Finding your calling in life takes time. It’s not unusual to be dreaming about a future in wallpaper design while sitting at your office desk, procrastinating with some very important vacation research. Leadership coach and organizational consultant, Cap Watkins, knows all about career changes. In fact, after years in the design industry, working at leading brands such as BuzzFeed, Etsy and Amazon, Cap made a sharp shift in his career.

After leaving his position as VP of Design at BuzzFeed, Cap opened his own Brooklyn-based leadership and organizational consultancy, Practical Works. Drawing from his rich experience in various tech companies and diverse roles, Cap coaches and supports teams, managers and leaders in all spheres of working life. With an active Medium account, regular public talks and a super honest and down-to-earth approach, Cap endeavors to help managers grow and evolve, create positive work environments and take their work to the next level.

We had the chance to speak to Cap for a spot of career therapy, plus hear his thoughts on working remotely, design leadership, knowing when it’s time to quit your job and more.

Playground Notes: Could you tell us about the process you went through, from leaving your role as VP of Design at BuzzFeed, to opening your own company?

Cap Watkins: It’s kind of a weird story. I left BuzzFeed because I wasn’t sure what I wanted to do with my life and wanted to take my time to figure out what made sense for me (which was an absolute privilege to be able to do). After taking a few weeks off to clear my head, I started interviewing with some really interesting companies for roles that aligned with what I thought I wanted. At the same time, I had started Practical Works and started coaching, mostly as an experiment. Some folks had asked if I’d coach them, and I felt like it was as good a time as any to give coaching a try.

Cut to two months later, I finally finished all my interviews, and my coaching business was doing pretty okay (I paid my rent with my coaching income that month!). I came home from a final week of onsite interviews, sat down with my partner, and said, “I don’t think I want any of these jobs. In fact, the only stress I feel about this whole process is that I’ll get an offer, take it and have to tell my clients that I’m not working with them anymore.” It was a really surprising and interesting realization. And, luckily, it turned out I didn’t actually get any of those jobs! So, after the final call with the last company, I bought an actual desk chair and officially dug into running my own business full-time with no distractions.

Playground Notes: You’ve mentioned that when you left BuzzFeed, you didn’t have a specific plan. How do you know when it’s time to leave? And how do you know what to do next?

Cap: The answer is different for everyone, but there are some things I think everyone can do to answer those two questions for themselves. In terms of knowing when it’s time to leave, I always ask people, “What would it take for you to stay? To not even think about leaving?” It’s surprising how many people don’t have that list! They just have a vague sense of discontentment or frustration, but haven’t figured out what is actually bugging them.

Once you’ve got your list of things that’d make you stay, the next step is (if you generally like your job, company, coworkers) to ask for those things. Again, so many folks I’ve managed or whom I coach today don’t even give their managers and companies a chance to make things better. Whether that’s because they assume nothing will happen, or are too nervous to ask. Ask! You might get exactly what you want and then you don’t have to go through the whole stress of finding a new gig, interviewing, taking time off work, etc. And if you ask and nothing happens? No big deal! You’re in the same spot you were before, but now you know you should move on.

Which leads to the second question. How do you know what’s next? That list from your previous company is a good starting point. If you were looking for a role with more accountability, you should go find that. If you were looking for more money, a more mature product development process, a manager who will help you grow… write those things down and look for that in the companies you interview with. Craft questions for the interviewers that help you figure out if that company will give you what you’re looking for.

Playground Notes: How did the idea for Practical Works come about? Was it born out of personal experiences?

Cap: When I got to BuzzFeed, a large portion of the managers at the company were first-time managers. Not only that, but their managers were also first time managers a lot of the time. And at that level, there typically just aren’t a lot of resources to help those managers. The same goes for senior-level practitioners. Most companies do not invest in those employees’ growth. You hear a lot about executive coaches who work with CEOs and that level of leadership, but what about the folks on the ground, in the thick of it, doing the work?

I always knew that if I started a coaching consultancy, it would be focused on helping that level of manager and practitioner grow.

Playground Notes: Since starting Practical Works, what are some of the biggest lessons you’ve learned? Has anything surprised you especially?

Cap: Having a bunch of Google Hangouts is not the same thing as being around people. I tell friends sometimes how lonely and isolating this job can feel at times, and they respond, “But you’re around people all day!” Wrong! Even my interactions with the folks I coach aren’t the same as coworkers. It turns out I’m a pack animal, and one way I recharge is by being around people in physical space. I’ve had to make a real serious effort to get out of my closet-office and make sure I’m getting that time in.

Playground Notes: As someone who spends their days communicating and working with clients from afar, do you have any tips for managers working remotely?

Cap: It’s really hard, and I can’t personally recommend it. You have to be way more hardcore about who you’re hiring and their ability to drive their own work and communicate hyper-effectively. Make sure you have budget to get your team together in the same geographic location at a reasonable interval.

I definitely distributed teams that are here to stay, but based on my own experience am not convinced it’s solved enough to be anywhere near as effective as co-locating your team. There are still a ton of unknowns, bad practices and even just gaps in technology that prevent it from being amazing.

Playground Notes: What makes a good leader in the field of design?

Cap: Someone who fully understands the business, as well as the other disciplines that impact design’s ability to execute. If you have a craft-oriented leader who isn’t engaged with the business and shaping design around the business, that’s a recipe for a pretty frustrated and siloed design team. Also, if you have a leader who doesn’t take other disciplines into account, you can either wind up under-staffed, or with a team who can’t negotiate thoughtful outcomes because their boss can’t work with their peers effectively.

Playground Notes: When working at BuzzFeed, you also managed the Corporate IT team, despite having little experience in the field. How important is it that a manager come from the same expertise as their team members, specifically in design?

Cap: I think the importance of having a manager from the same discipline really depends on what a team is facing. At that exact point in time, our IT team was going through a hard time culturally, mostly. It wasn’t a situation where they needed my help networking a building or managing the insane amount of storage for our video footage. They were all super talented, but weren’t sure how they should work together across offices or with other departments, lacked a set of core principles for decision-making and also were just missing management expertise to help grow the managers on the team. And hey, that’s all stuff I know about!

After about 18 months, the team was doing a lot better in those areas, and I looked ahead to us growing even more with the company and realized I was no longer the right person for that job. I spent the next six months advocating for, and eventually hiring, a VP of IT to replace myself.

So, it really depends, even for design! I’m certain there are design teams who could benefit from simply having a strong and empathetic leader, regardless of where they come from.

Playground Notes: What did you learn about leadership from running non-design teams at BuzzFeed?

Cap: Two things come to mind. Firstly, all teams need the same basic elements or they can’t move forward in a meaningful way. There are so many teams who are missing things as simple as role documentation and salary bands, for instance. If you don’t know what your job really is, how can you know if you’re doing it well? And if you can’t say with certainty how your pay relates to the market, that’s a constant source of stress.

A lot of leaders start with “what’s the vision for this team?” when that doesn’t matter at all if you don’t have some of the basics right. How and when does your team communicate with each other? What about with the rest of the organization? What are their day-to-day goals? What processes do they have? Should they even have them? Are the right people even on the team? There are so many questions you need to answer before you can even start to think about big picture things.

Secondly, starting from a humble place is so effective. I do this with my design teams too, but in particular with IT and the Ops team I managed, I was forced to admit to them that I didn’t know a ton about their jobs. But instead of that making it harder to work together, it meant that I needed to rely on them to do their jobs and help me understand their needs. It made figuring out those basic elements so much simpler when I could work directly with the team in a more collaborative way to understand the context. When I made decisions, they were informed ones! And people were far more receptive than if I’d come in hot, making changes left and right without knowing anything about them or their roles.

Playground Notes: How do you let go of your ego when giving design feedback? Any words of advice?

Cap: Make sure you always start with the goals of the project. Most of the design critiques I’ve seen go off the rails are those that don’t center around the goals of the work being shown. When you talk about metrics or user problems you’re trying to solve, or a business need, it not only helps others give you helpful, actionable feedback but also puts you in a position to better receive it.

If you feel like the feedback is overwhelmingly subjective, it means you probably haven’t done a good enough job setting up the context and helping the team understand what feedback would be most useful.

Playground Notes: How was your experience of your first managerial role at Etsy? What were your main learnings, and how do you think that experience eventually brought you to where you are today?

Cap: It was great! I finally found the thing I’m naturally both good at and interested in. With design, I was interested, but definitely lacked the raw talent that I saw in a lot of my peers. Hiring and managing people for the first time was an amazing experience, and I’m very lucky to have had it at Etsy, where I got to learn a lot about building strong culture, balancing empathy with pragmatism, etc. When I finally left to pursue a larger role, I felt super prepared by the work I’d gotten to do with the design team, my design manager peers, and the great folks in product and engineering.

Playground Notes: Do you have any advice for someone who made the move from team member to team leader, within the same team?

Cap: Accept and acknowledge that it’s weird at first, for you and everyone else involved. It can be awkward to start managing people who use to be your peers, but remember it’s as weird or weirder for your team! Try to be there for them, do what you say you’ll do and read as much as you can about how to be good at your job.

Playground Notes: Lastly, what are some of the proudest moments and accomplishments of your career so far?

Cap: In no particular order:

1. When the first major redesign of Etsy’s Seller Tools launched. It was my first project as a manager at Etsy, and I’d hired and managed the team of designers who worked on it. To this day, it’s one of the most interesting projects I’ve ever worked on, and the collaboration between product, engineering and design was so incredibly tight and amazing. I was so proud of the whole team when they launched (after I left the company!), because I knew how hard they all worked and what a complicated project it was.

2. There were a couple designers at BuzzFeed when I started who were so frustrated already that, during my first week, they told me they were probably going to quit. They wound up staying for many years afterward (one of them just got promoted to the highest design level they have, even!), and they had such a high impact on the team and are still a couple of my favorite designers of all time. It feels good to have talked them off the ledge and for them to then go on to such success.

3. Every once in a while a coaching client will email me to let me know how helpful I’ve been and that’s always such a nice moment for me. Like I said, it can be tough sitting in my closet all day on Google Hangout calls sometimes. Getting those notes really fuels me and reminds me all over again why I’m doing this.

This interview is a continuation of Cap’s recent career therapy session at the Wix Playground in NYC. Keep up with our upcoming design events at Wix Playground Presents.