Early in my MSP days, I spoke with a prospect who needed IT support. We talked through their current pain points and general setup over the phone, and I thought I understood what they needed. I met them onsite for an assessment, everything seemed straightforward, and we signed the agreement.
Then I discovered the legacy server.
It was running old software that nobody had mentioned. It wasn't in any documentation or located with any other IT equipment, but it was part of a critical workflow that only their previous IT person understood.
And I had completely missed it.
I had just committed to keeping their systems running, and there was a single point of failure sitting on their network that I knew nothing about. If that server failed, a critical workflow stopped. And I was now responsible for fixing it.
I paid a specialist out of pocket to migrate that system to something supportable. That cost was on me, not the client.
Here's what I learned: I stopped being curious too soon. I did a standard assessment, asked standard questions, and saw what I expected to see. A few more questions would've surfaced that legacy system before we signed anything.
Curiosity isn't about doubting your expertise. It's about staying open to what you don't know yet. The questions that feel obvious or redundant often surface the things nobody thought to mention.
If you're walking into a situation thinking you already know the answer, you've probably stopped asking the right questions.