23 October 2025
The leadership team gathered for the third time in six weeks. Same agenda: finalising the transformation roadmap.
The COO opened with familiar words: “We need to get this right before we commit.”
Another two hours of debate followed. Questions about resource allocation in Quarter 3. Concerns about capability gaps that might emerge in Year 2. Worries about market conditions nobody could predict.
The meeting ended with: “Let’s schedule another session once we have more clarity.”
Meanwhile, the board was losing patience. The window for moving was closing. Competitors weren’t waiting for perfect plans.
I’ve watched this pattern destroy momentum in organisations facing high-stakes culture and leadership challenges. Leaders confuse thorough planning with readiness. They try to map every turn before starting the journey. They demand certainty before taking the first step.
It feels responsible. It’s actually paralysing.
A colleague once described how mountaineering teams actually approach difficult climbs. It changed how I think about high-stakes decision-making.
They don’t stand at the bottom and plan every foothold to the summit. The summit is the goal, but it’s too far away to see the path clearly.
Instead, they commit to reaching base camp. That’s achievable. That’s visible. That decision they can make with confidence.
Once at base camp, they look around. Weather patterns are clearer. The route to the next pitch reveals itself. Some paths that looked viable from the bottom turn out to be impossible. Others that weren’t visible before open up.
So they make the next decision: which pitch to aim for. Not the summit—the next achievable stop. They reach it, look around again, and make another decision based on what they can now see.
This isn’t cautious. It’s how you actually reach summits when conditions are uncertain and stakes are high.
The difference isn’t about ambition. It’s about how you structure decisions to make progress possible when you can’t see the whole path.
After working with dozens of organisations where boards have major change programmes on the line, I’ve identified why the “decide everything upfront” approach fails predictably.
Information changes faster than plans
You spend three months building a detailed roadmap. Two weeks after approval, market conditions shift. A key leader leaves. Technology you planned around becomes obsolete. Customer needs evolve.
Now your perfect plan is outdated. But you’ve invested so much in creating it—and getting everyone aligned to it—that changing course feels like admitting failure.
So you either stick to a plan that’s no longer optimal, or you restart the whole planning process. Either way, momentum dies.
Commitment paralysing analysis
When you’re trying to make one massive decision that determines the next 18 months, the stakes feel overwhelming. So you keep asking for more data, more scenarios, more assurance.
This doesn’t improve decisions. It delays them whilst creating the illusion of rigour.
I watched a leadership team spend four months analysing a restructure, trying to anticipate every possible implication before committing. By the time they finally decided, the organisational problems they were trying to fix had evolved. The restructure they eventually implemented was solving yesterday’s issues.
Teams waiting for permission
When leadership hasn’t committed to the full journey, teams don’t know whether to start preparing. Should they begin building capability? Reallocating resources? Making trade-offs?
Without clear direction, everyone waits. Meetings happen. Progress doesn’t.
One organisation I worked with had teams asking for six months: “Are we doing this or not?” Leadership kept saying “We’re still finalising the approach.” By the time the decision came, the teams had mentally moved on. Energy was gone.
Board confidence eroding
Boards don’t lose confidence because decisions are imperfect. They lose confidence because leadership can’t demonstrate the ability to make decisions and execute under pressure.
When leadership asks for “just one more month to get clarity” repeatedly, boards see capability gaps, not thoroughness.
Through our Build phase work with organisations facing pressing culture and leadership challenges, we’ve refined an approach that makes progress possible when certainty doesn’t exist.
Define the next achievable milestone, not the perfect end state
Instead of asking “How do we get all the way to the summit?” we ask: “What’s the next stop we can commit to with confidence?”
This might be: “We’re implementing the new structure in Division A first. Three months, defined scope, clear success criteria.”
Not: “We’re restructuring the entire organisation over 18 months with these specific outcomes in every division.”
The first decision is achievable. The second paralyses.
A CEO I worked with was facing board pressure to transform their culture. Instead of committing to a three-year culture programme, we helped them commit to a 12-week diagnostic and pilot with their leadership team.
That decision they could make immediately. The board saw movement. Teams saw commitment. And critically, after 12 weeks they had real data about what actually worked—which informed the next decision with evidence, not assumptions.
Build in decision points, not just milestones
Traditional roadmaps show milestones: “Q2: Complete Phase 1. Q3: Launch Phase 2.”
We build decision points: “Week 12: Review pilot results and decide whether to scale as planned, adapt the approach, or pivot based on what we’ve learned.”
This isn’t leaving things open-ended. It’s acknowledging that you’ll know more at Week 12 than you do now—and that future decision will be better informed.
A CHRO told me: “This felt risky at first. What if we get to Week 12 and realise we need to change course? Then I realised: we’d rather discover that at Week 12 than at Month 9 after we’ve committed everything to a plan that isn’t working.”
Make decisions reversible when possible
Not every decision needs to be permanent. When you frame decisions as “We’re committing to this forever,” they become terrifying. When you frame them as “We’re doing this for the next three months, then assessing,” they become manageable.
Some decisions are genuinely hard to reverse—hiring senior people, large technology investments, major structural changes. For those, take time to get them right.
But most decisions are more reversible than leaders admit. Pilot programmes. Process changes. Team formations. New ways of working.
Make those decisions quickly, learn from them, and adjust. Speed of learning beats perfection of planning.
Create explicit criteria for the next decision
When you commit to base camp, don’t leave the next decision vague. Define what you’ll evaluate when you get there:
“At the end of Quarter 1, we’ll assess: Did capability improve measurably? Did the board see tangible progress? Did teams report clearer expectations? If yes to all three, we scale. If no to any, we adjust the approach before expanding.”
This does two things. First, it makes the current decision feel less risky because the next checkpoint is explicit. Second, it ensures the next decision is data-informed, not political.
Communicate the approach, not just the decision
When you announce “We’re implementing this change,” people hear a massive commitment and either resist it or wait passively to see what happens.
When you announce “We’re starting with Division A for three months, learning from that, then deciding the best way to scale,” people hear a thoughtful approach that values learning.
The second creates buy-in because people see you’re not gambling everything on one decision. You’re testing, learning, and adapting—which feels competent in uncertain conditions.
When we implement this approach through our Build–Embed–Sustain™ methodology, several shifts become visible.
Momentum returns
Instead of spending six months planning, teams are moving within weeks. Not recklessly—strategically, with clear next steps and defined checkpoints.
A COO told me: “The energy change was immediate. People stopped waiting for the perfect plan and started solving the problems in front of them. Progress became tangible.”
Risk actually decreases
This feels counterintuitive. Surely one big well-planned decision is less risky than multiple smaller ones?
No. Because big decisions made with incomplete information are gambles. Small decisions with frequent checkpoints are experiments.
You learn faster. You catch problems earlier. You adjust before small issues become crises. Risk doesn’t disappear—you manage it more actively.
Board confidence improves
Boards don’t want perfect plans. They want evidence that leadership can execute under pressure.
When you demonstrate the ability to make decisions, implement quickly, learn from results, and adapt based on what you discover—that builds confidence.
A CEO facing board scrutiny told me: “Once we started showing progress in three-month increments with clear decision points, the board stopped questioning our capability. They could see we were learning and adapting, not just hoping our initial plan was perfect.”
Teams become more engaged
When people see that decisions aren’t set in stone—that leadership is willing to learn and adjust—they engage differently.
They raise concerns earlier because they know those concerns will inform the next decision. They offer ideas because there’s a mechanism for incorporating learning. They commit more fully because the approach feels realistic, not aspirational.
Culture becomes more adaptive
This is the deeper shift. Organisations that practice iterative decision-making don’t just make better decisions. They build cultures that learn faster.
Through our Learning Organisation Framework™, we’ve seen this transformation repeatedly. Teams stop defending original plans and start focusing on outcomes. Feedback loops tighten. Problems surface earlier. Adaptability becomes organisational muscle memory.
When boards have major programmes on the line and culture or leadership issues are jeopardising delivery, iterative decision-making isn’t optional. It’s survival.
You can’t wait for perfect information when windows are closing. You can’t commit to 18-month plans when conditions change monthly. You can’t build confidence through perfect execution of rigid plans—you build it through demonstrated ability to adapt intelligently.
This is why iterative decision-making sits at the heart of how we work with organisations facing pressing challenges. Not because we’re avoiding commitment, but because we’re structuring commitment in ways that make success possible under uncertainty.
If your organisation is trapped in planning paralysis and your board is losing patience, try this:
Identify one major decision you’re struggling to make. Instead of asking “How do we solve this completely?” ask: “What’s the smallest meaningful step we could take in the next four weeks that would teach us something valuable?”
Make that decision. Take that step. At four weeks, gather the team and ask: “What did we learn that we didn’t know before? Based on that, what’s our next step?”
You’ll notice something: the second decision is better informed than the first could ever have been. And you’ve made progress whilst others are still planning.
Then apply this approach systematically. Replace annual planning with quarterly decision points. Replace “Here’s the 18-month roadmap” with “Here’s where we’re going, here’s our next three-month commitment, and here’s what we’ll evaluate before deciding the next phase.”
That leadership team stuck in their third planning meeting revealed a pattern I’ve seen repeatedly: confusing thoroughness with readiness, and mistaking perfect plans for executable strategy.
Climbers reach summits not by planning every step from the bottom, but by committing to achievable milestones, reaching them, looking around, and making the next decision based on what they can now see.
In high-stakes situations where boards are watching and programmes must succeed, this isn’t caution. It’s how you actually make progress when conditions are uncertain and perfect information doesn’t exist.
Stop trying to commit to the summit in one decision. Commit to base camp. Get there. Look around. Make the next decision better informed.
Then keep moving—look around, take stock, move forward. Again and again until you’ve climbed mountains that others said required perfect plans you’d never achieve.
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Dr Ioan Rees
Ioan is a Chartered Psychologist and founder of SYCOL, the psychology-led consultancy that works in stakes, not sectors. Leaders call him in two situations: when culture and leadership issues are undermining major change programmes, or when they need high-performance infrastructure for ambitious growth. He’s spent over 15 years helping CEOs and executive teams build the culture and leadership systems that make strategy succeed, especially under pressure. Known for his direct approach and blend of science and pragmatism, Ioan created the Build–Embed–Sustain™ methodology after working with organisations across tech, media, finance, and public service. He also contributes regularly to national television as a psychology expert.
