Start with the Experience

Make My Mess My Message · Issue 2 · Friday 19 June 2026

Most standard software you buy is a solution looking for a problem.


Why the software your team hates is the problem you didn’t see.

In the early 2000s I had two seats at the same company. One was on the team deciding what software the sales divisions would use. The other was running one of those divisions.

We bought a new CRM platform. I read the deck. Easier quotes. Better pipeline analysis. Disciplined follow-up. Professional sales management.

Twelve months later, my sales team called Friday afternoons “CRM afternoons.”

That was when they sat at their desks populating fields, updating win percentages on deals they hadn’t won, answering automated triggers generated by a logic that did not match how a real sales cycle actually works. The system was eating the day that should have been spent in front of customers.

I asked them what we could do better as a division. Product, marketing, engineering, service, anything.

They came back with one answer. Unanimous.

Get rid of the CRM.

Not the idea. This one.

That was the Collective Brain at work. The people closest to the work, given access and asked the right question, knew what the rest of us never saw. The system had been sold to the C-suite. It was being used by the people in the field: the ones who had to bear the flag and go win business. It was actively making them worse at the job.

That is when the realization landed. It was not only that the software was wrong. It was that the way it had been sold and built was wrong.

What good salespeople want to do is sell. That includes writing quotations: quotations are sales, not paperwork.

Software should make that work easier and faster. It should enable the people who use it.

When it does the opposite, when it eats the time the team needed to spend selling, you have not bought a CRM. You have bought the perfect sales prevention tool. Something has gone wrong well before the software was bought.


Most standard software you buy is a solution looking for a problem.

The vendor writes the answer first. Then their marketers find the questions the answer can be sold against. Then their salespeople find buyers, usually in the C-suite, where the people who will never have to operate the software are the people with the budget. Then their consultants implement, which is a word the industry uses to mean: translate your reality into our template.

By the time the system reaches the people who have to use it on a Friday afternoon, the experience has been pre-decided by everyone except them.


The fix is one move.

Start with the experience. Work your way back to the technology.

The experience is the customer in their actual moment. What they are trying to do. What is frustrating them. What would make them feel served. Map that first. Stay with it.

Then ask: what is the smallest, simplest, most intuitive system that delivers that experience?

That is the answer. The technology is whatever stays out of the way of the experience you mapped. Not whatever the vendor’s deck said it could do. Not whatever consultants said you would need. Not whatever flatters your title in the procurement decision.

I did not invent this principle. I just keep noticing it works.


When we built another business years later, we made this the operating discipline from day one.

Two people joined to run it. Both had spent their careers buying from companies like the one we were now building. They knew, from their own lived experience on the other side of the table, exactly what mattered.

Three words.

Speed. Simplicity. Stock.

Speed: responding fast, faster than the customer expects, faster than anyone else.

Simplicity: easy to work with, simple logical workflows, no friction in the daily transaction.

Stock: having the product available when it was needed.

That was the whole experience, mapped by people who had lived it.

Everything else got built backwards from those three words. The technology stack. The team structure. The hiring criteria. The metrics. Every weekly meeting had to demonstrate movement on one of the three S’s, or the meeting was wasted.

We built systems. We did not buy them. The difference is everything.

It worked.


We still run this. Every six months we get together for our Work Together Week off-site. Everyone on the team gets HomeWork.

Two questions. Think about the business broader than your current job: a whitepaper, a framework, anything that pulls them above their daily lane. And: what can or should we do better.

The quiet ones often turn out to have the longer view, the better priorities, and the analysis that goes to root cause instead of stopping at symptom.

Everything goes into the Collective Brain. The Brain keeps building.


If you want to start with the experience this Monday morning, here is the starter version.

Pick the one thing that frustrates you most in your business right now.

Interview five people about it this week. All internal or customers. No consultants.

Ask each one what they would change and what the ideal outcome looks like.

List every answer before you change anything.

That is the whole technique.


This week was four versions of one move.

Monday: read the relationship the contract is built on, not just the clauses.

Tuesday: build the camel that outlasts the cycle, not the unicorn that does not.

Wednesday: see the explicit learner who teaches, not just the learner who absorbs.

Friday: build from the experience the people in the field already understand, not the vendor’s deck.

The pattern stays the same in every domain.

Read what is underneath.

Most operators read the surface. The operator who survives reads what is underneath.


Start with the experience.

Be water, my friend. 🌊


Make My Mess My Message is a book written in public, one Friday at a time. This issue first appeared on LinkedIn. Every issue lives here.

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