The Entrepreneurial Leader's Challenge: Knowing When To Hug And When To Kick

If I have learned anything over the past decade, it’s that leadership, and entrepreneurial leadership in particular, is incredibly difficult.

The challenges faced are deceptively simple on the surface, but the solutions are complex and nuanced.

There are a myriad of solutions and approaches that can be adopted to cope with these challenges, but they vary from situation to situation.

I’ve found that only one tactic holds true in every single situation: authenticity.

Authenticity requires taking the time to reflect on your personal weaknesses.

Everyone has different faults that influence their decisions and behaviors.

One of my big weaknesses as a leader is that I tend to be too soft when it comes to dealing with employees and partners.

When it comes to the old “stick or carrot” approach to motivating those around me, I overwhelmingly favor the carrot.

I have a deep desire to see my team and partners find success, happiness, and fulfillment in the work we do.

Unfortunately, this approach can cause problems if left unchecked. When a leader tries too hard to be a friend rather than a manager, it becomes almost impossible to make the tough decisions that are right for the business.

Know when to hug and when to kick

One of my favorite books is Jack Welch’s 2001 management treatise “From the Gut.” In it, he talks about how leaders can be both firm and fair. “This isn't about being tough-minded and straightforward,” says Welch.

“That's the job. But so is sensing when to hug and when to kick.”

I’ve struggled in the department in the past. If I’m honest with myself, I have to admit that I have historically let underperformance and bad behaviors go on too long, only to reach a breaking point and snap.

When this happens, my response seems out of the blue and team members can easily be frustrated or confused. I've learned that It is far better to be consistent in your approach, remaining friendly but “kicking” when necessary.

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