Dear Lewis, I think my star performer is interviewing elsewhere. Should I just ask?
Many managers sense when a top performer is exploring new opportunities—but should you address it directly? In today's edition, a VP grapples with this dilemma and learns a simple framework for having
Today, I'm revisiting a coaching client from last month. He's a VP of Corporate Development who noticed his star team member suddenly taking mysterious "appointments."
It's not uncommon for managers to sense when someone's interviewing elsewhere. And as always, I'm here to offer some guidance including:
When to trust your gut and just ask the question
How to have that conversation without making it awkward
A framework for addressing what's really happening
Keep building stronger teams,
Lewis C. Lin
One of my clients is Marcus (not his real name). He runs corporate development at a mid-size healthcare company. He's been there for three years and built a reputation for closing strategic partnerships that competitors couldn't.
Marcus comes to me with a problem he can't shake: His top dealmaker, Alicia, is suddenly behaving differently.
"She blocked off three afternoons in two weeks with vague calendar holds. Showed up in interview clothes after a two-hour 'dentist appointment.' Her LinkedIn profile is freshly updated. I'm not an idiot, Lewis."
I ask Marcus what he's done about it.
"Nothing yet. I've been dancing around it. Making comments about our exciting pipeline. Reminding her about the bonus structure. Yesterday I even joked about her 'fancy outfit' being for a hot date."
I stop him right there. This passive approach is just making things weird. It's creating distance exactly when he needs connection.
"Why not just ask her directly?" I suggest.
Marcus looks at me like I've suggested he jump off a cliff. "Isn't that inappropriate? What if she's not interviewing? What if she is but doesn't want to tell me?"
This is where most managers get stuck. They think directness is somehow unprofessional. It's not. It's the opposite.
"Marcus," I tell him, "mature professional relationships can handle direct questions. Dancing around issues is what creates awkwardness."
We develop what I call the ASK approach to this situation:
The ASK Framework for When You Think Someone's Interviewing
A: Acknowledge Your Observation
Start by simply naming what you've noticed, without interpretation:
"I've noticed you've taken several afternoon appointments recently and there seems to be a shift in your schedule pattern."
NOT: "So I guess you're secretly interviewing?"
The key is stating observable facts, not conclusions.
S: Straightforwardly Ask
Then just ask the question directly:
"I'm wondering, are you exploring opportunities elsewhere?"
NOT: "You're not planning to leave us, are you?"
The phrasing matters. It's a neutral question, not an accusation or guilt trip.
K: Keep Space for Honesty
Create room for an honest answer by showing you can handle the truth:
"If you are looking, I'd rather know so we can talk openly about what's driving that. I'd like to understand if there are things we should address."
Marcus was skeptical but agreed to try. The next day, he created privacy, took a deep breath, and followed the framework with Alicia.
Her response surprised him.
"Yes, I've had two interviews," she admitted after a brief pause. "I wasn't sure how to bring it up."
Instead of panicking, Marcus asked what was prompting her search. It wasn't money. It wasn't the work. It was her desire to lead deals independently without having each strategy approved by the CFO – a frustration Marcus shared but hadn't realized was a breaking point for her.
"The conversation completely shifted," Marcus told me later. "Once it was in the open, we could actually problem-solve. I'd been thinking about proposing a restructure that would give her that autonomy. Now I had the motivation to push it through immediately."
Two weeks later, Alicia was heading a new special projects division with direct reporting to the CEO. She canceled her remaining interviews.
"The wild thing is, if I hadn't just asked," Marcus reflected, "she would've been gone before I ever knew there was a problem I could solve."
The ASK framework doesn't guarantee you'll keep everyone. Some people need changes you can't offer. But it does guarantee that you'll have real conversations instead of awkward dances around the truth.
Remember: The most respected leaders aren't the ones who avoid difficult conversations. They're the ones who make difficult conversations feel safe.
Just ASK. Your team will respect you for it.
Simple, right? Well, not always
I'm here to help. Email me if you have any management or employee challenges. I've got your back, and your identity will remain anonymous.
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