Managing Up: A Key to Success in Your Career

One thing that I didn't think about earlier in my career was managing up, especially when it came to thinking that my manager is my manager and they should manage me. I thought, "Well, my manager is my manager so they should manage me." But I realized that this mindset can actually create a more collaborative and productive relationship with your manager. By taking the initiative to think about what your manager might need from you, you can avoid having to answer ad hoc questions all day long, which disrupts your workflow.

When you take a step back and consider why your manager is asking for updates or information, you may realize that it's because they're not aware of what you're working on. And ultimately, their head is on the chopping block because they're responsible for all the work that comes out of their team, including yours. So, if you think about it that way, it becomes very reasonable why your manager might be asking for XYZ updates.

Empathizing with your manager and understanding what they want can also make a big difference. Some managers like more context, while others prefer less. Some only want bullet points, while others want to know more data. They're more quantitatively driven or focus on getting good core insights before making a decision. The key is to figure out what your manager wants and cater to that. Luckily, you don't need to know what all managers want - you just need to know what your specific manager wants.

By understanding your manager's style and preferences, you can reduce the sample size of people you're catering to from everyone in the company to just one person. This means that you can tailor your approach to each individual manager, which is incredibly effective. Every manager has quirks and idiosyncrasies, so the more you understand yours, the better you'll be able to manage up.

When you start managing up, you're not just writing weekly recaps of what you've shipped - that's a small part of it. You're taking on a holistic posture where you're anticipating what your manager might need and thinking about how you can make their life easier while also keeping them in the loop on what you're working on.

Managing up takes effort, but it does take time to do it right. The alternative is spending 10 times as much time answering ad hoc requests from your manager instead of proactively managing their expectations. In my experience, investing time and effort into managing up has paid off tenfold - it's absolutely worth the investment. By being proactive, you can create a seamless relationship with your manager and reap the benefits of having someone who trusts you, seeks your thought partnership, believes in your competence, and wants to give you more autonomy.

Finally, learning to be concise is another key takeaways from managing up. Especially when presenting to senior leadership or to an all-hands meeting, rambling can be very common. My advice is to pause and gather your thoughts before speaking out loud - it's not natural to speak in a stream of consciousness! Preparation is the only surefire way to be concise.

So, if you're looking to take your career to the next level, focus on learning to manage up and being concise in your communication. With these two skills under your belt, you'll be well on your way to success in your career.

"WEBVTTKind: captionsLanguage: enthe biggest thing for data folks is to not just offer a fact or data point as a standalone thing but to offer your interpretation around what does this mean what's the so what there how can you help this make sense for your audience hi W thank you for joining me on the show hey Richie excited to be here excellent so I actually want to start with something that's been bugging me so you know there's this common thing where it's supposed to take $10,000 to become an expert but I've been working for several decades now well more than the 10,000 hours but I don't feel like an expert at my career so why is it so hard to get career skills o uh that's a banger to start with Y uh I think it's actually because career skills are a combination of a bunch of separate skills it's not just one skill um being good at your career involves being great at execution thinking about strategy uh being a good communicator project management dealing with conflict uh negotiating uh there's so many small negotiations that happen on a on a daily or weekly basis um at work and so managing up managing down managing expectations pushing back um being able to advocate for your ideas in a way that's effective and productive um so there's so much Nuance that goes into every one of those things uh which is why I think it's it's a lifelong Endeavor to get good at work essentially okay yeah uh that makes me feel better there's like so many different possible skills that you could learn so many different contexts so uh there's a lot to talk about so um we're probably get all now otherwise it's going to be a 24-hour podcast but uh maybe we'll start with uh something I think a lot of data people struggle with is like talking to other people so uh we go with communication so uh maybe communicating technical ideas is one of the most common things data people have to do and they struggle with so do you have any advice for this I think that data people tend to be logical and rational and they like numbers and uh I think when you have this mindset it's easy to assume that the numbers will speak for themselves the data will speak for itself in my experience very few things actually speak for themselves and even if they could your audience would probably appreciate a bit of narrative around what is your interpretation of what these numbers mean so I think the biggest thing uh for data folks is to not just offer a fact or data point as a standalone thing but to offer your interpretation around what does this mean what's the so what there how can you help this make sense for your audience okay yeah I like the idea of you can't just spout load the numbers and expect people to care you've got to give them the reason for why something is important oh I was going to say I think um the other thing is that very few things are um very Obviously good or obviously bad so in our own minds with full context we might think oh I mean this is clearly bad or this is clearly good but when you share something with someone else um it's pretty common that they're not sure how to react right like most of us have had people say wait is that good or bad you know and I've definitely said that you know to to folks who shared something with me that I could tell in their eyes was so obvious uh but for me it wasn't and so offering that interpretation of you know here's what this means here's why it matters here's how it relates to the work that we're talking about um that all helps to facilitate meaning which helps to create a more thoughtful conversation and discussion that leads to eventually a better decision yeah that makes a lot of sense um and I suppose um I think that like uh buying or selling stocks there's only two possible things you want to do it's like this is a good thing this is a bad thing and trying to reduce um a complex situation down to those two states this is good or this is bad it's going to help your audience okay uh so uh one of the um sort of common abys of advice for communications you got to tailor what you say to uh your audience do you have any advice on how to go about doing that yes so I have a couple Frameworks here um one is if you think about concentric circles you are in the bullseye of the concentric Circle Circle you have full context about all of your work um anyone outside of your own head is in the next rung so these are people who you work with on a daily basis they might be fellow data analysts data scientists all the people who do something similar maybe for a different team um and then you know on the next rung might be your manager depending on how closely they are uh in the data world uh some some managers are more Hands-On others are a little bit further away and then in the outer rungs you might have have cross functional Partners you might have product managers marketers that you work with Ops people uh and then you might have leadership team members who have even less insight and visibility into the day-to-day workings of of what your work might entail uh and then if you go even in the very further outer rungs you have people who are outside your company so if you're talking to a journalist you know about a product launch or if you're on a podcast whatever um how do you tailor your what you're saying to those different audiences so I like thinking about the concentric circles because it helps remind me that uh people can't read my mind and they are not immersed in the world that I'm immersed in and so it's up to me to share context and to educate my audience on the things that I need them to know in order to be able to have you know whatever conversation that we're having so that's one is a concentric circles the other is to think about the altitude that would make the most sense when when answering a question so uh there's you know altitude that's too high if you're if you speak at too high of an altitude you might be too vague too high level you're not giving people enough to chew on or enough detail uh but if you swing the pendulum and you're 5 Ines above the ground then you're too low altitude so that might be describing the step-by-step process of how you did you know something behind the scenes so you want to be somewhere in between those two uh and for an executive audience for example um you you want to be uh you want to give them enough detail for them to be able to chime in and be able to understand um what the situation was what the problem was but not so much nitty-gritty detail that you're getting lost in the weeds and they're they're you know not sure what the plot line really is anymore that last point is very interesting like um trying to figure out the altitude and do you need to start at high altitude and go lower or is it the other way around so I have an example here so let's say that there is uh a project delay and you're explaining in you know an all hands meeting why why this big project was delayed um and uh and one of the exacts asks you know was the delay um our fault or the vendor's fault so an answer that is too high altitude would be something like it was both of our fault okay and then just ending there something that is too low altitude would be getting into the nitty-gritty of well in January we started this project you know by March we knew we were a bit delayed then in June we res scoped the project and then later that month the vendor also missed a deadline and so really it was a bit of their fault and a bit of our fault right and then you know going into a lot more detail there right so that would be too low altitude and something that is I would say a right amount of altitude would be to say uh it was probably a bit of both of our faults the vendor missed a deadline which pushed the timing back but we also expanded the scope which meant that we needed to add a couple more weeks to be able to finish the project I have say I've definitely know people who tell stories at that very low altitude level and you get every bit of detail and 10 minutes later you can't remember what you were talking about so I do like that idea of just um trying to think about is anyone going to understand understand what you say and just adjust the uh the altitude accordingly okay um so a lot of this seems to be out the sort of flow in the general sort of a style of communication um do you need to go deeper on like Are there specific phrases or words that you can change according to your audience to make things easier to understand I think adjusting the jargon level depending on your audience uh is something good to keep in mind so you know going back to concentric circles if you're talking with fellow data scientists you know you can uh get very technical you all speak the same language if you are talking to a marketer like me or a founder or an exec um you might want to uh pull up a little bit and uh and kind of adjust uh the phrases and and words potentially all right and does it make a difference if you are a manager talking to your um employees on your team or if the way around if you're talking to a manager when you got that power imbalanced does the um does the way you communicate need to change I would say yes and no um traditionally people would say you know the manager is in a position of power so they don't have to explain themselves as much so I think that kind of you know logically tracks uh personally I like sharing my thought process even when I'm talking with director ports um I think it builds a lot of trust to explain why are we doing this why does this matter how does this fit into the the broader business instead of just tossing something over the wall and saying do this by this date um I think when people are more um engaged in whatever task are working on and they care about it they know how it fits uh they're more likely to do a better job uh and come out with with you know better output so that's one thing um and then you know if you are the direct Port thinking you know how much should I explain to my manager uh I think it depends on how much existing context your manager has on your work so some managers are are quite Hands-On uh and they are player coaches so they're individual contributors themselves and they're very close to the primary data other managers uh have very little visibility in to your work and maybe your manager uh you know isn't in data themselves and so they don't they have even less visibility and understanding of what it is that you do and so in that case um educating your manager when you are explaining what you're working on I find to be very very helpful in general I like thinking about how much does this person whether they're my manager or anyone else know about this topic when was the last time they thought about this topic where what what else you know might they need to know in order for them to either give me useful feedback or give me useful input uh or for them to be able to make a good decision uh so I like thinking about uh the existing amount of context and then I can fill in the blanks right so for some audiences I might need to explain a little bit more for others you know if I talk to my manager yesterday about this thing I don't need to give a ton of context they are already in the loop and we can we can uh you know go to the next thing without missing a beat in general um if you're trying to persuade someone to do something rather than just inform them about something how does that change your communication style I think traditionally people see informing and persuading as as two different things I actually think that it's it's a bit more of a spectrum um even when you are informing someone of news or informing someone of information um you want to think about how can I make sure that they receive this well uh because you might think I'm going to inform them of this and then move on right I'm just letting you know and I'm moving on uh but they might not be ready to move on if they hear this from you they might have a ton of questions they might disagree they might challenge some of your assumptions they might want to do something different so if you inform someone and don't think about how is this person going to receive it you might open up a can of worms where uh you're dealing with a bunch of Downstream issues of needing to cater to their questions and whatnot so I like thinking about informing and persuading as as you know a little bit more of a spectrum um if you are persuading uh it depends on how bold and how controversial is the thing that you are trying to convince someone of so if if you go to your CEO and you say we need to scrap our entire business and pivot to something completely different that is a bold claim and uh I forget which TV show this is uh I think it's Breaking Bad I don't quote me on that but uh there's a there's a quote that says if you come for the king you best not miss which I love nice so so you know if you are making a big swing like that you should have evidence ready to support what it is that you're saying you should have data points you should have examples you should be able to share your logic your first principles um to convince that person because otherwise why should they be convinced right um on the other hand uh let's say you say that same thing you know hey CEO we need to completely change our our business model and that's something that the leadership team had been talking about for a couple years now well then that's not so controversial anymore is it right the entire team has already been thinking about this it's been on their radar you know the team has been debating on it and so it's not so much you know what is the actual thing you're saying it's more what is it in context of how shocking would this be for your recipient to hear then then that would would inform how much you need to prepare to really build a business case okay yeah I can certainly see how um the Wilder your ideas are the more evidence you need to back up and the more preparation you need to do before having that conversation I'm was imagining trying to persuade persuade our CEO that we need to radically change data Camp's business and yeah uh it it would take an awful lot of persuading um okay so um I think giving feedback is one of the trickier types of communication so do you have any advice on how to do that one of my favorite Frameworks for giving feedback is what I call strategy not self-expression so what I mean by that is most of the time by the time we are giving feedback to someone we have already been sufficiently frustrated that we can no longer put up with whatever it is that you know that they've been doing that bothers us and so you go into this conversation uh you know you're feeling resentful you're feeling frustrated and it doesn't take much for you to get derailed you start giving that feedback and the other person your recipient raises their eyebrow or they scoff or they look surprised and that's it all of a sudden you're like oh you're surprised by this how are you surprised by this right like I mentioned this multiple times blah blah blah blah blah and so it's so easy to go off the rails trying to get the last word trying to teach that person lesson trying to get them to admit that they had wronged you um and none of that is productive the only thing that is productive in a feedback conversation is what will get that person to change their behavior Behavior change that is the ultimate goal and so you want to trim the 90% of stuff that you're saying that does not contribute to behavior change and only keep that 10% that will contribute to behavior change so that 10% I call strategy the rest is all self- expression that's you offloading your emotional baggage on that person um and I find whenever I go into a feedback conversation with this in mind this shapes what I say to that person this might mean focusing Less on all the ways that they wronged you and all the damage they caused and more on motivating that person to want to change to help them understand how changing would benefit them and the company and maybe offering some tactical ways to incorporate that change so they're more likely to do it because they realize that changing is actually really doable and not as hard as they thought it was right so your entire the entire content of what you might say to that person changes when you think about only focusing on the part that's going to get them to change their behavior I have to say offloading your emotional baggage on other people is having a good rant at them very satisfying but I agree it's probably not very useful totally totally I mean you want to get that out of your system just not with with that person right so maybe talking your a friend your spouse your therapist you know get it all out so that by the time you talk to that person you know you you no longer feel that need to offload absolutely but yeah I do like the idea you should probably focus on the behavioral change aspect just to get people to do what you want them to do um and after at work it's one of the few places where uh feedback just gets given to you whether you want it or not but there cases at work where you should actually go and seek out feedback without someone just thrusting it upon you oh definitely especially feedback on work output so feedback you know there's there's maybe multiple types but I see two major buckets one is behavioral feedback the other is feedback on workout output so especially with the latter category with work output um I think all of us should be eager to get more feedback on that especially because it will make us better at our craft so uh especially if you don't feel like you're getting enough of it I encourage you to seek it out from your manager and really let them know that it's okay for them to tear your work apart you know I think so many managers are are afraid of giving feedback um I actually uh read this fascinating quote uh study that was in Harvard Business Review that 67% of managers are afraid to give their direct reports feedback that's almost 70% of managers which is insane I mean that's wild right so these are people in quote unquote positions of power and even they feel self-conscious about potential conflict or retaliation or you know demotivating employee you know their team member taking it the wrong way and so if you are someone who wants more feedback your manager likely wants to give it to you they're just afraid of how you're going to take it uh and so I like being very explicit that you know I want you know red lines go for it right or you know do I want high level directional feedback to check in and make sure I'm going in the right direction um you know you can be specific about the kind that you were looking for uh but be explicit that you love that feedback you know you want them to be honest with you don't pull punches because your manager might actually need to be convinced that it's it's safe and that you actually do want feedback I wonder whether managers have that sort of uh bad experience of like employee just um taking feedback incredibly badly and that that makes them afraid so are there anything things you can do as an individual to make sure it's easy to give you feedback I mean I guess Beyond like just not bursting into tears as a manager I've definitely given feedback to people who said that they wanted feedback and then the minute I gave it to them they reacted extremely poorly and so for me that was like okay you say you want feedback but when I give it to you you know then then I find out if you really want it um and so I think many managers have had that uh had that happen where they're burned from past experiences and so therefore they're cautious about giving feedback um so yeah I think the biggest thing with with uh receiving feedback is um don't be defensive it can be very hard not to be defensive especially if you disagree in the moment with what the person is saying um and so you know I think of feedback very much like a gift if someone gives you a gift you don't have to love the gift it might not have been exactly what you were looking for but the fact that that person was thoughtful enough to put together this gift for you and then give it to you with good intent means something and so as a recipient you want to honor that you want to thank that person for trusting you enough to be honest with you and then you can look at the gift in more detail after they leave right you can decide do I want to keep this do I want to regift it do I want to donate it that is all fine you do not need to put into practice every piece of feedback that you are ever given you need to use your own judgment uh and so this requires intellectual honesty so that's very very important it's really easy to say well my manager is a micromanager they're just nitpicking this doesn't actually matter they're just on a power trip it's so easy to write off feedback like that uh in that way um so you want to be intellectually honest about is there validity in what this person is saying is there some truth in what they're saying if I disagree with the way they express that feedback is there still a grain of something that I can take with me that is actually valuable absolutely and yeah definitely I've had cases of feedback where it's the equivalent of like a set of socks or or some batteries or Something Different Strokes for different folks all right uh so you use the phrase there uh which um sounds easy but is probably suspiciously hard so intellectual honesty so uh can you talk through like how you get better at that it's it's so hard um to catch yourself when you're being intellectually honest or not because our brains are very good at um justifying the things we want to justify um and protecting our psyche from feeling threatened or challenged so I think the way to get better at calling yourself out is to make the decision that you want to start calling yourself out that you want to start challenging whatever your initial knee-jerk reaction might be uh I really do think that deciding to be intellectually honest is half the battle at that point it's you know constantly questioning um am I reacting this way because because I feel hurt or because I feel threatened and I'm you know telling myself that this feedback doesn't make sense and my manager sucks so that I don't have to change or that I don't have to admit that I contributed to the situation in a negative way you know uh so it's really calling yourself out in these ways and um and not letting not letting yourself scir out when good things happen I want I want to take credit when bad things happen out it's like it's other people's fault but yeah intellectual seems like a much more sensible approach if you can persuade yourself to do that okay uh so do you have any advice for when things go wrong because I mean in business things go wrong all the time there are disasters um are there any sort of uh strategies you can use in general to cope with problems and uh bad feedback and things like that yeah I think it depends on the kind of thing that's going wrong um but uh you know I would say to always reflect on how did I contribute to situation and what might I want to do differently going forward um I really like reflecting on anything that is happening you know especially you know things that are uh particularly good or particularly bad I think with things that are particularly good it's it's easy to chalk it up to well finally I've been so excellent all along finally something worked out uh versus being equally critical about what did I do that really made this work um and then same with with anything that didn't turn out as expected um you know was there a way I could have foreseen this was this avoidable in any way were there's signs of this that I can watch out for next time so that I can predict uh more accurately and save myself the heartache of you know learning from a mistake uh I think mistakes are totally normal and we should learn from mistakes but they're also expensive so if there's a way that you can learn without making the mistake personally then that's a better way to learn the L and what happens if um you disagree with colleagues or about some strategy or whatever um like cuz there always going to be differen his opinion um are there any ways to deal with I fundamentally uh disagree with what's going on here but still um it's something I've been asked to do one of the principles I like thinking about is not seeing conflict as conflict and what I mean by that is through a certain lens everything almost everything at work can be seen as conflict of some sort right conflict isn't just we are arguing and debating explicitly it's also a difference of will right one person wants to do something the other person wants to do something else and sometimes you know those two can be very far apart or very close uh but these are all examples of friction of conflict um and so I like thinking about you know how do I not see any of this as conflict because conflict means means that we need to overcome the conflict right we need to address this we need to figure out you know we need to fix this thing um when when in reality very often at work it's we're two people trying to figure this out together we are both aiming for the same thing which is making an informed decision based on the information that we know and usually there is some information asymmetry where you know some information you have some lived experience or you know visibility into things that I don't and vice versa so how can we put our heads together and figure out what is the best decision so there's a negotiating concept that I really like uh about being position about being uh issue driven not position driven position driven is you know Richie thinks this Wes thinks this like let's duke it out right whereas issue driven is we are figuring out this issue together and want what's best for resolving this issue regardless of who came up with what idea or or whatever um and so I think adopting that posture um uh can be really productive okay uh I do like the idea of um just working together in order to resolve some issue rather than just fighting about stuff um suppose you get to the point where you've just um you end up having to do something where you say okay I disagree with this but it's going ahead anyway um is there some way to um to do that gracefully so disagreeing and committing I think that's something that all of us have have heard of at this point um I like thinking about when when should you disagree and commit um I think that some people disagree and commit a little bit too early where you know there's a little bit of push back on their idea and they throw up their hands and say all right fine you know if you don't want to do it that way that's fine we'll do it your way right uh and there's a little bit of this martyrdom feeling of self-righteousness of like okay you know I said my peace I did my part uh if the Train's going to crash then the Train's going to crash um I personally don't like that I think that that is um a little bit immature and that uh the struggle of needing to convince other people and to have them understand why we think something is so important and why something is worth listening to um that is the work that is such a big part of our work as professionals so to to kind of Sher that responsibility I think you know I think I think we have a moral responsibility to to follow through and try our best to convince people if we think an idea is is uh uh really important um and and then I think on the other hand there are people who um hold out a little bit too long um before disagreeing and committing uh and so you know you also don't want to be the person who has tunnel vision who is digging in their heels who you know everyone feels like they need to bend over backward just like try to bring back on the boat um and so with disre committing you know I think if you feel like you've truly done your best you can be honest about that that you have reached into the depths of your creativity and powers of persuasion to to convince people um and and folks really are not still are still not seeing the point that's the point where uh relenting makes sense um and I also think it depends on the stakes that are involved so the higher the stakes uh and the worse the potential outcomes the more I think you should continue to advocate um if the stakes are relatively low and the worst thing that can happen is not that bad um maybe you disagree and commit earlier you know you can only pick so many battles you know one thing that I as someone who has many thoughts on many things um I've had to train myself to let go of having an opinion on certain things of having you know a point of view on certain things uh because it's not worth um the advocacy and I trust my colleagues who making the decision so those are all factors that I take into account uh when deciding do I want to disagree in command or not so uh we talked a lot about communication and whenever I've asked managers about like what the most important skill like soft skills that you value in your employees communication is always number one but the number two thing is acting like an owner and I think that one's a bit more vague like what does acting like an owner mean for me acting like an owner means being responsible for the outcome not only the tasks and the means to an end leading to that outcome um and you know I think for folks who are a bit more Junior earlier in their career you know by the time something arrives on your desk a task uh it's oftentimes very clearly scoped very clearly defined you know you do this thing you check off the Box you move on to the next thing but the more senior you get um the more that you might be handed an ambiguous problem that hasn't been shaped yet where you you have to be the one to define the parameters and to follow through and see this thing to completion and it doesn't matter if you took you know five six different attempts and and you still haven't reached the outcome you don't just get to check off the Box saying well I tried these five things and they didn't work back over to you now manager you know uh that might work you know earlier on but but doesn't work uh the more senior you get and so having this owner mentality means not assuming that you can throw this problem back on someone else for them to figure out but for you to sit with that problem you to own that problem until it is solved wow uh so I guess you could potentially be stuck in this for uh an awful long time if you keep trying things that fail or I guess maybe you probably get fired if you don't solve it eventually but uh yeah is uh is there a point where you say okay enough is enough then yes so acting like an owner also doesn't mean um blindly doing something just because someone told you to if you if you are an owner you have to exercise judgment on when it's time to change course and to own that decision not Sher that responsibility and have someone else make that decision for you so basically it's not blindly doing anything you know I think that a non-owner mentality is someone told me to do this so I'm going to do it or I'm going to keep doing it until someone tells me to stop right both of those are not that productive because you are uh not actively using your own judgment I would say it's more like Auto autopilot you know mode just doing the thing I was told versus I'm actively thinking about what makes the most sense in this situation maybe after a certain number of attempts you realize you have updated your thinking on this problem and you've changed this from being a problem to a constraint that this is actually something we should work around and here's what we might do to work around it right or you might call in reinforcements you might realize that my skill level or my domain expertise is limited to be able to solve this thing that I've tried enough things to come to that conclusion and therefore I'm going to pull in other people to help out um and and if that doesn't work I'm going to try something else right and so it's that it's that idea of of the buck stops with me there's no one else who I can just hand this off to who's going to tell me what to do I need to tell myself what to do and live with the decisions that I'm making okay I like the idea of just use your judgment about uh what the best way way to proceed is you sort of uh doing meta thinking about the problem about like what how do I do the strategy as well as just like going about trying to solve the problem itself um and you can call him reinforcements if necessary all right so uh on the subjects of judgment is that something that you can train yourself to get better at judgment is a topic that is endlessly fascinating for me and with every week in my newsletter I try to teach a bit of judgment um it's such a multifaceted complex topic because so much of judgment is tacit um if you talk to someone who's really experienced in something who's an expert in something sometimes they can't explain to you how they see differently than a lay person right uh how they pick up on things that other people don't even see don't even realize um and so trying to translate trying to capture that and trying to translate it put it into words so that people who are um who are trying to increase their level of judgment on something can learn that um I think is is really fascinating very very difficult um but uh you know I do think that it can be trained um I think that if you were to go through you know 10 15 20 years of your career um without reflecting and without questioning your decisions and trying to learn from them uh I think you can spend decades without improving your judgment very much so I don't think that it's something that just comes with time or comes with experience I think it takes active thinking to um try to pattern match and try to update the mental model in your own mind you know we have so many mental models about how things work um and ideally these mental models are as predictive as possible so you know the last three times I was in the situation blew up in this way and so this fourth time I'm going to do things a little bit differently right or you can do things the exact same way and then feel surprised when blows up again right so that active um the the act of thinking about what happened you know in similar situations how do I pattern match and update my mental model um all of that allows you to have better judgment which allows you to make better decisions which allows you to have I think a bunch of positive things like more ease more cooperation more excitement from other people less stress less headache less friction conflict skepticism um so I think there's so much goodness that happens when we continually improve our judgment okay I like that so it seems like a variation on the old saying there so it was like uh fool me three times shame on you fool me a fourth time shame on me yeah uh okay yeah so I like the idea of just uh learn from your experiences and then uh try and do things a bit smarter next time so um it seems like uh analytical thinking is going to be contributor to making better decisions can you talk me through um how do you get better at analytical thinking this is another meta skill that um can really help I think in everything that you do um I like thinking about the root cause of whatever might be happening you know I think often there's a surface level conclusion we might jump to we might even have pet theories about something um but getting closer to the root cause allows you to think about what actions might I take to solve that thing so I have a framework that I call brawl b r o l um and uh it's Behavior right what Behavior are you observing um the RS root cause what are potential root causes that might be causing this Behavior Uh the O is the ideal outcome so what's the ideal outcome you would like to have happen and then L are levers what are levers within your control that uh you can pull that will get you closer to this ideal outcome um and so by breaking it down this way you can get more specific about what exactly do you want to change um and so I actually a good example one of my clients is a head of data at a a Marketplace uh company and um he was saying that he feels like the product team doesn't really take into account data's uh perspective on thingss at least not soon enough and not often enough and so he always feels like he's trying to play catchup on features that the product team has already decided on has already latched on to uh that the data doesn't support at all um and so so he was saying I want data to listen to or I want product to listen to my team the data team more um so that's an example of an outcome that I would say is not specific enough so you want to get more specific on uh what that ideal outcome is uh because being Listen to More what does that mean what does that look like right how much how much are they listening to now and what would more really be um and so I worked with them on identifying uh what that would really look like which is um product seeking data's input or taking taking account taking data into account before creating uh product plans okay so like that is a more specific outcome and then there's from there there's a lot of levers that we can pull for you know how do we achieve that right um and so if you look at behavior for example uh you know the product managers were uh shipping uh strategy docs and whatnot and starting to pitch them to senior leadership without consulting the data team right so that's that's a behavior um and what are the levers you know oh what are the root causes of that behavior potentially right it's um you know product has a lot going on the are excited by certain features they're also hearing from customers who might be saying like oh we really want this or you know so they're looking at other sources of data in their mind probably so they're not looking at the same sources of data that that the data team are looking at but they are talking to customers to you know the sales team the marketing team Etc to leadership team and so all these sources are probably data in their mind so they probably think well we are looking at data right we just don't talk to our data team you know more than once a week but we already feel like once a week is really is quite a lot right and so getting to the minds of the person or the team that you're wanting to to appeal to um that all allows you to think about okay what are the levers then and so what we came up with was you know uh each data scientist has a corresponding product manager for whatever project they're working on and so they have a one-on-one each week and so in that one-on-one can data uh can the data scientists bring um insights proactively to share with their product managers on what is working what's not anything that's unexpected and then also use that as an opportunity to ask the product person what are you seeing and what are you thinking about are there certain features that you starting to ponder on right because right now the data team is not getting that information until they're seeing the you know the fully written out strategy docs that are you know quite Downstream already and so that is the lever that is totally within your reach right you already have those one-on-one meetings you already have the PM that you work closely with and so what is a small change that you can make that can increase uh the chances that product takes data more into account so that's an example of you know if you break down a problem and really analyze it into the Behavior Uh root causes ideal outcome and levers you can get a clearer understanding of what can I change that will lead to the result I'm looking for that's a very cool framework and I like that everything uh gets broken down into smaller parts and it's very specific so you mentioned at the start it was just well product need to listen to the data team more but that's kind of very vague and you want something to become uh more concrete and actionable okay so uh you mentioned that like one of the solutions to that was or one of the levers in that would be just changing how meetings work between product and data teams and I think meetings are something we spend way too much of our lives in how to do meetings better is always an important thing so uh what are your top meeting tips I think um it really depends on the meeting culture within each company there are some companies where the default is to hop on a call is to hop in a meeting other companies are allergic to meetings they try to do as much outside of a meeting as possible um and so I'm more in the lad Camp um I prefer not to meet live unless there is uh no other way to discuss this than to discuss live um and so I love creating uh even in advance of a meeting so let's say I have to meet even then if there's anything I could put in a pre-recorded video a loom video where I can explain something that is pure knowledge transfer that you can watch on 1.75x speed on your own time amazing when we hop on the call we're going to have more shared context um I also like putting together a few notes or a dock beforehand that the person again can read on their own time uh they can even comment on a few areas that they especially want to discuss or they have question on which for me um gives me more information right instead of going in blind for this meeting I now know that this person has questions on XYZ areas so I'm more prepared to be able to talk about those and address those and make the best use of our time um so I'm very big on you know what are things we can do asynchronously so that when we actually do meet we are focusing on discussion debate conversation uh this is a working session versus one directional information uh you know dispelling you know sharing information and uh you know all of that is Is some much of it is stuff that you can do asyncronously okay I like the idea um it's like you do the homework before the class rather than afterwards uh flip classroom approach yeah so uh yeah certainly information dump is probably better done in a document rather than just getting everyone together uh in a call and let's going to be lots of questions okay uh so uh we talked about um a lot of the ideas for improving your career I'm curious as to what mistakes people make have you seen any examples of like what of the most common things people do wrong at work it's a tricky one right there's so many things so many things um there's that uh Tolstoy anak kinina quote that uh I'm going to butcher the quote but essentially um all happy families are are alike in the same way and all unhappy families are uh uh different in a bunch of different ways uh which to me applied to the workplace means there are infinite ways to mess things up or to you know to be unhappy or to you know uh fall into various traps uh but there's there's only a few things to keep in mind you know when uh to be successful I think um but uh oh gosh what are some common mistakes in the workplace um I think one of them is not managing up uh that was something that I did not think about at all especially earlier in my career um you know I thought well my manager is my manager so they should manage me you know why should I have to manage up um but you know I I realized that uh managing up will create a much more collaborative and productive relationship with your manager where um it's often one of the best ways to avoid your manager breathing down your neck you know if your manager is coming to you every day with a bunch of ad hoc questions that Tak so much time to answer that disrupt your flow um instead of just continuing on with this Dynamic if you take a step back you might realize that it's because my manager is not aware of what I'm working on and ultimately their head is on The Chopping Block because they're responsible for all the work that comes out of their team including my work right and so if you think about it that way it becomes very reasonable why your manager might be asking for XYZ updates because you aren't proactively providing them right and so thinking about uh thinking about that um Dynamic and getting into your manager's mind empathizing with them um uh I think that that can really do wonders uh and so for me that meant proactively sharing updates proactively sharing how I was thinking about certain decisions especially for higher uh Stakes projects higher visibility projects um and really catering to my manager style and the way they want to your information so some managers are you know they like more context some like less some only want bullet points some like more data they're more quantitatively driven they want to know that you are looking at the numbers other managers really want to know that there is a good core Insight or that you're exploring a variety of options before picking one right and so uh luckily you don't need to know what all managers want you only have to know what your manager wants so it drastically uh reduces you know the sample size you're catering to is n equals one that's awesome like every manager has quirks and idiosyncrasies so the more you understand your manager the better you can uh manage up to create a more seamless relationship and when you do manage up uh there are a lot of benefits you know your manager trusts you more they uh seek your thought partnership they believe in your competence and your ability they believe that you are someone who is reliable and trustworthy and shows good judgment all of those things mean that they want to give you more autonomy they want to give you bigger projects they want to elevate you more within the company they want to back you they want to support you um so managing up I think is one thing that uh I think many people don't think enough about and it goes beyond you know writing a weekly recap of what you shipped that is one thing you can do to manage up but it's much more of a holistic posture where you are anticipating what your manager might need and thinking about how can I make my manager's life easier and also them in the loop on what I'm working on okay I have say when you started answering that and you talking about managing your manager I was like wait I've got to manage my boss now that sounds like hard work to do this another one yeah yeah yeah uh but no I think certainly like communicating status updates before you get asked for them that's that's a brilliant uh tip something fairly simple just to get you started with uh with managing up yeah and one last thing with managing up you know it does take effort it does take time the thing to keep in mind is that not the managing up takes even more time so it's either you decide to manage up proactively or you spend 10 times as much time answering all those ad hoc requests uh you know having your manager breathe down your neck needing to task switch so it's really a trade-off of is a bit of investment UPF front going to prevent all these headaches down the line and in my experience it is absolutely worth that investment absolutely um all right so uh just to finish up do you have any final advice for how to get better at your career I think that managing up piece was a big one um I think the other one is learning to be concise I think that especially if you are presenting to senior leadership presenting in you know all hands meetings um rambling is very very common and so my advice there is to pause and gather your thoughts to try to figure out what your point is instead of speaking out loud in a stream of Consciousness uh in my experience preparation is is the only Sure Fire way to be concise uh and so figure out what you think and then and then you know say communicate what you think after that absolutely um all right so in the spirit of being concise we should wrap up here then rather than carrying on another 10 minutes so yeah uh thank you so much for your time West that was fantastic awesome thank you so much Richiethe biggest thing for data folks is to not just offer a fact or data point as a standalone thing but to offer your interpretation around what does this mean what's the so what there how can you help this make sense for your audience hi W thank you for joining me on the show hey Richie excited to be here excellent so I actually want to start with something that's been bugging me so you know there's this common thing where it's supposed to take $10,000 to become an expert but I've been working for several decades now well more than the 10,000 hours but I don't feel like an expert at my career so why is it so hard to get career skills o uh that's a banger to start with Y uh I think it's actually because career skills are a combination of a bunch of separate skills it's not just one skill um being good at your career involves being great at execution thinking about strategy uh being a good communicator project management dealing with conflict uh negotiating uh there's so many small negotiations that happen on a on a daily or weekly basis um at work and so managing up managing down managing expectations pushing back um being able to advocate for your ideas in a way that's effective and productive um so there's so much Nuance that goes into every one of those things uh which is why I think it's it's a lifelong Endeavor to get good at work essentially okay yeah uh that makes me feel better there's like so many different possible skills that you could learn so many different contexts so uh there's a lot to talk about so um we're probably get all now otherwise it's going to be a 24-hour podcast but uh maybe we'll start with uh something I think a lot of data people struggle with is like talking to other people so uh we go with communication so uh maybe communicating technical ideas is one of the most common things data people have to do and they struggle with so do you have any advice for this I think that data people tend to be logical and rational and they like numbers and uh I think when you have this mindset it's easy to assume that the numbers will speak for themselves the data will speak for itself in my experience very few things actually speak for themselves and even if they could your audience would probably appreciate a bit of narrative around what is your interpretation of what these numbers mean so I think the biggest thing uh for data folks is to not just offer a fact or data point as a standalone thing but to offer your interpretation around what does this mean what's the so what there how can you help this make sense for your audience okay yeah I like the idea of you can't just spout load the numbers and expect people to care you've got to give them the reason for why something is important oh I was going to say I think um the other thing is that very few things are um very Obviously good or obviously bad so in our own minds with full context we might think oh I mean this is clearly bad or this is clearly good but when you share something with someone else um it's pretty common that they're not sure how to react right like most of us have had people say wait is that good or bad you know and I've definitely said that you know to to folks who shared something with me that I could tell in their eyes was so obvious uh but for me it wasn't and so offering that interpretation of you know here's what this means here's why it matters here's how it relates to the work that we're talking about um that all helps to facilitate meaning which helps to create a more thoughtful conversation and discussion that leads to eventually a better decision yeah that makes a lot of sense um and I suppose um I think that like uh buying or selling stocks there's only two possible things you want to do it's like this is a good thing this is a bad thing and trying to reduce um a complex situation down to those two states this is good or this is bad it's going to help your audience okay uh so uh one of the um sort of common abys of advice for communications you got to tailor what you say to uh your audience do you have any advice on how to go about doing that yes so I have a couple Frameworks here um one is if you think about concentric circles you are in the bullseye of the concentric Circle Circle you have full context about all of your work um anyone outside of your own head is in the next rung so these are people who you work with on a daily basis they might be fellow data analysts data scientists all the people who do something similar maybe for a different team um and then you know on the next rung might be your manager depending on how closely they are uh in the data world uh some some managers are more Hands-On others are a little bit further away and then in the outer rungs you might have have cross functional Partners you might have product managers marketers that you work with Ops people uh and then you might have leadership team members who have even less insight and visibility into the day-to-day workings of of what your work might entail uh and then if you go even in the very further outer rungs you have people who are outside your company so if you're talking to a journalist you know about a product launch or if you're on a podcast whatever um how do you tailor your what you're saying to those different audiences so I like thinking about the concentric circles because it helps remind me that uh people can't read my mind and they are not immersed in the world that I'm immersed in and so it's up to me to share context and to educate my audience on the things that I need them to know in order to be able to have you know whatever conversation that we're having so that's one is a concentric circles the other is to think about the altitude that would make the most sense when when answering a question so uh there's you know altitude that's too high if you're if you speak at too high of an altitude you might be too vague too high level you're not giving people enough to chew on or enough detail uh but if you swing the pendulum and you're 5 Ines above the ground then you're too low altitude so that might be describing the step-by-step process of how you did you know something behind the scenes so you want to be somewhere in between those two uh and for an executive audience for example um you you want to be uh you want to give them enough detail for them to be able to chime in and be able to understand um what the situation was what the problem was but not so much nitty-gritty detail that you're getting lost in the weeds and they're they're you know not sure what the plot line really is anymore that last point is very interesting like um trying to figure out the altitude and do you need to start at high altitude and go lower or is it the other way around so I have an example here so let's say that there is uh a project delay and you're explaining in you know an all hands meeting why why this big project was delayed um and uh and one of the exacts asks you know was the delay um our fault or the vendor's fault so an answer that is too high altitude would be something like it was both of our fault okay and then just ending there something that is too low altitude would be getting into the nitty-gritty of well in January we started this project you know by March we knew we were a bit delayed then in June we res scoped the project and then later that month the vendor also missed a deadline and so really it was a bit of their fault and a bit of our fault right and then you know going into a lot more detail there right so that would be too low altitude and something that is I would say a right amount of altitude would be to say uh it was probably a bit of both of our faults the vendor missed a deadline which pushed the timing back but we also expanded the scope which meant that we needed to add a couple more weeks to be able to finish the project I have say I've definitely know people who tell stories at that very low altitude level and you get every bit of detail and 10 minutes later you can't remember what you were talking about so I do like that idea of just um trying to think about is anyone going to understand understand what you say and just adjust the uh the altitude accordingly okay um so a lot of this seems to be out the sort of flow in the general sort of a style of communication um do you need to go deeper on like Are there specific phrases or words that you can change according to your audience to make things easier to understand I think adjusting the jargon level depending on your audience uh is something good to keep in mind so you know going back to concentric circles if you're talking with fellow data scientists you know you can uh get very technical you all speak the same language if you are talking to a marketer like me or a founder or an exec um you might want to uh pull up a little bit and uh and kind of adjust uh the phrases and and words potentially all right and does it make a difference if you are a manager talking to your um employees on your team or if the way around if you're talking to a manager when you got that power imbalanced does the um does the way you communicate need to change I would say yes and no um traditionally people would say you know the manager is in a position of power so they don't have to explain themselves as much so I think that kind of you know logically tracks uh personally I like sharing my thought process even when I'm talking with director ports um I think it builds a lot of trust to explain why are we doing this why does this matter how does this fit into the the broader business instead of just tossing something over the wall and saying do this by this date um I think when people are more um engaged in whatever task are working on and they care about it they know how it fits uh they're more likely to do a better job uh and come out with with you know better output so that's one thing um and then you know if you are the direct Port thinking you know how much should I explain to my manager uh I think it depends on how much existing context your manager has on your work so some managers are are quite Hands-On uh and they are player coaches so they're individual contributors themselves and they're very close to the primary data other managers uh have very little visibility in to your work and maybe your manager uh you know isn't in data themselves and so they don't they have even less visibility and understanding of what it is that you do and so in that case um educating your manager when you are explaining what you're working on I find to be very very helpful in general I like thinking about how much does this person whether they're my manager or anyone else know about this topic when was the last time they thought about this topic where what what else you know might they need to know in order for them to either give me useful feedback or give me useful input uh or for them to be able to make a good decision uh so I like thinking about uh the existing amount of context and then I can fill in the blanks right so for some audiences I might need to explain a little bit more for others you know if I talk to my manager yesterday about this thing I don't need to give a ton of context they are already in the loop and we can we can uh you know go to the next thing without missing a beat in general um if you're trying to persuade someone to do something rather than just inform them about something how does that change your communication style I think traditionally people see informing and persuading as as two different things I actually think that it's it's a bit more of a spectrum um even when you are informing someone of news or informing someone of information um you want to think about how can I make sure that they receive this well uh because you might think I'm going to inform them of this and then move on right I'm just letting you know and I'm moving on uh but they might not be ready to move on if they hear this from you they might have a ton of questions they might disagree they might challenge some of your assumptions they might want to do something different so if you inform someone and don't think about how is this person going to receive it you might open up a can of worms where uh you're dealing with a bunch of Downstream issues of needing to cater to their questions and whatnot so I like thinking about informing and persuading as as you know a little bit more of a spectrum um if you are persuading uh it depends on how bold and how controversial is the thing that you are trying to convince someone of so if if you go to your CEO and you say we need to scrap our entire business and pivot to something completely different that is a bold claim and uh I forget which TV show this is uh I think it's Breaking Bad I don't quote me on that but uh there's a there's a quote that says if you come for the king you best not miss which I love nice so so you know if you are making a big swing like that you should have evidence ready to support what it is that you're saying you should have data points you should have examples you should be able to share your logic your first principles um to convince that person because otherwise why should they be convinced right um on the other hand uh let's say you say that same thing you know hey CEO we need to completely change our our business model and that's something that the leadership team had been talking about for a couple years now well then that's not so controversial anymore is it right the entire team has already been thinking about this it's been on their radar you know the team has been debating on it and so it's not so much you know what is the actual thing you're saying it's more what is it in context of how shocking would this be for your recipient to hear then then that would would inform how much you need to prepare to really build a business case okay yeah I can certainly see how um the Wilder your ideas are the more evidence you need to back up and the more preparation you need to do before having that conversation I'm was imagining trying to persuade persuade our CEO that we need to radically change data Camp's business and yeah uh it it would take an awful lot of persuading um okay so um I think giving feedback is one of the trickier types of communication so do you have any advice on how to do that one of my favorite Frameworks for giving feedback is what I call strategy not self-expression so what I mean by that is most of the time by the time we are giving feedback to someone we have already been sufficiently frustrated that we can no longer put up with whatever it is that you know that they've been doing that bothers us and so you go into this conversation uh you know you're feeling resentful you're feeling frustrated and it doesn't take much for you to get derailed you start giving that feedback and the other person your recipient raises their eyebrow or they scoff or they look surprised and that's it all of a sudden you're like oh you're surprised by this how are you surprised by this right like I mentioned this multiple times blah blah blah blah blah and so it's so easy to go off the rails trying to get the last word trying to teach that person lesson trying to get them to admit that they had wronged you um and none of that is productive the only thing that is productive in a feedback conversation is what will get that person to change their behavior Behavior change that is the ultimate goal and so you want to trim the 90% of stuff that you're saying that does not contribute to behavior change and only keep that 10% that will contribute to behavior change so that 10% I call strategy the rest is all self- expression that's you offloading your emotional baggage on that person um and I find whenever I go into a feedback conversation with this in mind this shapes what I say to that person this might mean focusing Less on all the ways that they wronged you and all the damage they caused and more on motivating that person to want to change to help them understand how changing would benefit them and the company and maybe offering some tactical ways to incorporate that change so they're more likely to do it because they realize that changing is actually really doable and not as hard as they thought it was right so your entire the entire content of what you might say to that person changes when you think about only focusing on the part that's going to get them to change their behavior I have to say offloading your emotional baggage on other people is having a good rant at them very satisfying but I agree it's probably not very useful totally totally I mean you want to get that out of your system just not with with that person right so maybe talking your a friend your spouse your therapist you know get it all out so that by the time you talk to that person you know you you no longer feel that need to offload absolutely but yeah I do like the idea you should probably focus on the behavioral change aspect just to get people to do what you want them to do um and after at work it's one of the few places where uh feedback just gets given to you whether you want it or not but there cases at work where you should actually go and seek out feedback without someone just thrusting it upon you oh definitely especially feedback on work output so feedback you know there's there's maybe multiple types but I see two major buckets one is behavioral feedback the other is feedback on workout output so especially with the latter category with work output um I think all of us should be eager to get more feedback on that especially because it will make us better at our craft so uh especially if you don't feel like you're getting enough of it I encourage you to seek it out from your manager and really let them know that it's okay for them to tear your work apart you know I think so many managers are are afraid of giving feedback um I actually uh read this fascinating quote uh study that was in Harvard Business Review that 67% of managers are afraid to give their direct reports feedback that's almost 70% of managers which is insane I mean that's wild right so these are people in quote unquote positions of power and even they feel self-conscious about potential conflict or retaliation or you know demotivating employee you know their team member taking it the wrong way and so if you are someone who wants more feedback your manager likely wants to give it to you they're just afraid of how you're going to take it uh and so I like being very explicit that you know I want you know red lines go for it right or you know do I want high level directional feedback to check in and make sure I'm going in the right direction um you know you can be specific about the kind that you were looking for uh but be explicit that you love that feedback you know you want them to be honest with you don't pull punches because your manager might actually need to be convinced that it's it's safe and that you actually do want feedback I wonder whether managers have that sort of uh bad experience of like employee just um taking feedback incredibly badly and that that makes them afraid so are there anything things you can do as an individual to make sure it's easy to give you feedback I mean I guess Beyond like just not bursting into tears as a manager I've definitely given feedback to people who said that they wanted feedback and then the minute I gave it to them they reacted extremely poorly and so for me that was like okay you say you want feedback but when I give it to you you know then then I find out if you really want it um and so I think many managers have had that uh had that happen where they're burned from past experiences and so therefore they're cautious about giving feedback um so yeah I think the biggest thing with with uh receiving feedback is um don't be defensive it can be very hard not to be defensive especially if you disagree in the moment with what the person is saying um and so you know I think of feedback very much like a gift if someone gives you a gift you don't have to love the gift it might not have been exactly what you were looking for but the fact that that person was thoughtful enough to put together this gift for you and then give it to you with good intent means something and so as a recipient you want to honor that you want to thank that person for trusting you enough to be honest with you and then you can look at the gift in more detail after they leave right you can decide do I want to keep this do I want to regift it do I want to donate it that is all fine you do not need to put into practice every piece of feedback that you are ever given you need to use your own judgment uh and so this requires intellectual honesty so that's very very important it's really easy to say well my manager is a micromanager they're just nitpicking this doesn't actually matter they're just on a power trip it's so easy to write off feedback like that uh in that way um so you want to be intellectually honest about is there validity in what this person is saying is there some truth in what they're saying if I disagree with the way they express that feedback is there still a grain of something that I can take with me that is actually valuable absolutely and yeah definitely I've had cases of feedback where it's the equivalent of like a set of socks or or some batteries or Something Different Strokes for different folks all right uh so you use the phrase there uh which um sounds easy but is probably suspiciously hard so intellectual honesty so uh can you talk through like how you get better at that it's it's so hard um to catch yourself when you're being intellectually honest or not because our brains are very good at um justifying the things we want to justify um and protecting our psyche from feeling threatened or challenged so I think the way to get better at calling yourself out is to make the decision that you want to start calling yourself out that you want to start challenging whatever your initial knee-jerk reaction might be uh I really do think that deciding to be intellectually honest is half the battle at that point it's you know constantly questioning um am I reacting this way because because I feel hurt or because I feel threatened and I'm you know telling myself that this feedback doesn't make sense and my manager sucks so that I don't have to change or that I don't have to admit that I contributed to the situation in a negative way you know uh so it's really calling yourself out in these ways and um and not letting not letting yourself scir out when good things happen I want I want to take credit when bad things happen out it's like it's other people's fault but yeah intellectual seems like a much more sensible approach if you can persuade yourself to do that okay uh so do you have any advice for when things go wrong because I mean in business things go wrong all the time there are disasters um are there any sort of uh strategies you can use in general to cope with problems and uh bad feedback and things like that yeah I think it depends on the kind of thing that's going wrong um but uh you know I would say to always reflect on how did I contribute to situation and what might I want to do differently going forward um I really like reflecting on anything that is happening you know especially you know things that are uh particularly good or particularly bad I think with things that are particularly good it's it's easy to chalk it up to well finally I've been so excellent all along finally something worked out uh versus being equally critical about what did I do that really made this work um and then same with with anything that didn't turn out as expected um you know was there a way I could have foreseen this was this avoidable in any way were there's signs of this that I can watch out for next time so that I can predict uh more accurately and save myself the heartache of you know learning from a mistake uh I think mistakes are totally normal and we should learn from mistakes but they're also expensive so if there's a way that you can learn without making the mistake personally then that's a better way to learn the L and what happens if um you disagree with colleagues or about some strategy or whatever um like cuz there always going to be differen his opinion um are there any ways to deal with I fundamentally uh disagree with what's going on here but still um it's something I've been asked to do one of the principles I like thinking about is not seeing conflict as conflict and what I mean by that is through a certain lens everything almost everything at work can be seen as conflict of some sort right conflict isn't just we are arguing and debating explicitly it's also a difference of will right one person wants to do something the other person wants to do something else and sometimes you know those two can be very far apart or very close uh but these are all examples of friction of conflict um and so I like thinking about you know how do I not see any of this as conflict because conflict means means that we need to overcome the conflict right we need to address this we need to figure out you know we need to fix this thing um when when in reality very often at work it's we're two people trying to figure this out together we are both aiming for the same thing which is making an informed decision based on the information that we know and usually there is some information asymmetry where you know some information you have some lived experience or you know visibility into things that I don't and vice versa so how can we put our heads together and figure out what is the best decision so there's a negotiating concept that I really like uh about being position about being uh issue driven not position driven position driven is you know Richie thinks this Wes thinks this like let's duke it out right whereas issue driven is we are figuring out this issue together and want what's best for resolving this issue regardless of who came up with what idea or or whatever um and so I think adopting that posture um uh can be really productive okay uh I do like the idea of um just working together in order to resolve some issue rather than just fighting about stuff um suppose you get to the point where you've just um you end up having to do something where you say okay I disagree with this but it's going ahead anyway um is there some way to um to do that gracefully so disagreeing and committing I think that's something that all of us have have heard of at this point um I like thinking about when when should you disagree and commit um I think that some people disagree and commit a little bit too early where you know there's a little bit of push back on their idea and they throw up their hands and say all right fine you know if you don't want to do it that way that's fine we'll do it your way right uh and there's a little bit of this martyrdom feeling of self-righteousness of like okay you know I said my peace I did my part uh if the Train's going to crash then the Train's going to crash um I personally don't like that I think that that is um a little bit immature and that uh the struggle of needing to convince other people and to have them understand why we think something is so important and why something is worth listening to um that is the work that is such a big part of our work as professionals so to to kind of Sher that responsibility I think you know I think I think we have a moral responsibility to to follow through and try our best to convince people if we think an idea is is uh uh really important um and and then I think on the other hand there are people who um hold out a little bit too long um before disagreeing and committing uh and so you know you also don't want to be the person who has tunnel vision who is digging in their heels who you know everyone feels like they need to bend over backward just like try to bring back on the boat um and so with disre committing you know I think if you feel like you've truly done your best you can be honest about that that you have reached into the depths of your creativity and powers of persuasion to to convince people um and and folks really are not still are still not seeing the point that's the point where uh relenting makes sense um and I also think it depends on the stakes that are involved so the higher the stakes uh and the worse the potential outcomes the more I think you should continue to advocate um if the stakes are relatively low and the worst thing that can happen is not that bad um maybe you disagree and commit earlier you know you can only pick so many battles you know one thing that I as someone who has many thoughts on many things um I've had to train myself to let go of having an opinion on certain things of having you know a point of view on certain things uh because it's not worth um the advocacy and I trust my colleagues who making the decision so those are all factors that I take into account uh when deciding do I want to disagree in command or not so uh we talked a lot about communication and whenever I've asked managers about like what the most important skill like soft skills that you value in your employees communication is always number one but the number two thing is acting like an owner and I think that one's a bit more vague like what does acting like an owner mean for me acting like an owner means being responsible for the outcome not only the tasks and the means to an end leading to that outcome um and you know I think for folks who are a bit more Junior earlier in their career you know by the time something arrives on your desk a task uh it's oftentimes very clearly scoped very clearly defined you know you do this thing you check off the Box you move on to the next thing but the more senior you get um the more that you might be handed an ambiguous problem that hasn't been shaped yet where you you have to be the one to define the parameters and to follow through and see this thing to completion and it doesn't matter if you took you know five six different attempts and and you still haven't reached the outcome you don't just get to check off the Box saying well I tried these five things and they didn't work back over to you now manager you know uh that might work you know earlier on but but doesn't work uh the more senior you get and so having this owner mentality means not assuming that you can throw this problem back on someone else for them to figure out but for you to sit with that problem you to own that problem until it is solved wow uh so I guess you could potentially be stuck in this for uh an awful long time if you keep trying things that fail or I guess maybe you probably get fired if you don't solve it eventually but uh yeah is uh is there a point where you say okay enough is enough then yes so acting like an owner also doesn't mean um blindly doing something just because someone told you to if you if you are an owner you have to exercise judgment on when it's time to change course and to own that decision not Sher that responsibility and have someone else make that decision for you so basically it's not blindly doing anything you know I think that a non-owner mentality is someone told me to do this so I'm going to do it or I'm going to keep doing it until someone tells me to stop right both of those are not that productive because you are uh not actively using your own judgment I would say it's more like Auto autopilot you know mode just doing the thing I was told versus I'm actively thinking about what makes the most sense in this situation maybe after a certain number of attempts you realize you have updated your thinking on this problem and you've changed this from being a problem to a constraint that this is actually something we should work around and here's what we might do to work around it right or you might call in reinforcements you might realize that my skill level or my domain expertise is limited to be able to solve this thing that I've tried enough things to come to that conclusion and therefore I'm going to pull in other people to help out um and and if that doesn't work I'm going to try something else right and so it's that it's that idea of of the buck stops with me there's no one else who I can just hand this off to who's going to tell me what to do I need to tell myself what to do and live with the decisions that I'm making okay I like the idea of just use your judgment about uh what the best way way to proceed is you sort of uh doing meta thinking about the problem about like what how do I do the strategy as well as just like going about trying to solve the problem itself um and you can call him reinforcements if necessary all right so uh on the subjects of judgment is that something that you can train yourself to get better at judgment is a topic that is endlessly fascinating for me and with every week in my newsletter I try to teach a bit of judgment um it's such a multifaceted complex topic because so much of judgment is tacit um if you talk to someone who's really experienced in something who's an expert in something sometimes they can't explain to you how they see differently than a lay person right uh how they pick up on things that other people don't even see don't even realize um and so trying to translate trying to capture that and trying to translate it put it into words so that people who are um who are trying to increase their level of judgment on something can learn that um I think is is really fascinating very very difficult um but uh you know I do think that it can be trained um I think that if you were to go through you know 10 15 20 years of your career um without reflecting and without questioning your decisions and trying to learn from them uh I think you can spend decades without improving your judgment very much so I don't think that it's something that just comes with time or comes with experience I think it takes active thinking to um try to pattern match and try to update the mental model in your own mind you know we have so many mental models about how things work um and ideally these mental models are as predictive as possible so you know the last three times I was in the situation blew up in this way and so this fourth time I'm going to do things a little bit differently right or you can do things the exact same way and then feel surprised when blows up again right so that active um the the act of thinking about what happened you know in similar situations how do I pattern match and update my mental model um all of that allows you to have better judgment which allows you to make better decisions which allows you to have I think a bunch of positive things like more ease more cooperation more excitement from other people less stress less headache less friction conflict skepticism um so I think there's so much goodness that happens when we continually improve our judgment okay I like that so it seems like a variation on the old saying there so it was like uh fool me three times shame on you fool me a fourth time shame on me yeah uh okay yeah so I like the idea of just uh learn from your experiences and then uh try and do things a bit smarter next time so um it seems like uh analytical thinking is going to be contributor to making better decisions can you talk me through um how do you get better at analytical thinking this is another meta skill that um can really help I think in everything that you do um I like thinking about the root cause of whatever might be happening you know I think often there's a surface level conclusion we might jump to we might even have pet theories about something um but getting closer to the root cause allows you to think about what actions might I take to solve that thing so I have a framework that I call brawl b r o l um and uh it's Behavior right what Behavior are you observing um the RS root cause what are potential root causes that might be causing this Behavior Uh the O is the ideal outcome so what's the ideal outcome you would like to have happen and then L are levers what are levers within your control that uh you can pull that will get you closer to this ideal outcome um and so by breaking it down this way you can get more specific about what exactly do you want to change um and so I actually a good example one of my clients is a head of data at a a Marketplace uh company and um he was saying that he feels like the product team doesn't really take into account data's uh perspective on thingss at least not soon enough and not often enough and so he always feels like he's trying to play catchup on features that the product team has already decided on has already latched on to uh that the data doesn't support at all um and so so he was saying I want data to listen to or I want product to listen to my team the data team more um so that's an example of an outcome that I would say is not specific enough so you want to get more specific on uh what that ideal outcome is uh because being Listen to More what does that mean what does that look like right how much how much are they listening to now and what would more really be um and so I worked with them on identifying uh what that would really look like which is um product seeking data's input or taking taking account taking data into account before creating uh product plans okay so like that is a more specific outcome and then there's from there there's a lot of levers that we can pull for you know how do we achieve that right um and so if you look at behavior for example uh you know the product managers were uh shipping uh strategy docs and whatnot and starting to pitch them to senior leadership without consulting the data team right so that's that's a behavior um and what are the levers you know oh what are the root causes of that behavior potentially right it's um you know product has a lot going on the are excited by certain features they're also hearing from customers who might be saying like oh we really want this or you know so they're looking at other sources of data in their mind probably so they're not looking at the same sources of data that that the data team are looking at but they are talking to customers to you know the sales team the marketing team Etc to leadership team and so all these sources are probably data in their mind so they probably think well we are looking at data right we just don't talk to our data team you know more than once a week but we already feel like once a week is really is quite a lot right and so getting to the minds of the person or the team that you're wanting to to appeal to um that all allows you to think about okay what are the levers then and so what we came up with was you know uh each data scientist has a corresponding product manager for whatever project they're working on and so they have a one-on-one each week and so in that one-on-one can data uh can the data scientists bring um insights proactively to share with their product managers on what is working what's not anything that's unexpected and then also use that as an opportunity to ask the product person what are you seeing and what are you thinking about are there certain features that you starting to ponder on right because right now the data team is not getting that information until they're seeing the you know the fully written out strategy docs that are you know quite Downstream already and so that is the lever that is totally within your reach right you already have those one-on-one meetings you already have the PM that you work closely with and so what is a small change that you can make that can increase uh the chances that product takes data more into account so that's an example of you know if you break down a problem and really analyze it into the Behavior Uh root causes ideal outcome and levers you can get a clearer understanding of what can I change that will lead to the result I'm looking for that's a very cool framework and I like that everything uh gets broken down into smaller parts and it's very specific so you mentioned at the start it was just well product need to listen to the data team more but that's kind of very vague and you want something to become uh more concrete and actionable okay so uh you mentioned that like one of the solutions to that was or one of the levers in that would be just changing how meetings work between product and data teams and I think meetings are something we spend way too much of our lives in how to do meetings better is always an important thing so uh what are your top meeting tips I think um it really depends on the meeting culture within each company there are some companies where the default is to hop on a call is to hop in a meeting other companies are allergic to meetings they try to do as much outside of a meeting as possible um and so I'm more in the lad Camp um I prefer not to meet live unless there is uh no other way to discuss this than to discuss live um and so I love creating uh even in advance of a meeting so let's say I have to meet even then if there's anything I could put in a pre-recorded video a loom video where I can explain something that is pure knowledge transfer that you can watch on 1.75x speed on your own time amazing when we hop on the call we're going to have more shared context um I also like putting together a few notes or a dock beforehand that the person again can read on their own time uh they can even comment on a few areas that they especially want to discuss or they have question on which for me um gives me more information right instead of going in blind for this meeting I now know that this person has questions on XYZ areas so I'm more prepared to be able to talk about those and address those and make the best use of our time um so I'm very big on you know what are things we can do asynchronously so that when we actually do meet we are focusing on discussion debate conversation uh this is a working session versus one directional information uh you know dispelling you know sharing information and uh you know all of that is Is some much of it is stuff that you can do asyncronously okay I like the idea um it's like you do the homework before the class rather than afterwards uh flip classroom approach yeah so uh yeah certainly information dump is probably better done in a document rather than just getting everyone together uh in a call and let's going to be lots of questions okay uh so uh we talked about um a lot of the ideas for improving your career I'm curious as to what mistakes people make have you seen any examples of like what of the most common things people do wrong at work it's a tricky one right there's so many things so many things um there's that uh Tolstoy anak kinina quote that uh I'm going to butcher the quote but essentially um all happy families are are alike in the same way and all unhappy families are uh uh different in a bunch of different ways uh which to me applied to the workplace means there are infinite ways to mess things up or to you know to be unhappy or to you know uh fall into various traps uh but there's there's only a few things to keep in mind you know when uh to be successful I think um but uh oh gosh what are some common mistakes in the workplace um I think one of them is not managing up uh that was something that I did not think about at all especially earlier in my career um you know I thought well my manager is my manager so they should manage me you know why should I have to manage up um but you know I I realized that uh managing up will create a much more collaborative and productive relationship with your manager where um it's often one of the best ways to avoid your manager breathing down your neck you know if your manager is coming to you every day with a bunch of ad hoc questions that Tak so much time to answer that disrupt your flow um instead of just continuing on with this Dynamic if you take a step back you might realize that it's because my manager is not aware of what I'm working on and ultimately their head is on The Chopping Block because they're responsible for all the work that comes out of their team including my work right and so if you think about it that way it becomes very reasonable why your manager might be asking for XYZ updates because you aren't proactively providing them right and so thinking about uh thinking about that um Dynamic and getting into your manager's mind empathizing with them um uh I think that that can really do wonders uh and so for me that meant proactively sharing updates proactively sharing how I was thinking about certain decisions especially for higher uh Stakes projects higher visibility projects um and really catering to my manager style and the way they want to your information so some managers are you know they like more context some like less some only want bullet points some like more data they're more quantitatively driven they want to know that you are looking at the numbers other managers really want to know that there is a good core Insight or that you're exploring a variety of options before picking one right and so uh luckily you don't need to know what all managers want you only have to know what your manager wants so it drastically uh reduces you know the sample size you're catering to is n equals one that's awesome like every manager has quirks and idiosyncrasies so the more you understand your manager the better you can uh manage up to create a more seamless relationship and when you do manage up uh there are a lot of benefits you know your manager trusts you more they uh seek your thought partnership they believe in your competence and your ability they believe that you are someone who is reliable and trustworthy and shows good judgment all of those things mean that they want to give you more autonomy they want to give you bigger projects they want to elevate you more within the company they want to back you they want to support you um so managing up I think is one thing that uh I think many people don't think enough about and it goes beyond you know writing a weekly recap of what you shipped that is one thing you can do to manage up but it's much more of a holistic posture where you are anticipating what your manager might need and thinking about how can I make my manager's life easier and also them in the loop on what I'm working on okay I have say when you started answering that and you talking about managing your manager I was like wait I've got to manage my boss now that sounds like hard work to do this another one yeah yeah yeah uh but no I think certainly like communicating status updates before you get asked for them that's that's a brilliant uh tip something fairly simple just to get you started with uh with managing up yeah and one last thing with managing up you know it does take effort it does take time the thing to keep in mind is that not the managing up takes even more time so it's either you decide to manage up proactively or you spend 10 times as much time answering all those ad hoc requests uh you know having your manager breathe down your neck needing to task switch so it's really a trade-off of is a bit of investment UPF front going to prevent all these headaches down the line and in my experience it is absolutely worth that investment absolutely um all right so uh just to finish up do you have any final advice for how to get better at your career I think that managing up piece was a big one um I think the other one is learning to be concise I think that especially if you are presenting to senior leadership presenting in you know all hands meetings um rambling is very very common and so my advice there is to pause and gather your thoughts to try to figure out what your point is instead of speaking out loud in a stream of Consciousness uh in my experience preparation is is the only Sure Fire way to be concise uh and so figure out what you think and then and then you know say communicate what you think after that absolutely um all right so in the spirit of being concise we should wrap up here then rather than carrying on another 10 minutes so yeah uh thank you so much for your time West that was fantastic awesome thank you so much Richie\n"