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Scale & Strategy

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• The Real Way to Keep Top Talent? Ask These 4 Questions

The Real Way to Keep Top Talent? Ask These 4 Questions

Companies are hemorrhaging talent, and the usual retention tactics – higher pay, shinier titles, and lofty promises of “purpose”- aren’t solving the problem.

The reason? People are switching jobs more than ever. On average, every 3.9 years globally, and even more frequently among younger workers. While surveys list common reasons like pay or status, the real answer is more nuanced.

After studying over 1,000 job moves across 15 years, we’ve found that employees are driven by a web of 30 different push-and-pull forces. These include frustrations with their current role (pushes) and enticing opportunities elsewhere (pulls). Money and benefits may delay a departure, but rarely stop it.

In fact, using perks as a bandage can backfire. When employees feel misunderstood, a bonus might just be ammunition for their next salary negotiation at a different company.

So how can you actually uncover what matters to your people before they walk out the door?

Here’s the key: Stop guessing. Start asking smarter questions, ones that help employees reflect on their true motivations. These four questions, asked thoughtfully during regular check-ins, can give you clarity before it’s too late.

1. When was the last time you almost quit?

A CFO we know asks this during every performance review. After discussing the employee’s performance, she shifts the focus to herself and says,
​“Is there anything I can do to make your job better or easier?”​
Then comes the big one: “When was the last time you seriously thought about leaving?”

The goal isn’t to dig into one dramatic incident. It’s to surface patterns: what consistently frustrates this person, or what outside opportunity might be tempting them.

Skeptical they’ll tell the truth? That’s fair. Unless you create a safe space for candor, they won’t. That’s why this CFO anchors the question in improvement, not blame.

There are two more things that make this work.

Show you’re listening by taking even small actions quickly. And follow up.
​Give people language. We found 14 push forces and 16 pull forces that shape career decisions. Showing these can help employees pinpoint the real reasons they’ve considered leaving without needing to name names or share overly personal stories.

One employee told the CFO she felt disrespected in her current role and had considered a competitor’s offer. Instead of reacting defensively, the CFO asked how she could show more respect. That led to giving the employee ownership over a key, high-profile project. She stayed.

2. When was the last time work didn’t feel like work?

Once people reflect on a negative experience like almost quitting, it becomes easier to shift to the positive. Ask them to name a moment when they felt completely energized or “in flow.”

This isolates the pull factors that keep people engaged.

Let’s say someone says they loved a project because they had real impact. Ask them to define “impact.” Was it about helping clients? Shaping strategy? Getting recognition from peers?

Others might describe enjoying a cross-functional project. Maybe it wasn’t the task, but the feeling of being part of something bigger. That tells you something powerful. This person thrives in team environments and may be drained by isolated work.

Now you know how to shape future projects to keep them engaged.

3. What trade-offs are you making to stay in this role?

No job is perfect. Every employee is balancing priorities, and those priorities evolve.

Asking this question reveals what someone is silently sacrificing. For instance, an employee caring for elderly parents might trade career advancement for flexibility. In a few years, that might flip.

But here’s the issue. Employees often don’t know how to ask for what they need, or they worry about sounding entitled. That’s where you come in.

Let’s say that same caregiver hears about a return-to-office mandate. They might be upset, but they might not say anything until they’ve already lined up another job. If you know the context, a simple solution like two remote days a week might keep them around for years.

Push the wrong lever, though, like offering a promotion that increases their in-office time, and you might accelerate their exit.

4. If this job disappeared tomorrow, what would you do next?

This one might feel awkward. But it’s based on truth. No job lasts forever, and everyone’s passively scanning for what’s next.

The answer reveals aspirations, especially the ones you might not expect.

Most managers assume people want to climb the ladder. But our research shows over 75 percent of job switchers weren’t chasing promotions. They were switching departments, industries, locations, or just looking for more control over their time.

So ask. You might learn that your top engineer has no desire to be a manager, but dreams of becoming an expert in a new technical field. Instead of funding an executive MBA, you might reallocate that time and money toward skills training that actually aligns with what they want.

Why It Matters

Most companies learn why someone left when it’s too late—via an exit interview or secondhand whispers.

But if you have these conversations while people are still on your team, you don’t just gain insight. You gain time. Time to act. Time to adjust. Time to show you care about more than output.

Retention isn’t about perks. It’s about understanding people. When employees feel heard, supported, and seen, they stay and thrive.

Stop guessing. Start asking.

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