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3 Leadership Shifts to End ‘Play Not to Lose’ Culture

Debra Kilsheimer
Posted by Debra Kilsheimer on Jan 6, 2026 8:01:27 AM

My girlfriend calls me and sounds defeated. She says, “I really hate my job.” Now, this is someone who started this position with real enthusiasm. She wanted to contribute, and she actually cares about customers. So, when she said that, I listened.

We keep hearing, “Nobody wants to work anymore.” But what if people do want to work and we build workplaces where the safest move is to ‘Play Not to Lose’? Not because employees get lazy, but because leaders set the rules of the game.

Here’s what happened to her. She gets hired into a role she wants. Trained for three months. She sees a future there, then leadership moves her into a different position with zero explanation.

There’s no growth path and no stretch assignment, just a surprise swap. She wants to leave but her family needs the salary and benefits, so she stays. Then the fog rolls in. Nobody gives her a job description, and nobody defines her title. Nobody agrees on what success looks like, but everyone still expects results.

High performers don’t need micromanagement. They need structure. When you remove the target and keep the pressure, you don’t get brilliance. You get anxiety.

If your best people are quiet, your culture is loud

Her next questions turned into crimes. She asks for clarification on a process and her manager calls her “difficult.” Later, her manager flips the story and accuses her of lying about the conversation. That moment teaches a brutal lesson: “Don’t speak up”. When leaders treat curiosity like insubordination, the team shifts focus from improving the work to self-protection.

Then the scoreboard shows up and leadership tells her, “Spend as much time as needed helping customers.” But the actual rules say: finish in 21 minutes, never make a mistake, be perfect every time while expecting 5-star Google and Yelp reviews. That’s not accountability. That’s contradiction with a timer. Your best people figure out how to survive it, and they stop trying to win.

She found a smart workaround, and she tells customers the truth. She wants to help completely, but she gets measured on speed and satisfaction. So, she asks permission from the customer if it’s okay to take the time to do it right. And the customers say yes because people want correct over fast when it’s their money, their accounts and their problem.

Leadership shuts that down. Transparency forces change and change feels inconvenient. The employee takes the hit, the metrics stay and the whole team learns the real rule, “Keep your head down and Play Not to Lose.

I see this in accounting firms too. We tell the team, “Be thorough”. Then we track every six-minute increment, we act shocked when burnout shows up. You can’t demand perfection and speed at the same time. Physics says no and your staff agrees.

Now to the business case because feelings are real and cash is loud. Gallup says replacing an employee costs about one-half to two times their annual salary. For a $60,000 employee, that’s $30,000 to $120,000. The cost further increases when you consider the loss of innovator and institutional knowledge, a decline in morale and your clients taking their business elsewhere.

Here’s the positive part. This is fixable. You fix it when you build a place where people can play to win. You don’t need “soft culture.” You need a high-trust environment with clear standards, fair feedback and curiosity that counts as competence.

The shifts

Shift 1: Move from ambiguity to clarity

If you want people who can’t wait to show up, you match words to systems. If the role is “strategic advisory work,” don’t reward mindless task volume. Match metrics to mission. Your best people stop guessing what you actually value.

Clarity isn’t bureaucracy. A job description and a visible scorecard show respect because nobody hits a target they can’t see.

Shift 2: Move from control to curiosity

Treat questions like intelligence. The people asking “why” usually try to do the work correctly and protect the client relationship. They answer questions well, document the answers and reward the person who spots the gap. As a result, you get better systems and stronger retention. When you punish questions, you get silence and silence costs money.

Shift 3: Move from ego to ownership

Apologize when you’re wrong. My girlfriend never gets an apology and that absence does more damage than any workload spike. Owning mistakes doesn’t make you weak, it makes the workplace safe for the truth and improvement lives in the truth.

Start simple. Pick one role this week and write what “great” looks like in plain language. Then pick one metric and ask: “Does this reward the behavior I want or the behavior easiest to count?” Can you change it? You can.

In your next team meeting, reset your story out loud. Tell them what you’re changing and why. They know the old you and they need reps with the new you. Ask one question, “What is confusing right now?” Fix one thing quickly and publicly so they see follow-through.

Build firms where people thrive

Are you rewarding safety over excellence? What changes in your firm when your best people stop holding back and start winning? Let’s build firms where people thrive and still hit high standards. Please share in the comments the feelings you want to cultivate within your team this next year.

Topics: Management Advisory, Human Resources


 

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