The Most Valuable Lesson I’ve Learned as a CEO


I was recently invited to join the CEO of a Silicon Valley tech company for a fireside chat at his annual global leadership summit. He’s been interviewing other CEOs at the event for years as he and his team value hearing the perspectives, experiences, and best practices of other companies. He did a great job moderating and I truly enjoyed the event.

One of the questions he asked is one I get frequently: What’s the most valuable lesson you’ve learned as CEO?

My answer was simple: Don’t leave the pitcher in the game for too long.

For those less familiar with baseball, some explanation may be necessary. Picture the following:  It’s the eighth inning of a game. A star pitcher is on the mound and has been pitching well. His team is up by a few runs. The bullpen is well rested and ready for action should he start to tire. The inning opens and the pitcher gets the first out, continuing his already strong performance. Then it begins.

The opposing team gets a hit.


And then another.

It’s increasingly clear the pitcher’s arm is tiring and his velocity is wavering. His manager, recognizing the situation, approaches the mound and asks how he’s feeling. The pitcher replies exactly as you’d imagine (remember he’s a star pitcher; he didn’t get that way for lack of confidence):

“Skip, you’ve got nothing to worry about. I misplaced that first pitch and that last hitter got lucky. I’ve got this.”

The manager returns to the dugout and watches in disbelief as the opposing team eventually ties the game and goes on to win in extra innings. For baseball fans, you may be nodding in agreement with how familiar this scenario is. (To Red Sox fans, my apologies for reminding you of this.)

I’ve seen the same scenario play out countless times, both directly and indirectly. However, I’m not referring to baseball. I’m talking about business.

Leaving a member of your team in a key role when it’s no longer the right fit is one of the most common — and costly — mistakes a manager can make. The good news is that with practice and experience it’s also one of the most avoidable.

Here are a few of the lessons I’ve learned to help address the issue:

  1. In nearly 20 years of doing business, no one has ever approached me and said they couldn’t do their job. Not once.  
    No matter how challenging the role, people will be inclined to believe they can get it done. It’s human nature, equal parts ego and optimism. Simply put, we’re programmed to finish what we’ve started. Admitting that we can’t do it is just too hard for most of us, a particularly acute trait among overachievers.
    As a result, just like the star pitcher in the late innings of an important game, most individuals are not in a position to objectively evaluate their own performance. That’s where management comes in.
    As a manager it’s up to you to identify the potential performance issue and act accordingly. Perhaps that will result in leaving that individual in the role, perhaps not. Regardless, it’s ultimately your responsibility, not theirs. The sooner you hold yourself accountable for that decision, the better for everyone involved.
  2. If you have to ask whether or not someone is up to the task, you already know the answer
    Deep down, we all know how to identify performance issues as soon as we see them. The challenge is that given the consequences, many of us may not want to admit the issues exist. In turn, we may end up asking others for their opinion in the hope we’ve somehow got it wrong, which may only serve to further muddy the waters.
    There is a simple rule of thumb here: If you have to ask yourself (or others) whether or not someone on your team is doing their job, you likely already know the answer. They’re not.
    The key to managing out under performers or poor cultural fits is not so much about identifying the fact they’re falling short of expectations. If we’re being honest with ourselves, we’re already well aware of the problem. The key is in determining whether or not that person will ever be capable of doing the job. Which brings us to #3…
  3. Create a timetable
    Once you’ve recognized a performance issue with a member of the team, more often than not, the natural inclination is to rationalize it away. This is typically a byproduct of fear: Fear of how difficult it will be to replace the individual, fear of hurting them, fear of how their team will react, etc. That fear will inevitably lead to sub-optimal decisions that have the potential to do far more harm than the fear itself.
    The solution is to create a timetable as soon as you’ve recognized an issue exists, i.e. how long will you give the situation until making the final determination that the person can’t perform in the role?
    Bear in mind, there is not a single, uniform answer for this. It all depends on the individual and the situation. Whether one month, three months, six months, or a year, make sure you are doing everything possible within the allotted time to help the individual clear the bar. Be transparent about your timing and expectations. Let them know the specific measures you’ll be putting into place to assist them, e.g. coaching, access to specific learning and development tools, reduced workload, organizational changes, etc. Hopefully, the changes work and that individual begins to flourish over time.
    However, if it’s still not enough, do everything within your power to transition them out of the role compassionately.
  4. Managing compassionately should not be confused with avoiding difficult decisions
    Whenever talking about this subject, inevitably the question arises: How can you transition someone out of their role compassionately? Given how much it’s going to hurt them, isn’t that an inherent contradiction?
    My response is that the least compassionate thing you can do in this situation is leave someone incapable of doing their job in that role for too long.

Think about the last time you saw someone on your team that was struggling: The slumped shoulders, the increasingly hushed tone of their voice, their overall lack of presence during important discussions. It’s all a byproduct of the fact they know consciously or unconsciously that they aren’t getting the job done. Subsequently, it’s draining their self-confidence, and man-doing-yoga-in-business-suit-on-beachit’s only going to get worse over time. Their inability to perform is hurting them, their team, the company, and perhaps worst of all, they are bringing that energy home to their families.

The most compassionate thing you can do in this situation is to alleviate their suffering by transitioning them out of the role as gracefully and constructively as possible.

One person I know who went through this kind of transition returned several months later and said as much as they fought to hold onto their job, and as fearful as they were about the repercussions, moving on was one of the best things that had ever happened to them, both professionally and personally.

One final thought on the subject: After responding to the question about the most valuable lesson I’ve learned as a CEO, the moderator of the fireside chat added a somewhat unexpected observation. He said that while the other interviewees had not used the same baseball metaphor, 100% of the CEOs he’s interviewed thus far responded with the same answer. 

Hope you can benefit from the lessons we’ve learned.

Jeff Weiner, CEO at LinkedIn learned-as-a-ceo?trk=tod-home-art-list-small_1