There’s No Such Thing as a Difficult Person

How to work with people who drive you a little crazy (OR, how to drive people less crazy)

Jess Skylar with Rayne Martin


Long Story Short

“Difficult” is almost always an unmanaged strength. Once you learn to work with the strength — theirs or your own — pretty amazing things become possible. We built you a free Working With Difficult People Toolkit to do exactly that.


I’m one of These Difficult People. AND I’ve been Driven a Little Crazy by Them Too.

Jess here!

I’ve got a LOT of empathy — seeing things through other people’s eyes comes pretty naturally (people-pleasing is basically in my body… or maybe that’s just what happens when you grow up a middle-class white girl in the 90s). AND I can get really bullish — lost in a thing, sure I’m right.

Back in my Revolution Foods days, I was responsible for driving revenue and frequently butted heads with our ops team (classic story!). One day I was venting about one particular human I found “difficult” to Pat Donovan, my beloved boss and mentor, who has more grace and patience than anyone I’ve ever met. We were both driving around in different states, between a school meeting and a tasting, when he stopped me mid-sentence (which he’d never done before) and said, bluntly: I don’t have time for this.

I was probably some combination of shocked, defensive, and angry. But it came from someone I trusted implicitly — so I let it in.

Looking back, it was exactly the turning point I needed. Was that person difficult? Yes. Could they have said the same thing about me? Also yes! AND it was not my job to catalog everything they were doing wrong. If I was going to keep working at Rev Foods, it was my job to work with them and get more healthy food to more kids.

I stayed at Rev Foods, and not only did I stop thinking of that person as difficult, they became someone I genuinely admired. Someone who was GREAT at their job and helped build the company build in ways we couldn’t have without them.

Here’s how I think about it now: the word “difficult” carries way too much baggage. We all have strengths, and strengths are neutral — neither good nor bad. When we figure out how to work with someone based on who THEY are and who WE are, pretty amazing things become possible. We ALL share that responsibility — including the “difficult” person. And we all get to decide when it’s working, or when it’s just not worth the energy.


Meet Rayne (who’ll happily tell you she’s difficult)

Rayne Martin self-identifies as a difficult person. She’s an executive coach who’s spent her career in the rooms where strong personalities and big stakes collide. At 26, with no department and no staff, she built the Chicago Housing Authority’s relocation operation from a team of 6 into a 50-person department running a half-billion-dollar budget. In the process, she turned one of her fiercest early critics into a genuine partner by showing up, over and over, even when showing up required three buses and a subway ride. 

Twelve years ago she turned all of that into a coaching practice called It’s the Impact, for exactly the high-stakes, strong-personality leaders most people find hard to work with.

My favorite thing she said? “I’m unbossible.” She used to joke to her bosses that they were “nothing more than a paycheck,” not as an insult, but because she was always there for a reason bigger than the job. That’s a difficult employee! (And an effective one!) Rayne has built an entire practice out of understanding why people like her get that label — and what to actually do about it.

By the end of our conversation, I knew two things: I wanted to bottle whatever she does and hand it to every leader I know, AND I wanted to work with her myself.


The Key Takeaway

Rayne’s reframe on difficult people kind of blew my mind: there’s no such thing as a difficult person — just a person with an unmanaged strength they need help aiming.

The whole point is that “difficult” isn’t an insult. It’s usually a strength nobody’s learned to work with yet.


Rayne’s Process for working with a Difficult Person

First things first: figure out where you are in the equation to know which moves to try. Almost everyone reading this falls into one of these categories:

  • You ARE the “difficult” one. (Welcome. Me too.) You’ve got the vision and the drive, and you’ve started to notice the effect you have on a room. → Moves 1, 4, 5.
  • You manage someone “difficult.” Talented — maybe your strongest person — AND every interaction takes something out of you. → Moves 1, 2, 3, 5.
  • You work alongside someone “difficult.” A peer whose intensity you’re constantly absorbing or working around. → Moves 1, 2, 3, 5.
  • Your boss is “difficult.” You spend real energy managing up, decoding, and bracing. → Moves 1, 2, 3 (the managing-up version), 5.

Once you know where you stand, test out Rayne’s moves that apply. Here’s a very abbreviated version for the “Just give me the template!” type of people (aka Libby, Helia’s COO):

  1. Everyone, start here: Reframe — strengths are neutral, not good or bad.
  2. Working WITH one: Get out of your own head — separate the thought (they don’t respect me) from the fact (they were late three times).
  3. Working WITH one: Name the behavior, not the story — Notice → Impact → Suggest.
  4. If you ARE the one: Own your strengths AND your wake — aim the strength instead of muting it, and build the skill to see how you land.
  5. Everyone, end here: Keep the main thing the main thing.

If you’re a “tell me WHY this works” person (aka our Founder Jess), read on.


Move 1 — Reframe: strengths are neutral, not good or bad

When Rayne looks at a “difficult” person, she doesn’t see a personality problem. She sees a profile, and a consistent one: people who see what’s possible when others can’t. People who aren’t stopped by the barriers that stop everyone else. People who have confidence and who can communicate. 

Every single one of those is a strength. They land as “difficult” because the very traits that make someone a visionary make them intimidating to be on the other side of.

Here’s a reframe that helps lower the temperature: strengths are neutral. There’s no good or bad version of “sees what’s possible and won’t be told no,” it just is what it is. Like any strength, it can be harnessed or it can run unmanaged.

There’s data that supports and makes sense of this, not just vibes from years of coaching conversations. Rayne has the trait of Command in her own top five strengths — a strength that lands in the top five for only about 2% of women (and roughly 5% of men). It lives in Clifton Strengths’ “influencing” domain, which is the domain that shows up LEAST often in leaders, period. So when someone reads as intimidating, it’s often because they’re carrying genuinely rare wiring. The people we call difficult aren’t broken. They’re rare — which is a very different thing.

So if it’s not a character flaw, what IS the gap? Usually one specific skill: the ability to see something through someone else’s eyes. The visionary who steamrolls a meeting often genuinely can’t feel what the room is feeling — and that’s a skill gap, not a character flaw. So Rayne treats “difficult” as a skill, knowledge, or will gap — something that can be named and worked on — instead of a verdict on who someone is. Not “this person is an asshole,” but “this person hasn’t built that muscle yet.”

That shift sounds small. It is not. The second you stop asking “why are they LIKE this?” and start asking “which strength is running unmanaged, and which skill is missing?” — you’ve got something you can actually work with. For them, or for yourself.

Which strength is running unmanaged?


Move 2 — Get out of your own head: thought or fact?

Most of the exhaustion of dealing with a “difficult” person doesn’t come from them. It comes from the story we’re telling ourselves about them.

Rayne is wonderfully blunt about this. When thoughts like they don’t respect me, they’re trying to undermine me  are running over and over in your head, you are, in her words, wasting your intellectual firepower. Our thoughts are finite, and you’ll never actually know someone’s intent (they often don’t know it themselves). So assigning it with total certainty is as unhelpful as it is tiring.

So the first move is a question to ask yourself: Thought or Fact? “They were late to our last three meetings” is a fact. “They don’t value my time” is a thought you created. The behavior might be real, but the intent you’ve assigned is a story, and the story is what’s eating you alive.

Rayne developed her Thought or Fact exercise before she ever took on a coaching client. Rayne has OCD, and deals with intrusive thinking she describes as “waterboarding for the brain.” So, she had to get genuinely good at interrupting her own thought spirals. Out of that came this tool she now uses with leaders. Once you’ve recognized that the thing gnawing at you is a thought, not a fact, you run it through four questions:

  1. Is this thought helpful to my mental and physical well-being?
  2. Does it take into account all the positive alternatives — or just the worst case?
  3. Would I tell a friend to think this way?
  4. Is it helping me move forward?

Here’s Rayne’s favorite part: it’s a trick. The answer to all four is always no. That’s the point. The power isn’t in the answers, it’s in the asking, which cracks the window just enough to set the thought aside for a moment and look at the actual behavior in front of you. This matters because if you walk into a conversation still telling yourself they don’t respect me, that’s the conversation you’ll have, no matter what words come out of your mouth.


Move 3 — Name the behavior, not the story: Notice / Impact / Suggest

Now you actually have to say something — and this is where most of us fumble, because we still lead with the story we just worked so hard to set aside. You don’t respect my time. You’re being dismissive. You steamrolled that meeting. Every one of those is an interpretation, and the second a “difficult” person hears it, you’re not talking about the work anymore — you’re in a fight about character.

Rayne’s move is a clean four-part structure that keeps the conversation on the behavior and off the character verdict:

  • Notice — name what you observed, like a camera would. “In our last two meetings, you cut me off before I finished my point.” No adjectives, no intent.
  • Impact — say what it did. “When that happens, I lose my train of thought, and I leave unsure if my piece was heard.” Your experience, not their motive.
  • Suggest — offer a path. “Could we try letting each person finish before we jump in?” A request, not a referendum.
  • Question — hand it back. “How does that sit with you?” This is the move that turns this into a true conversation.

What makes this work — especially with someone “difficult” — is that there’s nothing to argue with. You can debate “you’re dismissive” all day. You can’t really debate “you cut me off twice.” And because you’ve stripped out the intent, they don’t have to get defensive to protect themselves. (Remember the skill they’re often missing — seeing through someone else’s eyes? Notice/Impact/Suggest gently hands them that view.)

Two things Rayne would want you to know. 

  • It usually feels stiff the first few times — do it anyway. She makes leaders role-play it three or four times out loud before the real thing. Yes, everyone hates a role-play, AND it works. 
  • You can adapt this to whoever’s across from you.

Managing UP at a “difficult” boss? Same three parts, softer suggest: “The plan shifted twice this week. The impact is I’m not sure which version to build against. Could we lock it in before I start?” You’re not managing their personality — you’re naming a behavior and its cost to the work, which almost any boss can hear.

A peer, no authority in the room? Same structure, and it works because it never pulls rank: “When the deck changed the night before, I had to redo my section at 11pm. Could we lock shared docs 48 hours out?”


Move 4 — If you ARE the difficult one: own your strengths AND your wake

If you read that profile in Move 1 and felt a little seen — the vision, the drive, the effect you have on a room — this part’s for you.

The trap most “difficult” people fall into once they realize they’re landing as difficult: they try to shrink. Talk less. Push less. Soften every edge until they’re a smaller, more palatable version of themselves. It almost never works — partly because it’s miserable, and partly because the sector NEEDS what you do at full power. The vision and the refusal to accept “that’s just how it is” aren’t the problem. They’re the point. A leader is literally paid to be out front with a point of view. Having one isn’t the bug. Not knowing how to bring people with you is.

Rayne’s the proof. She’s not interested in becoming less command-y, less direct, less her. What she’s built instead is the ability to aim the strength rather than fire it indiscriminately, and that’s the difference between a strength harnessed and one running unmanaged. The work isn’t to have less of your strength. It’s to know it well enough to drive it.

Rayne developed a simple tool to help folks harness these strengths: The RID Process.

  • Reflect: Briefly describe an upcoming project, meeting, or relationship that is important to your goals and legacy — and may be challenging.
  • Identify: Which strength could show up and, if unmanaged, hinder your success? Name the strength and how it could get in the way.
  • Decide: Choose one specific action you will take to manage the potential negative side of this strength so it supports — rather than undermines — your goals. Describe how this action keeps you aligned with your desired outcome.

Here’s how this could look in real life:

  • Reflect: I am preparing for a high-stakes presentation to a board of directors, where success will set the stage for a large-scale project approval.
  • Identify: My Achiever strength could push me to work tirelessly to complete every detail — overloading the presentation with unnecessary detail, skipping delegation, and losing sight of the bigger picture.
  • Decide: I will set a clear boundary on preparation time and prioritize three key points that align directly with the board’s interests. I will assign supporting tasks to team members and trust their contributions.

And, when you’re in the moment and the RID-process doesn’t apply, she has a couple almost-embarrassingly simple tactics for the big personalities who tend to take up all the oxygen in the room:

  • The pre-speak gut check. Before you jump in, ask yourself: Is what I’m about to say of value — at this moment, with these people? If not, hold it. (Yes, sometimes the move is just to not talk.)
  • Doodle. Genuinely. Giving your hand something to do is one of the simplest ways a dominant voice makes room for everyone else’s.

But you can’t aim what you can’t see — and you genuinely can’t see your own wake. So the other half of this move is building the one missing skill: seeing how you come off through others’ eyes.

You know what you meant. What you can’t see from the inside is how it landed. So ask. “How did that meeting feel from where you sat?” Then don’t defend. Just take it in. 

Here’s the catch this type of person always runs into: you’ll swear you ask for feedback. You tell people you want it. And it doesn’t come — because roughly 9 in 10 people are uncomfortable challenging their boss, and the very confidence that makes you effective also makes you hard to push back on. (People with this wiring often don’t even feel the power dynamic, which is exactly why they underestimate it.)

So you can’t wait for honest feedback to arrive. You have to lower the bridge, on purpose, over and over: be transparent about what you’re working on, ask people to affirm it when they DO see you doing the new thing — not only flag when you don’t — and thank them specifically when they push back. 


Move 5 — Keep the main thing the main thing

Remember Pat’s words: I don’t have time for this. That worked on me not because it dismissed the difficulty, but because it pointed at something more important — the work. We were driving food to schools so kids could eat. THAT was the main thing. My frustration with one colleague was real, AND it was not the main thing.

When Rayne talks about keeping the main thing the main thing, she doesn’t mean a tagline either. She means a person — a girl she started kindergarten with in a Louisiana town of 200, someone who took 40 years to finish her college degree. THAT’s the main thing. The reason she’s in the room at all. It’s the same engine under all her work: as she tells her own clients, some of whom she’s coached for YEARS — I love you AND I’m a big cheerleader for you, and the reason I do this is because I expect you to go do something with the privilege of the seat you’re in. The more supported and brave a leader gets, the more they spend that privilege on the people who don’t have it.

This is the move that keeps all the others honest. None of this is about being conflict-free for its own sake — it’s in service of the mission. So you get to keep asking two questions, on purpose:

  • What’s the main thing here? When you zoom out to why you’re actually in this work — the kids, the community, the mission — a startling amount of the friction gets smaller. Not gone. Smaller. Worth less of your energy. (It’s also just freeing.)
  • Is this working — for the mission AND for me? Because keeping the main thing the main thing is NOT a mandate to tolerate anything forever. Sometimes the honest answer is that the dynamic isn’t worth what it’s costing, and the most main-thing move you can make is to change the role, change the team, or walk. (Rayne names this straight up: sometimes the spinning is really code for I’m ready to move on — and naming that is its own kind of progress.) That’s not failure. It’s clarity.

For me, all those years ago, the answer was to stay, and that “difficult” colleague became someone I deeply admired. Your answer might be different. The point isn’t the answer. It’s that you get to ask the question from a place of what serves the work — instead of from the middle of the thought spiral.


If you want help

A lot of this you can do on your own, starting today — and the toolkit below is built to get you going. But some of it you can’t see or do alone: when you keep having the same conflict with different people, when you ARE the “difficult” one and need someone to show you your real-time impact, or when you’ve done the reframe and the feedback and it’s still not working.

Rayne Martin coaches leaders to harness their strengths and get out of their own way — and she loves this work from BOTH directions: working directly with the “difficult” leaders themselves, AND helping you manage the difficult people around you.

She might be the person to call if:

  • You see some of the “difficult” in yourself — and want to aim your strengths instead of muting them
  • You’re constantly drawn to difficult, intense, big-personality people and want to get better at working with them
  • You’re managing someone brilliant and exhausting and want a real strategy, not just a place to vent
  • You keep running the same interpersonal pattern and you’re ready to look at your own part in it

Connect with Rayne!

Book a chat Email

Try this yourself

Working With Difficult People Toolkit (FREE)

  • Notice / Impact / Suggest — The 60-Second Feedback Guide — when you have to say the hard thing and don’t want it to become a fight about character
  • Empower Your Thinking — when you’re spiraling on what they “really meant” and can’t put it down
  • Managing the Side Effects of Your Strengths — when your own intensity is landing harder than you mean it to
  • Raising Feedback With a Manager Who Can Be Intimidating — when the difficult one is your boss, and you need to open the door and say the thing clearly

Go deeper: Take Clifton Strengths Strengths Finder — the backbone of how Rayne reads strengths, including the “influencing” ones that so often get labeled difficult.


Questions to Sit With

  • Who have you labeled “difficult” — and what’s the strength underneath the label?
  • Think of your last real frustration with that person. Which parts were fact, and which were the story you added?
  • If you’re the “difficult” one: what strength of yours lands hardest on others — and what would it look like to aim it instead of mute it?

Forward this to someone who’d see themselves in it — or who’s working with one of us. (No one has to feel called out: the whole point is that “difficult” isn’t an insult. It’s usually a strength nobody’s learned to work with yet.)

Not sure Rayne‘s the right fit? Talk to Helia directly!

Book a chat

This article comes from a coffee chat with Rayne Martin in July 2026. These conversations are the heart of the Helia Library — because we’ve learned the most from doing, and from talking with other doers willing to share what they know. We don’t need to start from blank pages or do everything alone.

As always, take what’s helpful, leave what’s not, and make it your own.


Professional headshot of Rayne Martin smiling, wearing a red blazer over a floral blouse against a dark background.

About Rayne

Rayne Martin grew up in a tiny north Louisiana town of about 200 and has spent her career in the seats where strong personalities and big stakes collide — VISTA community mediation in Philadelphia, political campaigns and a chief-of-staff role in the Bay Area, and then Chicago, where she built the Chicago Housing Authority’s relocation department from a team of 6 into a 50-person operation running a half-billion-dollar budget, executing a federal consent decree while buildings closed on 24-hour notice. After Katrina she returned to Louisiana as chief of staff in the Recovery School District, served as the state’s chief of innovation and lead author of its Race to the Top application, and founded a Stand for Children affiliate — before opening her coaching practice, It’s the Impact, twelve years ago.

Her purpose is specific: help leaders push past their own limiting beliefs so they can make the world better for the people who don’t have access to the seats they’re sitting in. It traces back to her mother, who grew up being taught she was worthless — and to a need Rayne came to understand in herself, to help people in a way she couldn’t help her own mom growing up. Today the engine under the work is equity. She has OCD, calls herself “unbossible,” and will cheerfully tell you she’s a difficult person — which is exactly why she’s so good at helping other people work with theirs.

Work with Rayne
Take what’s helpful, leave what’s not, and make it your own.
Subscribe For More

More Articles You’ll Love

Helia’s Social Contract
We keep all Helia articles and resources free because, in the world we want to live in, people share generously and we all feel less alone! If anything in our library helps you, pay it forward — share an article, recommend a contributor for our Library, and when you need support, hire one of our brilliant Collective members.