Over the course of my career, I've made hundreds of difficult decisions. Decisions to let people go, to rework orgs and where people fit, to change compensation plans for my team, to lay off people, to say no to what appears to be exciting new ventures for the department, and everything in between.
I've learned one thing through twenty years of difficult decision-making.
It never gets easier.
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Difficult decisions are exactly what they sound like. They're difficult. They usually involve letting people down, hurting some feelings, and generating emotions that range from anger to frustration to just downright sadness.
It never gets easier.
After twenty years, I can still tell you the names of the people I had to let go. I can still tell you the moments I made the wrong difficult decisions that impacted others, and I can tell you the nights I went sleepless before and after having to make the hard decisions.
I will say it once again, it never gets easier.
Ok, that's sort of a lie, because it does get easier, but the emotions of it never make life simpler.
It gets easier because you have experience, because you know how to approach things like a seasoned adult, and because you are able to clearly communicate the why through the process. But if you're a human who cares, you always carry that weight with you no matter where you go.
I think one of the biggest misconceptions about leadership is that the longer you do it, the less you care about the difficult stuff. Somehow, people think that when you reach a certain level, you become immune to the emotions that come with making tough decisions. You become this seasoned executive who can make a decision, walk out of the room, grab a coffee, and move on with your day. I can assure you that's not how it works, at least not for me.
The reality is that the higher you climb in your career, the more difficult some of these decisions become. You're no longer making decisions that impact one person or one team. You're making decisions that impact entire departments, people's livelihoods, their families, and sometimes the future of the business. The stakes get bigger, the consequences become more significant, and the responsibility sits squarely on your shoulders.
I've also learned that avoiding a difficult decision is usually worse than making one. I've seen leaders drag their feet for months because they didn't want to have an uncomfortable conversation or deal with the fallout of a decision they knew they needed to make. All they did was prolong the inevitable, create more confusion, and in some cases make the situation significantly worse. I've been guilty of this myself, and it's something I've had to work on throughout my career.
Experience has taught me how to make difficult decisions, but it hasn't taken away the weight of making them.
There's also a big difference between making a difficult decision and making a careless one. You owe it to the people impacted by your decisions to think through the consequences, understand the alternatives, and make sure you're doing what you believe is right. You don't owe everyone the answer they want to hear, but you absolutely owe them the respect of knowing you didn't arrive at your decision without putting some serious thought into it.
One of the things I tell people who are stepping into leadership for the first time is that you need to get comfortable being uncomfortable. There are going to be days when someone is upset with you, when someone disagrees with you, or when you have to make a decision that isn't going to win you any popularity contests. That's part of the job. If your goal is to make everyone happy all the time, you're going to have a very difficult time being an effective leader.
But here's the other side of this that I think is important. Just because a decision is difficult doesn't mean it's the wrong decision. Sometimes doing the right thing feels terrible. Sometimes you walk away from a conversation wondering if you could have handled it differently, even when you know the outcome needed to be exactly what it was. You can have empathy for someone, care deeply about how a decision impacts them, and still recognize that it was the decision you needed to make. Those things aren't mutually exclusive.
Twenty years into this journey, I still don't enjoy making difficult decisions, and I hope I never do. I hope I continue to lose a little sleep, question my approach, and think about the people on the other side of the table. To me, that's a reminder that I still care about the responsibility I've been given. Experience has taught me how to make difficult decisions, but it hasn't taken away the weight of making them. Frankly, I think that's exactly how it should be.