Why Leadership In Startups Can Sometimes Feel Impossible & How To Thrive Anyway
In a high-growth startup, nothing stands still. Every new hire, new function, new customer, and new product surfaces the need for processes, systems, and workflows that don’t exist yet. Most of the way teams are going about their work isn’t right and will need to change. Temporary fixes that inevitably need to be iterated can make it feel like you’re spinning your wheels. And the change you need changes because the company is so small, you can double the number of customers, employees, or initiatives within a matter of months, if not less. There’s pressure from the board at the top of the organization because they have their own set of expectations for what success is that may no longer align with reality, and there’s equal pressure (sometimes more) at the bottom of the organization because the team at that level lacks the control and context to be fully aligned with your decisions.
What’s worse is that as a leader, no consultant or mentor or management book is going to help all that much because everything you’re doing is new. Management is situational, and you’re facing a new situation in almost every way. Even the most seasoned managers, to some degree, actually have no clue what they’re doing.
For these reasons, even the best-run companies feel chaotic because, by definition, the creation of something new must start with chaos. It’s this chaos that becomes a sort of workshop where ideas are created, tested, iterated, and, through multiple cycles, turned into stability and order. The turbulence inside a startup isn’t a side effect; it’s the thing that ultimately shapes the company.
One day, you’re telling your team you believe in a product strategy, and you get the team rowing in that direction, only to have to tell them you’re changing the plan (again) and heading in another direction. You make a decision, then change your mind. Every situation is unique, and everyone sees only a piece of the picture; and many don’t see their picture the way you do. People will think they can do things better than you. And they’re telling each other. And they might be right.
The reason all of this can feel so painful for leaders is our human nature. Humans want to belong. And when you’re making fast decisions on behalf of other people in an unfamiliar, dynamic environment, you can become an outcast. In addition, humans want stability. And as a leader in a startup, given the above, it’s almost impossible to provide your team with consistent stability.
Here are some ways to thrive through all of this chaos, and maybe even enjoy it:
1/ Get the team focused on three things (or fewer). There are multiple books written on how to set goals, OKRs, etc., so I won’t dive into that here. But in short, I like to have three company-level goals that everyone knows by heart. I worked at a company a while back that would walk around with a drink cart on Friday afternoon and ask people what the three company-level goals were. If they answered correctly, they’d get a free drink. The idea here is that when things get crazy, and people are thinking, “What are we doing?”, they know to point back to those three things.
2/ Context, context, context. I’ve written about this at length here in the past, but this is so important. I’ve often made the mistake of assuming people think what I think or know what I know. You have an obligation to get out there and communicate decisions and the context around decisions. People need to hear it over and over. It’s safe to assume you’re never doing this as well as you could. Also, it’s a good idea to build alliances with a few of your senior managers or influencers within the company that can help you with this. Different people are going to be more effective than you are at communicating certain things.
3/ Make decisions with 75% confidence. In this kind of environment, speed is so much more important than perfection. Your cost of capital is too high to be idle.
4/ Be vulnerable. This is probably the hardest one of them all, given the points around human nature. People want to look like they know what they’re doing even when they don’t. And you don’t want the team to lose confidence in you. Regardless, I’ve found that leaning on the vulnerable side is far more effective than the opposite. I can assure you that if you try to pretend you have all the answers, your team will see right through it. As you grow, there’ll be several people who disagree with your decisions and many who don’t like you personally. It comes with the job. Get comfortable with this.
5/ Create tight operating rhythms and tie everything back to metrics. I really believe that the effectiveness with which a company runs its OKR or goal-setting/management process is directly correlated with the success of the company. Companies that do this really well are almost always run really well. It can be a trap, though, because taking it really seriously welcomes analysis paralysis and too much time talking and not executing. Obsessing over goals also allows people to hide because it becomes philosophical instead of practical. Police this dynamic personally and very carefully. Insist on creating the perfect balance between great management of goals and keeping the team focused on producing. Be very active here.
6/ Create a publicly available, easy-to-access strategy document. Similar to the ‘three most important things’, everyone should understand the company’s strategy; that is, “how you’re going to accomplish what you want to accomplish.” This will change a lot. So, find a place or a mechanism to update the team on it regularly and describe why it’s changing.
7/ Get comfortable saying ‘no’. The old saying about “knowing what not to focus on” is very, very true. There will be an endless number of ideas, opportunities, and distractions. Bad leaders let these sit out there and frustrate their team by not making a call. A culture where this happens regularly is much worse than missing a big opportunity. People don’t work well when they’re in limbo.
8/ Encourage debate. This is so easy to say and so rarely done. If people across the organization are not comfortable respectfully debating important topics with leadership, that is a blatant failure of leadership, and your company will be much worse off for it. If you or the leadership team around you don’t encourage debate, don’t change their mind, and don’t admit mistakes or poor decisions, everyone in the company will know about it, and they won’t like working for you. Creating a safe, respectful environment around debate is crucial in a startup. You must give this to employees. In return, their obligation is to disagree and commit. Once the decision is made, they’ve got to move on and chase after it. That’s the trade.
9/ Celebrate wins and highlight failures. Given the crises you’ll inevitably go through, it’s really important to have systems in place to celebrate wins, highlight the best contributors, and the big exciting events. People want to work for winning companies, so make sure when you win, people know about it. On the other hand, people also want to work for a company that is balanced and tells one another the truth. So have regular retros on failures. At a team meeting, have a “win of the month” and a “loss of the month.” Failures scale more than wins because you learn from them, and humans tend to avoid future failures more than they do chase future success.
10/ Zoom out. Refer back to the beginning of this post. By creating something new, you’re breaking ground and leading the charge to create something special that may live on long after you’re gone. Most people never get that opportunity. Take pride in that. And remember that the stress you’re feeling is a structural requirement of creating something new. Nobody has all the answers, and right or wrong, someone has to make the hard decisions and drive action. That’s you. ‘It’s not the critic who counts’ applies here.
Take care of yourself, be proud of your work, and try to enjoy it.