The story of Gary.

I’d like to share a story about how leadership can work for you and against you sometimes in the very same situation. I hope you can take something positive from it.

A few years ago I had an opening on my team and we went through the standard hiring process. We interviewed several candidates, many with great skills and a few that didn’t make the cut. I always include some of my team members in this process because, for me, the best candidate is not always the smartest or the most experienced. I place a very high value on personality. Yes, I want qualified candidates, but I also prioritize how well a new team member will fit in with, and support, the people already there and the mission we are working toward.

We got lucky this time.

Gary was obviously passionate and knowledgeable about technology, and he was just so naturally compatible with the team. During his interview we never even got through all of our questions because Gary would start with a very direct and confident answer and then drift wonderfully off into the weeds, offering examples, pontificating on some strange technical occurrence, or just telling a great story about the subject. He loved to talk and we loved listening. After the interviews were wrapped up we sat together, laughed about it, and unanimously agreed. Yeah, Gary would fit right in. After the second round of interviews, it was settled. Gary was our guy.

From day one it was clear we hadn’t just hired someone we enjoyed being around. We hired a genuinely brilliant, forward-thinking person who was passionate about sharing his knowledge with the team. What a find. Things were looking very good.

For a while.

A few weeks in, Gary came to me wanting to discuss something. My door is always open, so in he came. He explained that he had been talking with his fiancée about his new position and she had some concerns about how he was being managed. Specifically, did his manager meet with him regularly? Were there formal scheduled check-ins? To which Gary had apparently told her, no, he just lets me work and we talk throughout the day but nothing too formal.

Now, to his fiancée, and I’m sure to many people reading this right now, that sounds like a red flag. Lazy manager. Checked out. Not doing his job. I understand that perception completely. But here is my side of it.

The project outcome was clear. We both knew where we needed to go and I had suggested the initial technology stack to get us there. Gary, being Gary, almost immediately identified a flaw in my approach that would have made the result less efficient and less secure. He tested a few alternatives, documented his findings, and came back and convinced me that his method was the better path. I agreed, encouraged him to continue, and that was that.

All of that happened quickly, comfortably, and almost entirely informally. Some of it came from me walking around the office and checking in. Most of it happened at lunch, where the majority of the team ate together at a picnic table behind our building. It was open, transparent, honest, and relaxed. In many cases the entire team heard Gary’s suggestions and reasoning, and they also heard that my initial recommendation had been the inferior one.

That is exactly where and how I want those conversations to happen.

Because here is what else occurred at that picnic table. The other team members gained knowledge and critical thinking skills just from listening to Gary walk through his research, findings, and testing. And they also gained something arguably more valuable. They watched their leader be wrong, embrace it, and change course without ego or embarrassment. That is the environment I want every person on my team to feel. The confidence to challenge what they are being asked to do, and the comfort of knowing that my mind can be changed when there is a better idea on the table.

Would scheduling formal one-on-one meetings in my office, where I am comfortable and Gary might not be, have produced a better result? Not to me. Why keep it in a vacuum when you can discuss it openly as a team? Why micromanage someone who is clearly smarter than you in this area? If I had pushed Gary to move faster based on my original suggestion we would have ended up with a subpar and insecure result. That would have been my failure, not his success.

Sorry, like Gary, I tend to go a little long when I’m passionate about something. Let me get back on track.

Gary had never experienced this kind of freedom in a workplace before. And once he got comfortable with it, he became even more Gary. Diving deeper into the technology, testing theories on his own time at home, and absolutely bursting to share what he was learning with me and his teammates. That kind of passion, excitement, and genuine enthusiasm for the work is exactly why I lead the way I do. That is what team growth looks like to me. That is what I am building toward every single day.

So, what happened?

During Gary’s six-month probationary period, another position opened on the team, one with a higher title and salary. I assembled a hiring committee that included several team members, Gary among them. We saw some solid candidates but nobody who truly stood out, and we decided to reopen the search and look again.

In our organization, restarting a failed search involves a fair amount of procedural red tape and can take a few months. My plan was to move as quickly as possible and bring the same hiring committee back together. In my mind they had worked well, so why change it.

That’s where I went wrong.

What I had not fully considered was Gary. He was now cleanly past his probationary period, still performing at an exceptional level, and he believed, reasonably, that he was the right person for this position. First, I genuinely didn’t see that coming. Second, what I did next made everything worse.

When Gary asked to be released from the hiring committee so he could apply for the position, I discouraged him from doing so.

Now before you close the browser tab, let me explain.

In that moment, with Gary standing in my office, I quickly ran through the situation and identified a few concerns I hadn’t yet had the chance to fully think through, let alone articulate.

First, I had moved through the organization fairly quickly during my career, starting as a part-time consultant and eventually becoming a high-ranking director over roughly 25 years and nearly ten different role changes. After a while, rapid advancement starts to raise eyebrows. People quietly wonder why, and when those questions form it can erode the trust and camaraderie someone has worked hard to build. I had seen it happen. I did not want that for Gary.

Second, I always try to prioritize the health and happiness of the entire team over any single individual. The sum and the synergy of the group produces more than any one person ever could. How would the team respond to Gary being promoted so quickly after just completing his probation? I genuinely did not know.

Third, what if the next round of interviews produced an outstanding candidate, someone even stronger than Gary? I would much rather have Gary be part of selecting a great new colleague than lose a position to someone he now had to defer to on projects. That kind of situation can quietly damage someone’s confidence and change who they are at work. I hadn’t known Gary long enough yet to know how he would handle it.

So I made my decision. I discouraged Gary from applying and swallowed that bitter pill.

Gary choked on it.

And I blame myself entirely for that. The conversation was already in motion and while those reasons were clear in my own head, I could not get them out of my mouth in a way that made any sense to him in that moment. On the surface my position contradicted almost everything I stood for. I understood why he was angry. I would have been too.

Things went bad quickly. The more I tried to explain my reasoning the less he wanted to hear it. He became argumentative, dismissive, and at one point pretty colorfully insulting. In his eyes I had become the exact kind of unsupportive, top-down manager he had spent his career trying to escape. I gave him space, stepped back, and hoped for the best.

Out of obligation to the organization, and frankly to protect myself, I filed a report with HR documenting the exchange. I want to be clear that I was very complimentary of Gary throughout, his performance, his abilities, his character. But I had to describe what had been said. It was the right call, because Gary contacted HR as well, and if I had said nothing it would have looked like I had something to hide. HR heard both sides. No further action was taken by anyone.

Here I am again, like Gary, saying far too much to get to the point.

So here is what happened.

I could not and would not force Gary to sit on the hiring committee, so I let him step away. He applied for the position, interviewed, and was clearly the strongest candidate in the room. He earned a second interview and ultimately was offered the job. He had proved, entirely on his own merits, that he was the right person for that role. He was treated fairly and honestly throughout the entire process. And why wouldn’t he be? He was a great candidate, and I genuinely wanted to see him succeed.

In the end, Gary and I rebuilt our relationship. I apologized again for how I had handled the initial conversation, but I held firm on why I had made the decision I made. And I think over time Gary came to understand it, because he also came to realize I was never going to hold him back or punish him for the way things had gone between us. We had some very honest and personal conversations about it over the years and we both came out of it stronger and closer than before.

What more could you ask for.

As for Gary in his new role? Just incredible. Talented, generous, always willing to go the extra mile and share his knowledge and support with everyone around him.

Gotta love Gary.