There’s a quiet habit among leaders that drains energy and dissolves trust: people pleasing.
It’s a pattern that hides in plain sight, wrapped in kindness, obligation, and the hope of being seen as reliable. It’s a cultural “should.” An automatic yes feels easier than bucking the system, easier than trying to stem the flow of external pressure.
Yet underneath this veneer sits a heavy truth: saying yes out of pressure, fear, or duty has a cost- a cost for both sides.
Time slips, resentment grows, and work suffers.
There is a simple, powerful alternative. Simple and not easy: a pause.
The Pause
A moment of pause is the necessary first step to break the spell of reflex and open space for alternatives. Learning to pause is the single most important thing a leader can do. Without it, the automatic kicks in and opportunity and possibility disappear into what’s always been.
Leadership is about increasing clarity through awareness, not furthering compliance via status quo. That means being able to stop the runaway train that is the conditioned mind, to break the habitual response.
In a recent podcast, Stephanie shared a story about a contractor she’s known for decades. He agreed to fix her roof. He’s known her and her family forever—they have a history. He can’t say no; he doesn’t want to disappoint her. Yet, he doesn’t actually have time to do the job, so he doesn’t show. And he doesn’t show, and he doesn’t show. And suddenly 5 years have passed and the roof is still not done.
It’s not malice; it’s care, it’s family history, it’s not wanting to disappoint. Unfortunately, the result is more than disappointment—five years of delay, mounting damage, and lost trust on one side. Guilt, mounting unease and a degraded relationship exist on the other.
This is the hidden math of people-pleasing. It feels generous in the moment and becomes costly over time.
Any promise we make out of habit, without pausing, has the potential to go down this road. Saying yes to not let someone down, without the time or space to be able to deliver, is trading short-term comfort for a long-term fracture.
Real care speaks the hard truth early.
Real service means knowing your truth and directing others to the right person when the fit is wrong.
To move from theory to practice, the conversation distills four questions that guard your yes.
- First, pause. Delay your answer long enough to check the source of your impulse. Is it love mixed with fear, or genuine alignment?
- Second, ask, Is this mine to do? Capability is not the same as calling.
- Third, project yourself into the future: in three to six months, with current commitments, does this choice feel heavy or light? If it’s light, what must you offload to keep it light?
- Fourth, admit uncertainty. If you’re not sure, propose a trial with a clear time frame and an agreed check-in. Trials surface truth with less risk, and they normalize not knowing—an undervalued skill in a culture that worships instant certainty.
Each question pulls you out of autopilot and into awareness. Together, they replace reflex with discernment and make space for a ‘no’ that serves everyone.
Boundaries aren’t walls; they’re pathways. A clear no can be a generous act, pointing someone toward a better fit. When you decline, offer alternatives if you can: a referral, a resource, a timeline that would work, or a smaller slice you can do well.
This is the hidden math of people-pleasing. It feels generous in the moment and becomes costly over time.
The best time to plant a tree is 20 years ago
There’s a buddhist saying: the best time to plant a tree is 20 years ago, the next best time is today. That’s true for speaking our truth as well – especially in regards to people-pleasing.
We will all have moments of saying yes when it should have been a no. What do we do then?
Like Stephanie and her roofer, our tendency is to ignore the elephant in the room and hope it goes away. And we all know that it doesn’t work.
Our body tells us.
When a yes isn’t rooted in what we’re skilled for, called to, or available for, we know. Our energy rejects it. This can often look like procrastination, anxiety, or sometimes even depression. Our body is saying no even though our mouth said yes.
The body knows the moment something is off, and instantly, the mind explains it away.
- I didn’t sleep well
- I had too much sugar yesterday
- my boss has been at me all week
Those things may all be true, so how do you know what’s eating at you?
Enter the practice of getting to know yourself. Self-inquiry. Not as an inquisition, out of genuine curiosity, out of love, care and concern. This is true self care.
Self-reflection builds the skill of discernment: the second power skill for every leader to develop. This makes the space within to know when something is off and we need to change the narrative – renegotiate, delegate, or decline.
“You wouldn’t worry so much about what others think if you realized how seldom they do.”
~ Eleanor Roosevelt
Setting Up a New Paradigm
Pausing, refusing to get on the runaway train, stopping a train that’s already run away—the road less taken. A different route, an empowered route, a route that takes both awareness AND courage.
Awareness notices: whether noticing the yes that wants to emerge in the moment, or noticing the internal reaction rising after the hasty yes.
Courage resets the stage: it sets clean, timely conversations about expectations that can feel costly in the moment and yet build abundance and trust over time.
Many of us have stayed too long—at jobs, on teams, in romances— for all the “reasons”: the other person is “a good person”, we don’t want to cause pain, we don’t know what to say, we’re expected to, etc.
Yet we know that the pain of a late exit outweighs the uncomfortableness of an early, honest boundary.
Every misaligned yes consumes enormous amounts of resources, inner and outer, for all parties involved. Resources better spent finding the right match.
Investing in practices that build inner awareness is not a luxury, especially for leaders. It’s good business.
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