Employee Retention: Learn To Ask The Right Questions

Almost 10 years ago, I wrote an article about why employee retention is such a challenge. Things haven’t changed much. At the time, I basically said: How can employers ensure that employees will stay? There are a few ways, but they all fall under one large umbrella topic: leadership must focus on the employee experience.

Employee retention is challenging because it sits at the intersection of leadership, culture, purpose, and modern expectations, and most companies underestimate how much all of those have evolved.

Why Is It A Challenge?

Here’s why retention remains a stubborn problem.

• There’s a mismatch between expectations and reality. Today’s workforce wants more than a paycheck; they expect meaning, flexibility, growth, and well-being.
• There’s poor leadership and management. People don’t leave companies; they leave managers. Leadership misalignment and weak people-management skills are persistent, under-addressed issues.
• The culture is weak or misaligned. People don’t leave managers, they leave cultures. When the stated values don’t match day-to-day experiences, trust erodes.
• Career development and growth are lacking or non-existent. Employees want to see a future. If you don’t invest in their development or map clear growth paths, they’ll find it elsewhere.
• Compensation and benefits matter, but they’re not enough. Fair pay is table stakes. But without culture and leadership alignment, no compensation package can buy loyalty for long.
• Employees are burned out and overloaded. Heavy workloads, constant change, and poor boundaries (especially in hybrid/remote settings) are leading to widespread burnout.
• Leaders fail to act on feedback. Companies listen to employees and gather feedback through surveys but rarely close the loop in meaningful ways. “Inaction fatigue” is a silent killer of engagement and trust.
• External competition is truly ruthless. With remote work, talent pools are now global – and so is your competition.
• Employee experience ownership is fragmented (or non-existent). No one truly owns the employee experience end to end. HR is often too focused on recruiting and compliance.
• It’s approached reactively, not proactively. Most companies only think about retention when it becomes a problem. (And, sadly, that applies to both employees and customers.)

What Can You Do?

Well, as I noted 10 years ago, what you can do to address each of these reasons is to focus on the employee experience. Let’s look at a different approach as part of that. Let’s look at the conversations you’re having with – and the feedback you’re getting from – your employees. It’s time to build a listening/feedback culture. It’s time to have better, smarter conversations. It’s time to ask the right questions.

What does that look like? Well, prompted by an article in the Wall Street Journal titled, The Secret to Retaining the Best Employees: Ask Them These Four Questions, I took a look at what various folks are recommending in terms of the questions or types of questions to ask.

Let’s start with that WSJ article. The four questions proposed there are:

1. When was the last time you almost quit?
2. When was the most recent time that work didn’t feel like work?
3. What trade-offs are you making to stay in this role?
4. If this job disappeared tomorrow, what would you choose to do next?

When I asked Google AI, I got these four questions:

1. What excites you about coming to work?
2. What do you find challenging or frustrating about your job or work environment?
3. What would you like to see changed or improved in your role or within the company?
4. What are your career aspirations, and how can we support your growth within the company?

Harvard Business Review offered up these questions on LinkedIn:

1. What’s your frame of mind today?
2. Who do you feel connected to at work?
3. What do you want to learn that will excite you and help you grow?
4. What barriers can I remove for you to help you do your job better?

Justin Wright suggested the following conversation starters:

1. When do you feel most energized or capable?
2. How do you like to receive feedback or input?
3. What kind of communication helps you feel supported?
4. Where do you want freedom, and where do you want guidance?

Seth Godin said these are direct questions worth answering:

1. Do you care enough to do great work?
2. Can we agree on what great work looks like?
3. When the world changes, do we have a process to redefine great work?
4. Do you have the tools you need to reach your goals?
5. How could we create a system where great work is easier to do?

Ten years ago, he proposed 10 other questions to ensure we’re doing work that matters.

Why Is This Important?

Well, imagine if you could save your (best) employees? Wouldn’t you want to have regular conversations to find out what goals they have, what inspires them, what they need to do their jobs well, what keeps them in your employ, etc.?

According to Gallup…

The good news? Employee discontent and voluntary exits are highly preventable, at least from the employee perspective.

An astounding 42% of employees who voluntarily left their organization in the past year report that their manager or organization could have done something to prevent them from leaving their job.

Forty-two percent!

Among those, nearly half said that no one (manager or business leader) had proactively talked with them about job satisfaction, performance, or anything about their future with the business within three months before they left. Among those who did have a conversation within three months of leaving reported that it wasn’t likely that they talked about their future with the business (29%), their job satisfaction (28%), what they need to be effective at their job (18%), or what it would take to stay (17%).

Stay interviews and 1-on-1s with your employees are not over-rated!

Stay Interviews For The Win

Stay interviews are critical to employee retention because they uncover why people stay – and what might cause them to leave – before they walk out the door, while you can still do something about it. Unlike exit interviews, which are too little too late, stay interviews offer real-time insights into engagement, motivation, and potential friction points.

They demonstrate that the organization values employee voices and is willing to act. (Act! You must use the information you are giving!) When done well, they build trust, surface hidden issues, and help leaders proactively address concerns, whether those concerns are workload, career development, team dynamics, or recognition.

In short: stay interviews are an underused, high-impact tool for retention – as long as you listen, act, and follow up.

In Closing

At its core, employee retention is hard because it requires companies to consistently deliver on the promises they make to their people – and most fall short. It demands a deep understanding of what employees value, the discipline to design systems and a culture around those values, and the courage to confront uncomfortable truths about leadership gaps, cultural misalignment, and operational blind spots.

Retention isn’t a perk problem; it’s a leadership, culture, trust, and experience problem. It’s the result of daily decisions, not annual programs. And in a world where employees have more options, louder voices, and higher expectations, companies that treat retention as a passive outcome rather than a deliberate strategy will continue to bleed talent.

Remember this – retention in it’s simplest form: Retention is hard because it’s not a single initiative. It’s the outcome of everything you do. To fix retention, you have to fix culture, leadership, employee understanding, and trust.

A crucial part of the equation around employee recognition and retention is gaining insights into what matters to your team. Employees will tell you what matters to them, so it’s important that we listen and take action. ~ Bryttani Graddick, MidSouth Community Federal Credit Union

Image courtesy of dlxmedia.hu on Unsplash