Planning Isn’t the Problem. Pretending Is.
Stop chasing certainty. Build structures that help you adapt when predictions fail.
“Plans are worthless, but planning is everything.” ~ Dwight D. Eisenhower
That line has been on my mind as 2026 gets underway. It captures a truth we all bump into sooner or later. The value of planning isn’t perfect prediction. It’s in the structure planning gives you, so you can adapt when reality disagrees with your plan, when uncertainty kicks in.
A little story...
A few years ago, as a consultant, I walked into a leadership meeting that had all the ingredients for a slow-motion train wreck.
If you’ve ever wondered, “Why are we here?” you’ll recognise what happened next.
Six senior people had shown up, busy, distracted, and already annoyed. It quickly became clear why. The person who’d called the meeting hadn’t defined what “success” would look like. In other words, the uncertainty started before anyone even walked into the room. So the room did what rooms often do in that situation. Confusion turned into frustration, and frustration turned into anger at the feeling that their time was being wasted.
Here’s the thing: I don’t think the convenor was being careless. In their mind, there was already a kind of certainty: “I’ll get the right people in a room, and we’ll sort this out.”
What they underestimated was how quickly lack of clarity creates uncertainty, and how uncertainty changes how people show up.
I’ve seen this dynamic for years, not only in organisations, but also through music. When you’re performing live, you can’t control everything in the moment. The room. The energy. The unexpected mistake. But you can rely on structure: a shared rhythm, cues, listening, and a clear sense of where you’re going next.
That structure doesn’t remove uncertainty. It makes it workable. In a sense, it becomes the plan. Not a prediction of what will happen, but the structure that lets you adapt when what you expect doesn’t materialise.
So in that meeting, we did something similar.
I invited the convenor to explain the problem they were trying to solve and why they’d brought everyone together. Then I asked each person, one by one:
“What would make this meeting worthwhile for you? What would you like to have at the end that you don’t have right now?”
Within minutes, we synthesised their input into two or three clear outcomes, prioritised them, and agreed on a simple way of working. I also made a deal: if we achieved the outcomes early, we’d end early.
What happened next stunned the group. Not only did they reach better agreements than expected, but they also did it faster than expected. Afterwards, more than one person said they’d never experienced a meeting like that before.
My takeaway is simple: clarifying outcomes gave people their why for being there. That reduced the uncertainty that was fuelling frustration, and the meeting became productive again.
Which is why I’ve been thinking a lot about this as we set big plans for 2026. The goal isn’t to eliminate uncertainty. It’s to stop pretending we can. Then lead in a way that gives people enough structure to think clearly and move forward anyway.
There’s a big difference between trying to remove uncertainty (which is often impossible) and creating enough process clarity that people can work with it.
Planning isn’t the problem. The problem is pretending a plan can remove uncertainty, and then being surprised when people react like humans.
That distinction sits at the heart of three conversations on the Leading People podcast, each one providing unique insights. I’ll link to each episode at the end, as usual.
Stop over-investing in predictability
Margaret Heffernan challenges a deeply embedded leadership reflex: the idea that the job is to forecast, plan, and execute, as if prediction is the primary path to performance.
But in a world where forecasting is fragile, “forecast–plan–execute” can become a kind of false comfort. The stronger capability is adaptation. Learn fast. Course-correct fast. Build organisations that don’t collapse when the plan meets reality.
Practical takeaway:
Treat your 2026 plan as a hypothesis, not a promise. Then design for learning loops: short cycles, frequent review, and rapid adjustment.
“Plans don’t fail because people didn’t think hard enough. They fail because the future refused to cooperate.”
In other words, planning still matters. It’s the pretending that the future will cooperate that trips leaders up.
Change breaks when the threat system takes the wheel
Hilary Scarlett's message is both practical and reassuring: a lot of what looks like “resistance” to a plan is often a human response to uncertainty.
When uncertainty is high, and people can’t find their footing, especially when the “why”, the “what”, the "how", and the “what happens next” are unclear, the brain fills in the gaps. Usually with worst-case stories. That’s when you see behaviours that look like a lack of buy-in. Often, it’s a threat response doing what it was designed to do.
Practical takeaway:
Don’t only communicate the vision. Communicate the stabilisers: outcomes, roles, next steps, update rhythm, and small wins people can actually feel.
“Change doesn’t fail in the org chart. It fails when uncertainty triggers threat, and thinking shuts down.”
Uncertainty tolerance isn’t evenly distributed
This conversation with Professor Patricia Riddell & Ian McDermott adds a crucial layer: leaders often assume uncertainty lands about the same way for everyone.
It doesn’t.
Some people stay calm and curious. Others experience uncertainty as an immediate risk. If we ignore those differences, we misread people. Then we design and plan change in ways that accidentally overwhelm.
Practical takeaway:
When you can’t reduce uncertainty, translate it. Make the “known/unknown/next update” explicit, and increase choice where possible.
“The same change can feel like possibility to one person, and danger to another.”
So the question becomes: if we can’t eliminate uncertainty, what can we do, practically, to stop it from derailing performance?
When uncertainty rises, lead with “process clarity”
One of the simplest leadership moves I’ve learned (and re-learned) is this:
You don’t need to pretend you can predict the future.
But you can prevent uncertainty from turning into frustration by increasing process clarity.
When you can’t remove uncertainty, you can still reduce the brain-load it creates.
A practical way to do that is to answer three questions explicitly, even if the answers are imperfect:
What are we trying to achieve right now?
(Outcome. What “worthwhile” looks like.)
What do we know, and what don’t we know yet?
(Knowns and unknowns, said out loud, not assumed.)
What happens next, and when will we review?
(Cadence. The moment people stop catastrophising and start thinking again.)
This is especially important because people don’t experience uncertainty in the same way.
For some, it activates curiosity and creativity. For others, it activates threat and drains mental bandwidth. Naming the three things above doesn’t remove uncertainty. It makes it workable.
If you take one thing from these conversations, it’s this: don’t abandon planning. Abandon pretending. Then replace it with process clarity.
One small experiment for this week
Next time you call a meeting or launch a change conversation, open with these three lines:
- Outcome: “By the end of this, we will have…”
- Boundary: “What we probably won’t solve today is…"
- Next step: “After this meeting, here’s what happens next, and you’ll hear more by [date]”
Two reflection questions
Where are we mistaking planning for certainty right now?
What’s one place we could increase process clarity (outcomes, next steps, rhythm) without pretending we can predict everything?
Want to explore this further?
If you’re planning a major change, leadership development, or a culture shift in 2026, it may help to pressure-test where uncertainty is predictable and where you can strengthen process clarity so people stay constructive.
At Wide Circle, we apply neuroscience and behavioural science to help leaders and organisations build practical capability in three areas:
- Talent Insights (getting the right people in the right roles)
- Performance Leadership (strengthening leadership habits that drive engagement and results)
- Collaborative Capacity (building trust and conflict-resilient teamwork)
🌐 Visit our website https://www.widecircle.eu
Let’s start a conversation
What’s one leadership move you’ve seen that instantly reduces uncertainty in a team?
Where do you notice leaders accidentally amplifying uncertainty (usually without meaning to)?
If you’d like, comment here or message me. I read everything, and I genuinely enjoy the back-and-forth.
And if you know someone making big plans right now, feel free to share this edition with them. It may save them at least one frustrating meeting.
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