Growth in organizations requires growth in their leaders.  Good leaders learn to make the hard transition from player to coach – doer to teacher of doers. [more]

As a big fan of NBA basketball, it’s been interesting to notice that few star players become great coaches or managers. The most recent failure in this transition is Isaiah Thomas.

Thomas was a joy to watch as a point guard leading his team to several NBA championships. Since then, among other teams he’s failed with, he brought the previously mighty New York Knicks to a new low as their general manager, then coach.

Of course there are exceptions, like Lenny Wilkens and Larry Bird, both of whom succeeded on the court and on the sidelines, but they are rare.

This analogy came to me recently as I see good friends, having been amazing entrepreneurs, falter repeatedly as they try to become great professional managers of their businesses.

And I’m feeling for them because it’s a transition I failed at myself. Just ask those who were with me at the time.

Years before that, I have painful memories of the first time my boss assigned me another employee to report to me. To this day, I remember the pain I put her through.

So, why is this transition – from player to coach; from worker to boss; from entrepreneur to professional manager - so difficult?

Firstly, and most obviously, is that developing our own knowledge, skill and self-discipline requires completely different skills than leading others to do the same.

The hard skills are the organizational architecture, strategic planning, financial strategy and human resource management. Books and seminars on these skills are easily found.

The softer and even more important side is leadership.

Here again, there are many sources for learning, my favorite of which is on our website’s “Bookshelf” titled On Becoming a Leader by Warren Bennis. I also believe in Jim Collins “Level 5 Leadership” theories.

Bennis and Collins made a splash by extolling the value of such (previously considered too soft) virtues such as honesty, humility and candor.

These traits, particularly the humility, are not usually found in our best workers, NBA star players or great entrepreneurs.

But after studying both the hard and soft sides of professional management and leadership, I believe there is actually another issue that causes the transition to be very difficult.

That is the concept of reaching for the middle ground.

Here’s what I mean.

Let’s say I’m a really good entrepreneur who decides his company is getting to a size where I must become a professional manager, more than an entrepreneur.

And let’s say I get past the first hurdles of the hard sciences – I’ve learned how to create the right structure to my company; put great financial controls in place; create processes for product development and project management.

In addition, I’m humble, honest and I learn to speak with great candor.

There is still a problem.

That is, what made me successful likely was operating on the extremes.

Extreme focus and passion is required of any great NBA player. The same holds true for a young worker rising up to management. And the same is true for entrepreneurs who are rewarded for great focus and passion as the company grows.

But what gets you to where you are is not what will get you to where you’re going.

For me, the extreme has been that when it was time to let go, I went from deciding nothing to delegating everything.

Other folks I know say they’re letting go but still decide everything. (True story: I know of an entrepreneur who ran a $2 billion enterprise who still reviewed every Federal Express bill for that week on Sunday nights.)

It doesn’t work.

Extremes may work when you’re a player; worker; entrepreneur. It doesn't work as well when you are challenged to become the leader.

The choice is not “control or delegation”; it is rather knowing when to delegate and when to control.

Great corporations and non-profit organizations are not the product of perfect flow charts and processes; they are the product of good (sometimes flawed) processes operated by good (sometimes flawed) people.

Much trickier, methinks.

Actually meknows because me screwed this up many times.☺