Entrepreneurs are often used to working alone. They do it all. They have ideas, and they know how to execute them.

But once you reach capacity as a one-man team, your business is no longer scalable. Growth screeches to a halt. After a few sleepless nights you realize, “I need help!”

The tough part of bringing in a team to support your entrepreneurial efforts is bridging the gap between working alone — and leading a team. All of the sudden, you have people looking to you not only for direction, but for support, encouragement, and leadership.

I reached out to a few entrepreneurs and asked how they learned to make the transition — and wanted to share their ideas with you.

Learn From Books

John Turner, the Founder of QuietKit, said:

The best book to help you transition from working alone to having employees is High Output Management by Andy Grove. Instead of giving a shallow, high-level view of how to manage, it goes into specifics and breaks down why certain approaches work so well, as well as the specific mechanics of practical management.

Ben Landers, CEO of Blue Corona, also had a list of books that helped him accomplish this goal.

“Start with the classics: The Great Game of Business and A Stake in the Outcome by Jack Stack and Bo Burlingham, Up the Organization by Robert Townsend, and Managing Oneself by Peter Drucker. Finish your education by reading every book written by Patrick Lenconi,” he said.

Focus on People

Dupray owner Sebastien Dupere says that the bridge between entrepreneur and boss happens when you focus on being a leader who cares about his or her team — instead of about just being “The Boss.”

“First thing I do in the morning: I greet my employees. I talk to each of them for around 2-5 minutes. It allows me to read how their personal life and work life is going. I can tell if they need help, if they need leeway or if they need to be motivated back onto the right course. Yes, it takes me 45 minutes to finally sit down in my office, but guess what? The fact that I care about my employees and their lives has probably been the best team-building, positive-work-environment thing we’ve done for our business,” he said.

Bill Fish of ReputationManagement.com echoed this sentiment. He noted that the gap was best bridged when an entrepreneur strives to be a coach and mentor rather than just the Boss.

“In a startup, you aren’t going to have perfectly defined roles. Rather, you have to bring everyone together, set the crew up for success in obtaining team goals. It is a fast moving environment, and you have to have trust in your team and prepare them with the skills they need not only for them to succeed on their own, but the business as a whole,” he explained.

Use Tools that Make Team Management Easy

Entrepreneur Makenzie Marzluff said that using team management tools helped her more effectively manage the transition between working alone and working with a team.

“I use Slack, a task management software, to delegate tasks out and keep the communication going on each project. It keeps me as involved or not involved as I want to be,” she said.

Seth Sinclair of Sinclair Advisory Group recommended Modern da Vinci, a toolkit for building leadership skills.

"Members are led through a learning process that begins with developing a better sense of their strengths and weaknesses and then moves into identifying personal and business goals, developing leadership skills most aligned to those goals, and then putting learning into action with tools and coaching support to maximize their effectiveness," he explained.

Bring in a Coach

If you’re not sure how to transition from an entrepreneur to a boss that leads a team of employees, working with an executive coach can bring in some external perspective. Georgette Blau owns a tour business, and said that working with a coach helped her finally understand how to bridge the gap between the two roles.

“I was a very weak manager for a number of years, and finally this past December, with the help of an executive coach, restructured my company. I approached him after initially meeting at a networking event because I knew I wanted to make a change. He helped me develop both long-term and short-term plans, and even helped me with the actual termination of a few employees,” she said.

Mind the Gap: Learn to Become a Leader

It’s not easy to transition from entrepreneur to boss, but with the resources outlined here (the books, the tools, the people) — it is possible. Get the help you need to effectively transition into this new role, and you’ll succeed.

The bottom line: Be open to learning, to help, and to improving your skillset in this new world.