Your Most Loyal Employee Might Be Costing You Your Best One

Your Most Loyal Employee Might Be Costing You Your Best One

October 16, 2026•4 min read

The Spreadsheet and the Sticky Note

It’s 7:12 on a Monday morning in October. Your coffee has gone cold, and the year-end review spreadsheet is open on your screen. Row four is Gary. He’s been with you seventeen years. He helped you haul desks out of the garage back when the company was three people and a fax machine.

Row eleven is Dana. She’s three years in and has the best numbers on the team. Stuck to your monitor is a note in her handwriting: “Can we talk Friday?”

You already know what it’s about. Dana has quietly picked up two of Gary’s accounts again, because Gary still won’t use the new system.

You tell yourself Gary has earned some slack. He’s family. You’ll deal with it after Q4.

Peanut Butter Season

It’s budget season, and the timing is a little on the nose. Payscale’s 2026–2027 Salary Budget Survey found that 36% of organizations gave everyone the same across-the-board raise this year. Ruth Thomas, Payscale’s chief compensation strategist, warned that treating everyone the same “can also fail to recognize the people, skills and contributions that are most critical to the business.” Pay isn’t the only thing companies spread like peanut butter. Standards get spread thin too.

The Tax Nobody Voted For

Here’s what’s really going on. Every time Dana covers for Gary, you’re collecting a tax, and it isn’t coming from Gary. It’s coming from her: her evenings, her patience, her belief that effort matters here. High performers don’t file complaints about that tax. They file resignations.

Gary isn’t the villain. He’s just been allowed to stay in 2014, and that’s on you, not him.

Confession time: I’m loyal to a fault. I’m the guy who’d rather redraw the whole org chart than have one uncomfortable conversation with someone who’s been there since the beginning. I used to call that kindness. My best people had a different word for it. Usually several.

The Coach’s Take: Honor the History and Not the Habit

Loyalty is a two-way street. You honor what someone built, and they commit to building what comes next. When only one side keeps the deal, loyalty quietly turns into a subsidy.

In Core Energy terms, avoiding the conversation feels gentle, but it’s catabolic. Resentment builds in your stars, anxiety builds in your long-timers, and everyone learns that the standard bends if you’ve been around long enough. That’s a breakdown in all 3 C’s: Commitment, Communication and Conflict.

Brené Brown puts it plainly in Dare to Lead: “Clear is kind. Unclear is unkind.” Keeping Gary in the dark isn’t servant leadership. Serving him means telling him the truth while he still has time to rise to it. You can respect history without compromising your company’s future.


Your Playbook for This Week

  1. Run a zero-based talent review. For every person on your team, ask one question: if they walked in the front door today, would I hire them for the exact role they’re in? Write down a gut-honest yes, no or not sure.

  2. Separate the person from the role. A “no” doesn’t always mean goodbye. Seventeen years of customer knowledge might belong in a different seat, one where Gary’s strengths actually lead.

  3. Have the adapt-or-sunset conversation. Name the new standard in plain words, offer real support to meet it, and set a date. Thank them out loud for the history. Then let them choose to rise to the standard or to plan a dignified exit with you. My accountability group calls this “care-frontation”: honesty delivered with respect.

  4. Stop taxing your stars. Before Friday, tell Dana what you’re doing about it. Then take the extra accounts off her plate today, not “after Q4.”

Back to Monday Morning

Picture that spreadsheet again. Same rows, same names. This time you book two conversations before your coffee gets cold. The first is with Gary, honest and kind, about where the company is going and how he can come along. The second is with Dana, so Friday turns into a thank-you instead of a two-week notice.

So who are you protecting at the expense of someone you can’t afford to lose?

If you want help raising the standard and getting everyone pulling in one direction, head over and grab your complimentary Core Energy Session today.

And remember,
When focus, purpose, and action align, success follows.

Leadership clarityintentional leadershipleadership communicationteam growthleadership empowermentleadership development
Matthew Hoffman
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