Entrepreneurial Leadership

human. Good bosses aren’t robots or automatons. They have feelings, and they recognize that employees who are being fired will feel a complex and unpleasant mix of emotions. Managers must deal with them appropriately, which mostly involves listening patiently and avoiding responding with negative emotion of their own.

Don’t hand off the dirty work. No one likes to fire people. No one likes being fired either. (I know this firsthand: it’s happened to me.) The only thing people like less than being fired by their boss is to be fired by a hired gun or an HR director.

It’s smart and advisable to rehearse a termination conversation with an HR professional beforehand; he or she has more expertise and experience in this task than most managers, and rehearsing may be the single best way to prepare for difficult conversations.

It’s smart and advisable to rehearse a termination conversation with an HR professional beforehand; he or she has more expertise and experience in this task than most managers, and rehearsing may be the single best way to prepare for difficult conversations. In certain cases, it’s useful to have an HR person accompany the manager to the meeting to serve as a witness.

“I’m just the messenger.” This is a cop-out. The person communicating the decision should take personal responsibility for it—and not pass the buck to others.

(Letting this person go is one of my most important tasks. I will do it with the utmost sensitivity.)

I deserve some of the blame for the failure.

To avoid becoming defensive, I focus on the end result we both desire. (I want to help this person find a place where she can maximize her potential—a place that better fits her skills, personality, and ambitions, her style of working.)

I also focus on my duty to the team to remove an underperformer.

“Stop thinking about the guys you fired and start thinking about the guys you still employ. They’re the ones who deserve your attention,”

“And by letting the person go, the people I left behind felt better about working for me. . . . They worked harder, with more pride, as long as I held the whole crew to the same high standard and did my job by weeding out those who didn’t meet it.”

As an entrepreneurial leader, your job is to put the best team on the field at all times. You owe it to those who stay to not burden them with those who should move on.

Since removing a teammate is an emotional and difficult passage for all, be gracious, generous, and thoughtful, remembering that you, too, failed to make the situation work.

Entrepreneurial leaders rarely have the luxury of making perfect choices. Instead, they’re choosing between imperfect options, making bets in the face of uncertainties, or making a call they know is suboptimal because of constraints that observers or the public may not even recognize.

Decisions are destiny. Making tough ones is the measure of the entrepreneurial leader.

If you’re making a lot of easy calls, you’ve failed to delegate.

Good decisions are necessary to great execution. Yet some leaders delay making them. Others make them before having the information that would alter the probability of success. Entrepreneurial leaders know big from small, likely from unlikely, and urgent from optional. They tend to know when to take a decision—especially one of the close-vote, 51-percent-to-49-percent variety.

Those with the best wiring for decision making stood at a reasonable but challenging distance, where success depended on a combination of skill, pattern recognition, and good fortune.

Eliminate the excuse that life isn’t fair. Get comfortable with making optimal decisions from the array of possible options, rather than wishing you lived in an alternate reality.

Make good small decisions. Use small decisions as a way to practice pattern recognition, to learn what works and what doesn’t.