Career Skills for Data Professionals with Wes Kao, Co-Founder of Maven

Richie Cotton: Hi Wes, thank you for joining me on the show.

Wes Kao: Hey Richie, excited to be here.

Richie Cotton: Excellent. So I actually want to start with something that's been bugging me. So, there's this common thing where it's supposed to take 10, 000 hours 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? 

Wes Kao: That's a banger to start with. I think it's actually because career skills are a combination of a bunch of separate skills. It's not just one skill. Being good at your career involves being great at execution, thinking about strategy being a good communicator, Project management, dealing with conflict negotiating there's so many small negotiations that happen on a, daily or weekly basis at work, and so managing up, managing down, managing expectations, pushing back being able to advocate for your ideas in a way that's effective and productive so there's so much nuance that goes into every one of those things which is why I think it's a, it's a lifelong endeavor.

to get good at work, essentially.

Richie Cotton: Okay, yeah that makes me feel better. It's like so many different possible skills that you could learn. So many different contexts. So, there's a lot to talk about. So, we're probably going to get through them all now. Otherwise, it's going to be a 24 hour podcast, but maybe we'll start with something I think a lot of data people struggle with, which is like talking to other people.

So, we'll go with communication. So, 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?

Wes Kao: I think that data people tend to be logical and rational and they like numbers. And 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 for data folks is to not just offer a fact or a 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?

Richie Cotton: Okay, yeah, I like the idea of you can't just spout a load of numbers and expect people to care. You've got to give them the reason for why something is important.

Wes Kao: Oh, I was gonna say, I think the other thing is that very few things are 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 it's pretty common that, They're not sure how to react, Like, most of us have had people say, Wait, is that good or bad? and I've definitely said that, to folks who shared something with me that I could tell in their eyes was so obvious. But for me it wasn't. And so, offering that interpretation of, here's what this means, here's why it matters, here's how it relates to the work that we're talking about that all helps to facilitate meaning, which helps to create a more thoughtful conversation and discussion that leads to, eventually, a better decision.

Richie Cotton: Yeah, that makes a lot of sense. And I suppose I think that like, buying or selling stocks is 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 a complex situation down to those two states, this is good or this is bad, it's going to help your audience.

So, one of the sort of common bits of advice for communication is you've got to tailor what you say to your audience. Do you have any advice on how to go about doing that?

Wes Kao: Yes, so I have a couple frameworks here one is, if you think about concentric circles, you are in concentric circle, you have full context about all of your work. 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.

And then, on the next rung, might be your manager, depending on how closely they are in the data world. Some managers are more hands on, others are a little bit further away. And then in the outer rungs, you might have cross functional partners. You might have product managers, marketers that you work with, ops people and then you might have leadership team members who have even less insight and visibility into the day to day workings what your work might entail.

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, about a product launch, or if you're on a podcast, whatever how do you tailor what you're saying to those different audiences? So I like thinking about the concentric circles because it helps remind me that 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, 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, there's, altitude that's too high. 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, but if you swing the pendulum and you're five inches above the ground, then you're too low altitude.

So that might be describing the step by step process. Of how you did, something behind the scenes. So you wanna be somewhere in between those two. And for an executive audience, for example you want to be you wanna give them enough detail for them to be able to chime in and be able to understand what the situation was, what the problem was, but not so much nitty gritty detail that you are getting lost in the weeds and they're, not sure what the plot line.

Really is anymore.

Richie Cotton: That last point is very interesting, like, trying to work out the altitude and do you need to start at high altitude and go lower or is it the other way around?

Wes Kao: So I have an example here. So let's say that there is project delay and you're explaining in, you know, an all hands meeting. Why, this big project was delayed. and one of the execs asks, you know, was the delay our fault or the vendor's fault? So an answer that is too high altitude would be something like, Okay.

It was both of our faults. Okay, and then just ending there. Something that is too low altitude would be getting to 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 re 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. And then, 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 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.

Richie Cotton: I have to say, I 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 trying to think about, is anyone going to understand what you say and just adjust the altitude accordingly.

So a lot of this seems to be how the sort of flow and the general sort of a style of communication. 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?

Wes Kao: I think adjusting the jargon level depending on your audience is something good to keep in mind. So, going back to concentric circles, if you're talking with fellow data scientists, you can get very technical. You all speak the same language. If you are talking to a marketer like me, or a founder, or an exec, you might want to pull up a little bit kind of adjust the phrases and words, potentially.

Richie Cotton: and does it make a difference if you are a manager talking to your employees on your team or if it's the other way around if you're talking to a manager? When you've got that power imbalance, does the way you communicate need to change?

Wes Kao: I would say yes and no. Traditionally, people would say, the manager is in a position of power, so they don't have to explain themselves as much. So, I think that you know, logically tracks. Personally, I like sharing my thought process, even when I'm talking with direct reports.

I think it builds a lot of trust to explain, why are we doing this? Why does this matter? How does this fit into broader business? Instead of just tossing something over the wall and saying, do this. I think when people are more engaged in whatever task they're working on, and they care about it, they know how it fits they're more likely to do a better job and come out with, better output.

So that's one thing. And then, if you are the direct report thinking, how much should I explain to my manager? think it depends on how much existing context your manager has on your work. So some managers are quite hands on, and they are player coaches. So they're individual contributors themselves, and they're very close to the primary data.

Other managers have very little visibility into your work. And maybe your manager, isn't in data themselves. And so they have even less visibility and understanding of what it is that you do. And so in that case 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? what else, you know, might they need to know in order for them to either give me useful feedback or give me useful input or for them to be able to make a good decision.

So I like thinking about 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 talked 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.

go to the next thing without missing a beat.

Richie Cotton: In general, if you're trying to persuade someone to do something rather than just inform them about something, how does that change your communication style?

Wes Kao: 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. Even when you are informing someone of news or informing someone of information, You want to think about how can I make sure that they receive this? Well, because you might think I'm going to inform them of this and then move on.

I'm just letting you know, and then moving on. 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 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, you know, a little bit more of a spectrum. If you are persuading it depends on how bold and how controversial is the thing that you are trying to convince someone of. 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 I forget which TV show this is. I think it's breaking bad. don't quote me on that, but there's a, there's a quote that says, if you come for the King, you best not miss, which I love.

Richie Cotton: Nice.

Wes Kao: So, 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 to convince that person.

Because otherwise, why should they be convinced, On the other hand 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 of years now. Right. Bye. Bye. Well then, that's not so controversial anymore, is it?

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, 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 that would, would inform how much you need to prepare to really build a business case.

Richie Cotton: Okay, yeah, I can certainly see how 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 was imagining trying to persuade our CEO that we need to radically change dating apps business. And yeah, would take an awful lot of persuading.

So, I think giving feedback is one of the trickier types of communication. So do you have any advice on how to do that?

Wes Kao: 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've already been sufficiently frustrated that we can no longer put up with whatever it is that, that they've been doing that bothers us.

And so you go into this conversation 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, they're like, Oh, 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've 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 a lesson, trying to get them to admit that they had wronged you 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 percent of stuff that you're saying that does not contribute to behavior change. And only keep that 10 percent that will contribute to behavior change.

So that 10 percent 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.

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.

Richie Cotton: 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 in a work

Wes Kao: Oh, totally, totally. I mean, you want to get that out of your system, just not with, with that person, right? So maybe talking to your, a friend, your spouse, your therapist, you know, get it all out so that by the time you talk to that person, you no longer feel that need to offload.

Richie Cotton: 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. And I have to say, at work, it's one of the few places where feedback just gets given to you whether you want it or not. But are there cases at work where you should actually go and seek out feedback without someone just thrusting it upon you?

Wes Kao: Oh, definitely. Especially with feedback on work output. you know, there's, maybe multiple types. I see two major buckets. One is behavioral feedback. The other is feedback on work output. So, especially with the latter category, with work output I think all of us should be eager to get more feedback on that.

Especially because it will make us better at our craft. 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. I think so many managers are, are afraid of giving feedback.

I actually read this fascinating quote study that was in Harvard Business Review that 67 percent of managers are afraid to give their direct reports feedback. That's almost 70 percent 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 an employee 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. And so, I like being very explicit that, I want it. red lines go for it, Or, do I want high level directional feedback to check in and make sure I'm going in the right direction?

You know, you can be specific about the kind that you were looking for, but be explicit that you love that feedback. you want them to be honest with you. Don't pull punches because your manager might actually need to be convinced it's safe and that you actually do want feedback.

Richie Cotton: I wonder whether managers have that sort of bad experience of, like, employee just just taking feedback incredibly badly and that, that makes them afraid. So are there any 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.

Wes Kao: 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, then I find out if you really want it. And so I think many managers have had that had that happen where they're burned from past experiences, and so therefore they're cautious.

about giving feedback. So yeah, I think the biggest thing with, receiving feedback is 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. 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. 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 re gift 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. 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. In that way. So you want to be intellectually honest about that. 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?

Richie Cotton: Absolutely. And yeah, definitely had cases of feedback where it's the equivalent of like a set of socks or or some batteries or something like that.

Wes Kao: speaking talk. Different strokes for different folks. It's, it's so hard um,

Richie Cotton: all right. So you use the phrase there which sounds easy, but it's probably suspiciously hard. So intellectual honesty. So, can you talk through like how you get better at that?

Wes Kao: Justifying the things you want to justify 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.

I really do think that deciding to be intellectually honest is half the battle. At that point, it's, constantly questioning Am I reacting this way because I feel hurt? Or because I feel threatened and I'm, 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, So it's really calling yourself out in these ways and not letting yourself squirm out.

Richie Cotton: When good things happen, I wouldn't, I want to take credit when bad things happen. Now it's like, it's other people's fault. But yeah, intellectual honesty seems like a much more sensible approach. If you can persuade yourself to do that. So do you have any advice for when things go wrong? Cause I mean, in business things go wrong all the time.

There are disasters. Are there any sort of strategies you can use in general to cope with problems and bad feedback and things like that?

Wes Kao: Yeah, I think it depends on the kind of thing that's going wrong. But I would say to always reflect on how did I contribute to the situation, and what might I want to do differently going forward. I really like reflecting on anything that is happening. especially, things that are particularly good or particularly bad.

I think with things that are particularly good, it's easy to chalk it up to, Well, finally, I've been so excellent all along, finally something worked out. Versus, being equally critical about what did I do that really made this work? And then same with, with anything that didn't turn out as expected.

was there a way I could have foreseen this? Was this avoidable in any way? Were there signs of this that I can watch out for next time so that I can predict more accurately and save myself the heartache of from a mistake. 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 a mistake personally, then that's a better way to learn the lesson.

Richie Cotton: And what happens if you disagree with colleagues or about some strategy or whatever like, because there's always going to be differences of opinion are there any ways to deal with, I fundamentally disagree with what's going on here, but still It's something I've been asked to do.

Wes Kao: 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. Conflict isn't just we are arguing and debating explicitly, it's also a difference of will, One person wants to do something, the other person wants to do something else, and sometimes, those two can be very far apart or very close. But these are all examples of friction, of conflict. And so I like thinking about, how do I not see any of this as conflict? Because conflict means that we need to overcome the conflict.

Right? We need to address this. We need to fix this thing. 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 about being issue driven, not position driven.

Position driven is, Richie thinks this, Wes thinks this, like, let's duke it out, 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. And so I think adopting that posture can be really productive.

Richie Cotton: Okay I do like the idea of just working together in order to resolve some issue, rather than just fighting about stuff. Suppose you get to the point where you end up having to do something where you say, okay, I disagree with this, but it's going ahead anyway. Is there some way To do that gracefully.

Wes Kao: So disagreeing and committing, I think that's something that all of us have, have heard of at this point. I like thinking about when should you disagree and commit? I think that some people don't disagree. Disagree and commit a little bit too early where, there's a little bit of pushback 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? And there's a little bit of this martyrdom feeling of self righteousness of like, okay, you know, I said my piece. I did my part. And if the train's going to crash, then the train's going to crash. I personally don't like that.

I think that that is a little bit immature. And that 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 that is the work. That is such a big part of our work as professionals. to kind of shirk that responsibility, I think, you know, I I think we have a moral responsibility to follow through and try our best to convince people if we think an idea is, Really important. and then I think on the other hand, there are people who hold out a little bit too long before disagreeing and committing. And so, you know, you also don't want to be the person who has tunnel vision, who is digging in their heels, who, everyone feels like they need to bend over back or just like try to bring back on the boat.

And so with disagreeing and committing, I think if you feel like you've truly done your best. And you can be honest about that, that you have reached into the depths of your creativity and powers of persuasion to, to convince people and, and folks really are still not seeing the point.

That's the point where relenting makes sense. And I also think it depends on the stakes that are involved. So the higher the stakes and the worse the potential outcomes, the more I think you should continue to advocate. If the stakes are relatively low. And the worst thing that can happen is not that bad.

Maybe you disagree and commit earlier. you can only pick so many battles. You know, one thing that I, as someone who has many thoughts on many things, I've had to train myself to let go of having an opinion on certain things of having, a point of view on certain things because It's not worth the advocacy, and I trust my colleagues who are making the decision.

So those are all factors that I take into account when deciding do I want to disagree in command or not.

Richie Cotton: So, 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 was a bit more vague. Like what does acting like an owner mean?

Wes Kao: 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. And, you know, I think for folks who are a bit more junior earlier in their career, by the time something arrives on your desk, a task 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 the more that you might be handed an ambiguous problem that hasn't been shaped yet where 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, 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, that might work. earlier on, but, doesn't work 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.

Richie Cotton: Wow. So I guess you could potentially be stuck in this for an awful long time if you keep trying things that fail, or I guess maybe you'll probably get fired if you don't solve it eventually. But yeah, is is there a point where you say, okay, enough is enough then?

Wes Kao: Yes. So acting like an owner also doesn't mean blindly doing something just because someone told you to. if you are an owner, you have to exercise judgment on when it's time to change course and to own that decision. not shirk 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, Both of those are not that productive because you are not actively using your own judgment, I would say.

It's more like auto autopilot, you know, brainless 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, 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. and if that doesn't work, I'm going to try something else.

Right? And so, it's that, it's that idea 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.

Richie Cotton: I like the idea of just, Use your judgment about what the best way to proceed is. You sort of, do 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. And you can call in reinforcements if necessary.

so on the subject of judgment, is that something that you can train yourself to get better at?

Wes Kao: 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. It's such a multi faceted, complex topic because so much of judgment is tacit. 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 layperson, How they pick up on things that other people don't even see, don't even realize. And so, Trying to translate, trying to capture that and trying to translate it, put it into words so that people who are trying to increase their level of judgment on something can learn that I think is, is really fascinating.

Very, very difficult. But you know, I do think that it can be trained. I think that if you were to go through, 10, 15, 20 years of your career without reflecting and without questioning your decisions and trying to learn from them 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 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. And ideally, These mental models are as predictive as possible.

the last three times I was in this situation, shit blew up in this way. And so this fourth time, I'm going to do things a little bit differently, Or you can do things the exact same way and then feel surprised when shit blows up again, So the act of thinking about what happened in similar situations, how do I pattern match and update my mental model?

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. So I think there's so much goodness that happens when we continually improve our judgment.

Richie Cotton: Okay, I like that. So it seems like a variation on the old saying there. So it's like, fool me three times, shame on you. Fool me a fourth time, shame on me. Yeah. Okay. Yeah. So I like the idea of just learn from your experiences and then try and do things a bit smarter next time. So, it seems like analytical thinking is going to be a contributor to making better decisions.

Can you talk me through how do you get better at analytical thinking?

Wes Kao: this is another meta skill that can really help I think in everything that you do. 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. 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 BROL, B R O L. And it's behavior. Alright, what behavior are you observing? The R is root cause. What are potential root causes that might be causing this behavior? 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 you can pull that will get you closer to this ideal outcome. And so by breaking it down this way, you can get more specific about what exactly do you want to change? And so actually a good example, one of my clients is a head of data at a marketplace company.

And he was saying that he feels like the product team doesn't really take into account perspective on things, at least not soon enough and not often enough. And so he always feels like he's trying to play catch up on features that the product team has already decided on, has already latched onto that the data doesn't support at all.

so he was saying, I want data to listen to, or I want product to listen to. My team, the data team or so that's an example of an outcome that I would say is not specific enough. So you want to get more specific on what that ideal outcome is because being listened to more. What does that mean?

What does that look like? how much are they listening to you now and what would more really be? And so I worked with them on identifying what that would really look like, which is product seeking data's input or taking, taking data into account before creating product plans.

that is a more specific outcome from there, there's a lot of levers that we can pull for, how do we achieve that? And so if you look at behavior, for example the product managers were shipping 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. And what are the root causes of that behavior potentially, right? It's product has a lot going on. They 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, you know, the data team are looking at, but they are talking to customers, to, the sales team, the marketing team, et cetera, 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, more than once a week, but we already feel like once a week is really important. It's quite a lot, And so getting to the minds of the person or the team that you're wanting appeal to that all allows you to think about, okay, what are the levers then?

And so what we came up with was, 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 the data scientists bring 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 are starting to ponder on, because right now, the data team is not getting that information until they're seeing the fully written out strategy docs that are, quite downstream already. And so that is a lever that is totally within your reach, 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 could make? That can increase the chances that product takes data more into account. So that's an example of, if you break down a problem and really analyze it into the behavior root causes, ideal outcome, and levers, you can get a clearer understanding of, you know, What can I change that will lead to the result I am looking for?

Richie Cotton: That's a very cool framework. And I like that everything gets broken down into smaller parts and it's very specific. So you mentioned at the start, it was just, well, Product needs to listen to the data team more, but that's kind of very vague and you wanted something to become more concrete and actionable.

so you mentioned that like one of the solutions that 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 is something we spend way too much of our lives in. How to do meetings better is always an important thing. So, what are your top meeting tips?

Wes Kao: I think 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 on a meeting. Other companies are allergic to meetings. They try to do as Much outside of a meeting as possible. And so I'm more in the latter camp. I prefer not to meet live unless there is no other way to discuss this than to discuss live.

And so I love creating 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 prerecorded 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.

I also like putting together a few notes or a doc beforehand that the person, again, can read on their own time They can even comment on a few areas that they especially want to discuss or they have questions on, which for me gives me more information, right? Instead of going in blind for this meeting, I now know that this person has questions on X, Y, Z areas.

So I'm more prepared to be able to talk about those and address those and make the best use of our time. 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 this is a working session versus one directional information sharing information and much of it is stuff that you can do asynchronously.

Richie Cotton: Okay, I like that idea. It's like you do the homework before the class rather than afterwards. Flip classroom approach. Yeah. So, yeah, certainly information dump is probably better done in a document rather than just getting everyone together in a call unless there are going to be lots of questions.

Okay. So. We've talked about a lot of the ideas for improving your career. I'm curious as to what mistakes people make. Have you seen any example of like one of the most common things people do wrong at work? It's a tricky one, right? There's so many things.

Wes Kao: So many things. Um, There's that Tolstoy, Anna Karenina quote that I'm going to butcher the quote, but essentially all happy families are, alike in the same way. And all unhappy families are different in a bunch of different ways. Which to me, applied to the workplace means, There are infinite ways to mess things up or to, to be unhappy or to, fall into various traps.

But there's, there's only a few things to keep in mind, to be successful, I think. But oh, gosh, what are some common mistakes in the workplace? I think one of them is not managing up. That was something that I did not think about at all, especially earlier in my career. You know, I thought, well, my manager is my manager, so they should manage me.

You know, why should I have to manage up? But, I realized that managing up will create a much more collaborative and productive relationship with your manager. where 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 take so much time to answer that disrupt your flow 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, 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, And so thinking about that dynamic and getting into your manager's mind, empathizing with them think that, can really do wonders. And so for me, that meant proactively. Sharing updates, proactively sharing how I was thinking about certain decisions, especially for a higher stakes projects, higher visibility projects.

And really catering to my managers style and the way they want to hear information. 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, whether you're exploring a variety of options before picking one, right? And so, luckily you don't need to know what all managers want. You only have to know what your manager wants. So it drastically reduces, the sample size you were 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 manage up to create a more seamless relationship. And when you do manage up there are a lot of benefits. You know, your manager trusts you more. They 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. So managing up, I think, is one thing that 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 keep them in the loop on what I'm working on.

Richie Cotton: Okay. I have to say, when you started answering that and you were talking about managing your manager, I was like, wait, I've got to manage my boss. Now that sounds like hard work,

Wes Kao: all the things I need to do, I can add this, another one? Yeah, yeah.

Richie Cotton: But no I think certainly like communicating status updates before you get asked for them, that's, that's a brilliant tip, something fairly simple just to get you started with managing up.

Yeah,

Wes Kao: And one last thing with managing up. it does take effort. It does take time. The thing to keep in mind is that Not managing up takes even more time. So it's either you decide to manage up proactively, or you spend ten times as much time answering all those ad hoc requests, having your manager breathe down your neck, needing to task switch.

So it's really a trade off of, is a bit of investment up front going to prevent all these headaches down the line? And in my experience, it is absolutely worth that investment. I

Richie Cotton: absolutely. All right. So, just to finish up, do you have any final advice for how to get better at your career?

Wes Kao: think the managing up piece was a big one. I think the other one is learning to be concise. Think that especially if you are presenting to senior leadership, presenting in, you know, all hands meetings rambling is very, very common. And so my advice there is to pause and gather your thoughts. Try to figure out what your point is instead of speaking out loud in a stream of consciousness.

In my experience, preparation is is the only surefire way to be concise. And so figure out what you think, and then, communicate what you think after that.

Richie Cotton: Absolutely. All right. So in the spirit of being concise, we should wrap up here then rather than carrying on another 10 minutes. So yeah thank you so much for your time, Wes. That was fantastic.

Wes Kao: Awesome. Thank you so much, Richie.