The High Cost of People-Pleasing Leadership
You have a rockstar on your team.
Someone brilliant, fast, and seemingly irreplaceable.
But lately, you’ve noticed the spark is gone. They’re bored. They’re disengaged.
And as a leader who cares deeply about your people, your internal alarm starts screaming: “I have to do something to keep them.”
In the moment, it feels like leading with empathy.
We look for a shiny object like a new project, a massive challenge, or a pivot in strategy just to capture their interest again.
However, when you make strategic business decisions based solely on the emotional state of a single employee, you aren't leading on purpose. You’re people-pleasing.
Leading on purpose means staying anchored to your mission and your lane, even when it feels like that anchor might cause a talented team member to drift away. If someone is already halfway out the door, throwing a treat at them just delays their departure and leaves you holding a bag you never intended to carry.
When a Yes to Them is a No to You
Dr. Troy and I recently interviewed Wes Towers, founder of the digital agency Uplift 360, for our UH-OH Conversations with Cohesive Leaders podcast. Wes shared a transparent story that perfectly illustrates this trap.
He had a brilliant lead developer who was getting bored with their standard (and profitable) web projects. To keep him engaged, Wes accepted a massive proposal for a complex dating website. This was totally outside their expertise.
But the developer quit just a few weeks later.
Wes was left with a high-stakes project he didn't know how to build, $80,000 in lost opportunity costs, and months of sleepless nights. By trying to save one employee, he accidentally compromised his own peace of mind and the agency's focus.
5 Ways to Support a Disengaged Employee (Without Sacrificing the Mission)
So, how do you help a bored or drifting team member without making a reckless strategic pivot? Here are five things to do instead:
- 1. Conduct a Stay Interview: Before they have an offer in hand, ask them: "What would make you leave?" and "What work here makes you feel most alive?" This identifies if their boredom is a temporary slump or a fundamental misalignment with the company's direction.
- 2. Offer Skill-Based Development, Not Project-Based Pivots: If they are bored, offer them a course, a certification, or a conference in a field that benefits your current niche. This invests in their growth without changing the company's lane.
- 3. Facilitate a Job Crafting Session: Allow them to tweak their current role to include more of what they enjoy and less of what drains them, as long as the core KPIs and business goals remain the priority.
- 4. Address the Disengagement Directly: Sometimes the most on purpose thing you can do is have the hard conversation. "I can see you aren't as excited about our core work lately. Let's talk about why." Acknowledging the elephant in the room is better than throwing money or shiny projects at it.
- 5. Prepare for the Departure: If their heart is no longer in the mission, the kindest thing you can do for the rest of the team is to begin succession planning. Don't let the fear of them leaving dictate your next five business moves.
You don’t have to know everything as a leader, but you do have to be teachable.
Sometimes the hardest lesson is learning when to let go.
Want to hear the full story of Wes’s $80,000 UH-OH? Check out the latest episode of the podcast to hear how he navigated the muscle tear of overextension and came out stronger on the other side.
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