Episode 23 - How To Fire People Properly - Part 1: When Waiting Too Long Goes Wrong With Dr. Dennis Davis
Most leaders know when someone isn't working out. They've known for months, sometimes years. But instead of acting, they rationalize, delay, and quietly accumulate what Dr. Dennis Davis calls management debt: the compounding cost of performance conversations they didn't have and feedback they softened into meaninglessness. Dennis, a clinical psychologist who works for Ogletree Deakins, a labor and employment law firm, argues that the leaders who struggle most with terminations aren't the ruthless ones. They're the ones who were too nice.
Why do managers avoid performance conversations and what does that avoidance actually cost?
Managers account for 70% of the variance in team-level employee engagement. And yet manager engagement itself fell from 31% in 2022 to 22% in 2025 (the largest single-year category decline Gallup has ever recorded). That means the people most responsible for creating the conditions where others do their best work are increasingly checked out themselves.
Dr. Dennis Davis, clinical psychologist and conflict resolution expert, says organizations are not letting people go enough, or early enough. The problem isn't cruelty – it's the opposite. It's avoidance dressed up as patience, and it's expensive.
“When we have someone in that position, others in the organization don't see that as an open position. So they don't strive toward it. They don't show you what they can do. You're losing out on many other people's potential by keeping someone in a position that doesn't fit.”
– Dr. Dennis Davis, National Director of Client Training, Ogletree Deakins
The executive who's quietly operating at 35% capacity isn't just a productivity problem, they're a ceiling. Every ambitious person on their team is watching that role stay filled and adjusting their own ambitions accordingly. Replacing an executive-level employee can cost between 200 and 213% of their annual salary when you factor in recruitment, onboarding, and lost productivity. The math on keeping the wrong person in a role for an extra 18 months because “35% is better than nothing” simply is not mathing.
The restraining forces are real though. Dennis identifies two of them: ego on the part of the hiring leader (acknowledging someone needs to go means acknowledging the hire was wrong), and fear on the part of the employee (if I admit this isn't working, what comes next?). Neither of these gets better with time. In fact, both get dramatically worse.
How do you give honest performance feedback without making it personal?
Most performance management breaks down not at the termination, but months or years earlier, in all the moments where a manager chose diplomatic fiction over useful truth.
The pattern is almost universal: give the underperformer a raise, write a glowing review, then turn around six months later and tell HR they need to go. HR and legal, quite reasonably, say no. Not because they're blocking the decision, but because the paper trail tells a completely different story. You don't get to say someone's performance is unacceptable in September if you said it was exceptional in March. HR has receipts. HR always has receipts.
Dennis has a reframe for this he calls the myth of niceness.
“Being nice means we have a frank discussion. Giving honest-to-goodness feedback is actually being nice — not faking it like things are going well. That's not being nice. That's being fake.”
– Dr. Dennis Davis
The practical alternative starts before any difficult conversation happens. Dennis advises leaders to stop telling employees what they need to do and start asking what they plan to contribute and how.
When someone designs their own performance commitments (in alignment with what's expected), they own them differently. They can't claim they didn't know the bar. And the manager has a genuinely collaborative document to refer back to, rather than a unilateral decree that breeds resentment.
The skill/will matrix helps here too: skill on one axis (can they do this?), will on the other (do they want to?). Someone who has the skill but not the will isn't a coaching project. They're someone who has quietly outgrown the role and is waiting for someone to give them permission to say so.
People want to know where they stand. They want to be challenged. As far as we know, no one's ever left their boss a positive GlassDoor review for having low standards (let us know if you find one and we will complete a dramatic reading in our next episode recording).
What actually makes a performance improvement plan (PIP) work and why do most of them fail?
A performance improvement plan (PIP) is too often Latin for “we need paperwork to get legal or HR to approve firing someone.” That's not a performance improvement plan, it’s a risk reduction plan. Treating it as the former while operating it as the latter is a failure of organizational integrity that employees can feel immediately.
Approximately 41% of employees placed on a PIP successfully complete it. That means nearly 60% fail. Most of those failures were predictable from the day the PIP was issued, because it was never actually designed to succeed – it was designed to create a paper trail. This check-the-box version exists in almost every organization and in turn most employees believe that a PIP means the decision has already been made.
The genuine version looks different. It starts with a real conversation about agreed-upon expectations, both parties able to say yes to what's on the table. It builds in specific, milestone-gated checkpoints with clear pass/fail criteria, set in advance rather than determined retroactively when the relationship has deteriorated past the point of honest assessment. And critically, it gives the employee the ability to negotiate; to say, “I don't think I can complete this in 60 days,” rather than signing something that's designed to document their exit.
What to do this week:
Identify one person on your team whose performance has been lagging and schedule a deliberate sit-down with them to discuss what you’re seeing, what you need from them, and what you’re committing to do differently as well.
Then flip the dynamic: instead of handing them a performance improvement plan, ask them to draft their own. What do they see as the gap? What do they plan to do about it, and by when? That kind of agency is usually what's missing, and it separates a genuine development conversation from a paper trail masquerading as one.
And if the honest answer is that you already know this person needs to go? Start there. The conversation you've been avoiding is almost certainly the kindest thing you can do for everyone involved, including them.
Tune in next week for part two, where Dennis returns alongside labor and employment attorney James Bryton to cover the mechanics of actually letting someone go with dignity.
Related Episodes
– Conflict at Work: Amy Gallo on How to Have the Hard Conversation You've Been Avoiding
– Managing Yourself First: Margaret Andrews on Self-Awareness and Leadership
– Toxic Leadership Explained: What Makes a Bad Boss with Mita Mallick
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