My Entrepreneurship Principles: Leadership

In my first piece on Mindful Entrepreneurship, I laid out several principles to optimize the entrepreneurial process.  In my second piece, I argued that culture is extremely important to startups. In this final (?) piece I will now examine how leadership can create an optimal startup culture and execute the entrepreneurial process.

Entrepreneurial Leadership

• Culture starts at the top; in a startup, all eyes are on the founders and the management team. Mission statements, declarations of values, and pronouncements of "our culture" have little effect on a venture's actual culture, which is determined much more by the actions of its leaders. If a company claims to have a culture of psychological safety but everyone sees a software engineer getting reamed out by the CTO for not doing things his way, then that culture is not actually safe. It is crucial that that startup leaders walk their own talk; however they act, that will be the culture.
• Bring the right people onto the team. Startup hiring can definitely be a challenge; finding people who are not only good but will also succeed in a less stable context isn't easy and many of the hiring best practices used by larger organizations fail at a startup. The best advice I can offer here is to seek out candidates who exhibit both humility and curiosity. These attributes are a perfect storm for contributors who thrive in the highly uncertain, rapid learning environment of a startup.
• Hire for diversity. Recall the effectuation principles from my first post: I was brought into a rapidly scaling startup to talk about how to apply those principles to leadership. One key take away is to prioritize the additional means that new hires bring to the team. Hiring for a very specific skillset is folly at a startup, where everyone wears multiple hats and what you think you need changes on a daily basis. Rather than evaluating candidates purely based on some pre-fab job description, give weight to all the additional skills, experiences, and perspectives they bring to the table.
• Encourage divergent thinking. Instead of asking your employees, "What is the right answer," ask, "What is possible?" Follow up with, "What else is possible?"
• Ask questions. Rather than barking orders, ask employees how they think problems should be solved. This serves the dual purpose of empowering employees with agency while also reinforcing a culture of skepticism. "Why?" "Why not?" "Is that a fact or a hypothesis?"
• Foster collaboration. It can be tempting in a startup to divide and conquer as much work as possible. Remembering that groups make better decisions in the face of uncertainty than do individuals, though, it is beneficial to reduce employees working in isolation as much as is practical. Use techniques like pair programming, team huddles, and strike forces to increase collisions among team members.
• Push employees out of the building. It is also important to increase collisions between team members and the outside world. Bring internal staff along on client visits. Provide incentives for employees to give talks (tech or otherwise) in the appropriate domains of the community. The more your team interacts with the outside world, the higher your venture's chances of benefiting from serendipity.
• Maintain a constant feedback loop. It is hard for startup employees to take big swings if they aren't standing on solid ground. Use 360 feedback to ensure that employees always know where they stand, how they are perceived, and how they can improve.
• Put the fish on the table. Feedback need not be limited to anonymous tools and it is important that it be provided - sensitively - in person. We use the term "fish on the table" to motivate team members to share open, honest feedback with each other. If there is a rotting fish kept under the table, it will start to stink. If it is brought up above the table, however, it can be dealt with. When a team member asks to put a fish on the table, others listen and try to accept the feedback openly because they know it is for the good of the team.
• Be a secure base. As babies learning to walk, we know that, if we fall, Mommy or Daddy or another care giver will be there to pick us up. We develop the confidence to take risks through reliance on these secure bases. This circuitry persists through adulthood such that, if you want your employees to take risks, you need to be a secure base for them. Let them know frequently that you will still love and value them even if they fail - show them rather than just telling them. A major role of being a startup CEO is also being the CPO - Chief Psychology Officer! Joining a startup is scary; being a secure base to your employees emboldens them to be fearless.
• Create meaning for your team. Working at a startup can be daunting. The work can be hard, the hours can be long, the pay and benefits can be below market . . . remind your employees of the purpose of their work. Mission and meaning are like secret weapons for startups; they make up for many other shortcomings so you can't let anyone forget about them. At my startups, we have very visible indicators of our progress toward meaningful metrics and periodically bring in speakers who have been impacted by our mission.
• Keep your integrity. Startups are hard and there is temptation to cheat in some ways even just to keep your venture afloat. At the end of the day, though, the only think you will take with you from one startup to the next is your integrity. If you fail, people will forgive you as long as you were honest. (I know an entrepreneur who lost all of an investor's money but did so honestly and transparently; that same investor then backed the entrepreneur's next venture as well.) If you are dishonest, however, your reputation will be trashed forever. 
• Never stop learning. Leadership is like other skills: it can be practiced. It can be improved. It can be developed. Just as a startup organization should never stop learning, neither should its leaders.