SALES STRATEGY
tactically. The work is knowing which situation you are actually in. That migration is what carried John to an unlikely place: the cock- pit of a fighter jet. The Air Force strategist John Boyd built a deci- sion model called the OODA loop – observe, orient, decide, act – after recognizing that winning a dogfight was never really about who had the faster plane. It was about who could read a changing situation and de- cide faster than the pilot across from them. See the sidebar for more. John has adapted the same loop to how a salesperson should work alongside AI, and his version is not complicated. Let AI do most of the observing. It can scan an account, detect what has changed, and compress information at a speed no seller can match. Orienting becomes a genuine partnership – with AI proposing what a leadership change or a funding round might mean, and the salesperson supplying the con- text and the relationships AI does not have. However, John insists that the de-
ciding stays entirely human. Pursue the opportunity or not. Challenge the customer’s assumption or not.
Hold the price or not. I think he is right, for a reason simpler than any framework: The AI does not have to look the customer in the eye afterward. We do. Acting is the one stage where the balance is shifting: meeting prep, follow-up drafts, CRM updates, the repeatable work sales teams are increasingly comfortable handing off once the system proves it can be trusted.
WHAT COMES NEXT? Near the end of our conversation, John brought the whole arc back to something you could do this afternoon. Take the most important deal on your desk right now. Do not ask AI to write another email. Ask it to investigate. What has changed inside this account? An acquisi- tion, a departed executive, a new market, a missed target, a strategy shift. Then push further. What might those events actually mean? And what problem might be developing underneath them that the customer has not fully connected yet? John recently used this exact
approach to revive a deal that had stalled in operations, and the break- through came from research into
circumstances the buyer had never disclosed. In miniature, it’s precisely what John did with his own two feet 30 years ago: walking through a Wall Street building – meeting after meeting – until he found the thing nobody had connected yet. AI did not replace that instinct. It gave it a much faster engine. Which is, I think, the real answer to
the question everyone keeps asking about AI and sales. We keep asking whether it will replace salespeople. AI will certainly replace pieces of what salespeople do. It will research faster, write faster, summarize faster, prepare faster. But none of that was ever the deepest reason a customer needed a great salesperson in the room. Great salespeople help cus- tomers see.
Thirty years ago, a CIO dismissed a young John Stopper in one sentence. John could have heard rejection. He heard an assignment instead, and he came back with something the man did not know. AI has now handed every buyer on Earth the ability to say the same thing to every salesperson they meet. The only difference is what it now takes to answer it.
Who Should Fly the Plane? John Stopper’s OODA Model for AI and Sales, from The Compass
Fighter pilot and military strategist John Boyd developed the OODA loop – observe, orient, decide, act – to explain how people prevail in fast-moving situations. John Stopper applies it to today’s sales situation, where a salesperson and AI share the same cockpit. 1. Observe: AI takes the lead – scanning accounts, researching, surfacing patterns a human would miss. 2. Orient: Human and AI work together – AI proposing what the signals mean, the salesperson supplying con- text and relationships.
3. Decide: The human takes the controls – AI can recommend, but the salesperson owns what to pursue, chal- lenge, risk, or promise the customer.
4. Act: Control shifts gradually to AI as trust is earned – starting with meeting prep, follow-up drafts, and CRM updates. The lesson is not that humans have to do everything. It is that automation and authority are not the same thing. AI can help you see faster, think faster, and increasingly act faster. But when the decision matters, someone still has to own it. That is the salesperson’s seat.
You may contact John at
jstopper@northstar8.com.
14 | SEPTEMBER/OCTOBER 2026 SELLING POWER © 2026 SELLING POWER
Page 1 |
Page 2 |
Page 3 |
Page 4 |
Page 5 |
Page 6 |
Page 7 |
Page 8 |
Page 9 |
Page 10 |
Page 11 |
Page 12 |
Page 13 |
Page 14 |
Page 15 |
Page 16 |
Page 17 |
Page 18 |
Page 19 |
Page 20 |
Page 21 |
Page 22 |
Page 23 |
Page 24 |
Page 25 |
Page 26 |
Page 27 |
Page 28 |
Page 29 |
Page 30 |
Page 31 |
Page 32 |
Page 33 |
Page 34 |
Page 35 |
Page 36 |
Page 37 |
Page 38 |
Page 39 |
Page 40 |
Page 41 |
Page 42 |
Page 43 |
Page 44 |
Page 45 |
Page 46 |
Page 47 |
Page 48 |
Page 49
