Towards a theory of entrepreneurial bosses

The fact that it’s Labour Day got me thinking about the relationship between entrepreneurs and “labour.”

Entrepreneurs tend to be benevolent dictators. They love their employees. They think of them as family. But in my experience, this relationship lasts only as long as the employees don't threaten the entrepreneur in any way. Question the boss too much, press too hard for more money, recognition or – gasp! – equity, and you unbalance the family aspect. You may even put your career at risk.

Organized labour is rightfully suspicious of entrepreneurial leaders. In a way, the entrepreneur is like the leader of a wolfpack. Challenge the alpha wolf and you could get killed. Try to start a union at an entrepreneurial company, and you’ll evoke two sequential reactions:

1) Puzzlement and genuine sadness as to why this step was necessary – “Why didn't you just come to me and tell me you were unhappy?”
2) Total war. “I’ll shut this company down before I let a union tell me what to do.”

In other words, entrepreneurs can be generous employers – but they like to do it from a sense of personal generosity (and yes, paternalism), not out of a sense of need.

The talent shortage in today’s job market also presents entrepreneurs with great difficulties. They feel aggrieved that employees are less loyal than ever – and they dislike having to bend over backwards, suck up and shell out the big bucks to get qualified professional or technical help. The talent shortage alters the balance of power, and entrepreneurs don't like that one bit.

On the other hand, if you need help, if you show promise, if you work hard – most entrepreneurs are delighted to help you succeed. They’ll make exceptions for you, and find ways to train and strengthen you. They won’t try to hold you back if you decide to move on, and they’ll take pride in your progress as you advance in life.

Entrepreneurs are usually self-made people with well-honed egos who truly believe they alone (or with partners) made their business a success. But as the business grows, they come to realize that they depend on their employees for continued success. It's a difficult transition to make, but it perhaps indicates why trust is so important to them.

On the whole, I think entrepreneurs adapt marvelously to a very difficult job that probably no one ever trained them to do – employing others.

A toast to the worker on Labour Day. But spare a cheer also for the boss - imperfect but still trying - who makes their work possible.