Most roundtable sessions follow a familiar script. People shuffle in with coffee and polite smiles, someone flips open a notebook and the waiting game begins. Who’s brave enough to go first? Not this time. At our Now to Next roundtable, we skipped the warm-up. Within minutes, half-baked challenges were flying; raw, messy, but refreshingly real. Then we brought in Jane.

Jane is our AI agent, but in the room she felt more like a sparring partner. She nods thoughtfully, then asks the question no one else will. Sometimes too direct, always useful. Because let’s face it: we all want sharper strategic thinking. We just don’t always get the nudge that gets us there. That day, Jane was the nudge.

Every strategy needs that person, the one who pokes at the logic without poking at you. But let’s be honest, that role gets awkward fast. No one wants to sound harsh. We’re all trying to be collaborative, polite… nice.

We brought in Jane. Jane asked the tough questions in a way that felt, well, nice. Suddenly, the mood shifted. We stopped clinging to our first ideas and explored what was underneath them. Even though the questions got harder, the whole conversation felt easier.

As we added detail, Jane pushed us further. She highlighted implications most leaders only see later, usually because there’s no time to pause and really inspect a strategy. Simple and obvious-in-hindsight. But that’s the thing, direction always feels brilliant once it finally shows up, doesn’t it?

• A broader ICP lowers lead quality.
• A weak distribution plan kills momentum before it starts.
• If sales isn’t involved early, the strategy gets rewritten anyway.
• If success is vague now, it’ll still be vague later.

We all tidy up our strategy more than we think. We smooth the edges, skip the awkward bits and share the neat version instead of the real one. But Jane kept poking at the parts that don’t fit into summaries, the constraints no one wants to deal with, the mess we hope will sort itself out. And once we stopped cleaning things up, something shifted (again!).

The quality of thinking jumped. The logic got sharper, we finally had shared context and not just the polished headline, but everything underneath it. Turns out, the unpolished version of a problem is often the most useful one, because that’s where the context lives.

Looking back, the surprising part wasn’t the AI. It was how the presence of a calm, steady challenger changed us. When something in the room refuses to let weak assumptions slide, we show up sharper. When the hard question’s already out there, no one has to tiptoe. When future consequences show up early, decisions get simpler. That’s what strategy often miss: the right kind of friction, at the right time.

We talked about the conversation rather than the tool. And that is the most encouraging part. AI is accelerating the part of strategy that usually takes the longest, is working as a sparring partner, is creating the room so that moving from now to next doesn’t feel like a leap. It feels like the natural way forward for any leader who wants to build better strategies.

Want to sit at the table next time? Keep an eye on our events page. We love new thinkers!

– Written by Marijke Vreugdenhil, Managing Director at Tech to Market.