The Decision Founders Wait Too Long to Talk Through
You don't have to be in it alone...
There’s a moment I see over and over again.
A founder knows something isn’t quite right.
Not broken. Not on fire.
Just… off.
So they do what most capable founders do.
They start scanning for the fix.
“Maybe we need to hire someone for this.”
“Maybe we need a VP.”
“Maybe this is a marketing problem.”
“Maybe it’s ops.”
They move quickly toward a title because it feels like progress.
What they don’t do (at least not right away) is talk the decision through with a trusted mind.
You can’t narrow it down by stage in my experience.
I see this with bootstrapped founders.
Seed-stage founders.
Series A founders.
The common thread isn’t funding or headcount.
It’s being a first-time founder or just a founder who feels alone in the game.
Sometimes they have a cofounder who’s deeply technical.
Sometimes they’re the only non-technical voice in the room.
Sometimes they’re surrounded by smart people, but still carry the judgment calls themselves. (I talked about the leak of all leaks, founder bottlenecks in an earlier post.)
So they think alone.
Here’s where things go sideways behind the scenes.
Founders often reach for hiring when what they actually need is a moment of clarity.
They are hiring to solve an undocumented/undefined problem.
By the time we talk, they’ll say things like:
“I think I know where the issue is.”
“We’ve had a couple blips.”
“This role should fix it.”
And then we slow down.
We lay the whole thing out.
What’s happening now.
Where signals are getting crossed.
What people are compensating for without realizing it.
Almost every time, the founder realizes one of two things:
Either the problem isn’t where they thought it was.
Or it’s deeper and more structural than a single hire can fix.
That realization usually happens in one conversation.
This is the part that doesn’t get talked about enough.
The most expensive decisions aren’t always the dramatic ones.
They’re the quiet, reasonable ones that get made without being pressure-tested.
Hiring to fix confusion.
Adding process to fix misalignment.
Layering roles instead of clarifying ownership.
Once a team starts working around a decision, it hardens.
People adapt.
Workarounds become habits.
Assumptions turn into systems.
By the time it’s obvious something’s wrong, the cost is already baked in. (And let me tell you, once this is set in the team’s mind, the mess just becomes massive. The project balloons by the time you want to actually make things right.)
What founders are often surprised by is how little it takes to avoid that.
They don’t need a full engagement.
They don’t need execution.
They don’t need someone to take over.
They need space to talk the decision through with someone who can:
listen without jumping to solutions
reflect back what’s actually happening
connect the dots across people, systems, and incentives
slow things down just enough to choose intentionally
Most of the clarity shows up before anything gets built or hired.
This is why the founders I work with often tell me the same thing afterward:
“I thought I was coming in with clarity.”
“I didn’t realize how much I was carrying.”
“I see it differently now.”
I didn’t hand them an answer, but the conversation helped them hear their own situation more clearly.
That’s the part founders wait too long for.
The cost of thinking alone doesn’t appear in a financial model.
It shows up as:
rework
unnecessary urgency
roles that don’t quite land
teams trying to read between the lines
None of that means you’re doing something wrong.
It usually means you’re doing something alone that was never meant to be carried solo.
Founders, we know you don’t need more hustle.
You don’t need to be faster.
You don’t even always need more help.
They need a second brain before a decision turns into a direction.
That’s the moment most people skip, and it’s the one that quietly determines how hard everything feels later.
If this feels familiar…
If this piece resonated, this is often the point where founders ask how to get support before a decision turns into a direction.
I work with a small number of founders as an advisor, as that second brain, while they think through decisions like this.
It’s typically lightweight: one or two conversations a month, plus occasional async touchpoints when something needs perspective.
If that kind of partnership would be helpful, you can learn more or reach out through my Substack.
It’s hard to see all the parts of a system when you’re responsible for it, and even more difficult to understand how others experience it. An impartial perspective is very helpful for that.
Yes, it is lonely, nigh impossible, and, in my case, ironic to do it for yourself even when it is exactly what you do for customers. Building a startup from scratch is not the same as coming into someone else's operation to help fix what's broken. The emotional investment you have in your startup is absent when working on someone else's business/venture/baby.
Basically, what @Janna McGregor said. ;-)