Will You Go To The Dance With Me?

ATJ — My Learnings on Building A Startup Team 

[This is an ATJ— an “Along The Journey” post. They’re written in the heat of the moment, vs. after the fact with proof of success. I hope that sufficiently counts as a caveat emptor ☺With that, here we go! ]

If I could do it all differently, I would have found the team first. But not all beginnings are as clean, and it came down to “move now, recruit later.” My experience with building a team has gone through three phases:

Phase 1: Willing friends: Three friends that joined to help make the vision a reality, giving 10 hours a week and being compensated with stock options;

Phase 2: Potential partners: Two colleagues that joined at 20 hours a week, with the intent of becoming full partners once we achieved financial stability;

Phase 3: Full-time team members: Members who started full-time (with salary + benefits) whom I brought on as senior members of the team compensated with salary + stock options.

Phase 1 was filled with excitement. Our collective skill set was design, technical, and business development. We started from scratch, and were able to knock out 3 product releases and land meaningful conversations with Quizno’s, the Port of Seattle, Butter London, Alaska Airlines, and many more.

Our momentum was cut short when we realized the time commitment was insufficient for meaningful contributions, as the majority of the team operated on a Maker/Creator schedule. 10 hours a week can produce almost nothing, & it was unfair for all for us to work on projects that demanded more than the time we had. I was also unknowingly growing expectations that their full-time schedules simply couldn’t permit. I was lucky enough that we were able to talk about the mounting challenges and difficulties. We parted amicably, with great learnings across the board.

Phase 2 also began with excitement. I opened up the kimono significantly to my new colleagues that were eager to help make the vision a reality. We onboarded successfully, partially succeeded in setting up meeting times, and delivered on a few small projects. Over time, issues cropped up with availability, work quality, and design direction. The thought of upcoming meetings became uncomfortable. Over discussions, I realized we just saw things differently. After ~90 days, I asked that we part ways.

This experiment failed for two reasons — mainly availability and a misalignment of values. 20 hours a week is not a lot of time, especially when working with busy individuals. We weren’t able to take the time to discover our communication styles, deal with availability, move from coaching to pure ownership, & discuss directional differences. Over time, the larger issue we uncovered was that we had very different approaches for solving problems and dealing with challenges. It became about values, what we thought about work/life balance, decision making, and much more.

Looking back, it was the right call for all of us. It wouldn’t have made anyone happy to continue working with discomfort, compromise, and a strong lack of alignment. I’m thrilled at what we all learnt, and I wish those colleagues the best life has to offer.

Phase 3 began with clarity — I would probe for values as well as skill set, and give it enough time to where we could deeply understand each other’s styles and approaches. This led to two strong candidates — an engineer based in Los Angeles and a designer based in Seattle. After flying down for a weekend and meeting my potential engineering partner in LA, I was convinced this was our guy. I gave the offer after several dicussions, of which he accepted. Two weeks later, he reneged and took another role. The designer whom I was also courting declined to join after two full months of conversations. It was a confusing and frustrating setback, knowing that I had just spent two months ‘dating’ two potential partners, and wasted another 2 months sketching a roadmap that would drive product progress and investor dollars. But setbacks create opportunities.

Seeking Counsel & Thinking Differently

I reached out to a few mentors about my challenge with finding team members, esp. after trying the usual startup talent outlets. I realized things weren’t working, despite my best efforts. (Translation — if things aren’t what you want them to be, they’re not working). In our discussions, I learnt that I was hiring by feelings/gut, feeling my way toward my future team. I was reviewing their published work, studying their blogs and twitter posts for attitude and values, and aligning that to what we needed as a company. But that alone wasn’t enough. I had to articulate our values more clearly, introduce more structure to the interview process, and focus on a core set of requirements that were comparable across the board. (A lot of this was influenced by some of the principles outlined in Thinking Fast & Slow) I decided to break my hiring approach into three distinct points within a non-negotiable two-week window, with advancement being conditional on each meeting.

Meeting 1: Culture and values. We’d talk about who you are, what you enjoyed, work style, schedules, what type of environments you thrived in, and what you on liked/didn’t like. I’d then share what type of environment/culture we were trying to create. This was critical — if there was no alignment here, we would not move forward.

Meeting 2: Hard Skills. This was all about your craft. We’d look at multiple projects completed, as well as brainstorm on opportunities. We’d look at different sites and platforms, and critique/discuss what could be better. At this point, I’d watch for passion, communication ability, and hunger to better the craft. Experts aren’t always the best business partners — hungry people fare far better.

Meeting 3: Business Deep Dive. Here, we look at the company — our plans, org structure, resources, tools, operations, etc. At this point, the dynamic shifts, where I ask folks to interview me and ask the hard questions.

Epilogue

The above refinement has greatly increased the number of individuals that have reached out to our team, and has helped me clarify what and who we’re looking for to take us to the next level. I fully expect the approach above to evolve as we learn, fail, grow, and evolve. I’m also delighted to say that after ~20 screens/interviews, we’ve found our new VP of Design/UX — a great guy that’s a culture fit, skilled, hungry, and totally groks the business. As with all things — success isn’t guaranteed, and we still have to hire more team members. But we’re learning from our mistakes and refining our approach. I also believe we’re another step closer to building an unstoppable team.