"That's how we've always done it" is not a strategy.
Imagine a sharp new colleague joins your team. They haven't yet learned how things are "supposed" to work — which sacred cows not to touch, which questions not to ask.
Then they ask one that makes you uncomfortable. What do you do?
Leadership experts Kevin and Jackie Freiberg have spent decades coaching leaders through consequential decisions, ongoing change, and complicated teams. Across more than 50 leaders they worked with in 2026 — from emerging talent to seasoned executives — one theme kept surfacing: *a surprising amount of clarity can come from simply asking better questions.*
Their advice? Don't pick the easiest question to answer. Pick the one that stings a little.
1. Curiosity: What would a new hire ask that I'd find irritating?
The longer you've been somewhere, the harder it becomes to see your organization the way an outsider does. Every workplace develops routines and traditions that eventually become invisible.
You hold the same meetings. Follow the same approval processes. Serve customers the same way.
Eventually, "That's how we do things around here" replaces "Is this still the best way to do it?" A new employee hasn't been trained to accept those assumptions yet.
Think about the questions a new hire might ask you. *What's the purpose of this weekly meeting? Does this really need three approvals? Why must customers do that? What if we tried this instead?*
Now notice which question irritates you the most. Chances are, that's the one worth investigating.
2. Courage: What am I avoiding — and what is it costing me?
Most of us have something we're avoiding. Maybe it's a colleague who isn't performing. A project everyone knows isn't working. A client relationship that's become more trouble than it's worth. Or a difficult conversation you've been promising yourself you'll have tomorrow — and tomorrow has a funny way of becoming next week, next month, and sometimes next year.
The second half of the question is the powerful part: What is your avoidance costing you?
Don't think only about money. What is it costing you in time? Team morale? Lost opportunities? Goodwill? Stress? How much energy are you spending working around a problem instead of dealing with it?
Avoiding a difficult decision doesn't eliminate its cost. It often increases it.
3. Impact: What are people doing, believing, or avoiding because of the way I show up?
As a leader, you have an impact on people every time you walk into a room — and sometimes when you're not in the room at all. If you shoot down new ideas, people eventually stop offering them. If you punish honest mistakes, employees learn to hide them. If you're constantly checking up on people, don't be surprised when they stop taking initiative.
The opposite is true, too. When you listen, people speak up. Give your team room to make decisions, and they'll grow more confident making them. And admitting you don't have all the answers gives everyone else permission to do the same.
Your behavior teaches people how to behave around you.
These three questions are worth asking yourself occasionally. You may not always like the answers — that's the point. Sometimes the question that makes you the most uncomfortable is exactly the one you most need to answer.
So the next time a new hire's question annoys you, don't brush it off. Write it down. That irritation might be pointing you toward your next big improvement.