A few days ago I had a conversation with a friend of mine: a high-integrity entrepreneur, someone who genuinely cares about his team and is doing the inner and outer work to build something meaningful.
He was preparing for a conversation with one of his coaches — someone who works for him — to talk about how to keep them engaged, excited, and committed. My friend had the intuitive sense this person wasn’t quite happy and might want to leave the company.
He said he was planning to ask something like: “What’s it going to take for you to really want to be here?”
Which is a solid question! Positive, forward-thinking, nothing wrong with it.
Yet I asked him anyway: “Can we play around with something a little different?”
(This is consent — always ask before offering pushback).
He said yes, and I said: “What would it feel like for you to ask them, ‘What are some of the reasons you want to leave this company?’”
He was silent. Then: “Whoa. I never would’ve thought to ask that.”
Exactly.
Because most leaders — even really good ones — don’t even think of this question. And not because they’re avoiding hard truths (although sometimes, yes), because it doesn’t occur to them.
Asking this question assumes something radical:
- That you’re strong enough to hear the truth.
- That someone’s reasons for leaving are just as valid as their reasons for staying.
- That feedback — even difficult feedback — is welcome here.
It opens a can of worms, yes. And maybe that’s the point.
Don’t Just Shine a Light — Invite the Shadow
When a leader only asks, “What would it take for you to stay?” it forces all the reasons for leaving down into the shadows.
It sends the message — even unintentionally — that the only valid perspective is the one that benefits the company. That if the “brightness” of staying is compelling enough, you’ll ignore the whispers telling you to leave: you’ll tolerate the little things, bottle up the resentment, silence the inner voice that says, “This might not be the right fit.”
However, those whispers never fully go away. They wait and gather weight. And if we don’t ask about them directly… they fester.
This is why inside my company, we ask our team to reflect every six months with a framework we call: Rose, Bud, Thorn, Earth.
Everyone’s invited to share:
- Rose — What’s going well, what they’ve accomplished and want to celebrate.
- Bud — What’s emerging, what’s on their current agenda.
- Thorn — What’s frustrating, what’s painful, what’s not working (with themselves, their team, leadership and even home life).
- Earth — What’s their long-term vision, both personally and with our company.
And we require that everyone share at least one thorn. Because the thorn is where the tiny resentments live: the little frictions and sharp edges we often don’t want to look at or social constructs say we can’t. They’re the truths we’re afraid to speak because we’re not sure how they’ll be received.
However, if we never name the thorn, it grows roots. And if those roots rot… we lose good people, even if they love the work.
“What Are the Reasons You Want to Leave?”
This question doesn’t mean someone should leave, and it doesn’t mean they will leave. In fact, it doesn’t even mean anything is wrong. It simply acknowledges the full spectrum of human experience. It invites transparency, and models trust.
Maybe most importantly? It invites truth to come to the surface before it becomes a crisis.
When you have the courage to ask why someone might want to leave, you may be surprised that the answer reveals something from their personal life they may not have shared unless asked directly. It’s tender, vulnerable. And gives them a chance to share without being judged.
It builds trust.
Because when you genuinely care about someone and you’re not just trying to keep them on, a bond develops naturally. And that bond turns into loyalty. And loyalty turns into more enjoyment at work — and ultimately, more productivity: because they care, too.
So whether you’re leading a team, holding space in a coaching container, or building something you want to last…
Ask the question.
Invite the thorn.
And listen with your whole self.
Because when you create a culture where every part of someone’s experience is welcome — not just the rosy parts — you build a foundation strong enough to hold real growth.
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Marla Mattenson
With a 25+ year career, Mattenson is a trailblazer in transforming sales paradigms from transactional to relational for professionals who prioritize the integrity & fulfillment of their services. She is a champion of consent-based sales.
www.instagram.com/marla.mattenson
