A conversation with Heather Graves Ramsey, executive coach and founder of Coach to Brilliance, on why telling people what to do is the path of least resistance, what it actually takes to pull answers out of someone instead of pushing them in, and the moment a hiss changed everything.
The Hardest Shift in Leadership
Heather Graves Ramsey has spent 20 years coaching leaders and working with teams across industries, and she’ll tell you the most common mistake she sees has nothing to do with strategy or execution but with conversation mode. Specifically, leaders defaulting to the wrong one.
Most leaders, she argues, move through the world as pushers. They have something in mind, they know how they’d handle it, and they communicate accordingly. This is a natural response to a system that promoted them precisely because they were good at solving problems and knowing answers. The trouble is that what got them promoted is exactly what limits them once they’re responsible for other people.
“If everybody would just do what I said, then life would be easy, and you all would be successful,” she told me. “But you aren’t gonna listen to me.” And so the work of becoming a more effective leader, in her view, is largely the work of learning when to stop talking and start asking.
Managing, Mentoring, and Coaching. Three Modes, One Common Mistake
Heather sorts leadership conversations into three types: managing, mentoring, and coaching. Each has its place, and each requires a different posture.
Managing is the most familiar. You have something in mind, you tell the person what to do and how to do it. This is necessary in a crisis, but less useful when you’re trying to develop someone or get genuine buy-in on a change. Mentoring looks like coaching from the outside, but is still fundamentally a pushing conversation. You’re sharing how you’d approach something, modeling the behavior you want to see, laying out a path, and inviting the other person to take it.
Coaching is where most leaders struggle. It’s a pulling conversation, built on the belief that the person in front of you is creative, resourceful, and capable of figuring things out once they’re genuinely engaged. “The monkey that was on my back is now on their back,” Heather said. “And it’s such a beautiful thing, because it is equally exciting for the other person who feels trusted and respected, and also great for the leader because there’s less pressure on them.”
The problem is that pulling takes longer and feels less productive, at least in the moment. You can’t point to what you said or what you solved. The results show up later, sometimes much later, and often without any direct credit flowing back to you. “I never know if what I’m doing is really making a difference for sure,” she admitted. “Because it’s really that person I’m asking that question [to]. They may not have the answer right then, but they’re gonna drive down the road and think, that’s it, that’s what I need to do, and I’m not gonna get credit for it. And I have to be okay with that.”
When Finance Meets Fear
One of the clearest examples Heather offered came from a group she’s working with now: a finance team undergoing a mandatory systems overhaul driven by audit requirements. The leaders have been living with the change for months. The team, some of whom have been doing things the same way for 25 years, found out more recently.
The leaders came in pushing. Here’s the new process, here’s where you need to go, here’s the timeline. Reasonable, except that it wasn’t working. People were digging in, resisting, and no amount of process explanation was moving them. What they actually needed, Heather said, wasn’t more information. It was to feel that they would still matter on the other side of the change. “A pulling conversation helps get the emotional part of that change out of the way. What’s going on for you? What do you need during this time? What’s getting in your way?”
The questions that unlock a stuck conversation are almost never about the logistics of the situation but rather about the person’s experience of it.
The Intuition No One Talks About
One of the more interesting threads in Heather’s coaching philosophy is her emphasis on intuition, specifically, on the value of the question you can’t quite explain but feel compelled to ask anyway.
She described working with a leader who was terrified of presenting to his board. They’d been working on it for months. He talked about how the board judged him, how he dreaded the scrutiny, how the anxiety would build for weeks in advance. And then during one session, something made Heather ask, “Who’s judging who?” She didn’t know exactly where it came from, but the leader stopped, sat with it, and landed somewhere he hadn’t been before: he was judging them. His fear had been about their evaluation of him, but the question flipped the frame entirely. The stress never fully disappeared, but he stopped losing sleep over it for three months before every presentation.
“The best questions are the ones that you just throw out there,” she said. “If you have a relationship with somebody where you’re comfortable enough to say, […] ‘What’s going on over here?’ That is one of the most powerful questions you can [ask].” Getting to that place requires both trust and a willingness to look a little uncertain. Most leaders would rather ask the polished question than the honest one.
The other side of intuition is knowing when something is off in a room and naming it. Heather describes scanning for what’s not being said, the ambient tension, the distracted energy, the conversation running just slightly sideways from where it should be. When she notices it, she asks about it. “It just seemed like you were distracted or frustrated. I just want to make sure I’m giving you what you need.” That kind of reaching out, she said, usually opens something that wouldn’t have opened otherwise.
The Girl Who Hissed
The most memorable story Heather told came from early in her career, when she was working as a counselor in Seattle schools. She’d been assigned to work with an 11-year-old girl who had been through enough counselors to stop trying with new ones. Every session, when Heather tried to ask a question, the girl literally hissed at her. Heather kept coming back, kept trying, and kept getting hissed at.
On the third session, running out of ideas and sweating through the silence, Heather hissed back. The girl stood up, walked over, and they played Uno. And then she talked.
“Sometimes you just gotta do what you gotta do,” Heather said. The lesson wasn’t about hissing. It was about reading the room accurately enough to abandon the plan entirely and meet someone exactly where they are. That willingness to throw out the script when the situation calls for it is, in her view, one of the rarest and most valuable things a leader can develop.
The POWER Model for Preparing for a Difficult Conversation
For leaders with a difficult conversation on their to-do list, Heather walks through a framework she calls the POWER model. She’s careful to frame it as a preparation tool rather than a script to follow.
Start with a P for purpose. What do you actually want to move forward in this conversation? Not the ultimate resolution, but the next honest step. Sometimes the purpose is simply to understand what’s going on for the other person, because you’ve been making up a story that probably isn’t accurate.
The O is for open space, which means safety. Establishing your intention before the hard part begins. “I’m coming to you directly because I think you deserve that rather than me going behind your back.” The way you start the conversation sets the tone for everything that follows.
The W is for what matters, both to you and to them. Heather pays close attention to values here. When two people’s values are running in different directions, and neither person names it, conversations stall in ways that feel mysterious but aren’t. Knowing what’s important to the person you’re talking to, and making sure you’re not inadvertently trampling it, changes how much they can actually hear.
The E is about embodiment, showing up as the version of yourself this conversation requires. Heather asks leaders to consider which adjectives they’d want used to describe them if someone watched a video of the conversation afterward. Calm. Curious. Direct. Warm. That intention, held before you walk in, shapes more than most people realize.
And the R is for relating through listening, specifically the level of listening you’re aiming for. Level one is when you’re filtering everything through your own experience. Level two is when you’re orienting everything toward theirs. Level three is when you’re reading the room itself, noticing the energy, catching what’s not being said. Most leaders live at level one and think they’re at level two.
A Few Questions Worth Keeping
Heather keeps a running list of questions she’s collected over 20 years of coaching, circling two or three before important conversations and keeping them close. A few she returns to most often: What’s working and what’s not? What would success look like? What do you need to move this forward? And her favorite, the one that sounds a little cheeky until you sit with it: How fascinating.
That last one isn’t meant to be said out loud, at least not usually. It’s what she says to herself when someone is behaving in a way that’s hard to understand or frustrating to deal with. How fascinating that they would be doing this. What are they protecting? What’s going on underneath? The question shifts her from judgment to curiosity, which changes how she shows up for the rest of the conversation. “You can get yourself in a different place,” she said. “Powerful questions are important not just for what you say out loud, but for what you think in your head.”
What Happens When Leaders Learn to Ask Instead of Tell
What Heather keeps coming back to is something deceptively simple: most workplace frustration, most stalled change, most relationship friction between leaders and their people, lives in the space of conversations that either didn’t happen or happened in the wrong mode. Leaders pushed when they should have pulled. They told when they should have asked. They filled silence that was actually doing something useful.
Pulling conversations takes more patience than most leaders feel they have. They produce results that are harder to trace back to you. They require sitting with uncertainty and trusting that the person across from you can find their own way forward. But the leaders who develop that capacity, Heather argues, are the ones whose people don’t need them to have all the answers because they’ve learned to find them themselves.
Brandon Laws is the host of Transform Your Workplace and the VP of Marketing and Product at Xenium HR, an outsourced HR and payroll partner for small and mid-sized businesses in Portland, Oregon.