What I Need to See Before I Agree to Work With a Business
Not every business is ready for systems work. There are preconditions — real pain, willingness to constrain, and capacity to let systems carry weight.
I turn down work regularly. Not because the businesses are bad, but because the conditions aren’t right.
Systems work requires specific preconditions. When those preconditions exist, the work succeeds. When they don’t, it fails — regardless of how good the systems are or how much money gets spent.
After enough failures, I learned to check for the preconditions first.
Precondition One: Real Pain
The business needs to be experiencing actual pain. Not theoretical pain. Not “we should probably” pain. Real, present, measurable pain.
Real pain looks like: we lost three customers last month because of fulfillment errors. We’re working sixty-hour weeks and still falling behind. We had to turn down a contract because we couldn’t handle the volume.
Theoretical pain looks like: we want to be more organized. We’re thinking about scaling eventually. We read an article about operational excellence.
The difference matters because systems require change. Change requires motivation. Motivation comes from pain that’s bad enough to demand a solution.
When the pain is theoretical, people nod along during planning and then resist during implementation. The old way is comfortable. The new way is uncertain. Without real pain pushing toward change, comfort wins every time.
I need to see pain that the business can’t ignore. Pain that’s costing money, losing customers, or burning out the team. Pain that makes the discomfort of change seem preferable to the discomfort of staying the same.
Precondition Two: Willingness to Constrain
Systems work by limiting options. That’s the whole point. Instead of infinite flexibility, you get reliable repeatability. Instead of handling every situation uniquely, you handle most situations identically.
This requires constraints. And constraints require willingness.
The conversation usually goes like this: “We need a system for customer onboarding.” Great. “But we have some customers who need special handling.” Okay, how many? “Maybe twenty percent.” That’s not special handling — that’s a second process. “Well, we can’t tell those customers no.” Then you can’t have a system.
Systems don’t accommodate unlimited exceptions. Every exception is a hole in the system. Enough holes and the system becomes meaningless — a set of rules that nobody follows because there’s always a reason not to.
I need to see willingness to say no. Willingness to tell some customers that this is how things work now. Willingness to eliminate the exceptions that have accumulated over years of ad-hoc accommodation.
This is harder than it sounds. Those exceptions often exist for good historical reasons. Eliminating them feels like abandoning relationships or breaking promises. But without constraints, systems can’t function.
Precondition Three: Capacity to Let Go
The hardest precondition is psychological. The owner — or whoever controls the operation — needs to be able to step back and let the system work.
Systems replace individual judgment with documented process. This means the owner can’t be involved in every decision anymore. The system makes the decision. The owner has to trust it.
For many small business owners, this is terrifying. They built the business on their judgment. Their involvement is what made it work. Stepping back feels like abandoning the thing they created.
But systems can’t function with constant override. If the owner reviews every decision, questions every output, and intervenes whenever something feels wrong, the system never develops authority. The team learns that the system is optional — that real decisions still go through the owner.
I need to see capacity for distance. The owner doesn’t have to be happy about it. They don’t have to feel confident. They just need to be willing to try — to let the system run for a week, a month, without intervening. To see what happens when they’re not the bottleneck.
The Conversation That Reveals Everything
I can usually tell within the first meeting whether the preconditions exist.
The pain is easy to assess. I ask what’s not working. If the answer is specific, detailed, and emotional, the pain is real. If the answer is vague or theoretical, it’s not.
The constraints are harder. I ask about exceptions. I ask what they’re unwilling to change. The businesses that are ready can identify what they’d give up. The businesses that aren’t want systems that accommodate everything.
The capacity to let go is hardest. I ask what the owner’s role would be after the systems are in place. If the answer involves oversight, approval, and review of everything, they’re not ready. If the answer involves new work — growth, strategy, customer relationships — they might be.
Why I Check First
I could take every project. The money would be the same. The initial work would be the same. Only the outcome would be different.
But failed projects cost more than money. They cost the client’s belief that improvement is possible. A business that tries systems work and fails often concludes that systems don’t work for them — that they’re somehow special, that their situation is unique, that the problem is unsolvable.
That conclusion is usually wrong. The problem isn’t that systems don’t work. The problem is that the preconditions weren’t there. The same business, two years later, with more pain and more willingness, might succeed easily.
I’d rather wait for the right conditions than create another failure that makes future success harder.
What I’m Looking For
To summarize: I need to see three things before agreeing to work with a business.
Real pain. Not aspirational improvement, but actual problems that are costing money, customers, or sanity. Pain that makes change preferable to staying the same.
Willingness to constrain. Acceptance that systems require limits. Readiness to say no to exceptions that would undermine the structure.
Capacity to let go. Psychological readiness to step back and let systems carry weight that the owner currently carries personally.
When all three exist, the work succeeds. When any one is missing, it doesn’t.
I’ve learned to check first.
Related
These preconditions are part of a larger question: when do systems make sense at all? For more on the timing and context of systems work, see: When Systems Are the Right Answer — exploring the conditions under which systematization creates value rather than overhead.