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The keys my employee had just thrown at me ricocheted off of my left shoulder and came to rest at my feet.
Our VP of People, stunned, responded by shooting a confident glance my way as if to say, “I’ve got it from here.” It was 9 a.m. on a Tuesday in the spring of 2017, and I had just fired my Director of Inside Sales.
He slouched down in his chair, gave me a disgusted look, and said, “This is such bullshit, and you know it.” Then he grabbed his office keys and chucked them at me. I sat there after the whole ordeal went down and thought about how stupid it was.
Because it never needed to come to this.
I had hired this guy, and he was relatively good at his job, although not what I’d describe as an “A player.” His sales team liked him enough, but he struggled mightily to build relationships with any leaders outside of sales and marketing. And the better his team performed, the worse his cross-departmental attitude seemed to get.
I’d known for months that I needed to sit him down and talk to him about it. Probably a 30-minute max conversation. I owed it to him to say exactly what I was seeing (and hearing) and give him a chance to fix it.
But I hesitated and stalled.
I knew he was always looking for a fight, and the thought of the conversation made me sick to my stomach a bit. I could already imagine how uncomfortable the whole thing would be, so I kept finding reasons to postpone it. I’ll do it next week. Or after the quarter winds down. Or once the commission plans have rolled out.
Any excuse to kick the can down the road, I made it.
I can remember a particular one-on-one where I had the whole conversation planned out. Then he walked in complaining about marketing, and I let the meeting devolve into a bitch and moan fest about marketing leads. But candidly, I felt relieved.
If you had asked me why I was doing this back in 2017, I can imagine I would have said I was being patient. Maybe giving him a chance to figure it out on his own.
But the truth is that I was afraid to handle it. And I think this is how a lot of bad situations get worse. We convince ourselves we’re being patient or keeping the peace, but we’re just avoiding feeling uncomfortable.
Eventually, as he saw his behavior go unpunished, he made poorer and poorer choices at the office. When he refused to interview a VP of Inside Sales candidate because he thought the job should be his, I fired him the next day for insubordination.
Cue the keys.
Looking back, I can’t believe how foolish I was to put off having one difficult conversation. I bought myself a little comfort in the moment and created a significantly worse situation later.
Luckily, I learned my lesson from the experience.
About a year later, I had a top-performing salesperson who was driving me crazy in a different way. He was 28, a quota-crusher, and had an opinion about how everything should be run. Compensation, promotions, strategic decisions. He marched into my office regularly to tell me what the leadership team was getting wrong.
But we’d worked together before and now had an ongoing relationship of almost five years. And, to his credit, I found him to be a reasonable person to have difficult conversations with.
So one day I asked him:
“Who on this team have you ever made better? What solution have you ever come to me with that’s even halfway realistic?”
He stammered around for a bit, but he didn’t have a good answer.
I told him that, if I was being honest, he was acting like a baby, not a top sales performer. If he wanted to get promoted or make more money or have more say in what was happening at the leadership level, he needed to stop complaining about everything and start making the business and the people around him better.
Go mentor someone. Bring me a real solution you’ve carefully thought through instead of another problem. Anyone can point out problems.
I challenged him directly: “Go step your game up and come back to me.”
And you know what? He did.
Over the next year, he mentored some of the newer salespeople, started bringing me thoughtful solutions, became one of the most respected people in the building, and got promoted. A few years later, he left and started his own successful healthcare company. And I’d like to think that challenging him to get better was a tiny sliver of what helped him do it.
The difference between these two uncomfortable situations bothers me when I think about it now.
I gave one guy useful information while he still had time to do something with it. With the other guy, I waited so long that the first truly direct conversation we had about his behavior came when I was telling him he was fired.
When you have an issue with someone, silence in the moment feels harmless because nothing happens right away. But that’s actually the entire problem.
The other person keeps on operating without the information that might change what they do. And you get to avoid discomfort and hope everything somehow fixes itself. Trust me. It doesn’t.
People deserve bad news while it can still help them.
I have no idea whether that first guy would have changed at all if I’d sat him down three months earlier. Maybe he would have been surprised and open to an attitude improvement. Maybe he would have gotten defensive, and we would have ended up in the same conference room even sooner. Maybe he would have thrown his keys at me right then and there.
But I never gave him the chance.
By the time those keys bounced off my shoulder, I had finally said what I should have said months earlier.
It was direct, it was honest, and it was totally useless.
