Before investing fully in AI, three questions worth sitting with
What is your AI strategy for sales?
There’s a conversation happening in most boardrooms at the moment, and it tends to go the same way.
A chair, MD or business owner asks the question: “So — what’s our AI strategy?”
It’s a very cluttered landscape right now and there’s no shortage of apps, tools or platforms that a sales team might benefit from.
I’ve heard that shout in a few meetings recently and often it feels like nobody quite knows what they’re really asking for and that can be a problem in itself.
(Does anyone remember how long it took to integrate a CRM into a business – ring-fencing budget, getting consent on vendor, integration, training?)
A shift in how I’m thinking about it
When AI first started showing up in the sales tools my clients were buying, I assumed — as I think most of us did — that it would change what we do. The reality I’m seeing across mid-market businesses is quieter than that, and in some ways more difficult.
AI isn’t so much changing what sales teams do. It’s amplifying what they already do and a lot of what they don’t
Where there’s discipline — clean qualification, honest forecasts, consistent sales rhythm, integrated coaching — AI seems to make it better.
Where there isn’t, AI seems to make things worse, faster. Either way, what AI is doing is making the underlying state of the business much more visible than it used to be.
That’s what I keep coming back to in conversations with sales leaders this year. AI is a magnifier, not a multiplier.
Three patterns I’m watching unfold
A few examples to share from the last twelve months.
One team turns on AI-driven forecasting on top of pipeline data that, if we’re honest, was already a bit of an “Are you sitting comfortably…?” job.
The forecast becomes more confident but not more accurate. By the third quarter the gap has widened — not because the model is poor, but because it’s working faithfully with data the culture has never been truthful about.
Another team buys an AI outbound platform and scales the volume of cold emails by ten. The reply rate doesn’t scale with it. Instead, it falls. The reps aren’t doing anything different. They’re doing the same thing but at a much greater volume.
The third rolls out AI call summaries. Every conversation gets transcribed, tagged, summarised. Six months on, the win rate looks identical. Nobody is acting on what the AI is surfacing — there’s no coaching rhythm in the business for it to plug into.
In each case the technology did exactly what it promised. The business just wasn’t ready to make use of it.
A more useful question than “what’s our AI strategy?”
Business owners and sales leaders should try a different question in those board conversations.
“If the way my team sells today were amplified x 10 tomorrow, would I want that?”
It’s a quieter question, and a little more challenging to answer. Most will, when they sit with it for a moment, come back with “not yet.” Not in the way we’re qualifying. Not in the way we’re forecasting. Not in the rhythm of conversations between managers and reps.
Which suggests that the AI question, when you follow it back, is really a sales question wearing different clothes.
Three things worth looking at first
Before making any decision, here’s 3 things to think about.
The honesty of your forecast. Can your team genuinely separate hope from commitment? When a deal sits in “commit”, is that backed by something specific, or is it the bucket where things go that we’re hopeful about? AI on top of an honest forecast can make it sharper. AI on top of a hopeful forecast just gives you “better presented” hope.
The depth of your qualification. If you asked your best rep, today, who specifically signs the cheque on their biggest open deal — and what changes in that person’s life if they don’t buy this quarter — how would they answer? AI works at the speed of the data the rep is gathering. If the gathering isn’t happening, there isn’t much for the technology to amplify.
The rhythm of your coaching. Does anyone in your business change how they sell from week to week because of a structured conversations with their manager? One-to-ones in many businesses are reporting meetings — useful, but not the same thing as coaching. AI can transcribe and summarise, but only a human conversation seems to change behaviour.
Answer these three questions honestly and you have a clear sense of how much your business will get from AI. Anything you find that needs work, work on it first.
AI is a chapter, not the spine
There’s no doubt AI needs to be embraced but if your sales set up is all wrong, AI will serve only to amplify the mess.
I would suggest a deeper dive into your sales strategy before you look at an AI strategy.
AI sits inside the sales strategy as a chapter — a significant one, increasingly — but the spine of the conversation is still what it has always been. “How are we selling?” “Are we doing it well?” “Do the fundamentals hold?”
If those fundamentals are sound, AI gives you real leverage. If they aren’t, AI tends to expose that more honestly than any consultant could. Which is uncomfortable, but useful.
Maybe the most interesting thing about where we are right now is that AI isn’t really the story but what it makes visible is.
Thanks for reading
