Saturday, November 20, 2010

Making the Transition from Entrepreneur to ‘Boss’

By Mark F. Herbert

Making the transition from individual contributor to manager, or entrepreneur to “corporate” executive, is one of the most difficult shifts most of us will face in our careers. A study conducted by a national management consulting firm a few years back indicated that more than 40% of newly appointed managers fail in their first 18 months on the job!

As a consultant working with many entrepreneurs attempting to grow their businesses either for continuity purposes or for sale I see them experience many of the same issues.

In many cases these issues boil down to developing and maintaining effective relationships.Our educational system has a bias towards “technical” skills and individual achievement. Winning means getting the best grades and “setting the curve” as an individual.

Here are some of the most common mistakes I have observed in “new” managers:

  1. They fail the “politics quiz.” Organizational politics are a fact of life. Don’t sacrifice key relationships because a colleague or subordinate has a talent for getting face time.

  2. Don’t try to “clone” yourself. Of course you’re brilliant, that’s why you were promoted. However, good management is getting the best out of the staff you have. Improving employee performance is a process not an event.

  3. Failing to communicate. You avoid giving feedback because you are sensitive to past relationships. People desperately need and desire good, balanced feedback.

  4. The Sprint. Don’t try to accomplish everything on day one to validate management’s decision. Learn your staff and their capabilities. All priorities aren’t equal.

  5. Trying to be Dr. Feelgood. Everybody wants something and it’s hard to say no. Special, confidential deals never stay that way. Your job is to be the boss, not their friend.

  6. You’ve arrived. Management is a continuing improvement and learning process. Seek out opportunities to improve your skills and refine them.

  7. You’re the star. It is very tempting to fall back into doing the “technical” things you did before. You were good at it. Competing with your staff is bad management. You need to transition from player to coach.

When you look at that list I have seen a number of those and a unique set of challenges for the entrepreneur. The common entrepreneur’s issues from my list are number 2, number 3, and number 7.

Even more so than the newly promoted manager, the entrepreneur is the business. There is a tendency to attempt to replicate yourself or in some cases turn the business over to a family member who doesn’t share your passion or acumen.

One of the things we learn in large organizations is that different leadership styles are appropriate in different stages of the business. The passion, vision, and daring of the entrepreneur often need to evolve to the calm hand and head of a professional manager.

Feedback often times is especially difficult for the entrepreneur. It is either provided inconsistently or not constructively. The business isn’t a hobby to them it is their life and others lack of “engagement” can be frustrating.

Similarly, transitioning to “coach” is difficult. Typically the entrepreneur makes all or most of the key decisions. Delegating those decisions is hard, especially without the skills to support effective delegation. Equally difficult is that some of your responsibilities will probably be have to be shared by more than one person. That can be especially difficult.

The entrepreneur also keeps much of the most critical information in their head and within their personal control. Giving up that control and trusting is hard!

As I summarized here, this transition is a difficult one. Achieving results through others is usually a critical component to long term success. As a corporate person it is the key to advancement. As an entrepreneur, if you are the business, the value leaves with you, or its ability to grow is gated by your personal skills. Either way, this is a critical transition.


Today’s article is presented by my friend Mark F. Herbert, now living in Phoenix, Arizona, who is an experienced corporate executive, and a consultant specializing in optimizing organizational performance. Find out more about him at or contact him directly at




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