The Most Expensive Mistake in Leadership: Delaying Hard Conversations
Wednesday, June 18, 2025 - Joe Kiedinger
Leader, beware! I’m speaking from experience here. I’ve learned the hard way how much it costs to avoid difficult conversations. I’m naturally a soft-natured person, and for years, I let my discomfort with confrontation shape how I managed my team. The result? Expensive lessons that I could have avoided had I simply been upfront when things weren’t right. If you’re a leader, here’s what you need to know about the costly consequences of delaying those tough talks.
Lesson #1: It’s going to happen anyway.
When your business starts changing, your projections become reality—whether you want them to or not. I learned this the hard way when my company transitioned from marketing to a SaaS and Leadership Development model. I had a fantastic team of marketers who were also great people, and I thought I could fit them all into the new model somehow. I kept convincing myself that we could make it work, that they would find their place. I was wrong. Instead of letting go early, I held on too long, burning through cash flow until I had no choice but to let them go. The reality? The new model didn’t need all their positions, and it cost me. When a shift happens, it’s crucial to act on the reality of the situation quickly. Delaying the conversation only makes things worse.
Lesson #2: Fear of confrontation and candor.
It’s easy to be afraid of the discomfort that comes with challenging conversations. I’ve seen employees go off the rails, undermining the work of others, simply because of personal issues they were dealing with at the time. I should have addressed the slipping performance immediately, but instead, I kept thinking, “Maybe it’ll get better if I wait.” Spoiler alert: it doesn’t. When an employee forgets their end of the contract, it’s time to address it. When they’re no longer delivering, the relationship needs to be redefined. Putting off that conversation doesn’t make it go away—it just prolongs the inevitable and costs your business time and money.
Lesson #3: This is a community, not a family.
One of the most painful lessons I had to learn was that business relationships are more like a community than a family. You don’t get to choose your family, but in a business, both sides have a say. I once thought my business was a big family, and I wanted to hold on to people even when they weren’t the right fit. But businesses have rules and expectations, just like a community. If you don’t uphold those rules, there are consequences. Whether it’s performance, behavior, or alignment with company goals, your team needs to understand that their contract is based on mutual benefit. If they’re not contributing, it’s time to part ways. That honesty is what keeps the organization strong, not false loyalty or sentimentality.
As a leader, you’re signing up for tough conversations. There’s no getting around it. You need to face the storm head-on, just like a buffalo does. Avoiding the tough talk may feel kinder in the moment, but it’s actually far more compassionate to be direct and set clear expectations. Not only will it lower stress and tension within your team, but it’ll save you time, money, and the heartbreak of unnecessary consequences. The sooner you address the issue, the better it will be for everyone involved. So, take it from me—don’t wait. Have the hard conversations, and do it quickly.
JOE KIEDINGER