I tend to give people a lot of chances. Sometimes they’ve worked out and other times they haven’t. And sometimes someone is paying for the decision you won’t make.

My desire to give people opportunities likely stems from becoming a CEO at thirty, well before I was probably ready. I made mistakes, both big and small, and I am forever grateful for the people who gave me grace to figure things out. The founders of StoneAge, in particular, saw something in me that I hadn’t yet developed into, and I know how different my life might look if they’d decided not to take a risk on me.

Their belief in me, and how it turned out, has shaped the way I lead. I have invested in people others said would never make it, and I’ve watched them grow into roles they weren’t yet ready for. I’ve seen how judgment develops with experience, and that sometimes the person struggling today becomes a rockstar six months later with the right kind of support. I’ve watched people stumble and eventually become exceptional leaders. For these reasons, I don’t ever want to lose my willingness to see what someone could become.

But as with anything, my belief in people has a downside. Sometimes, my belief doesn’t match their capacity, capability, and/or desire to grow.

The Decision You Won’t Make By Giving it More Time

This came up recently when I had to make a tough decision that, when it finally came, made it clear I had waited too long.

Someone I cared deeply about was struggling, and while I’d known for a long time there was a performance problem, I wanted it to work out for them and for me. I gave tactical feedback, and I saw some improvement, which gave me hope that if we both kept trying, we’d get to where we needed to be. But in the end, the gap was just too big to overcome, and I had to go in a different direction, which was painful for everyone involved.

As I was weighing my decision, I had no choice but to look in the mirror. My leadership, or lack thereof, got us both into this predicament. I was coaching around the edges instead of getting straight to the point: if performance doesn’t improve, your job is at risk. I hoped more time would fix it, but I was really avoiding the truth because I didn’t want the consequences of that next conversation.

But as we all know, hope is not a strategy, and avoiding an honest conversation almost always makes things worse.

I Was Focused on the Wrong Person

On reflection, I see that I viewed the situation primarily through the lens of the person who was struggling. I thought about how much they cared, how hard they were trying, and how much going in a different direction could affect their life. I imagined how they’d feel and whether they’d think I’d been fair.

But what I wasn’t paying enough attention to was everyone else.

Other people were finding mistakes and being frustrated by them. Some were compensating by taking on work that wasn’t their own. Others wondered why these bigger issues weren’t being addressed. And many of them were quietly, and not so quietly, complaining about it.

And this is the part that many of us well-meaning leaders miss. We’re so focused on giving someone a chance that we don’t see how closely others are watching, how much they are compensating, and how frustrated they are. But by avoiding hard conversations and trying to be fair to the person struggling, you ask everyone else to set aside their frustrations and be patient, which might not be fair to them.

The Cost Doesn’t Disappear

In this situation, my patience benefited the person who was struggling. I was empathetic because I knew their story and understood what they were going through. And it was easy for me to imagine their pain if I decided that their gap was just too much to overcome.

But the impact my patience had on everyone else was harder to see. A mistake was quietly fixed, someone else picked up the dropped ball, another person decided to just deal with it rather than bring up the issue again. Over time, people started adjusting their expectations around what was and wasn’t being addressed.

And this is what I didn’t see – at least not as clearly as I do now. By postponing a difficult decision, I’m not postponing its consequences; I’m just changing who feels the consequences.

That doesn’t mean the answer is always to move faster. Sometimes another chance is absolutely warranted, and I’d rather be the leader who gives direct feedback AND a chance to improve rather than one who cuts and runs too fast. But when I decide to give someone more time, I need to be honest with myself about what I am asking of everyone else.

The reality is that you can always talk yourself into trying one more thing, to have one more conversation, to coach in a different way, or to give it another thirty days (or more). And if you hold yourself to the unattainable goal of trying everything under the sun, you can find yourself looking for a long time.

But at some point, you have to ask yourself whether more time will really change the outcome. And whether you are avoiding the conversation or decision because you don’t want to be the one to decide it’s time to stop. Not easy questions to answer, are they?

Look Beyond the Person in Front of You

I still believe deeply in giving people chances, and I always want to be the leader who sees potential in someone before they’ve seen it in themselves. And I definitely don’t want difficult people decisions to make me less compassionate. But I also want to make sure my compassion extends beyond the person struggling and includes everyone affected.

If you find yourself in a similar situation, I encourage you to look beyond that person and consider what the rest of the team is doing to pick up the slack. Who’s fixing their mistakes? Who’s taking on work that shouldn’t be theirs? Who’s frustrated but has stopped bringing it up? Who’s lowering their expectations because they’ve decided this is just the way things are?

Then ask yourself why you’re still waiting.

Giving someone a fair chance matters, but so does being fair to everyone else. If you decide to give someone more time, make sure you acknowledge who else might bear the brunt of that decision.

Keep the Conversation Going

If this resonates with you, my book, Talk with Trust, goes deeper into how to navigate the hardest conversations, especially when you don’t have the perfect answer, and the truth may be uncomfortable. Buy Talk with Trust here.

I also bring this work directly into organizations through the Talk with Trust Leadership Experience. If you’re interested in bringing it to your leadership team or organization, book a 20-minute call with me, and we can talk about what you’re facing and whether it’s a good fit. And check out more about my speaking engagements here.