The Retention Problem Is Systemic
I once watched an organization lose its three best people in six weeks. Not to competitors offering more money. Not to burnout exactly. They left because the system they were working in had become intolerable—unclear direction, shifting priorities every quarter, a leadership team that talked about values but operated through fear—and managers who‘d never been taught how to have a real conversation about someone‘s future.
The exit interviews all said the same thing in different words: “I stopped believing this place was going somewhere. And nobody seemed to notice I was drifting.“
That‘s the retention problem most organizations face. The problem isn‘t compensation or perks. It‘s a failure of leadership at the system level.
Why the Standard Playbook Fails
Most retention strategies focus on what I call the hygiene factors—compensation benchmarking, flexible work policies, wellness programs, career ladders. These matter. They‘re table stakes. But they‘re not why people stay.
People stay when three conditions are met simultaneously: they trust their direct manager, they can see a future for themselves, and they believe the work matters.
Remove any one of those three and you have a retention risk. Remove two and you have an active departure in progress, whether the person knows it yet or not.
This pattern holds in every context—from post-conflict institutions trying to retain talent that could earn ten times the salary elsewhere, to Fortune 500 companies hemorrhaging mid-career women. The organizations that retain talent aren‘t the ones with the best benefits. They‘re the ones where people feel seen, stretched, and aligned with something real.
The Manager as Retention System
Your managers are your retention infrastructure.
A person with an exceptional manager will tolerate a lot—organizational ambiguity, imperfect compensation, difficult colleagues. A person with a poor manager will leave even when the salary is generous and the mission is inspiring. Kim Scott‘s Radical Candor framework captures this well: the managers who retain people are the ones who care personally and challenge directly. They don‘t just manage performance—they invest in growth. In my Manager to Leader programs, I teach that at a certain level, leadership is measured not by what you achieve but by who grows under your leadership. The best managers are multipliers—they create conditions for others to thrive.
This means retention strategy is, fundamentally, manager development strategy. Are your managers having real development conversations—not once a year during reviews, but monthly? Do they know what each person on their team wants to build toward? Can they articulate why each person‘s work matters to the larger mission?
I worked with an organization where I asked every middle manager the same question: “What does your best performer want to be doing in two years?“ Fewer than half could answer. The rest said some version of “I assume they‘re happy—they‘re performing well.“
Assumption is the enemy of retention. Performance is not the same as engagement. Your highest performers are often your highest flight risks because they have the most options.
The Stay Conversation
The most underused retention tool is the simplest one: asking people what would make them stay.
Not in an exit interview—when it‘s already over. In a stay conversation. Quarterly. One-on-one. With genuine curiosity, not a corporate template.
The questions that matter: What‘s energizing you right now? What‘s draining you? If you could change one thing about your experience here, what would it be? What would make you want to be here in two years?
When I introduced this practice in organizations I‘ve advised, the consistent feedback from managers was surprise—not at the answers—but at how simple most of the requests were. People didn‘t want radical change. They wanted to be heard. They wanted their development taken seriously. They wanted clarity about direction.
And they wanted someone to notice they were drifting before they‘d already decided to leave.
Building a System, Not Running a Programme
Retention isn‘t an HR initiative. It‘s an operating system.
Strategic clarity drives retention. When people understand where the organization is headed and how their work contributes, they‘re anchored. When direction shifts quarterly, when priorities conflict, when the strategy is a document nobody references—people feel adrift. Clarity is a retention tool. Get clear on three priorities and communicate them relentlessly.
Development pathways drive retention. People don‘t just want jobs. They want trajectories. If someone can‘t see how they grow here—not just upward, but laterally, into new skills, into deeper expertise—they‘ll find growth elsewhere. Build visible pathways. Not just promotion ladders. Learning opportunities, stretch assignments, cross-functional exposure, mentoring relationships.
Psychological safety drives retention. When people can be honest about what‘s not working—without being punished for it—problems get surfaced early. When they can‘t, frustration builds silently until it becomes a resignation letter.
Equity drives retention. People notice who gets opportunities, who gets credit, who gets protected, and who gets overlooked. If the system feels unfair—especially along gender or racial lines—you‘ll lose the people who have the least tolerance for inequity. Which are often the people you most need to keep.
The Diagnostic: Where‘s Your Retention Risk?
Before you build a retention strategy, diagnose where the risk exists.
Ask your managers: Who on your team is a flight risk? How do you know? What are you doing about it?
If they can‘t answer, you have a diagnostic problem, not just a retention problem.
Look at your attrition data with a systems lens. Is turnover concentrated in certain teams? Under certain managers? At certain tenure points? Among certain demographics? The patterns tell you where the system is failing.
Organizations invest heavily in company-wide retention programs when the actual problem was three managers who shouldn‘t have been managing people. Fix the system failure. Don‘t wallpaper over it with programs.
What High-Retention Organizations Actually Do
The organizations that retain talent exceptionally well share common traits. They invest in manager capability—not once, but continuously. They have honest feedback cultures where problems surface before they metastasize. They promote based on demonstrated capacity, not tenure or self-promotion. They take development conversations seriously. And their senior leaders model the behavior they expect—including vulnerability, accountability, and genuine investment in people.
None of this is revolutionary. All of it is rare. Because it requires sustained leadership attention, not a program launch.