“Leadership is the art of disappointing people at a rate they can stand.” – John Ortberg, Harvard.
That’s one of my favorite quotes on leadership because it’s both funny and relevant. I used to think good leadership meant doing what I could to make people happy, and I would try everything to avoid disappointing people. But I’ve learned that great leadership demands courage.
Sometimes that means saying no. Sometimes it means disagreeing with people and making decisions they don’t like. And when people mess up – which we all do – it means giving tough feedback.
I’ve watched many leaders struggle with this balance. They try so hard to be liked that they avoid any decision that might disappoint. They avoid tough conversations because they don’t want to upset people. In doing so, they make driving performance impossible. Don’t feel bad if you do this sometimes; I’ve been there too.
What’s fascinating is that when you do give people feedback and do it skillfully, it increases how much they respect you. I’ve seen it again and again. When people deeply respect their leader, they don’t just tolerate tough decisions and conversations; they’re motivated by them. With that foundation of respect, disappointment actually becomes fuel for growth and a driver of performance.
Navigating High-Stakes Conversations: From Avoidance to Skillful Engagement
Have you ever woken up at 3:00 AM worried about a difficult conversation you have to have the next day at 3:00 PM? And then found yourself ruminating about it the entire next 12 hours? Yup, me too.
When I was first a leader, I tended to come on too strong in tough conversations or react negatively if the other person got defensive or I felt like they weren’t listening, which I would counter with not listening to them by interrupting them. We call this “making a mess.” In our research, 32% of people default to making a mess in a difficult Last 8% situation.
Then I decided that I wasn’t good at having tough conversations and they weren’t worth the trouble, so I started avoiding them. I knew it was wrong to avoid them, so I’d feel regret and shame. I know many of you have been there too because avoiding is the default behavior of the other 68% of people.
The good news is that there is another option: learning insights and strategies to be able to step into difficult conversations skillfully. It’s something every leader and every person I know struggles with at times, including me.
Explore Bill’s Six Strategies to be Effective in Last 8% Conversations here.
Building a High-Performing Last 8% Culture
Some conversations are harder than others—and that’s exactly why they matter. In those moments when tension rises and emotions run high, many leaders pull back. We say most of what needs to be said, but avoid the hardest part.
For the last 3-4 years, our focus has been on what we call The Last 8%. These are the difficult moments we face – tough conversations, challenging decisions, or even uncertainty. It’s the final, emotionally loaded part of a difficult conversation that people tend to avoid. And while it may be uncomfortable, it’s also where trust is built, issues get resolved, and performance improves.
Our work explores how leaders can get better at having these Last 8% Conversations and why they’re foundational to building high-performing teams. We’ve introduced our Last 8% Culture Map, which helps organizations assess their culture based on two dimensions: courage (the willingness to speak up) and connection (the ability to stay caring and emotionally present). A high-performing culture lives in the top right—where people have the courage to be honest and the emotional intelligence to stay connected.
What a Math Guy Knows About Leadership
Whoever thought a guy with a degree in mathematics would be considered a thought leader on culture, leadership, and emotional intelligence? Well, at least my mom thinks so!
As a “math guy,” I always want to know there’s research and/or brain science behind something. As one of my good clients said to me, “Bill, I want to know what you are delivering to us wasn’t made up one night by two guys with a case of beer.” This principle guides our work at The Institute for Health and Human Potential (IHHP).
Leadership isn’t about delivering the perfect message every time. It’s about having the courage to tell the truth and the skill to do it in a way that deepens psychological safety. Even when it’s hard.
If you’re curious about how to build a high-performing Last 8% Culture in your team or organization, let’s talk!
