The Engagement I Turned Down
A founder I worked with came to me wanting to explore automating a role in his business. The reasoning made sense on the surface: cut the ongoing cost of a person, remove the dependency on any one hire, let a system handle what a team member had been handling. It's the kind of project most consultants say yes to right away. It's billable, it sounds forward-thinking, and "we automated it" is an easy story to tell afterward.
Client Overview
A founder-led business operating in a sector where client data is handled through third-party platforms governed by security standards the business itself doesn't set and can't change. The request: explore automating a role that touched those systems directly.
The Challenge
Before scoping anything, I looked at what the role actually touched. It included systems holding sensitive client data governed by standards belonging to the sector he operates in, not the business itself, enforced through third-party platforms his business only had access to, not ownership of.
That distinction is what made this a hard no rather than a scoping conversation. This wasn't a case of the right architecture not existing yet in his business, something I could design my way around with enough time and a clever build. The constraint sat one level up, in infrastructure the sector as a whole hadn't yet evolved to support this kind of automation safely. No amount of skillful system design changes what a third-party platform will and won't allow, or what a regulator still expects a human to be accountable for.
The Approach
I told him that directly. Not a scaled-down version. Not a phased approach. Don't do this, not with me and not with anyone else, until the sector's own infrastructure catches up to make it possible to do safely.
The Outcome
He didn't move forward with the project. That conversation cost me the engagement, and I still think it was the right one to have.
A diagnostic only means something if the answer can go against what the client wanted to hear, and against what would have been good for my invoice that month. If I only ever say yes to the project in front of me, I'm not diagnosing anything. I'm agreeing with the client and charging for the agreement. This is also why readiness and fit come before revenue in how I take on work: sometimes the honest answer isn't "not yet, but here's the workaround." Sometimes it's "not yet, and no one can build their way around that right now."
Ready to Find Clarity?
Not every engagement should move forward, and knowing which ones won't hold is part of the diagnostic itself. The five-minute Readiness Check is a place to start finding out where you stand.
