4 Questions to Help Retain Great Employees

Welcome back to the Mid Market Insider!

Today, I’m diving into the key to retaining your best employees, and how it starts with asking them a few simple questions.

Most leaders only find out why their best people are unhappy after they’ve already quit.

A recent Wall Street Journal article by Ethan Bernstein and Michael Horn hit on something that’s stuck with me over the last couple of weeks:

After studying 1,000+ job changes, they found that throwing money, promotions, and “purpose” at top performers doesn’t keep them around.

But asking better questions does.

Specifically, these four:

Simple questions on the surface.

But most managers never ask them (or they ask too late).

What I appreciate about this isn’t just the retention advice… It’s the mindset underneath it:

• You can’t buy loyalty.

• You build it by treating people like human beings, not headcount.

• And you don’t wait until they’re halfway out the door to do that.

Here’s a not-so-hypothetical situation:

An owner loses a great team member and scrambles to backfill the role. To them, it feels like it’s happening suddenly, as if the damage is happening now.

But in reality, the damage happened long before that, when they stopped listening or assuming things were fine.

What I learned from this article was if you want to keep good people, start asking better questions while they’re still on your team. Don’t just assume everything is all good and fine because they haven’t left yet.

Practical Application

Here’s how I’d apply this inside a $20M–$50M company:

• Make those 4 questions a quarterly rhythm, not just an exit interview tool.

• Don’t ask them all at once. Ask 1 question per quarter, spreading them out to give space and build trust.

• Use what you learn to reshape roles, not just as a retention mechanism.

Retention is usually a leadership issue.

If you’re on the edge of your seat wanting to give this a try, pick one team member this week and ask:

“When was the last time you almost quit?”

See what kind of answer you get.

You can read the full article here

Reader Question of The Week

For context, this is a new section I’ve decided to add. After receiving many questions in my day-to-day as the co-founder of Four Pillars, I wanted to share the most common ones in my newsletter in hopes that it’s valuable to you in some way.

If you have a question you want answered in a future newsletter, please reply directly to this email and I’ll do my best to answer it. Now, onto this week’s question:👇

Q: How do I know if I’m actually ready to sell… or just burnt out?

Well, I’ll start with the honest answer:

It depends. (Not super helpful, I know.) So instead, let me offer a better question:

As the owner, are you more focused on growing… or on not screwing up what you’ve built?

If your mindset has shifted from growing to protecting, then that might be a sign it’s time to think about an exit. You may disagree with me, but I firmly believe in the cliche “If you’re not growing, you’re dying.”

That’s all for today’s newsletter! Thanks for reading!

📅 Next Week:

Next week, I’ll be sharing 5 simple questions to help you spot owner dependence in your business… before it becomes a problem. If you want to scale (or someday step away), this is a great place to start to determine where you stand. You won’t want to miss it!

Keep building,
Nick

P.S. 

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