What's the biggest risk facing the leaders of most entrepreneurial ventures? It's not closing that first round of funding or landing a cornerstone customer. As with most things, it all comes back to people -- and your ability to lead those who don't have much practice following.
It's easy to get seduced by the investors, the technology, the contracts, and the customers. It's even easier to focus on those things when you don't want to take on the challenge of leading a green team. But, in the end, it's your people who hold the fate of your venture in their hands, and leading them well may be the most important work you do.
Whether you earned your stripes in corporate America or as a serial entrepreneur, you carry many embedded assumptions about the way people should follow their leaders. Unfortunately, no one has ever explained that to the members of your team. That's your job. You have to teach them how to be good followers and team members.
It's Not About Hierarchy
Most of your team members are part of your entrepreneurial venture because they enjoy the absence of excessive structure and bureaucracy. Try to teach the art of following by enforcing a hierarchy, and you've taken the first step toward killing your company culture.
Instead of explaining the org chart (trust me, everyone already knows it), help them understand the power of directing every team member's creativity, hard work, and determination toward a few key goals. Explain that it is your job to set that direction, monitor the course, and get them everything they need (money, people, resources, etc.) to move the organization toward its destination. Be sure to emphasize that their job is to accomplish the tasks along that path.
It's Not a Democracy or a True Meritocracy
Many entrepreneurs hold egalitarian management ideals. "The best idea wins!" we proclaim. Unfortunately, the best idea is not always practical or pragmatic. In that case, it falls to the leader (you) to squash it, which can inspire more than a little backlash from its most passionate supporters. So be careful in the expectations you set and assumptions you allow when canvassing your organization for good ideas.
Additionally, remember that incentives aren't always aligned. Younger salaried employees have very different goals than do personally invested founders or executives whose compensation hinges on the performance of the business. Those incentives lead people to assess decisions very differently, and it may lead your people toward projects that are at odds with your goals.
You set a tone with your decision making style. Set the wrong tone and you'll either never make a decision or your employees will grow frustrated when their recommendations are overridden. Simply explain the major constraints (time, money, technology, etc.) and how the decision will be made (democratically, by a committee, by you with input from others). Once the decision is made, be sure to explain why that path was chosen. Transparency helps your team see how you're keeping the organization on track with the goals you’ve previously articulated.
Help Them be Better Followers
By explaining that your role is to set direction, provide resources, and drive decisions, you'll help your newer team members understand how they fit into that broader organizational picture. Failure to do these things will result in frustration, disillusionment, and gridlock. The better you're able to teach your people to follow you, the farther along your desired path you'll go.