What's really
going on?
Most people who reach out to me know something isn't working. They're not always sure what. In six questions you'll get a clearer name for the situation you're in — and some honest thoughts on what it usually requires.
Question 1 of 6
Something shifted recently. What was it?
Pick the one that fits closest, even if it's a combination.
Question 2 of 6
Where does the real knowledge live right now?
Not where it should be. Where it actually is.
Question 3 of 6 — halfway there
What have you already tried?
Pick everything that applies.
Question 4 of 6 — almost there
How do you feel about it?
The honest answer, not the one you'd give in a board meeting.
Question 5 of 6 — nearly done
When it comes to AI — where are you?
This one matters more than it might seem.
Last one!
One month from now — how do you want to feel?
Not what you want to have built. How you want to feel when you sit down on a Monday morning.
The floor just dropped
Something — or someone — that was holding things together isn't there anymore. A departure, a restructure, a handover that didn't quite happen, a team that got leaner. What's left is exposed in a way it wasn't before.
This isn't a failure of planning. Most companies run lean by necessity, and lean works until it doesn't. The people who left knew things nobody had time to write down — not because anyone was careless, but because there was always something more urgent to do. What was working, worked. Until the ground moved.
The risk now is filling the gap with whatever's nearest — a junior hire, an agency, a tool — rather than understanding what the gap actually is first. The shape of what's missing matters more than the speed of the replacement.
What this usually requires
- Someone who can walk in without a brief and figure out what's actually fallen through — not what the org chart says should be covered
- Surfacing the institutional knowledge that left with the person, before anyone else leaves with the rest of it
- Stabilising the immediate gaps before building anything new — sequence matters here
- Honest assessment of what was working and what was already quietly not, before the departure made it visible
- Someone you can hand something to without having to manage them through it — who reads what's needed and starts doing it
The ceiling just got higher
Something arrived — a new mandate, a significant client, an expansion, a fundraising round, a push into new territory — and the setup that was sufficient before isn't sufficient anymore. The opportunity is real. The infrastructure isn't quite there yet.
This is a good problem to have, and a genuinely hard one. The temptation is to hire more people. But hiring into a team that hasn't defined the work properly yet just creates more coordination overhead. What you usually need first is someone who can figure out what the work actually is — and build the foundation that lets people do it.
The companies that navigate this well focus on building momentum. The ability to experiment fast, find what breaks before it breaks in front of a client, and carry the operational foundation across functions while the rest of the business accelerates around it.
What this usually requires
- Mapping what needs to be true operationally for the new stage to work
- Someone who operates at whatever level the situation requires: strategic framing one day, invoicing the next
- Building the onboarding, delivery, and client processes that don't exist yet — so everything can scale
- Keeping existing work from breaking while the new thing gets built alongside it
- Someone you can trust to run with it — who doesn't need the brief to be perfectly defined before they start
It runs on people,
not systems
Things work because the right people make them work. That's not a criticism — it's how most small companies survive the early stages, and for a long time it's the right call. Formal systems have overhead. People who know what they're doing don't need them.
But something has changed — a new hire who needs context that nobody knows how to transfer, a growth moment that requires consistency the current setup can't guarantee, a key person who's stretched or thinking about leaving. Suddenly the dependency is visible in a way it wasn't before.
The fix here isn't documentation for its own sake. It's making the real work visible — naming who owns what, surfacing what's assumed, writing down what everyone knows but nobody's said. The process of doing that usually reveals more than the documents themselves.
What this usually requires
- Someone who will start writing things down from day one — not waiting for sign-off, not waiting for the perfect structure
- Naming owners to things that have always been ownerless — and the conversations that follow
- Building what new hires actually need to land without draining the most expensive attention in the company
- Moving the critical knowledge somewhere it can survive a departure — before the departure happens
- Someone you can hand it to without creating a new management task — who gets on with it and tells you what they found
You've added complexity
before stability
New tools. New hires. A push to implement AI. New processes layered on top of old ones. Each addition made sense at the time — and collectively they've made things slower, not faster. More tangled, not cleaner.
This is one of the most common patterns in companies trying to grow quickly, and it's easy to misdiagnose. The instinct is to add more — a better tool, a clearer process, the right AI model — when the actual problem is that the foundation underneath isn't solid enough to support what's been put on top of it.
AI is making this more visible right now. A lot of companies are finding that AI tools underdeliver not because the tools are bad, but because the data is a mess, the workflows aren't defined, and nobody's quite sure what problem they're solving. The technology works. The foundation wasn't ready for it.
What this usually requires
- Slowing down before speeding up — understanding what was already broken before adding more
- Working out which tools are solving real problems and which are solving the symptom of a process problem
- Getting the data layer, the ownership, and the workflows in place before the next tool goes in
- Someone with a strong enough point of view to say: this isn't a tooling problem
- Someone you don't have to manage through the diagnosis — who comes back with what they found, not a list of questions
You're still here.
That's not nothing.
You've been through enough changes — restructures, pivots, new leadership, false starts — that it's hard to feel much about this one. The problems are real. You know that. It's just that you've known it for a while, and knowing hasn't made them easier to fix.
This isn't apathy. It's what happens when capable people absorb too much change without enough traction. The appetite to build something that works is still there — it's just buried under the accumulated weight of things that didn't.
What this moment usually needs isn't a plan or a framework or another tool. It's someone who will close their laptop, ask how things actually are, and listen to the answer before they start on anything else. The work comes second. Understanding what's actually going on — including what's worn people down — comes first.
Once that's visible, something usually shifts. Not because the problems got smaller, but because they're finally being looked at clearly, by someone who isn't exhausted by them yet.
What this usually requires
- Someone who reads the room before they start — and adjusts the approach accordingly
- Starting with what's actually happening, not what the brief says should be happening
- Finding the version of the work that reconnects to why people started — not asking them to do more of what's already draining them
- Small, visible traction early — not a big plan, but something that moves, so the team remembers what momentum feels like
- Someone who earns trust by doing, not by presenting — who doesn't add to the noise before they've understood what's actually going on
It's more than
one thing
Your answers point in more than one direction — and that's probably accurate. Most situations that are genuinely hard to fix aren't one clean problem. They're two or three overlapping ones, each making the others worse.
Something left and something new arrived at the same time. Or the infrastructure was already shaky when the pressure went up. Or the team has been through enough that adding tools and processes on top of the existing exhaustion just created more noise.
The risk with a mixed situation is treating the most visible problem as if it's the whole thing. Fix the gap the departure left, and miss that the team's been running on fumes for months. Build the new client process, and miss that nobody owns the knowledge it depends on.
What helps here is someone who looks at the whole picture before they start on any of it. Not to build a comprehensive plan — but to figure out what to touch first, and in what order, so that fixing one thing doesn't break another.
What this usually requires
- Mapping what's actually going on across the whole operation before deciding what to fix first
- Someone comfortable working across more than one problem simultaneously — without losing the thread on any of them
- Getting sequence right: some things need to be stable before others can be built
- Honest assessment of what's urgent versus what just feels urgent because it's visible
- Someone you can hand the whole picture to — not just one workstream — who can hold the complexity without needing it simplified first