The Translation Gap: A Candid Interview with Hillarie Kay

So who's actually showing up in your client roster these days?

People who have already done the work. They've read the books, they've done some therapy, they have some degree of awareness for how they operate. They might even know their Enneagram type. They've worked with coaches, probably some good ones. But there's still something not quite there… A team that doesn't work the way it should, a business that grew beyond their ability to fix everything themselves, but they feel like they're the only one who can. The friction is real and they've kind of run out of explanations for it. They're at the point where they know the answer isn't coming in another book, or course, or systems overhaul. That's where my work starts.

What do you call this thing? What's the umbrella?

I call it heart-centered strategy. Most coaching is head-centered… communication tactics, framework after framework, what to say in the next meeting. And AI can give you that now. AI has a brain. And it thinks it has a body. But it doesn't have a heart, and the heart center and body center can't be achieved or engaged through AI. AI can give you head-centered strategy. What heart-centered strategy does is it sees the nuance.

There's a lot of work like this on the market right now. Where are you finding the gap?

There's a variable in all of it that none of these interventions touch. Some people are like, "Okay, I just need to work on the inside. Understand my patterns, name my fears, learn my Enneagram type." And then there's the complete flip side, where some people believe, "I just need to have better communication, I need to dress better, go to speaking classes." So they're so focused out here that they're forgetting in here. None of these interventions touch it. It's the translation between the two. That's where I work. I call it the translation gap.

I want to sit on that for a second. Is there a more practical name for what happens when somebody actually closes that gap?

I call it actionable empathy. Empathy with a next move attached. So I can know — this is their fear, this is what I did to trigger their fear, so I can adapt, I can modify. I'm not changing who I am. I'm using a tactic. It's not empathy in the eye-roll, everyone-needs-empathy type of way. It's empathy you can actually do something with.

Let's go deeper on the translation gap. What is it, exactly?

It's the variable that nothing else is touching. So you've got people working entirely on the inside — patterns, fears, the Enneagram, therapy, all the internal stuff. And you've got people working entirely on the outside — communication, presentation, how I show up in a meeting, how I dress, all of that. Both are real, and both have value. But there's this variable that either side of these coins, none of these interventions touch. It's the translation between the two. That's the missing piece. And that's where I've spent the last however many years figuring out what's actually going on.

Why doesn't head-only work close the gap? Or external-only, for that matter?

Because head center is only one component. There's a heart center and there's a body center, and the heart center and body center can't be achieved or engaged through AI — or through a framework you read in a book, for that matter. AI has a brain. And it thinks it has a body. But it doesn't have a heart, and that's where most of this work actually has to happen. AI can give you head-centered strategy. What heart-centered strategy does is it sees the nuance.

You've told me there are basically three stages of awareness people walk in with. Walk me through those.

So there's completely unaware — they have no idea what they're doing or why. There's the middle group, the self-aware, who has some self-awareness, knows roughly what they're working with, and is honestly the easiest to coach. And then there's the over-aware, who are so self-aware that it's actually impacting the people around them. Both ends have a translation gap, just for different reasons. The unaware aren't translating because they don't know what they're working with. The over-aware aren't translating because they're so locked into their own analysis that they've lost the read on the people in front of them. That's the gap that I'm able to help people close.

Tell me about a leader you've watched fail to close the gap. What did it cost them?

I'm thinking of a corporate leader who led a very successful team. By the numbers, she was excellent. What she didn't know was that three of her best people had quietly stopped bringing ideas to the table. They'd figured out she already knew where she was going, and the fastest path through the meeting was to let her get there.

One of them resigned. The official reason was a better opportunity. The real reason came out later, through the grapevine — something to the tune of, "She never actually heard me. She'd ask what I thought, and before I finished, she was already on to her answer."

The leader genuinely wanted their input. She cared about her team. But her wiring processes fast and moves with precision, and when that's what you're transmitting, people on the receiving end experience it as a conclusion already reached. She meant invitation. They received finality.

She tried the fixes. Listened more. Slowed down. Practiced the vulnerability thing. Her team noticed the effort, and still felt like they couldn't quite reach her. Her behavioral changes on top of unchanged wiring read as performance. Her team trusted the wiring more than the adjustment.

Four strong performers left in two years. Every departure had a surface explanation. None of them pointed directly at the gap. And that's exactly the problem — the cost is invisible. It doesn't show up as a line item. It shows up as a team that functions fine but never reaches what it could have been.

What about a founder? How does the gap show up for them?

I worked with an entrepreneur who'd built a $2M-plus business. Strong offer, market that wanted what he had. From the outside, it was working.

From the inside, he was doing everything. Every deliverable came back at about 60% of what he'd described, and he'd spend his nights quietly fixing it. He'd hired four different people to fill key roles. Each one seemed capable. Each one eventually stopped taking initiative — because the pattern had trained them: he'll catch it, redo it, and explain what he wanted after the fact. So just do your best and wait.

He started thinking about selling. The business wasn't broken, he was just worn down by a friction he couldn't put his finger on. His logic was: maybe if I start over with something simpler, it won't feel like this.

He'd done his Enneagram. Read the books. Hired an ops manager to find the breakdown. The ops manager found process issues, fixed them. The friction stayed. Because it was never a process problem. It was a translation problem.

His communication moves in the language of vision and intensity. What lands on his team is urgency without a clear path. They hear where he wants to go. They don't receive how to get there.

He was genuinely three months from listing the business when I asked him: "Does this friction follow the business, or does it follow you?"

He already knew. He'd just never had language for what it meant, or what to do about it.

Both of those stories end badly before the work even begins. What changes for somebody when they're able to close the gap?

What changes is you realize you don't have to change who you are. You don't have to get the next self-help book or do the next best course. You have everything you need inside of you — you just have to learn how to operate it. That's the shift. It's not about becoming somebody else. It's about getting fluent in the person you already are, and then being able to translate that to the people around you in a way they can actually receive.

Before you were doing this work with clients, you were doing it on yourself. What did the methodology give you first?

It gave me my why language. I finally had words for why I could be who anyone needed me to be in any room. Why I was wired to read people that fast. Why some of the patterns in my life were patterns and not just one-offs. The Enneagram was the thing that named it, but the work… the actual translation work, the part where you go from understanding yourself to operating yourself… that took years. I couldn't unsee any of it after that. Not in me, and not in anyone I worked with. That's when this stopped being a job and started being the work.

When somebody starts working with you, what's the first thing you're actually doing?

So the first move is internal. I'm mapping how you see the world. What's actually motivating you, what your fears are, where your wiring sends you under stress, what your ego is protecting. The Enneagram is the primary tool for that because it gives us a shared language fast, and it's a map, not a stamp. We're not putting you in a box. We're locating where you're operating from.

Once you've identified the place they're operating from, what's next?

Then we work the other side. I'm using a research-based tool that maps how the world receives you; your communication style, how you come across in a meeting, what people think you're saying when you're saying something. This part isn't about how you feel internally. It's about what's actually landing on the people in front of you. Most people have never had this mirror held up to them with any precision. They have an idea of how they show up. They've never seen the data.

So you've got the inside read and the outside read. What happens when you put them together?

That's the work. That's the translation gap, and that's where everything I do actually happens. Because you can know yourself perfectly and still not be landing the way you think you are. And you can be polished externally and have no idea what's actually driving you. When we put both reads next to each other, the gap shows up immediately. People see it the moment they see it. Oh — that's why my team keeps responding that way. That's why my marriage keeps getting stuck in the same place. That's why I can't get out of my own way. The translation between the two is what I'm combining. That's the whole thing.

What are you actually doing in a session? Walk me through it.

Honestly, I'm diagnosing. It's like going to the doctor. You go in with symptoms, maybe your team isn't bringing ideas, your marriage feels stuck, you're working harder and getting less back… and now you've got someone who can diagnose what's actually causing those symptoms, and then tell you what to do about them. I'm going in and diagnosing the wiring problem. Most of what people are dealing with isn't a behavior problem. It's a wiring problem expressing itself as a behavior problem. Once we name the wiring, the behavior makes sense. And once the behavior makes sense, you can actually do something about it.

What's the thing that becomes possible once somebody actually closes their gap?

You can scan a room. That's the closest way I can put it. You can start to scan your team and say, they're just scared right now, they're acting out of fear. Or, this person is shutting down because they think they've already disappointed me. Or, this person isn't pushing back because they don't have an idea, or they're pushing back because they don't trust the timeline. You start seeing it in real time. Things that used to take you years of knowing somebody, you can see in the first ten minutes. And then you can adjust. That's the superpower. That's what the work is actually building toward.

What are the rules of working with you?

A few non-negotiables. The leader has to be bought in. I tried doing team work twice where a middle manager brought me in and the leader wasn't fully on board, and both times the team turned on the leader. That's not what I'm here to do. So if I'm working with a team, the person at the top has to be in the room and ready to do the work themselves, not just send their people. The other rule, and I say this at the start of every team engagement: you can share as much or as little as you want. But just don't lie. That's the whole thing. We can work with anything that's true. We can't work with anything that isn't.

Tell me about a session where you watched all of this work in real time.

I worked with a VP who ran an innovation lab at a Fortune 100. Smart guy, well-respected, doing real work. His communication assessment came back and his innovation score was second-to-lowest on his team. He was panicked. "How am I supposed to lead an innovation lab if I don't speak the language of innovation?"

So we sat with it. And what I realized — and what he hadn't seen — was that the data wasn't telling him he wasn't innovative. It was telling him he wasn't perceived as innovative in the way the assessment defines it. Those are completely different things. His actual job, the way his wiring actually contributes, is curation. He elevates things to excellence. He's the one who can listen to fifteen ideas from his team, immediately know which three are worth fighting for, and pair the right story to those ideas to get them approved by senior leadership. That's why he's in charge of the lab. Not because he's the loudest innovator in the room, but because he can recognize and shepherd excellence.

Once he had language for that, everything changed. He stopped trying to perform innovation and started leading from the actual strength his wiring gives him.

Section 1 talked about who's showing up in your work right now. Let's get more specific. Who's an ideal client for your coaching?

Founders past the scrappy years. People who've already built something that works on paper and now need to scale themselves to keep up with what they've built. Senior corporate leaders inside Fortune 100 teams who are tired of the surface-level executive coaching that didn't move anything that actually mattered. Operators who've been doing real work on themselves for a while and are at the edge of what self-help and standard coaching can give them. The work doesn't make sense for somebody who isn't already operating at a level where the cost of the engagement is small compared to the cost of the gap. That's not a values thing. I have a heart for everybody. The work needs the right container to work.

And who isn't a fit for the work?

I don't work with vanilla. People who are kind of comfortable where they are and want to stay there. Vanilla isn't a personality type — it's a posture. It's somebody who wants to feel a little better but isn't actually willing to change anything about how they're operating. I also don't work with people who treat coaching like content. They want to feel understood, they want the language, they want to nod along — but when it's time to actually do something with what they learned, they don't. I've watched it enough times to know the pattern. That's not somebody I can help. That's somebody who needs a different kind of support than what I do.

One-and-done workshops. You won't do them. Why?

Because this work isn't a parlor trick. You can't teach somebody to see in a half-day. What I do isn't transferring information — there's plenty of that already, and most of my clients have read all of it. What I do is helping somebody actually develop the muscle to read themselves and the people in front of them in real time. That takes practice. It takes coming back to the work after you've tried it in your actual life and watched what happened. It takes someone telling you, "that thing you just did, that's the wiring talking, not the new pattern." You don't get that in a half-day. So I'm not going to teach you about this and peace out. That's not what this is. If somebody wants the workshop version, there are good people who do that. I'm not one of them.

You've built firm guardrails around your work. What are they protecting?

Depth. Honestly, that's the whole answer. Every no I have is in service of being able to actually go deep with the people I do work with. If I take everybody, I can't be fully present with anybody. If I take the people who don't want to do the work, I'm spending energy trying to motivate somebody who'd rather be motivated than changed — and meanwhile the person three meetings later, who's ready, gets a tired version of me. If I do the half-day workshops, I'm putting language into people's heads without giving them the time to actually integrate it. None of that serves the work, and none of it serves the people I'm meant to serve. The no's aren't about gatekeeping. They're about being able to give what I actually do well to the people who can actually use it.

You're a fourth-generation entrepreneur. Tell me about the family business.

Grocery stores. My grandfather had one, my great-grandfather had one before him, and my dad took over the family store the day I was born. Literally the day. So I came into the world inside a family that was already running something. My hometown — if you were a Hight, it was prestigious. You had good integrity. You were always there to help. You were the one people confided in or came to if they needed something. I have never legally changed my last name, even when I got married, because I'm so proud of that legacy. Kay is my professional name, that's branding. Hight is the name.

What was it like growing up inside a family that was always building something?

Honestly, I was being primed to start my own company. I just didn't know that's what was happening at the time. I couldn't be good at something without one of my parents saying, "oh, let's create a business plan." I can't tell you how many business plans got drawn up on napkins at restaurants, and I wasn't even in high school yet. There was this expectation, never explicitly stated, that we figured things out and we built things and we made things work. I carried that responsibility without having to be asked. It was definitely more implied. This was just what our family did.

Walk me through your early career. What did the path look like before you started your own thing?

I went to school for PR and marketing — originally because I wanted to work in the sports industry. Life had different plans. Out of school I went into an ad agency, then I was director of marketing at a company, and I was on track to keep climbing inside corporate. And then I started my own agency in my early twenties, about two and a half, three years into corporate. I was the youngest person doing what I was doing in the rooms I was in, and I think part of what gave me permission to leave was the napkin business plans. I'd already been building things in my head my whole life. Starting one for real didn't feel like the leap it should have been.

There's a chapter that happened around the time you left corporate. Can you walk me through it?

It was a lot at once. I was 23, I had two kids, I was in the middle of a divorce, and I was just gonna go do the damn thing. My son was born with Down syndrome. I didn't know before he was born. And the first thought I had, and I hate saying this out loud, was that I was so resentful of him. Because I knew the second he was born, there was this feeling, like, he is going to slow down my career. That's the truth.

So I powered through. I kept building. And what I didn't see at the time was that he was teaching me something I would not have learned any other way. Parents of special needs children learn patience in a whole new lens. There is not a timeline. There is nothing quick. I have never been a patient human. I have never been one to play the long game — I like the quick wins.

And the other thing he taught me, which took me longer to be okay with, is that I'm a different kind of special-needs mom. I've had to learn to give myself a lot of grace, and that it's okay that I'm not like other special needs moms. I am not the president of that committee, of the support groups. I don't go to them. It took me a long time to be okay with that. And now I am — my kid's thriving, and I'm also doing well. He taught me that it's okay to do things differently. You don't have to fit a specific mold. That belief is the spine of everything I do now in my work. I just didn't have the language for it yet at 23.

When did the Enneagram come into your life?

It came in fast and hard. I had been a coach for a while at that point, but mostly working with women in the marketing and entrepreneurship space. The Enneagram was something I'd heard about, used a little, didn't fully know. And then I got typed myself, and within a very short time — three months — I'd left corporate America. It gave me my why language. I finally understood why I could be who anyone needed me to be in any room. Why I was wired to read people that fast. Why some of the patterns in my life were patterns and not just one-offs. And once I had that for myself, I couldn't unsee it in anyone else either. That's when the work started becoming what it actually is now.

Three years ago you walked into your first Fortune 100 contract. What did that change?

It changed everything, honestly. Up until that point I'd been working with solopreneurs, women in the entrepreneurship space, people who were good and trying to grow. And I had this assumption that the people at the top of major companies — director-level, VP-level, the actual senior leadership at a Fortune 100 — were going to be so much more evolved. They had to be. They got there. And then I walked in and realized: nope. That is not the case. People are people. They have the same problems, the same fears, the same patterns. It's just at a higher intensity, with more on the line. The people at the top have just learned how to mask their fears better. That changed how I thought about my work entirely. The methodology was the same. The clients I could serve with it just got a lot bigger.

You wrote a book a couple of years ago, The Burnout Recovery System. Where does that fit in the arc?

That book is honestly a snapshot of how I was thinking two years ago. It came out of real work I'd done with real clients on what burnout actually was and how to recover from it. I stand by it. But the world has shifted. Burnout has become such a common word that it almost doesn't mean anything anymore. Everyone's burned out. So when somebody comes to me now with that language, my work isn't to help them recover — it's to figure out what's actually underneath the word. Sometimes it is burnout. Sometimes it's a wiring problem they've been calling burnout because that's the language available. The book is the work of a previous chapter. The work I'm doing now evolved from it.

Where are you now in the work?

I'm doing the work I'm proudest of. That's the most honest way I can put it. I'm Chief of Culture and Strategy at a research-based assessment company, which is where I do a lot of the team and corporate work. And I'm doing my one-on-one and team coaching practice on top of that, which is where the translation gap work lives most clearly. For most of my career, I had a hard time saying I was good at this. I was always reaching for the next thing, the next certification, the next proof. And somewhere in the last couple of years, that stopped. I don't feel cocky saying it anymore. I truly feel like it is my purpose. Like it is why I am on this earth. That's a different relationship to my work than I've ever had before, and I'm finally able to say it without flinching.