The Hardest Leadership Habit to Break (Because It’s What Got You Here)

You got where you are because you did all the things and had all the answers.

Then you became a leader. And your job became empowering other people to do all the things and find all the answers.

Nobody tells you that transition is one of the hardest things you’ll ever do.

You’re sitting with someone. They’re struggling. You can see exactly what they need to do. And a quiet voice in your head starts asking, “How am I even adding value if I don’t give them the answer?”

That voice is your own discomfort with the idea that your job isn’t to fix them, save them, or show them the “right” way. Your job is to create the conditions for their own insight to emerge.

And it’s one of the most common ways well-intentioned leaders quietly undermine the people they want to see grow.

A reader named Katie, Head of Marketing at a global tech company, named it perfectly:

“One idea in particular made me pause and look inward: unconditional positive regard. It forced me to examine how subtle instincts to fix, rescue, or approve can quietly undermine ownership, even when they come from a good place.”

That word “subtle” is doing a lot of work. Because this isn’t about leaders who are dismissive or unkind. Leaders like Katie genuinely care about their people and want to help.

Unconditional positive regard is a concept coined by psychologist Carl Rogers, and it’s the foundation everything else in this newsletter has been building toward.

It means approaching the person in front of you with complete acceptance: trusting that they are capable, whole, and already in possession of their own inner wisdom, regardless of how stuck they seem right now. It means your job isn’t to fix them, save them, or show them the right way. Your job is to create the conditions where their own answers can surface.

This doesn’t mean you agree with every decision they make. It means you trust that they’re doing the best they can with the resources they currently have.

It’s not a technique. It’s a mindset. One that is harder to hold onto than it sounds.

Here’s the tension that makes this so hard: most of us have been rewarded, our entire careers, for having the right answer.

When someone brings us a problem, our brains immediately reference similar situations from our own experience, complete with the judgments and conclusions we drew from them. “If I were in that situation, I would…” is running in the background whether we say it out loud or not. We view their challenge through the lens of our own lived experience and biases. We inadvertently make them feel judged or misunderstood, which puts them on the defensive.

The result: the person shuts down. Their guard stays up. And real insight, ownership, and meaningful action never have a chance to emerge.

Well-intentioned coaching goes sideways not because we don’t care, but because we care in a way that’s really about us. Our need to feel useful. Our discomfort with not having the answer. Our anxiety about whether we’re actually helping.

Unconditional positive regard is the antidote to all of it. When you hold the genuine belief that the person in front of you is resourceful, capable and whole, you stop trying to prove your value by having the answer. You start creating the conditions where their answer can surface.

That shift, from proving your own worth to trusting in theirs, is what effective coaching actually looks like. And it changes the entire energy of a conversation. When someone feels genuinely accepted rather than subtly evaluated, they open up. They think more clearly. They access their own creativity and insight. The answers come from the person living the problem, not the person observing it.

Unconditional positive regard isn’t a grand gesture. It shows up in small moments, in the questions you choose and the ones you don’t. When you catch yourself about to say “Have you thought about…” (which is really a suggestion dressed up as a question), you pause and ask “How are you thinking about this?” or “what’s your gut instinct?” instead. When someone says “I know this sounds silly, but…” you don’t rush past it. Instead, you say “It doesn’t sound silly at all. Say more about that.” When you notice they seem hesitant about something, resist the urge to diagnose the cause and just notice: “What about this is giving you pause?”

Each of those small pivots is an act of trust. They communicate, in real time, that you believe the person in front of you is capable of finding their own answer.

And when the voice in your head asks what value you’re adding if you’re not sharing your own wisdom and experience, you answer it: the point is to be the person who trusts them enough to let them consult their wisdom and experience.

That’s not passive. That’s the whole job.

A quick watch-out for this week: notice when you catch yourself thinking “I would never…” or “they should just…” That’s the moment unconditional positive regard has left the room. Pause. Take a breath. Ask yourself: “What am I making this mean about me?”

When have you caught yourself jumping in with the answer instead of trusting? Tell me in the comments.

Jenn Farrer is an ICF and NeuroLeadership Institute-certified executive coach and the author of Make Them Think: How to Coach for Ownership, Insight and Action. Available on Amazon and Barnes & Noble.


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