Your Questions, Answered

Probably because you're busy, maybe a little overwhelmed, or not entirely sure it will help.

Legit reasons, not excuses.

But here's what I've noticed: the people who wait for the perfect moment usually wait a long time. If you're on this page, something brought you here. That's worth paying attention to.

Right here is fine. You don't need to have done any homework or know exactly what you're looking for.

Start by reaching out and telling me what's going on, in whatever words you have.

I'll ask questions, listen carefully, and we'll figure out together whether I'm the right person to help.

Often both. Most of the leaders I work with find the organizational stuff and personal stuff are more tangled together than they expected. That's not a problem — it's actually useful information. We start wherever makes the most sense.

Founders and executive directors navigating growth or complexity.

Senior leaders who are high-performing and yet, often overwhelmed.

Practitioners and founders who built something great and now need help running it smoothly before it grows legs and runs away.

Students, adults, and families navigating executive function challenges — from middle school through the retirement years.

And a lot of people with ADHD and other neurodivergent profiles, at every stage of life and leadership.

If you're looking for a quick fix, a templated solution, or someone who will tell you what you want to hear — I'm not your person.

My work is relational. It requires real engagement from both sides, and it takes some time to do well. I work with a small number of clients at a time, which means I'm selective. If I don't think I'm the right fit, I'll tell you, and I'll do my best to point you toward someone who might be.

I help people and organizations get unstuck and move forward.

Depending on what you need, that might look like stepping in as a fractional Chief of Staff or operational leader, coaching you one-on-one through a leadership transition, helping your team get clearer on roles and priorities, or working with you or your kid on the executive function skills that make everything else harder when they're missing.

The through line is the same: I help figure out what's actually in the way, and I help you do something about it.

Direct, warm, and practical. I ask a lot of questions before I offer anything. I'll tell you what I actually think, including when I wonder if we're looking at the right problem. But I will do that kindly.

I work in ways that are accessible and flexible—because many of the people I've worked with are neurodivergent, and one-size-fits-all has never fit.

I also know that real change isn't linear, so I don't pretend it is. You'll have a way to reach me between sessions, and I stay with you through the wobble, not just the wins.

It means you get a senior leader, in this case, someone with COO and Chief of Staff experience, without hiring one full-time. I work with you part-time or on a project basis, embedded in your organization in a real way. Not consulting from a distance. Not handing you a report and leaving. Actually in it with you, doing the work. It's a good fit when you need senior-level thinking and execution support, but a full-time hire isn't the right move yet.

Less than you'd think. The honest answer is that the line blurs in practice, especially when you're a founder or leader, because organizational and personal challenges are usually connected.

We'll figure out what kind of support actually fits your situation. I'm not attached to a label.

Neither, exactly — or both, depending on how you look at it.

Executive function is the set of skills that helps you plan, prioritize, start things, finish things, manage time, and regulate when things get hard. Everyone has them. Everyone struggles with some of them from time to time.

I work with people from middle school through retirement — students, founders, leaders, parents, and everyone in between.

If you've ever thought this should be easier than it is — about starting things, finishing things, managing time, or just keeping up — that thought is worth paying attention to at any age.

They're different tools that often draw from the same toolkit.

Executive function coaching focuses on the underlying skills that make everything else possible — planning, prioritizing, initiating, managing time, regulating when things get hard.

• It's about how your brain operates, and building strategies that work with how you're actually wired, not against it.

Leadership coaching focuses on where you're going, your goals, your team, your organization, your next stage of growth.

• It's about developing the skills, clarity, and confidence to lead well from where you are right now.

Here's where it gets interesting: the fundamentals of EF coaching are the same as the fundamentals of leadership coaching. A leader who can't prioritize, initiate, or regulate under pressure isn't struggling because they lack vision. They're struggling because the operating system underneath the vision needs attention. That's a distinction that matters — and one I'm trained to look for.

Whether you need one or both depends on what's actually in the way. That's what the first conversation is for.

It's all the same work, at different scales.

My career started in special education, so I began by learning how people learn. How brains work. How to pick up on what someone might need in a moment, adapt what you're doing, and meet them there — rather than where the plan assumed they'd be. That foundation never left.

From there, I moved through teaching, coaching, and eventually running a national behavioral health and EF coaching organization as COO and then President — a fourteen-year chapter that further shaped how I work today. Across twenty years of this work, I've watched behavior change and organizational change happen simultaneously, up close. I know what it actually takes.

I wasn't just coaching leaders through executive function challenges. I was the operating system for the business itself. Planning, prioritizing, building infrastructure, managing culture, driving change — at scale, across a distributed workforce, over time.

What that gives me when I work with a leader or an organization is something I can't fully summarize in a credential: I know what it feels like to run the system, debug it under pressure, and upgrade it while it's still running. I know that individuals, teams, and organizations all have operating systems — and that those systems need updating, the same way your phone does. When they don't get it, they start to fail in recognizable ways. They lose capacity. They freeze under load. They stop doing what you need them to do.

I also know that where you are in the process matters enormously. A first-time manager is in a different stage than a seasoned executive director. A startup runs differently than a twenty-year-old nonprofit. The approach that fits—the strategies, the pacing, the entry point—shifts with that stage. Ages and stages matter, for people and for organizations.

Where there is a way, there is a will.

Yes — and I want to be direct about that. ADHD is not a barrier to this work. It shapes how we do the work. I don't pathologize it and I don't work around it — I work with how your brain is actually built, developing systems and strategies that fit you rather than asking you to fit a neurotypical template that was never designed with you in mind.

A lot of the people I work with are neurodivergent. If you've tried approaches before that didn't work, there's usually a reason. Finding it is often where we start.

I believe they are different tools for different purposes — and both are worth taking seriously.

Clinical therapy encompasses a wide range of approaches — many of them rigorously evidence-based — and I'd do the field a disservice trying to compress it into a paragraph. What I can tell you is what coaching is, and when it's not the right fit.

Coaching is designed to build. It starts where you are right now and focuses on where you want to go—setting goals, building habits, removing obstacles, and taking action. Coaches aren't therapists, and good ones know the difference.

There's overlap, and that's okay.

Both care about the whole person. Both require trust. And sometimes the best thing for someone is both — therapy and coaching running alongside each other, with practitioners who respect what the other is doing.

I'm not a therapist. If something comes up in our work that I think belongs in a therapy room, I'll say so — directly and without judgment. I know a number of excellent ones, and I'm glad to make a connection.

It depends on what we're working on. Fractional engagements vary; some are project-based, some are ongoing.

Leadership coaching often goes three to six months, sometimes longer.

EF coaching with a student might run a semester or a school year.

I don't push for longer than what's useful, and I'll tell you when I think the work is done. The goal is not dependency.

 Both. Most of my work happens virtually, which means I can work with clients anywhere.

When it makes sense to be in the room — for a team session, a working day, or an onsite — I can do that too. I'm based in Massachusetts. If in-person would work better for you, let's talk about it.

Both. Much of my work is one-on-one — coaching individual leaders, students, or clients. But I also work with leadership teams, co-founder pairs, and small organizations on what's harder to solve individually: role clarity, decision-making, communication, culture. If you're not sure which one you need, we'll figure it out.

If you're overwhelmed, that's not a reason to wait. It's usually the reason to start.

I'm not going to add a heavy lift to an already full plate — the first conversation is usually 30 minutes, and we go from there at a pace that works.

A lot of the people I work with come to me precisely because they don't have margin in their day. Building margin is often part of the work.

 Yes. That's often exactly what this looks like in practice — not talking about the work, but doing it. Building the system, clearing the backlog, figuring out what's getting in the way and removing it. I'm not a coach who stays at the altitude of insight. I get into the work alongside you. If you need someone to help you execute, not just reflect, that's a good sign we're a fit.

That's a fair question, and I'd rather you ask it than not. A few honest answers: most things don't stick because they weren't built for how you actually work — your brain, your schedule, your real constraints, not an idealized version.

Also, accountability matters. Having someone in your corner who knows what you said you'd do makes a difference.

And sometimes things didn't stick because the timing wasn't right. That's allowed too. If you've tried before and it didn't land, tell me what happened. That's useful information.

Most of this work lives in the complicated. Simple situations don't usually need outside help. If things are messy — the team dynamics are hard, the history is complicated, you're not even sure you're asking the right questions — that's fine. Bring it as it is.

I've worked in complex organizations long enough to know the complicated parts are rarely the whole story, and they're usually worth understanding before anyone tries to fix anything.

  We talk about it. If you've tried before and it didn't land, tell me what happened. I'd rather start there than pretend we're starting from scratch. If the work needs to shift, we shift it. If I'm not the right fit, I'll say so and help you figure out what is. Holding onto something that isn't working doesn't serve either of us.

Not in the way you might think. Whether you're neurodivergent — ADHD, autism, dyslexia, twice-exceptional, or something that's never had a clean label — or simply someone whose brain has always moved differently than expected, that doesn't limit what's possible. It changes the starting point.

The work we do together doesn't require you to become someone you're not. It requires getting clearer on who you are and how to use that well. Some of the most effective leaders, builders, and thinkers I've worked with have felt exactly the way you're describing. That's not a liability. It's usually where the most interesting work begins.

You'll hear back from me directly. We'll find a time to talk, usually thirty minutes to start, and I'll come to that conversation ready to listen. No intake paperwork, no pre-work required. Just show up and tell me what's going on.

I'll tell you. The first conversation is as much about fit as it is about anything else, and I take that seriously. If I don't think I can help you, or if I think someone else could help you better, I'll say so.

I'm lucky to have a wide network of colleagues, both individual practitioners and organizations, doing strong work in coaching, consulting, fractional leadership, and behavioral health.

If I can't help you, I'll do my best to connect you with someone who can.

I work with a small number of clients at a time. That's intentional; it means every engagement gets real attention, not a template. Pricing reflects the scope and structure of the work, and I'm transparent about it once I understand what you need. I don't post rates online, but I won't waste your time. If it's not a financial fit, I'll tell you early.

The first conversation is how. There's no commitment in reaching out, just a chance to talk, ask questions, and get a feel for each other. I'll be honest with you about whether I think I can help, and I'd expect the same from you. If it feels right to both of us, we go from there.

Absolutely, and I'd welcome that.

I'm most active on LinkedIn, where I often share thoughts on leadership, neurodiversity, operations and organizational strategy, parenthood, and the messy reality of doing meaningful work.

You can find me at linkedin.com/in/rachelkrompinger.

Follow along, and reach out whenever the time feels right. There's no rush.

Click on REACH OUT. That's it. Use the button at the top or bottom of the page to send me a note about where you are and what's going on.

I'll take it from there.