Running a business can be lonely and all of us have weaknesses and blind spots. As you move from being a solo entrepreneur to running a small company you need to build a leadership team comprised of people who can fill the gaps. The right “first officers” are people you can brainstorm with and who will hold you accountable. After awhile, a good first officer can “take the bridge” so you can enjoy some much-needed shore leave.

Build your leadership team with people who aren’t exactly like you. I am not suggesting you look for someone who is your complete opposite – although that person would be good at all the things you weren’t – if you have no common ground you are sure to make each other crazy.

Instead, make a list of all your weaknesses. Then pick the one or two you know you aren’t likely to change and make those required skills for the next member of your leadership team. 

  • If you are fast, look for someone who is accurate.
  • If you prefer to work alone, find someone who enjoys getting out, meeting people and managing staff issues.
  • Maybe you are an optimist. You believe every project will be easy, every client will pay on time and you can always get everything done in the time remaining. While the positive attitude is good, you’ll definitely need someone to raise a red flag when they see a potential obstacle in the path.
  • If you are a big picture person who sees the objective and the general path but not the steps to get there then you need someone who is a stickler for details with strong process skills. Without someone to think th­rough and execute the details your ideas will be just that, ideas. 

Fight, Listen and Learn.

Once you start bringing people on to your team who have different opinions and skills, be prepared to compromise. It isn’t easy working with someone who views the world differently. You’ll find yourself answering tough questions and defending your ideas. The ones which hold up under scrutiny are the ones worth pursuing. This will only work if you can keep your ego in check, accepting the fact that you don’t always know the best answer.

Grow Your Leadership Team

While large companies have the budget to gamble on senior managers recruited from the outside, small businesses do much better with home grown talent. Identify someone in your organization who has potential and bring them along slowly. 

  • Start by delegating small tasks which they will own. Be prepared. They will not do the task exactly the way you would have done it. As you review their work, ask yourself if their solution is wrong, better or simply different. As you try to cultivate their leadership skills you need to be willing to accept different solutions as long as they are viable.
  • Solve problems, but don’t punish. People make mistakes. You need to create an environment where people are not afraid to fail. If they know the most important thing is fixing the problem, not assigning blame, they will be more likely to take risks. When things go wrong, it is ok to reach out to help them think through possible solutions. Just avoid the temptation to take over and resolve the issue for them.
  • Start documenting what you do. It is hard for someone to take over some or all of your responsibilities if there is no clear outline of what you do. Reviewing how you do things with someone else opens up opportunities to evaluate and simplify your processes or eliminate unnecessary steps.
  • Bring them along for the ride. Over the years you have probably developed a network of peers and strategic partners. Start bringing your candidate with you to formal and informal meetings. They need to know the people you trust and rely on. It will be helpful for them to see how you interact with each of your key advisors. Ultimately they will create their own circle, but understanding who you have chosen and why will help them make good decisions about their advisory circle.  
  • Develop action/coaching plan – Identify skill gaps and traits which interfere with their ability to lead. Look for appropriate training classes and opportunities for them to practice key skills. Getting a great first officer will free you up in the long term but is going to take a lot of work in the short term.
  • Test drive multiple candidates – If you are fortunate enough to have more than one potential candidate, give both people opportunities to expand their skills. 

The difference between being self-employed and owning a business is whether or not revenue continues to be generated when you aren’t there. If your goal is to own a business, a strong leadership team is critical to your success.

Strategic Plan