I Wish I Had A Do-Over

Here is a story about one of my leadership failures. At the time I was a Lieutenant Colonel in the Air Force and was coming on board as the operations officer of a fighter squadron—the #2 position just below the commander. The commander, who had been in his position about a month longer than me, assessed that the squadron was underperforming its potential due to two primary factors.

The first factor was that one particular officer had built his functional shop into a powerhouse. He had too many people along with the lion’s share of the squadron’s talent. His shop did great things, but that came too much at the expense of other squadron personnel needs, hindering our overall performance. The second factor was that this same officer had also taken on an informal leadership role beyond his normal duties that overshadowed and undermined the formal, mid-level supervisors in the unit (flight commanders, in Air Force terminology). The commander asked me to rebalance the squadron, which would mean deliberately tempering this officer’s role and influence to allow others to step up.

Make no mistake, this officer was a great guy – he was smart, hard-working, well-intentioned, charismatic, a terrific fighter pilot, and arguably our best instructor. My approach should have been to build some initial trust with him and listen to his perspectives. Armed with that knowledge I could then discuss with him why the commander and I thought we needed to make some changes that would impact him, but that we thought were best for the team overall. Ideally, I would be able to do that in a way that he could buy in to the changes.

Man, did I screw that up! Within my first few weeks on the job, there were at least three times I publicly undermined him. So much for building trust.

At my first meeting with the mid-level supervisors, this officer (who was not a formal supervisor) showed up because that was what he was accustomed to under the previous leadership. It caught me off guard and right in front of the other attendees, I asked him to leave. That was a mistake. A better move would have been to let it ride, talk to him after, and adjust the next meeting. Next, I publicly overruled him about implementing a training competition he had created. I failed to set clear expectations that I would want input on something like that before he pitched it to the squadron, and he assumed he didn’t need to clear the plan through me. So, he presented the plan to all the pilots.

As he was explaining it, I immediately knew it was not aligned with my and the commander’s intent. I put a hold on his plan there, in front of all the pilots. The smarter approach would have been to take it up with him after the meeting and allow him to fix it himself with the pilots later. For strike three, I publicly called him out for being overdue paying his snack bar bill. This was another instance I handled poorly.

I was arguably “technically right” on each issue, but my approach to dealing with each was flawed and I completely sabotaged my ability to build trust. From his perspective, I suspect it felt like a sustained attack from his new Operations Officer—one that he had done nothing to deserve other than bust his butt for the team. He was frustrated with me, which showed, and the palpable tension was not good for either of us or the organization.

I have always been a believer that it is primarily my job to figure out how to get along with my boss, more so than my boss’s job to figure out how to get along with me. However, in this situation, with me as the boss, I hold myself to account for that broken relationship. I turned an officer who should have been one of my best wingmen into an adversary because I failed to build trust, I failed to listen and learn, and I failed to effectively teach and communicate.

On a more positive note, over time our relationship improved and we came to a better mutual understanding. I also believe that I helped this officer become a better leader because I was willing to tell him what he needed to hear, even when it was not necessarily what he wanted to hear. Initially, because I mistreated him, that feedback fell on deaf ears. Eventually, as he came to understand that, despite my initial missteps, I truly did care about him and his success, he came to value my observations and advice. I also believe that the commander’s assessment that we needed to rebalance the squadron was spot-on. Over time, this officer aligned with the needed adjustments, and in doing so we became a much better organization for it.

I will always look back on how this relationship began and wish I could have a “do-over.” Since there are no “do-overs,” I’ve tried to at least learn from my mistakes. I’m more alive to the thought that embarrassing someone, intentionally or not, rarely leads to a good outcome. Also, I learned to more fully embrace the critical importance of building trust early in a relationship. Finally, in my communications, I try to be more mindful about what I want to achieve and am more apt to intentionally accept a suboptimal outcome on the smaller things to preserve my ability to meet my more strategic objectives.

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