What it’s Like to Work with Me
Two coffee cups and a notepad on a kitchen table
Most of the people who hire me already know me. They've worked with me, or someone they trust has, or they've been reading my thinking on LinkedIn for a while.
If you’ve been reading this blog for a while, you probably know that I log obsessively. Last month, I sat down and processed all of the sales data collected by Calendly, Stripe and Fathom for the past 3 years and noticed something interesting: People who experience this work tend to want more of it.
And people who only read a description almost never do.
I understand why. "Agile coaching for ADHD" isn’t terrifically informative for anyone not fluent in both ADHD and Agile. It doesn't tell you what I'll ask, what we'll actually do in a session, or whether you'll walk away with anything more than a pleasant conversation and a bill.
So this essay is my attempt to give you a small taste of the experience itself.
We start with something that actually happened
To get the most out of it, do one thing before you read on: think of a specific moment from the last few days when something you meant to do didn't happen. Your whole life is too big, and so is "I'm always behind." Pick one moment, and hold onto it (we're going to use it).
People usually arrive with an explanation already in hand. I need more motivation. I need a better app. I think I'm misusing my time. Most have tried plenty of tools before they get to me: task managers, Asana, paper lists, notes apps, whiteboards, color-coded calendars. Most of those tools work fine.
I don't assume your explanation is wrong. I don't assume it's right, either. And I won't try to tackle all of it at once, because "every ADHD problem in my life" can't be examined in thirty minutes (or thirty weeks). So I ask about one recent incident.
Take your moment. What happened immediately before it went sideways?
One person I spoke with was getting ready for a family trip. There were two tasks, one meant to lead into the other, and the first one never got done. As we walked through it, a picture emerged: his real working system was the end-of-day emergency. Things got done when the deadline arrived and made them unavoidable. And when the first deadline passed, what he felt was relief, because now it was too late to do it.
Those details matter, because they point to specific mechanics we can work with: how one task hands off to the next, where urgency actually comes from, what happens once a deadline is lost. "I need more motivation" gives you nothing to change. Mechanics do.
Here's another question for your moment: when you DO finish something that matters, what's different? What conditions were present?
We separate problems that feel identical
"I can't keep up with my work" is one sentence, but it can describe many different problems. You might not be capturing the work at all. You might be capturing it but unable to see it as a whole. You might see it fine and be unable to choose among it. You might struggle to start, or run out of energy by 2 PM, or have a workload no technique on earth will fix. From the inside, all of these feel the same. But they need very different fixes.
One client came to me convinced she was seriously misusing her time. She was responsible for a lot, couldn't fully name what she did, and was constantly forgetting things. Before we talked about any system, I asked her: if our work together succeeded, what would be different on an ordinary Tuesday?
She said she'd know what she needed to work on that day, and she wouldn't be scrambling to remember what she'd discussed with her supervisor.
So I asked whether success meant getting more done, feeling less overwhelmed, communicating more clearly, or some combination. She thought about it and said she wasn't sure "more" was the point. She wanted the work to be tangible.
That answer changed our direction. Instead of optimizing her output, we pulled her whole job into view: a map of her responsibilities, which we then compared against two weeks of what she actually did. The map turned out to be incomplete (there was more work than either of us could see at first). But her estimates of her major work were, in her words, “pretty spot-on”.
So poor forecasting wasn't the problem we'd suspected. What she discovered instead was that a handful of broad responsibilities contained a great deal of work, and that how important something was and how much time it consumed were two entirely separate questions. And "I'm misusing my time" stopped being the only available explanation for why she never had enough of it.
Then we run a small experiment in your real life
Once we have a hypothesis, we test it with the smallest thing that will give us useful evidence. We decide in advance what counts as success, and I usually set that bar at "good enough to learn from" rather than perfect.
Sometimes that means building something during the session: a map, a list, a simple spreadsheet. That kind of structure isn't a solution I'm handing you. It's a way of seeing what's going on. And when “getting started” is the obvious risk, we start right then, during the call.
With one client, we'd designed a simple experiment to track her energy through the day, and I pointed out that the most likely way it would fail was that she'd never get around to creating the tracking sheet. She agreed immediately: if it didn't happen now, it wasn't going to happen. She was already at her computer. So we made it together, before the session ended, with no new app involved.
After the first session, most of our time together follows a simple rhythm. You give me two quick scores from 1 to 10: one for how you're doing emotionally, one for how things are going logistically. We look at the step forward you chose last time and what actually happened with it. We look at your calendar and your list of work for the coming week. Then you choose your next step forward, and I ask: what, specifically, are you going to do? If the answer is fuzzy, we break it down until it isn't.
Those scores do real work. They tell us whether last week's plan still belongs to this week's reality.
"What if I don't do it?"
This is the question I hear most often, sometimes out loud and sometimes underneath everything else. People have watched a dozen systems work beautifully for three weeks and then vanish. They're afraid of paying for help and then failing to use the help.
It's a reasonable fear. Here's how I handle it: an undone step is information. When something didn't happen, I want to know what’s in the way under the conditions you actually live in. I start from the assumption that you did the best you could with what you had at the time, which is a promise I've made to every team I've coached and one I'll make to you. (I've written more about why compassion is part of Agile's foundation.)
Falling off a system doesn't erase what you learned while you were using it. As I once put it to a client: if you fall off the wagon, so what? You have some tools. Getting good at this kind of work looks a lot like getting good at meditation, which is mostly getting good at coming back.
Sometimes the thing that changes is your whole life. One client started with me to get a job search moving. Then illness happened, and travel, and then a family member needed care. We could have treated all of that as interference with the plan. Instead we changed the plan to fit her life. Over time she started naming the phase she was in: re-entry mode, caregiver mode, career can wait. By our later sessions, she was naming those shifts before I did. She described our sessions as an anchor, a reliable place to come back to while everything else kept moving.
Sometimes it doesn't work, and I'll tell you
I'd rather be straight with you about this than have you find out the expensive way. Sometimes a first conversation doesn't surface the real bottleneck. Sometimes our first hypothesis is wrong, or the experiment is. And sometimes what I offer simply isn't the right fit for what you need, in which case I'll say so rather than sell you more sessions.
That's why I start with a single Clarity Session. It stands on its own: we look at a real piece of your life, you leave with something to try, and then you test it in your actual work. After that, both of us can decide based on evidence whether it makes sense to keep going. You don't have to commit to weeks of coaching on faith.
Where this goes
Yes, I want your immediate problem to get better. But the longer-term goal is for you to get good at investigating yourself: noticing when a plan has stopped fitting your circumstances, telling apart problems you've been lumping together, treating a failed experiment as a clue rather than a verdict. The caregiving client I mentioned got there, and that's what I'm aiming for with everyone. Learning happens at the end of each cycle, which is why small, repeated iterations teach you faster than one big overhaul.
I have ADHD myself, and I've spent a long time building systems that work with my brain rather than against it. I don't expect you to become a more organized version of someone else.
Bring me one moment
You don't need to show up with the right explanation, or know what kind of help you need. Bring me the moment you've been holding onto while you read this. We'll look at what happened just before it went sideways, figure out what's actually going on, and pick one small thing that might make it better.
