The Strangest Feedback I Ever Received

Posted on August 17, 2026 Updated on August 17, 2026

My first job after my consulting company shut down was building a consulting organization for a spinoff database company. The CEO called me the week before, then invited me to meet him in Manhattan the following week. We met for a few hours, then he handed me a piece of paper with a title and salary. I thought about it for a minute, shook his hand, and said, “Thanks, boss.” We devoted the next few days developing a vision for the team that would boost sales and drive greater customer success.

We worked closely for the next six months, but there were times I could tell that I frustrated him. For example, we once met with a top 3 credit card company. They presented their needs, and he told them we could easily handle it.

On the way back to the hotel, I explained the architectural limitations that would make the project very challenging. Then I presented multiple ideas to accomplish what they needed – just not in the way they envisioned it. My focus was on creating a deal that worked, and not just closing a deal that could ultimately hurt our reputation.

A year or so later, I was on a multi-city road trip to visit customers and prospects with each member of the sales team. It was a Thursday afternoon; I had just arrived at a hotel in San Diego where I’d stayed dozens of times over eight years, and I was relaxed and feeling great.

The CEO called, telling me that one of the architects he hired had just given his notice, and asked me if I thought we should try to get him to stay. I explained that this person was extremely talented and worked well with everyone, but he wasn’t working on the things he was hired to do and had been noticeably unhappy for the past several months. I asked if we planned to revive the project this person helped develop, and the answer was ‘no’.

I went on to explain that while this guy was a great person and technical asset, he wasn’t a good fit for the company now or where it was heading, which is why I recommended letting him go. I said we could use his salary to hire one or two people interested in our current direction and get a better return on that investment.

To me, this was a logical decision, and not an emotional one. Most companies have limited resources, and to win, you need to find the greatest leverage for every dollar spent.

His response was, “The thing I love about you is also the thing that I sometimes hate about you.”

There was a brief pause of silence, then I replied, “OK, I’ll bite. What is that?” He said that, unlike everyone else who reported to him, I told him what he needed to hear instead of what he wanted to hear. He told me that he valued my perspective, which was why he called, but it was often frustrating for him to be told something contrary to his beliefs.

This candid conversation didn’t damage our relationship, and it reinforced a core truth about leadership: loyalty demands clarity first, then compliance.

Safe leaders surround themselves with “yes-men” to protect their egos. Exceptional leaders seek out individuals who care enough about the mission and its success to risk temporary friction. This is about doing the right thing, versus who is right.

Leaders should create an environment where all opinions and data are welcomed during the planning phase. Disagreement isn’t disrespect; it is a risk-mitigation strategy. This is where clearly articulating your concerns persuasively helps. True alignment sometimes requires strong debate behind closed doors to find the right path, and then executing the final decision as a unified team.

So, do you have the courage to provide the truth – even if it is unpopular? Can you do so in a convincing and professional manner? They might hate it in the moment, but they will value your integrity in the end, especially if you are seen as someone focused on improvement and success, and not just a contrarian.