On my first day on the job as the new CTO of a startup, I sat at my desk and looked at a team working their asses off: heads down, headphones on, fingers clacking on the keyboard. No one was talking. I quickly realized that revamping the site wasn’t my biggest challenge. My greatest task was to build out a large team without alienating the people who made the place special in the first place. The new team would need the same drive and passion as the old, but needed to add a sense of shared vision, some levity, and some camaraderie.
The team started with five engineers, shrank to three, and now has grown to twenty strong. I’ve learned quite a bit, and want to share insights gleaned along the way. Hopefully they may help any of you who are about to start a new role and/or face similar issues.
Respect the current team: Their domain knowledge, which you are probably lacking, is invaluable.
At first, these interactions can be confrontational. The trick is to strike the balance between being deferential to their insights, while asserting your own agenda. Push for change without treating your own vision as golden and infallible. While there always might be those who you need to replace, keep the core team in place — they were hired for a reason. Show that you value them and are not hiring new people to replace them. However, have the hard conversations; be honest about what you need from them. Involve them in the hiring process and clearly articulate the objective: You need to build out an even more robust team that’s a talented mix of veterans and newcomers.
Don’t go out and buy fancy new toys: It’s tempting for us techies to fall in love with the technology that’s shiny and new, eg we should be “SOAPing up our NoSql Rails that are Groovilly studded with Rubies in the cloud so we can Scala!” But make no mistake about it, often the “we need more new tech” mantra is a trap and a bunch of crap.
While jumping on a new platform may be warranted, an infatuation with new tech will result in a myriad of unmaintainable implementations, ultimately causing productivity to crumble.
Keep the baby, dump the bathwater: It’s easy to assume you have the right solution, and that what was done before was not up to snuff. Often the current solution evolved after a long series of trials and errors. Learn from it so you don’t repeat the mistakes.
Don’t rely on being remote: No, it’s not just the edict last month from Yahoo. Engineering thrives with the rapid fire of ideas, and for that spark to take place, you need to be in shouting distance or at least on the same floor. It’s not an easy thing for me to say as the father of a two year old and four month old waiting for me to come home, but propinquity matters.
If you’re at a startup that few have heard of, and you need to recruit the best people, you need to sell the vision, yes the dream, and implement quickly. Every bit of work you do can radically change the company’s future.
Hire for attitude, intelligence and then skill set: Personality, attitude and the ability to work collaboratively are first on my list. Avoid the stereotypical social misfits. Hire engineers with not just high IQs, but also ones you want to spend time with. They can quickly learn both the necessary skills and processes. Most importantly, avoid the “antisocial” variety of hacker, even if they have a stellar background, because no one will want to work with them.
Release constantly, sprint sanely: Like many others we iterate, but in a pretty distinct way. We leverage two week sprints, and have established a cadence with two alternating teams so that when one team’s sprint is being released the other’s work is cresting. We are able to naturally separate releases around deployables, but the same concept can be applied to functional areas as well.
Aim to create an engineering Mecca: I came from MLB and quickly learned never to rest on your laurels. Every year we focused on our core competency of streaming live baseball, so much so that our expertise for streaming live events became the best out there, period. These innovations aren’t just about engineering, they’re key to driving the business forward. Strive to build a team culture like Etsy’s where taking ownership is real and not just a buzzword. They continue to experiment and embrace risks, creating an engineering mecca that’s worth emulating.
Be the techie who talks: Board and executive meetings can be relatively easy for the CTO; other people in the room are often just too unfamiliar (or bored) with tech to question our decisions. So the best course of action is for the CTO to share with both the board and other departments, explain without being patronizing and point out the flaws in your own plans. Be honest with other interested parties and truly understand their perspective. Although it’s tempting to have your team focus purely on engineering needs, you often have to compromise and simply deliver features. Also, add a dose of humility, it will come in handy when, invariably, the excrement hits the whirling blades.
Culture is about attitude, being relentless, creative and embracing experimentation. It’s about taking responsibility, being honest, and knowing how and when to communicate. Culture is about the org, no doubt, but it’s really about the dynamic between people. Hire the right people, lead with humility, respect others insights, and your team’s productivity and quality of work will excel.