re:position
A monthly newsletter and community round-up, shining light on the art and science of powerful market positioning.
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Confidence tricks
When certainty feels like relief
Early last year, I incorporated AI as a participant in a live customer workshop for the very first time. A bold move for this naive but enthusiastic adopter of AI supported workflows. If all else fails I figured, at least it won’t scoff the sausage rolls at morning tea.
So there I was, face to the whiteboard, deep in a market segmentation exercise. Segmentation is the domain of fuzzy logic, where a team’s patience and imagination are eventually rewarded with a crisp new market planning model.
We asked the AI clarifying questions, to test our assumptions, and so it replied in the perfectly structured and certain tone of an LLM. In the midst of the intellectual fog of the exercise, I was amazed and energised by how crisp and sure its answers were. I could feel a weight being lifted off the team as our questions were responded to with apparent fact. It felt like we nailed it.
The danger of confident answers
Now, you can probably guess what was going on here, because I think we’ve all been there by now.
In the middle of this genuinely hard task, we were being offered an easy way out. A short cut. The answers, so clear and professionally expressed, didn’t invite doubt in any way. So as we lifted this human-AI cadence throughout the day, it didn’t occur to us that the AI might be mistaken in any way. And boy, was it wrong! Every answer that we didn’t challenge took us incrementally further away from the reality that we were seeking to understand.
It wasn’t the hallucinations
A year on, I think we’ve all experienced enough AI hallucinations to work with the tools in a different way. But the lesson from that day has stuck with me and neatly expresses the challenge we face as strategic problem solvers.
In market positioning we’re always working with hypothetical situations. It’s the OG of fuzzy logic in business planning, where we try to predict future outcomes using wildly disparate and disconnected sources of data or insight.
Hence my issue wasn’t that the facts got a bit jumbled by AI. It was that we didn’t bother to question them. And I want to really work out why. Because it’s not just the confidence of an LLM that does this to us. The confidence bestowed by hierarchy or personality are equally likely to lead us astray in the same way.
Confidence is not competence
When somebody says something strongly, when was the last time that you questioned the source? “Why exactly do you know that is true?” might be the most under-used question in business.
Now the psychologists amongst you will already be calling out why. The human brain, just like an LLM, seeks out patterns as it enables more energy efficient thinking. So when something is told clearly and definitively to us, it offers subconscious relief to our energy hungry brain. Our mind stops searching once we have an answer that fits our pattern or simply feels plausible enough for now.
Of course, this is severely compounded by our Authority bias, which nudges us to react more positively to senior figures in our social hierarchy. We are all part of this. We subconsciously protect our own status by making strong, authoritative statements that are unlikely to be challenged. We’re hard wired to enjoy being right, yet competence and confidence are not the same thing.
Beliefs masquerading as insight
So what's the simple lesson here for our positioning projects? After all, during any insight or strategic process we have to evaluate rock-hard, uber-confident statements all the time.
“Customers don’t value us anymore.”
“Our market is too crowded.
The clearer and more confident a statement sounds, the more suspicious we should be.
Such definitive statements are usually well intended. But when we’re trying to separate facts from feels, such confident statements as best gently challenged as they are often just personal beliefs masquerading as insight
Learning to sit with the grey
I have a simple rule, that you might want to adopt.
"Confidence prompts curiosity."
Not because a confident or clear statement is automatically wrong, but because the real world we’re positioning for just isn’t that neat. Markets are messy, and the most important truths in your business are never black and white. Taking statements on face value often misses something more valuable underneath.
So I’m learning to treat confidence as an invitation to find out more. And this has meant remembering to challenge my own thinking, as rigorously as anybody else’s. Which as a consultant whose ego loves an intellectual mic-drop, has been a challenge.
In 2026, let’s all be content to spend more time enjoying the grey areas. It’s usually where the magic lies.
Article from the January 2026 re:position
Why certainty should make you nervous. Confidence feels like relief. That’s the problem. READ THE FULL NEWSLETTER HERE and SIGN UP HERE if you’d like to receive this in your inbox next time.
Browse our past issues of re:position, and sign up at the bottom of the page if you’d like to get it in your inbox.
November 2025 re:position
Do it til it’s done. Celebrate the year's end with us. Read here
October 2025 re:position
The question every board should be asking. Who really owns your positioning? Read here
September 2025 re:position
The most valuable asset in your business. A simple exercise to reset positioning and performance around reality . Read here
August 2025 re:position
Value is the villain. Most businesses kill their positioning by talking about “our value” instead of the outcomes their customers actually care about. Read here
July 2025 re:position
In praise of Plan B. Rethinking the back‑up plan: why 2025 might call for a Plan B renaissance. Read here
June 2025 re:position
Is export the wrong problem to solve? Forget “build it and they will come.” It’s time to rethink how we scale. Read here
May 2025 re:position
A little south of Huntly. Inspired by a flight home from a recent workshop, I found myself connecting the dots of light below, which made me think about how our words work in similar ways - guiding decisions and perceptions. Read here
April 2025 re:position
Change is inevitable. 2025 has been a bumpy ride so far, and it’s not slowing down. Find out why focusing on what you can control is essential for your strategy. Read here
March 2025 re:position
Scared of similar? Marketers are obsessed with originality, but maybe it’s time to stand up for being more alike. Here’s why. Read here
February 2025 re:position
A productivity challenge for 2025. Execution is where strategy comes to life. Why do we get stuck, and how do we move faster? Read here
January 2025 re:position
2025, we made it. So what now? The truth about January. It’s tempting to let the month slip by in a summer haze, but January could be your most strategic month yet. Read here
December 2024 re:position
Wrapping up 2024 with gratitude and a special invitation. A quick thank you, a sneak peek at 2025, and a fun chance to kick off the year with an 'Ask Me Anything' clinic. Enjoy your holidays, and see you in the new year! Read here
November 2024 re:position
Embrace sales! It's time to grow 📈 Let’s address sales investment phobias and the impact this has on growth. Read here
October 2024 re:position
Don't let ghost value haunt your strategy - Ghost value can creep in unnoticed - let's explore how meaningful differentiation can keep your strategy sharp and scare off sameness. Read here
