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Episode 34: Interview with Cap Watkins, Founder at Practical Works + Prev. VP Design at Buzzfeed

As the founder of the leadership consultancy Practical Works (and former VP of Design at Buzzfeed, to boot), Cap shares what he wishes he would’ve learned earlier about our reliance on instincts instead of tools as a leader, and how being “people first” can actually be a pitfall.

Every few weeks as part of The Heartbeat, I ask one question to a founder, CEO, or business owner I respect about their biggest leadership lesson learned. This week, I interview Cap Watkins is the founder of Practical Works.

Claire: Hi everyone. I’m Claire Lew and I’m the CEO of Know Your Team. I am psyched today to have a very special guest. I have Cap Watkins who is the founder of a leadership and organizational consulting firm called Practical Works, but you might best know Cap for being the former VP of design at Buzzfeed and being a design leader at Etsy. And I know I’m a big fan of Cap’s writing and his work. We recently were on I think like a design leadership late night show on Youtube, which was a lot of fun. Yeah, it was my first time doing something like that, but an absolute blast and so thrilled to ask Cap this one question about leadership, both having been a leader and then also getting to give advice to a lot of leaders. So Cap, thanks for joining me today.

Cap: No, totally. Thanks for asking me to come on.

Claire: You bet. Okay. So here’s the question I’ve got for you that I’ve been asking leaders who I admire, which is what one thing you wish you would have learned earlier, as a leader?

Cap: Just one thing?

Claire: Yeah. Asterix!

Cap: Well you got to talk about this a little bit, I think I have two answers to this. I’ve one that’s what I wish I’d learned. And then something I think I’ve seen a lot of people that I talked to kind of learning as we’re talking.

I think the thing for me personally was, I wish I had learned sooner how to balance out the needs of the business with the needs of the people I was managing.

I think I went into management from the perspective of I’ve had some bad managers in the past. I’ve been treated badly. And I wanted to really understand why it was so hard to be a good manager. Why it was hard to support people that you manage. Why it was hard to tell them what was going on for real, and that kind of thing. And then I became a manager and realized that you can do whatever you want basically, and be whoever you want to be. And so I approached it though from doing the opposite of what my old managers had done. And so I think that meant was … a lot of them were probably going at it purely from a business perspective and that’s why I had such a bad time.

But that meant that by doing the opposite, I was coming at it purely from an empathetic perspective, which led me into situations I think where I might’ve been defending my team, or the people on my team, even in situations where maybe they were wrong or maybe what I should’ve been doing was helping them understand more why something was happening. Or why we needed to take things in a certain direction. But then I would refuse to do that. And I didn’t learn that until I think just much later than I wish I would have. And then be more effective to find that balance between business stuff and when to shield people and when not to.

I didn’t learn that until I think just much later than I wish I would have. And then be more effective to find that balance between business stuff and when to shield people and when not to.

Claire: That’s fascinating. There are a million questions I have on that too. If you want, we can start there and then circle back to the thing that you feel like people are telling you constantly “Here’s the thing that I’m learning.”

Cap, what you’re talking about is incredibly counterintuitive. It’s this idea that for so many of us as leaders, our model for leadership is usually in reaction to something that we’ve seen or experienced. Usually something positive or something negative in many cases. Actually this is true for myself. Negative. Very, very negative. And so you go, “Oh, I’m not going to do this. I’m not going to be that person.” But what you’re describing is that you can actually overcompensate for that reaction. And what’s counterintuitive about what you’re sharing is that I think it’s very popular, and rightfully so, to take a very empathetic people centered approach. A universe supportive, but then of course, you know your team. But I think also you’re saying that it can go too far. Right? So tell me, how do you know the difference? Where do you … How do you know how to draw that line then?

Cap: Yeah. It’s kind of tough. I think I’m making this up. I’m retro-ing a lot. Retroactively applying this logic. But I think some of it is kind of respecting the people that you manage a little bit. Do you know what I mean? I think there’s something that always helped me was when someone gave me critical feedback or explained to me why something was happening. Even if I didn’t like it. Even if I disagreed with it or whatever. I, looking back, grew a lot through those moments, where someone was actually able to level with me. Whether it was about me or about something happening to my team or whatever. And I think denying people … when you do that thing that I’m talking about where you just flat out defend the people that you manage no matter what, until the death, you’re denying them first of all access to what will help them grow into leaders. Because as a leader you have to understand that balance. You need to understand those objectives. You need to be able to adjust and pivot yourself around to meet those objectives or change the business.

Something I think about a lot is if I defend my team and they all feel good but the business fails because we didn’t adjust then we don’t have jobs. So what did it matter that I defended them until the end?

Do you know what I mean? So the balance there is … I want the business to be successful so we can continue to hire more designers, so we continue to hire more engineers so we can have a bigger team and work with more people and build more cool stuff. And in order for that to happen there are changes sometimes, the strategy or changes to teams or whatever that we need to make.

And then what I need to do with people that I manage is not just do it because that’s the thing I think that screwed with me so much when I was coming up, I wouldn’t. No one explained it to me. It just happened. And I think trying to say like, “I’ll give you exposure to everything I’m learning about why we’re doing this, to contextualize it for you and now we can disagree about it or whatever.” But at least you understand more than you did before. And even if you don’t realize it for two or three years down the road in your career, at some point you’re going to be faced with a similar decision and you’re going to go like, “Oh, I’m familiar with this because I’ve been told about these things before by people when it’s happened to me.”

And again, I think, a person hypothetically you don’t approach it cold. I understand when a decision’s going to be unpopular or when it’s going to upset somebody or maybe frustrate them. And I think even just acknowledging that upfront is very helpful and I think there’s a way to do both, I guess is what I’m saying.

You don’t have to choose to completely just abandon your team emotionally. You have to choose between that and going all in on just your team. I think you can find a good sentiment there.

Claire: Absolutely. That is a spectrum and they’re not necessarily mutually exclusive or even at odds with one another. I think one thing that I’ve heard a lot of leaders who I’ve interviewed over the past few years talk about is that yes, when you optimize for your team to feel good then perhaps the business suffers. But at the same time when people feel good, they actually perform better. So the business performs better at the same time. So I always have found that to be such an interesting paradox. And I always wonder … in your opinion Cap, if you were put on the spot right now and asked, which do you put first? Do you put the business results first? Do you put how people are feeling about how to achieve those results first? Or is that even the wrong question? And like you were saying, is there really just truly a spectrum?

Cap: If it came down to it, I think you put the business goals first. You have to, and I think the way that it manifests itself towards your team is I think you need to get them to buy into it too.

It can’t just be that I’m sitting there going like, “The business results matter to me.” It has to be that I’ve done the work over time and hired people who care about the business we’re creating.

That’s something I talk to people about when I’m hiring them is, what is the business ran like? What does success look like for us? To make sure they understand what they’re getting into. So at Etsy, it’s like … when Etsy sells things, our sellers make money, Etsy makes money. That’s a big … that’s awesome. I think that’s a cool mission. A huge portion of that money goes directly to sellers, it feels good.

And then you come to Etsy and it’s like, “Oh, well we’re doing work that maybe I think it’s kind of boring.” And in those moments I would like you to be able to go like, “Well, objectively though I’m aligned with this entire organization and the work I’m doing does feed into this work. Or when the company shuts down a project because it isn’t being that successful.” Going on like, “Well I don’t want us working on stuff that doesn’t help the people, our customers.” So again trying to get your team hyper aligned in business objectives makes those conversations simpler. And it doesn’t have to divorce the empathy and all. I can still … I understand it sucks. Things change. Change sucks. Period. Whatever, no matter what. And so I think there’s a … it’s not going to balance, it’s just trying to get everybody aligned on the same goal in the end. And so then your goal isn’t your one little thing you’re working on. It’s this bigger objective that we’re all feeding into.

Claire: Absolutely. I completely agree with you. I think if someone asked me this question, I would say, “Absolutely. You have to focus on the results first, because that’s the reason you’re there as the leader.”

Cap: That’s what the money’s for.

Claire: Well it’s to achieve the goal. To be very blind, you’re not there to be people’s cheerleaders or their friend or their family or … You’re trying to help them achieve this goal. And I think because of that, you want them to feel connected to the work, understand how their work fits into the bigger picture. You want to approach things from empathy because it actually helps them get the results better. And the person feels good when they do achieve the results. So I’m right with you. And I think it sometimes becomes blurry when you have to tell someone something they don’t want to hear or you have to make a difficult decision or you can’t protect someone from something that they might not want to be exposed to.

For you Cap, do you notice … or actually, let me ask this. So one thing that you mentioned is how that this insight has developed because of this reaction to a bad boss. In the work that you’ve been doing in advising different leaders, how much of an influence have you noticed that previous bosses have had on the way people choose to lead? This is something I’ve been really interested in lately. Is this something that happens a lot, do you think?

Cap: I think it does. Like you said earlier, I think it happens in both directions. I know people who are mirroring behavior that they’ve seen, that they agree with or align with. Even people who become the new head or whatever. Structuring their teams in ways that they’re familiar with. That’s a very straightforward example. Even if the organization they are in is not necessarily conducive to that particular way they want to set it up. Do you know what I mean?

Claire: I do. Yeah.

Cap: And I think that’s a very new manager type thing where it’s like I’m being handed this thing and I’m going to lean on what I know from the past because it feels comfortable to me. Something that worked for me. But I think hopefully as we all grow and evolve in these roles we get more and more tools.

I think it’s at a point where you’re lacking the tools. All you have is experience and so you’re leaning on those experiences either in the positive or negative and then over time developing the tools so you’re not running purely off of instinct or off of a singular experience you had.

That is kind of what I typically have seen.

Claire: I think you’re spot on. That’s something that I’ve noticed as well with the leaders that we’ve worked with. And what I’m curious to know, and I’m sure everyone who’s watching this is curious to know is, so how do you self correct for that tendency? If you’re leaning on experience instead of the tools and the frameworks perhaps that you learn and pick up over time or from talking to people or et cetera. What advice do you have for new managers who might be overly biased by just their prior exposure to leadership?

Cap: Well, the thing that helped me a lot is assuming I might be wrong. It’s very helpful. When I started at Buzzfeed, I had never run an entire design team before on my own. I had been a part of a management team previously. I’ve had people to lean on. We had a boss who ran the whole design team. We had a good … I was protected. I had my bubble of influence, but that was it. And so coming in, I was leaning on a lot of my past experiences. I knew that a lot of the things I was about to implement on this new team, were going to be things that I had seen or done in the past. Because I just didn’t know.

I remember the first day or my first week, I was giving a presentation to the team about who I was to reduce the fear factor a little bit. And I was going like, “Here’s what I believe, here’s my philosophical, here’s the three things philosophically I feel very aligned about.” And at the end I was like, “Here’s the deal. We’re going to try some stuff. Like we’re going to experiment with some things. It may make people uncomfortable, it may be different. And all I’m asking is for people to number one, try. And number two, tell me what’s not working as soon as possible. Because if it’s not working or something’s wrong, the sooner I know and I’m going to be wrong. I’m person with limited experiences. If something’s not working or wrong or whatever, the faster I know the faster I’m willing to change it.”

And I think that’s the thing a lot of people don’t feel like they can do.

As leaders or managers, they feel like they have to own the decision, they have to see it through, they have to forge the team into their way of thinking or way of doing things. And I feel like that leads into situations where you’re just being in way too brittle and you’re not learning because you’re not able to listen or see and you’re not inviting that sort of criticism.

And so I feel like that helped a lot because people would really quickly raise their hands to tell me like … for instance, our team grew and the critiques director broke and I didn’t notice. I kind of noticed, but I didn’t know how urgent it was. And then somebody came to me and they’re like, “This doesn’t feel like it’s not effective anymore.” And I was like, “Okay, so let’s do something about it.” We all talked and worked on it and fixed it.

Claire: Yes, absolutely.

Cap: And I think that’s just a thing you need to be able to get to. It’s a place where you’re open to criticism and you’re inviting it regularly even from people who aren’t above you or your peers, just so you can start or to learn.

Claire: Right. No, that progress. I mean, it doesn’t come without literally, like you said, assuming that maybe a lot of the assumptions that you have up front are wrong. So I think that’s a brilliant insight Cap. So I want to switch gears a little bit. You mentioned at the start of this little chat that you also have noticed something recurring from all the clients that you have, the things that they wished they would have learned earlier. I’d love to hear that is, or maybe many things.

Cap: Yeah, I think the thing that stuck out to me a lot recently, I’ve been meaning to write about it. I’ve had a lot of people talking to me about processed stuff. So either writing career tracks for their team or coming up with a way of recruiting quickly and efficiently or experimenting with design critique structures or product development, ways of doing product development. And I had someone asked me recently when I worked with them before a long time ago, and this was back when I’d been developing a reputation that Etsy is being a really good recruiter. I recruited really fast, I recruited really well. And I ran the process and ran all outsourcing and stuff.

This person was asking me because they were about to start embarking on their own recruiting adventure for the first time. And they were like, “So what was the trick? How did you do it so fast? How did that happen?” And I was like, “Well. I sat down on my desk for hours a day and I scoured the Internet and I wrote a ton of emails and I kept up with all those emails and I have them in a Google doc.”

And I just think sort of described the work involved and the person was like, “That can’t be true. That just can’t be true.” And then I was like, “That is true. That is what it takes to do it really fast and to do it really well.” Yes, I’m better at it now than I was when I started doing it. But it took a ton of work.

And the same thing with career tracks. I think I’ve seen it a few times, people taking either my career track or career track, open source to their career track from somewhere else and just plopping it into their organization. And it’s not working. It doesn’t work as well as it should. And I think there’s a lot of resources out there and probably now more than there’s ever been for all of this kinds of stuff. Managers are sharing more than they’ve ever shared. I think this is great. It’s a really good thing, but there’s this thing that I think people miss, which is it takes a lot of work to make it right and to understand why something’s happening and how to do it well.

That’s something that I’ve really been blowing people’s minds with is that career track that’s open source online was in development for three years and it got iterated on every year, multiple times, and tons of feedback and that’s why it’s where it’s at. And I still don’t think it’s very good. I think it’s fine. We worked on it really hard. I think it works for us, but when I use it again, I don’t know. I might change it. A lot. Depending on the situation and I feel like this taking of resources and shortcutting is a thing that I feel like we could do less of. And I think it’s kind of a thing we were talking about earlier, where it harms your progress as a manager or leader to take that stuff verbatim without really seriously sitting down and going like, “What do I think about this?”

Claire: Totally.

Cap: Which has another side to it, which I think a lot of leaders I’ve talked to and they have been challenged to think about what their philosophy is and this is why these things happen. And like I said when I started at Buzzfeed, I had a deck that I put together and I’m like, “Here are the three things you’re going to hear from me until I’m gone. Forever. And it’s transparency, collaboration and process familiar skillsets. Those are the three things and I’m not letting those go. That’s my leadership philosophy and you should just know that going in. But that’s how I make decisions.”

There’s a lot of room there. You can do a lot of stuff within that purview. There’s also a lot of stuff outside of that. It has nothing to do with that. But a lot of people don’t think about that at all. It’s very intuitive. They’re doing it without really saying it.

Claire: It’s reactionary.

Cap: Right. And I think people being very intentional about who am I as a leader? What does that mean for things like career tracks? What does it mean for things like reviews? What does it mean for how we recruit? All of that comes back to who am I as a manager? And that’s the thing a lot of people struggle with it. And I think maybe don’t even spend much time on. And I think it’s really important.

Claire: Absolutely. Well I think all of us are as humans suckers for recipes and quick paths to success. So anytime that you see, “Oh, here’s an open source career track. Oh, here’s what worked at this person.” You copy and paste and cross your fingers that it works. And your point is you know what? Do the work and most importantly do the self reflection to figure out what you stand for. What matters to you as a leader and how based off of that you want to make decisions going forward. So I guess my last question for you here then Cap is how do you know what you stand for as a leader? How do you go about that process or for yourself? When you were building that deck, what went into that?

Cap: That’s a big question.

I feel like my therapist. She told me something once, which was that her job with me and a lot of people she works with were to help people understand who they are better. That that is like the human condition. We should all be trying to constantly understand ourselves a little bit better.

And when I wrote that deck, the goal of the deck was to demystify people so there wouldn’t have to be confusion bubble in my expectations where they could expect certain things from me, I wanted them to understand. So that there wasn’t a lot of confusion or rumor. And so I sat down and had to write it for that reason. It’s not like I sat down and what’s my philosophy? Let me just write that down today.

Claire: I did it in 30 minutes. Yeah.

Cap: Right. But I think going through that process of people get caught up a lot in what is this team now? And so that’s my philosophy. They back it out from what’s happening currently. And I got lucky that it was a fresh start for me. I had no idea what it was like. And so I didn’t have to care, I don’t know, baggage. But for a lot of people they’re in an org, they’re working a certain way and they’re like, “Well, those are my values.” They must be. And it’s actually not. I was thinking about stuff like if you’re in an org right now, if you could snap your fingers and change anything, what would it be? Or if someone were trying to snap their fingers and take something and you were going to lay down on the tracks in front of it, what would that be?

Start to really think about what are your non-negotiables?

So if I believe that design should be shared broadly forever inside of a company and if that ever stopped, I wouldn’t want to work there anymore. That’s good to know. I should write that down somewhere because that’s actually how I’m making decisions and I should be intentional about it.

I read something once, I don’t remember where … they’re talking about how people watch what you do and not what you say. I know people who get up in front of their org and they’re like, “It’s really important to take our time and just make sure we’re shipping great products to customers.” And then two weeks later I’m like, “Why didn’t we ship this yet?” They actually sent the email. But why didn’t this go out yet? And you’re like, “Well no one’s listening to your all hands presentation. They are listening to that.” And so you’ve got to know what that is and own it and write it down somewhere and be like, “This is who I am.” Again, understand yourself. Who am I? What do I value? What would I quit a job over? What would I take the job for? And then that’s it. You got … that’s a start anyway of what those values would be.

Claire: I absolutely love that. I think letting go of baggage helps frame a clear perspective to see things as they are. I think defining what those non-negotiables are and I love the different questions that you post, are in essence what values are, the things that are immutable, that shape how you do your work, how you view your work. And then I think your point about the things that you consistently act on are often the things that you are, and so I think even the simple reflection of going, what are the things that people would just say that I don’t change about? That I’m just always doing it. That I just habitually do. Oftentimes you can trace this back and go, Huh, I think I’m actually pretty patient or maybe I’m impatient, but it’s the actions that that reveal reveal who you are to your point.

Cap: To examine that and you may not like that thing. It may be, maybe I find out I’m doing that interest and I am impatient and that’s not really a value. I know deep down it’s bad. But knowing that that’s even possible means a wall I’m working on it. It’s okay to receive feedback in a more open to the critical .. to being someone criticizing me about it. And I can say like, “Yes, that is true.” There are times and I am impatient. That is one of my things that I have trouble with. And I’m working on it. It makes you a lot more receptive I think to those things.

Claire: Absolutely. Even sometimes what is perceived as negative or in fact positives as well. Being impatient can be a great catalyst for getting things done and having a sense of urgency and just shipping things and not being held back by just things being perfect. And so I think either way, just figuring out what is actually true instead of what you want to be true.

Cap: Yeah. The fascinating thing to me and what I realized is and this was a long time ago, during that someone’s giving me critical feedback. And I realized it was the exact opposite side of the positive feedback I was receiving. So on the one hand, everyone at this company really loved how they could always trust that they knew what I was saying was my actual opinion. They liked that when I said something, I was shooting straight. They’d have to worry about no bureaucracy, no politics, no bullshit. So then the opposite side of that was, not everyone always wants to know what I think. So, I want opinions. But were they all useful? No.

I have noticed this ever since then, every review I’ve ever seen for anybody, everyone’s strengths also holds them back a little.

Claire: Totally.

Cap: Because it just has that opposite effect just a little, and I think a lot of the work people do or should think about doing is … you can’t really change that that con exists. It’s not like I can change that I’m going to have opinions about stuff. But I can minimize the points at which that could be a negative. I can start to try to hack my way around. I have an opinion, but maybe I just won’t say anything because it doesn’t seem that useful in this meeting. But if it is useful I’ll find out eventually, and then I can bring it there. I feel like a lot of people feel like they are in this place where the feedback’s not fair. Because if I do that, then I can’t be there doing the thing that everyone loves about me. And that’s actually not true. It’s just a lot about modulation and trying to minimize the risky scenarios for the thing you’re really good at.

Claire: Absolutely. I think that that nuance and awareness that comes with understanding that your greatest strength is also many times your greatest weakness. It’s something I feel like I learn more and more as a leader is so key and to adjust like you said. To adjust and not just say, “Oh this is my strength and I have to just go all in on it.” So I think that’s wonderful wisdom.

Cap: The saddest part is to go back to the first thing about shortcuts and stuff. As a manager I found there is no shortcut to learning that. It is the process that people must go through and you can tell them as many times as you want, that is what’s happening and they don’t believe you. And then eventually it becomes clear. It’s just really … I think a lot of managers hope that they can progress the human condition by helping people not do the dumb things that I did when I was coming up as a designer. Can’t do it. They still stick their hands on that stove and they’re like, “Ah, it hurts.” And you’re like, “Yup.”

Claire: Yup. No, I think, the most powerful way to learn anything, this is true of any skill is just to do it and to actually to get burned yourself. And self delusion is the most powerful fog. And so no one entirely alludes it, but we sure as can try and I love the helpful tips that you shared on how to do that.

Claire: So Cap, thank you so much for chatting with me today. It’s been a blast to have you.

Cap: No problem. Totally.

Claire: Cool. Thanks.

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.