What Kind of Leader Will You Be During The Tough Times? — by Dan Lynn
By Dan Lynn
I had a great boss at AT&T named Mary Upchurch. I learned a lot from her — lessons I've carried through my whole career.
During one of our downsizings, I had to let someone go. It was one of the hardest things I'd had to do as a young leader. Mary gave me a piece of advice I've never forgotten.
She said: "As a leader, you will always be remembered for how you are during the tough times."
I think about that lesson from her often. She didn't say "during the good times". Anyone can lead when the numbers are up, the team is winning, and everyone's happy. That's easy. Real leadership shows up in the hard moments — the layoff, the failure, the crisis, the day you have to look someone in the eye and deliver news that changes their life.
That's when people are watching most closely. The person across the table from you will remember how you treated them for the rest of their life. And so will everyone else on the team — because they're all quietly asking themselves the same question: if it were me, how would I be treated?
I've thought about Mary's words in every difficult moment of my career, and I've passed them on to more leaders and mentees than I can count. Because she was right. You are not defined by how you show up when it's easy. You're defined — and remembered — by who you are when it's hard.
So ask yourself, before the tough time comes — because it will: who are you going to be?
Questions this Key Learning answers
How do I handle laying someone off with dignity?
The author’s lesson is to treat the conversation as a moment the person will remember for life, not simply a task to complete. Our analysis emphasizes being candid, present, and humane. How a leader delivers life-changing news reveals whether people remain worthy of honesty and respect even when the organization no longer needs them.
Why does my team watch how I deliver bad news?
The author explains that colleagues are quietly asking how they would be treated in the same situation. Our analysis calls them the silent audience: they watch consequential conversations to understand the organization’s unwritten rules. A leader’s conduct in that moment communicates more about dignity, respect, and responsibility than any formal statement of values.
How can I prepare to lead well during a crisis?
The author suggests deciding who to be before the tough moment arrives. Pressure leaves little room to invent character, as our analysis notes. The central preparation is recognizing that leadership will be defined and remembered most clearly during layoffs, failures, and crises—when being candid, present, humane, and respectful matters most.