}); My Biggest Mistake As A Manager, and What You Can Learn From It | Corporate Wise Man

My Biggest Mistake As A Manager, and What You Can Learn From It

man sitting at desk

I remember it like it was yesterday. After spending months working on a nine-figure acquisition we finally closed the deal. The pressure was on: there were “day-one” presentations on site the day we closed, working with the communications team to create external communications, and even writing bullet points for the CEO of our $80B company to communicate to Wall Street. The best was still to come: I was 27 years old and my “reward” for architecting this acquisition (and seeing it through to conclusion) was that I would (finally!) get my very first direct report. Of course, I had worked on teams my entire career and had “dotted line” responsibility for many people throughout my career, but this was going to be my very first, completely mine, direct report who would support me as I was to manage my very first $48M P&L (profit & loss). My very first business! And my very first direct report, to boot.

Dave was one of the employees we “acquired” with the acquisition. I had worked with Dave throughout the acquisition process but, being a good manager (I hoped) I wanted some one-on-one time with him during the first week post-acquisition to learn a bit more about his background and to get him excited about his new role (and new manager: me). Our first one-on-one meeting was interesting, to say the least. Dave was one of the first dozen employees of the company we bought and, it turns out, he was personally hired by, and had a close relationship with, the former CEO and founder of the company we purchased (who, after receiving a very large check, was no longer with the company). I asked Dave to be honest with me and (much to his credit) shared an uneasiness with suddenly finding himself working in a multi-billion dollar international conglomerate as well as reporting to someone nearly half his age. “No worries!” I told Dave. “Things will get much better now that you are a small cog in a big, well-funded, sophisticated enterprise.” And I promised I would be one of those new “cool” bosses who would be heavily invested in his growth and development as an employee.

One month in, cracks began to show. Dave was missing deadlines and the quality of his work…well, it left a lot to be desired. In our weekly one-on-one meetings, I largely  brushed it aside. I mean, going through an acquisition can be traumatic, so I wanted to make sure I was providing enough space for Dave to spread his wings and be successful.  I reminded Dave of our core metrics, how the synergy of the acquisition was good for customers, and how being part of a larger company could do wonderful things for his career.

Dave, however, was not convinced. Three months in, there was little improvement. Dave was still missing major deadlines, key customers were complaining about Dave being late on important deliverables, and my boss was wondering if Dave was an “A” player and deserved a role on our team. “Don’t worry,” I responded. I was sure I could turn things around. I mean, Dave was my first direct report and I was not going to let him fail, right? To remedy the situation, I flew out to California to meet with Dave in person (I was headquartered in Minnesota at the time), took him to the most expensive restaurant in town, reassured him as to my commitment to the success of the business and his success as an employee on the team. Dave’s response was surprising: he was promised multiple promotions within the company we purchased (before the acquisition), was annoyed he was still at a low-level within the organization, and missed the scrappy, small attitude of the company post acquisition.

“Nothing to fear!” I said confidently. Acquisitions can be traumatic events (I had read all the Harvard Business Review articles, after all) and I was confident he would find his footing in a larger company post-acquisition. I thought maybe my guidance as a manager was unclear, so I reiterated his goals and metrics and instituted an every other day meeting cadence instead of our weekly check-ins. Warily (I didn’t notice at the time, but I see it now) Dave agreed.

Fast forward three more months. Dave’s performance hasn’t improved. It’s clear that he is not taking his job, or the metrics seriously. My boss is pressuring me to make a tough decision: either Dave needs to get on board or he has to go. I double-check my leadership style: share a vision? Check. Clear metrics? Check. Strong MOS (Management Operating System)? Check. Nothing seems to work. So, I finally ask Dave: “What’s going on?” Dave unloads, “I was one of the first employees of the acquisition, yet I was never given any equity. Everyone except for me made a pile of money when the company was sold. I used to be in a role where I had a direct line of control, but now I report into a manager who reports into a manger who reports into a director, etc. This is not what I signed up for, this is not where I want to be.”

Because I was a good manager, I listened politely, addressed his concerns, and tried to sell him on the benefits of being part of a multi-billion dollar global company. Grudgingly, Dave agreed with me and said he would improve his performance. The next day, I pleaded with my boss to let me keep Dave. I told him that we came to an agreement and his performance would improve. Three weeks later, Dave quit and went to a competitor.  

Was my first experience as a manager a complete failure? Maybe. I clearly messed up, but it’s not really failure if you learn from it. What did I learn? A very important lesson. Today, as a much more mature manager, I am willing to put up with a lot if an employee’s heart is in the right place. If an employee is trying hard, but not achieving metrics, I will work with them to ensure goals and tactics are aligned. If someone needs development, I will provide it.

However, what I learned from Dave it this: there is no cure for bitterness. If an employee is truly bitter, it is better for you and it is better for the employee to make the tough decision to remove him from the team. Do I wish I would have fired Dave? Yes. Why? Because he was clearly not happy and he was not giving the performance I needed on my team. Continuing to invest in Dave was not good for Dave and it was not good for the business, myself (as manager) or the broader cross-functional team. To continue to coddle Dave was to be “cruel to be kind.” Dave deserved better (he deserved to be in a small company where he belonged), I deserved better as I needed a committed employee, and the team deserved better as they needed someone who was committed and could deliver.

As I mentioned in an earlier post, I am fortunate to have grown up with a father who owned a construction company. My father is generally a pretty happy guy. On the rare days when he was in a terrible mood, I knew why: he had made the (heart-wrenching) decision to fire someone. Now, as a more mature manager, I have (unfortunately) had to do the same: I have fired more than a few employees. It is, unquestionably, the worst part of my job and I hate it every time. But the one benefit of getting Dave early in my career is that very early on, I learned a very important lesson: it is of no benefit to you, or to the employee, if you have a low performer/someone who is bitter/not engaged on your team.

Letting people go is a very, very difficult decision, as well it should be. Yet it is a reality of working in the corporate world. Be engaged with your employees and give them every opportunity to grow and develop. That is your obligation as a manager. However, employees have an obligation to perform and be engaged. We are paid to make hard decisions. In hindsight, I should have had an honest, difficult situation with Dave sooner. We probably both would have agreed he was not a good fit and both he and the business would have been better off had we come to this conclusion earlier.

In summary, I would like to leave you, as a leader, with the following advice:

  1. Invest in your employees. Allow them the ability to succeed.
  2. If your employees are under-performing, set clear expectations and metrics and invest time to get them to a point where they can succeed.
  3. There is no cure for bitterness. If an employee is truly bitter and unhappy, you are not doing them any favors by keeping them on the team: they can (and will!) likely succeed elsewhere.

My biggest mistake as a manager was not firing Dave sooner.  I know that sounds harsh but it’s the truth. I got in touch with Dave a few months later. I was happy (and so was he) that he was now a highly successful marking leader at a competitor. He found a job he likes at a smaller company for which he is a better fit. We both agree it was a mistake for him to stay with us post-acquisition and we laugh about it now. That said, you have an opportunity to learn from my mistake: don’t waste time dealing with performance/commitment issues on your team. If someone on your team is bitter, there likely is no path forward. It is better for you, your team, and the employee if you make the difficult decision to remove someone from your team.

Leave a Reply