The four conversations to have now.

Off the record: You’ve probably had a hundred conversations with your team. Could you name three things about their life outside of work?

The growth plan you built for them last quarter, is it built on what they actually love? Or just what they’re good at?

This has been coming up a lot lately. Between speaking events and workshops on the road this summer, I keep hearing the same thing from leaders. Leaders from different industries, with different roles and pressures. But the same regret:

“I didn’t know that about them.”

It usually comes out after a resignation. Sometimes after a hard conversation that could have gone differently. Sometimes after a project that quietly went sideways because they were leading the person and not the human.

Here’s what I’ve noticed. There are four conversations every leader is either having with their team, or avoiding.

The Future. What are they aspiring to? Where are they trying to go in the next three years? What role do they want that no one has ever asked them about? Most leaders have this conversation. It’s the safe one and the easiest one to schedule.

(💡 Listen: Learn more about leadership excellence with Garry Ridge, former CEO of WD-40)

The Fatigue. How are they actually doing? Not the “how’s it going?” you throw over your shoulder walking into a meeting. The real question. What’s been wearing them down? What are they carrying that you can’t see? Fewer leaders have this conversation. And it’s the one that makes the difference between someone staying and someone quietly starting to look.

The Family. Who are the people around them? Kids, partner, parents, roommates, dog. The stuff happening at home is showing up at work whether you know about it or not. You don’t need to be nosy. You need to be curious. There’s a difference.

The Fears. What are they worried about right now, about their career, about the company, about themselves? This is the hardest one. It requires trust you’ve built somewhere else first. But when it happens, it changes everything. Because you can’t lead someone through something they haven’t told you they’re scared of.

Most leaders spend all their time on The Future. The other three are what make The Future conversation actually work.

You can’t build a career plan for someone whose actual life you don’t know.

You know their title.
Do you know them?

THE TAKEAWAY

The Moral of the Story

01  GROWTH PLANS ARE NOT CONNECTION
Most leaders think they’ve been having deep conversations with their people. They’ve been having career conversations. That’s not the same thing. Read more on why Storytelling isn’t a Speaking Skill, it’s a Connection Strategy.

02  CURIOSITY IS NOT NOSINESS
You’re not overstepping when you ask someone about their life. You’re overstepping when you don’t ask and pretend that you know.

03  THE HARDEST QUESTIONS BUILD THE STRONGEST TEAMS
The Fatigue and Fear conversations are the ones people are hungry to have. They’re waiting for you to open the door.

04  THREE OUT OF FOUR IS THE BAR
This isn’t a judgment, it’s a diagnostic. Which of these conversations have you had this year? Which have you been avoiding?

DO THIS WEEK

The Cheat Code

Pick one person on your team. In your next 1:1, don’t lead with work.
Ask them:

“What’s something happening in your life right now that brings you joy?”

Then stop. Let them decide how much to share. Some will say something small. Some will say something big. Some will say “nothing much” the first time and something huge the third time.

None of that matters. What matters is that you asked.
Because it’s not the answer that builds the trust.
It’s the question.

Help someone see themselves differently this week.
– Danielle Krischik