The most common conversation I have with mid-market technology leaders starts with some version of “the board is asking about AI, and I don’t know what to tell them.”
If you’re in this conversation, the pressure is real. Board members want to hear about AI initiatives. Their peers at other companies are name-dropping tools and vendors. Not having an AI story feels dangerous. The temptation is to fabricate one — announce a few initiatives, sign a couple of vendor contracts, put “AI-enabled” into the next investor deck — and hope nobody looks too closely.
Don’t do it. That path leads to a portfolio of unmanaged AI experiments that eventually get audited, and that conversation is worse than the original board pressure.
Here’s a better approach. Reframe the conversation from “what AI are we doing” to “what problems are we solving that AI would help with.” That shift is subtle and enormous.
The first framing invites vague, tool-focused answers. The board asks “are we using AI,” you answer “yes, in these five ways,” and the conversation moves to details you can’t defend. The second framing invites specific, problem-focused answers. The board asks “what problems are you solving with AI,” you answer “our top three operational bottlenecks are X, Y, and Z, and here’s our approach to each,” and the conversation moves toward operational reality — which you can defend, because you know your operations.
If your business hasn’t done the inventory work, this reframe is harder to execute, because you don’t have the specific problems to name. That’s a signal to do the inventory before the next board meeting, not to fabricate initiatives before it.
A useful template for the executive presentation:
Slide 1: Here are the three operational problems we’re prioritizing this quarter.
Slide 2: Here’s what each costs the business today, measured in hours or dollars or delay.
Slide 3: Here’s where AI could plausibly help with each, and what we’d need to verify before investing.
Slide 4: Here’s what we’re piloting first, why, and how we’ll know if it worked.
Slide 5: Here’s what we’re deliberately not doing, and why.
That last slide is the one that convinces sophisticated board members you know what you’re doing. Anyone can list initiatives. Naming what you’ve decided not to pursue — and defending the reasoning — signals discipline. Discipline is the thing sophisticated boards want to see, more than novelty.
If you can’t fill that fifth slide because your business is currently pursuing everything, that’s the honest conversation to have with the board. “We are running too many initiatives to give any of them a fair chance. Here’s the sequencing plan for the next quarter.” Boards respect that more than they’d respect a padded initiative list, in my experience.
The diagnostic is a good tool for building the initial version of this presentation, especially the “what we’re deliberately not doing” slide.