S06 E13: Why Engaged Employees Still Leave - Retention Across a Multi-Generational Workforce

Hello everyone, and welcome to season six of CultureClub X, powered by CultureMonkey. I’m your host, Darcy Mehta. CultureMonkey is an AI-powered employee engagement platform that helps organizations listen to their employees and strengthen workplace cultures. CultureClub X is our global thought leadership forum where CHROs and people leaders share insights, discuss trends, and exchange practical strategies for building future-ready organizations.

Today we are so delighted to host Jeffrey Robinson, Human Capital Advisor at Mentone Avenue LLC, a seasoned HR executive with extensive experience helping organizations strengthen culture, develop talent, and navigate growth and transformation. Jeffrey, welcome. It’s so wonderful to have you with us.

Thank you so much for having me. I’m delighted to be here with you.

Jeffrey is a senior human resources executive and human capital advisor with deep experience helping organizations build strong workplace cultures, develop effective talent strategies, and lead through periods of growth and change. Throughout his career he has worked with organizations across multiple industries, helping leaders align people, culture, and performance to create sustainable business outcomes. Your experience advising organizations on culture, talent, and workforce strategy makes you the perfect person to join us for today’s topic: why is everyone engaged, but nobody staying, and how to rethink retention for a multi-generational workforce. Before we dive in, could you share a little about your own leadership journey?

I appreciate that. I spent my career in HR, working my way through every possible job in the function, building everything from benefits to strategic recruiting initiatives, retention, performance, and all of those kinds of things, all with an eye toward eventually becoming a CHRO.

I’m happy to have had that journey across a multitude of industries and companies. I’ve served five CEOs in one way or another, through their strategic growth stories, from companies that were literally on their last leg to companies that were the leader in their particular industry. That variety of experiences and backgrounds gives me a unique opportunity to provide insights to CHROs, CEOs, and the entire C-suite on what is happening in the workforce and how to deal with it.

You have such a breadth of experience, and it makes it so much more interesting to have that variety with so many different people and organizations. Thank you for sharing that. Let’s dive into our first question.

Engagement is rising in 2026, yet retention remains a persistent weak spot. From your CHRO experience, why does this disconnect exist, and why aren’t organizations connecting these two dots?

I think what happens is that employers conflate engagement and retention. They are two different things, so let’s separate them out. It’s a strategic error to think about engagement and retention as the same thing. People can love their company, love the things that company does, love their coworkers, and have real day-to-day experiences they enjoy. Yet they still leave, for stronger growth, greater flexibility, better rewards, or deeper alignment with personal values. There are things that happen in life where you can’t simply say they left us because of something we did. Sometimes their values changed and something else was calling them.

Engagement measures how I feel today. Hey Darcy, how are you feeling, come take our little survey. Maybe I’m overwhelmed, maybe I’m stressed by what’s happening in the company, or maybe I’m just having a good time, loving my project and delivering. Retention is confidence in the future. Does the employee believe this company has what it takes into the future? Too often companies want to celebrate engagement scores while underinvesting in the broader value proposition: career mobility, manager quality, workload sustainability, and development pathways. They celebrate how you’re feeling today while ignoring that someone has no career mobility, an unsustainable workload, no pathway, and a manager who isn’t working out. This persistent disconnect is what creates the issues in the workplace today. We have to do both. We have to find a balance between retention initiatives and initiatives to understand how people feel today.

I thought that was really interesting, even how you broke it down, that engagement is today and retention is more about tomorrow. And it’s not that people necessarily leave because they’re unhappy. They may enjoy the company, enjoy their coworkers, and have good engagement, but leave for their own reasons or because the growth is not there. That’s very interesting.

To get a little more specific, what does the engagement-retention gap actually look like on the ground, and what early warning signs do leaders consistently miss before people start leaving?

The engagement-retention gap doesn’t announce itself through poor performance. Yes, there are poor performers who may be ill-suited for their job, but that’s not where we’re going to understand the gap. More often it appears in high performers who continue to be productive while quietly disengaging. They start to step away from the future of the organization, and leaders misread those outputs and don’t do what they need to do to sustain commitment.

The early signals are subtle, but you can see them. Reduced participation: the person who was always gung-ho in the meeting takes a step back and sits quietly. Lower interest in development and in taking those stretch jobs. Those high performers who are usually first to step up and say, I want to get involved, I want that stretch, you’ll start to see them step away, and step away from enterprise goals. I always started the year with a performance management process on a calendar basis, introducing the goals for the organization early on. It’s the high performer who steps up and wants to talk about those goals that you want to keep engaging and retain. But by the time dissatisfaction is in your face, they’re already gone. So don’t look for signs of poor performance. A high performer is going to be a high performer, they’ll do whatever they do well, but in the background they are plotting the escape. The signs are subtle, but they’re there if you’re looking for them.

If you see the big ones, it’s probably already too late, like you said. The subtle signs are the ones to watch.

With up to four generations now working together, how does a one-size-fits-all engagement strategy quietly accelerate attrition in a multi-generational workforce?

A one-size-fits-all engagement model accelerates attrition because it ignores a fundamental reality: employees do not experience work from the same life stage, career stage, or set of priorities. Everyone comes to the workplace with a different set of priorities based on where they are. Early career talent wants rapid development, purpose, and mobility. They’ve barely done anything in this job, and they’re already on to the next one. Mid-career professionals want flexibility, project progression, and balance. They want to be able to step away, replenish their health, and do the things that balance the project and the day to day, because if you’re too focused on the day to day, the job becomes less interesting. Late career employees want stability and mentorship. They want to establish a legacy and leave an imprint on the organization.

When you design your organization around a single set of assumptions, there’s relevance for some and friction for others. Not everybody is the same. Attrition rises when employees feel the organization understands the workforce in aggregate, but not in the individual context. You’re not going to individualize every benefit, you have a global benefits strategy, but somebody needs to understand what I need in the context of those generations. I prefer to think about them as early career, mid-career, and late career stages.

That’s a good way to think about it. It seems so obvious that one-size-fits-all wouldn’t work, but it bears being said, and we can see the difference it makes.

How do you build purpose-driven cultures that retain Gen Z without alienating the later career stage, the older generation?

You need a broad vision around purpose. If you define purpose too narrowly, you limit yourself to a small group of people. But when you create a broad, credible mission that employees across generations can connect with in different ways, you can energize the whole organization. Some are energized by visible social impact and value alignment. More experienced employees may derive purpose from customer outcomes, expertise, mentorship, and legacy. So how broadly can you define your purpose to still be impactful while opening the door for everyone to get in? The leadership imperative is not to create a single interpretation of purpose, but to build a culture that has multiple expressions of how purpose can exist. The company that builds that, where we can all see ourselves inside it, will have the most success.

Research shows psychological safety, meaningful work, and flexibility are universal drivers across all generations. So why do most organizations still design engagement strategies around generational labels?

It’s simple. You put a label on it, and that’s the way of the world. Generational labels persist because they’re a simple narrative for a complex workforce. But that simplicity is not the same as accuracy. When you talk to employees across generations, the evidence is clear: they consistently value trust, respect, growth, flexibility, and meaningful work. That’s universal. The strategic lens is not age, but experience. High-performing organizations move beyond generational shorthand and design around career stage, life circumstances, and individual motivation.

As a manager, the workplace is much more complex now. You have to really get into people to understand what’s happening. The shift from broad-based labels to a more segmented approach around career stage leads to more precise decisions and stronger retention outcomes. And career stage isn’t an age thing. Some people are in their mid-careers in their forties, others in their early thirties, and they can have the same level of experience. The objective is a stronger retention outcome, so give yourself the best chance to retain the employee. That’s about understanding where they are in their career, why a certain project fits employee X versus employee Y, and being able to explain it.

So it’s not necessarily based on age, it’s experience. And certain things are universal, but it’s how that manifests in each specific experience group. The organization can grow with employees too, because what worked at one stage will be different later. That’s so interesting.

So what does a generation-smart engagement strategy actually look like in practice?

The key principle is to standardize the values but personalize the experience. As a company, this is who we are and what we’re about. Present that as a package. Then it’s up to me as a manager to show you how your experience and your goals fit inside that organization, and how you’re going to make a contribution. The foundation always remains the universal drivers: psychological safety, flexibility, recognition, and development. Am I getting better, am I learning new things, and am I included, do I feel part of the team?

The differentiation comes in how those drivers are delivered. That may mean offering multiple career paths and varied learning modalities, because how I learn may be different from how you learn. I want to do it with someone, you just want to read the book, so the learning modalities need to be flexible. Flexible work models too: I’m a night owl, you’re an early riser, so accommodate those things. Reverse mentoring matters as well. Sometimes the older worker has wisdom the younger worker could benefit from, and at the same time the early career professional knows things someone later in their career may not. So create those reverse mentoring opportunities. And tailor recognition, so employees get recognized for their roles on cross-functional teams and for contributions to their function and specialty.

The objective is consistency in culture without rigidity in design. In the companies I’ve led, we had some formalities at the umbrella level, but we gave managers the ability to do things in their own teams and cross-functional teams. A product team working with an operations team should have their own forms of recognition and their own reverse mentoring opportunities. Those are the strategies that help you standardize your values and personalize the experience. Company values are the values, but let’s personalize the experience and understand what different people need. Some things you won’t be able to accommodate, and I don’t want to be Pollyannaish about that, but you’ve built a culture without rigidity in its design, so as a leader I can do what I need to get my team moving in the right direction and executing against performance goals.

These are such actionable strategies, thank you. I love that tagline: standardize the values and personalize the experience. That really says it all. And the reverse mentoring is so interesting, because we usually think of it the other way, top down. Thinking of it in reverse is really interesting.

This might be hard, but what is the one non-negotiable action every CHRO should take in the next ninety days to close the engagement-retention gap, and how would you measure success six months later?

There are a lot of things to do in ninety days, and as a CHRO you know it comes and goes quickly. But the one thing you need to do is institutionalize structured stay conversations with high-performing and high-potential employees. Many companies do performance reviews and nine-box succession planning, so if I’m stepping into the role new, those are things I can draw upon, and if I’ve been in the role for some time, I already know who these high-potential, high-performing employees are.

Most organizations rely too much on exit interviews. That’s too late, it’s retrospective by its own definition. Stay conversations are a forward-looking signal. They reveal what’s sustaining commitment. Darcy, why are you still with us, what’s keeping you in the chair, what do you like, and what is still a little bothersome to you? What are you hearing from other employees, and where is friction building, on your team or between your team and another? And what interventions could materially strengthen retention? That’s what you’re asking in a stay interview. You want people to focus internally, not on what’s happening out there on social media, and understand what we can do to strengthen retention before a risk turns into a loss.

Six months later, I assess through leading indicators, not just the lagging sentiment of exit interviews. Internal mobility, manager effectiveness, intent to stay, and participation in development opportunities. And voluntary turnover. I always look at turnover in terms of voluntary and involuntary, and when my voluntary turnover is higher than my involuntary turnover, I know I have a problem. We are not managing our workforce. We need to encourage people to stay while at the same time managing out the poor performer. We look at those indicators within our critical talent segments, and how we’re retaining our people directly reflects how we’ve done in those areas.

That’s amazing, thank you. Catching it before it’s too late, with a forward-looking conversation instead of an exit interview, makes so much sense.

Specifically, how can pulse survey platforms like CultureMonkey help detect retention risk early across a multi-generational workforce?

First of all, I believe highly in survey platforms like CultureMonkey and others. I encourage CHROs to look at the ones they’re using, consider where they might need to get better, and use them strategically to move from this is how we’re feeling to continuous workforce intelligence, which can lead to workforce improvement. When you combine that with stay meetings with your high performers, you’ll understand better where the retention risks lie. They rarely come up all at once. There are patterns in employees’ intent to stay, their manager relationship, workloads, recognition, career growth, and psychological safety.

The strategic value lies in segmentation and predictive insights. Leaders can and should compare experiences across generations, functions, locations, and groups. CultureMonkey and other survey tools give you the ability to identify recurring themes within groups, the threads running through, and the pressure points. A well-used platform allows you to intervene early, look at actions more precisely, and translate employee feedback into a stronger retention strategy before the talent exits.

The key is before it’s too late. Jeffrey, thank you so much. I could keep talking to you all day. Your insights on the relationship between engagement, retention, and workforce expectations have been incredibly valuable. One of the key takeaways is that engagement alone is no longer enough. Organizations need a deeper understanding of what motivates employees across different life stages, career aspirations, and work experiences if they want to retain top talent. Successful retention requires leaders to move beyond assumptions and build cultures that are inclusive, flexible, and responsive to the evolving needs of a multi-generational workforce. That’s where CultureMonkey can help, with pulse surveys and real-time listening that help leaders identify retention risks early, understand employee sentiment across workforce segments, and take action before valuable talent walks out the door. Before we end, how can our listeners connect with you?

Thank you. LinkedIn is my preferred vehicle. I encourage folks to check me out and connect with me on LinkedIn, and let’s begin a conversation about employee retention and how we can rethink retention for a multi-generational workforce. LinkedIn is the place to go.

Sounds good. I’ll connect with you as well. And to all of our listeners, thank you so much for being here. Don’t forget to follow, share, and subscribe. That’s a wrap for this episode of CultureClub X, powered by CultureMonkey. Until next time, I’m your host, Darcy, signing off.