Since I take responsibility for my experience I’ll share that the biggest obstacles I’ve encountered in my career is myself. My biggest mistake is one that I’ve made a number of times throughout my career; leaving failed people in their roles too long. I can cite a number of examples.

The first example is an all too common mistake, actually in a sense a double down mistake. And that is assuming that the best salesman could be the best, or even successful, sales manager. I have made this mistake, regrettably twice, and it’s painful. Not only do you risk losing the productivity of taking your best salesperson out of that seat, but seldom do the skills and talents necessary to be a successful salesman translate effectively to sales management. As this becomes evident you become reluctant to make the tough decision to take the sales manager out of that role as it brings into question your judgment in making the initial decision. But as this person fails as a manager the productivity of the entire team suffers. And it’s not so simple as replacing the failed manager and putting that person back in the field as their morale and focus is severely compromised by their failure. And if you look at this under a microscope, it’s not really their failure, but yours.

Another example is a CFO that I inherited when I was appointed CEO of a manufacturing company. This was a long tenured employee with over 20 years service to the company. I quickly learned that he sat at the epicenter of the horrible political environment that permeated the company. I also learned that he had an “agenda” that was not in alignment with my direction and that of the Board of Directors. I tried to coach them through the necessary adjustments to his approach to his job, and this went on for many months. Ultimately the balance of the senior staff and much of the middle-management group started to believe that he had gotten the better of me. That compromised my credibility and leadership ability with this group. When I learned that he had taken some liberty with the financial reporting, “adjusting” some of the results to suit his purpose, rather than present the truth, I realized he had to go. In retrospect the price IN the company paid for keeping him on was far too great.

The final example all offer is definitely the most painful. I had developed a close friendship with a certain plant manager. Our family socialized together, we spent time together outside of work, and I got to know his kids and other relatives. As the performance of his operations started to fail I tended to turn a blind eye to that due to my personal relationship with him. As the marginality of his performance became more evident I try to coach him, offer additional resources, and make and implement decisions myself which should have been his. As his responsibility was very significant relative to the size of the whole business the performance of his operations severely compromised the results of the entire business. Eventually I had to make the difficult decision released him.

The “political” CFO bounced around several similar roles, over several years, and failed all. You can’t change a leopard’s spots. It is of note however, that both of the failed sales managers and the failed plant manager, went on to successful careers with another company. They found a situation that suited them better.

Although firing people is never pleasant, it sometimes has to be done. In many cases, it must be done. In virtually every case where my first instinct told me I should fire someone, it turned out that I should have, instead of hanging onto them and hoping their performance will improve. It virtually never happened.

I’m sure many of us who’ve been in the unenviable position of having to make these decisions has delayed them, feeling the poor performer might be able to “turn it around. When a decision becomes crystal clear, it’s important to act quickly. Hanging onto an under performer was bad for company performance, morale, and my own standing with other staff as it was usually clear that this person should be gotten rid of. Furthermore, it was seen by other staff that I was unable to make that decision, compromising my ability to lead effectively.

In firing people, if you ask yourself why they need to be fired: Is it their failure or the failure of the organization or their boss? In my experience, if you have someone in the wrong position, they’re often relieved and even grateful for the opportunity to find a position that’s a better fit for them. The positive side to all this is that a termination allows me an opportunity to recruit and hire a superstar and them, relief from the pressure of a bad fit.