Two Questions That Predict Retention

Kristine Goebel
Feb 2
3 min read

When was the last time you asked, and do you know what the response means?

The Two Questions You Should Know the Answer to:

What would make you want to stay?
What would make you want to leave?

These questions do something that exit interviews never can. They reveal what people value now, not what they tolerated until they couldn’t anymore. Most importantly, they give leaders insight they can actually act on.

You might think you already know the answers. Most leaders do. Proceed with caution if you haven’t asked these questions; assumptions don’t predict retention.

Most leaders ask some version of these questions informally. Not many leaders know what to listen for when the answers come. Retention happens when you know what patterns to listen for and how to respond.

“What Would Make You Want to Stay?”

This question reveals what currently fuels engagement. Listen beyond the words.

Listen for these 3 things:

Energy vs. obligation: Are they describing what excites them or what feels expected? Passion signals commitment. Neutral language often signals compliance.
Specifics vs. generalities: Vague answers like “the people” or “the culture” may mean they haven’t reflected deeply or don’t feel safe being honest yet.
Future orientation: Do they talk about growth, contribution, and impact ahead? Or do they speak only in present tense?

👉 What it means: When people can articulate why they’d stay, they’re showing you what to protect and strengthen.

“What Would Make You Want to Leave?”

This question surfaces risk factors before they become exits. It requires trust and emotional safety.

Listen for these 3 things:

Conditions vs. complaints: Statements like “If this continues…” signal thresholds. These are early warnings, not negativity.
Control vs. helplessness: Are they describing fixable issues or resignation? Helpless language often precedes disengagement.
Silence or deflection: A quick “Nothing” can be more concerning than a hard truth. Silence often means they don’t believe change is possible.

👉 What it means: People rarely leave suddenly. They leave after deciding it’s no longer worth raising concerns.

How Often to Ask These Questions

Quarterly: for formal check-ins or stay interviews
Monthly: for leaders with direct reports in transition or high-impact roles
Immediately: after role or schedule changes, leadership shifts, or major organizational changes

*Consistency matters more than perfection. One conversation won’t predict retention. Patterns over time will.*

PSA: If you have a workplace that is experiencing constant change, you must stay on top of these questions and responses.

What to do with the information:

Look for themes, not promises: You don’t need to fix everything. You do need to notice trends. Pay attention.
Close the gap: Even small follow-ups build trust. Silence will erode it.
Share responsibly: Share insights with senior leaders without sharing names, quotes, or individual stories. Protect individual voices.

When leaders act on what they hear, these questions stop being diagnostic and start becoming developmental.

Retention isn’t a mystery. The answers are already in the room. Act before it’s too late.

We are thrilled to announce that our Digital Marketing Intern, Maddie, has accepted a position here on our team. Click to read about her internship here!

Book a workshop or program today!

🤝 Retention Interactive Workshop:

(2 hrs) Our Retention workshop is designed to strengthen the current workplace retention program or be the launch of a new one!

🤝 Developing a Purposeful Hiring to Termination Process Program:

(4 Sessions) This interactive program guides you through the full employee lifecycle—from hiring and onboarding to retention and termination/succession—using a values-aligned, people-first approach.