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Humility in Leadership: The Year Between Planning and Pressure

I’ve written before that humility in leadership isn’t about modesty.

It’s about accuracy.

Accuracy about what you know.

Accuracy about what you don’t.

And accuracy about how your decisions land on the people doing the work.

The turn of the year invites reflection, but reflection only matters if it sharpens judgment. For me, 2025 was the year leadership stopped being theoretical and became operational.

When the Work Gets Real

2025 wasn’t about bold ideas. It was about exposure.

It was the year plans stopped being safe. Slide decks turned into contracts. Assumptions ran headfirst into budgets. Timelines met weather, labour constraints, permitting realities, and the simple fact that people are not infinitely elastic.

This is the point where leadership either matures or becomes performative.

When the work is still conceptual, confidence is cheap. When the work becomes real, confidence has to be earned. Every decision starts to carry weight beyond the room it’s made in, and every gap in thinking shows up somewhere downstream, usually on someone else’s shift.

Earlier in this series, I’ve written about humility in decision-making: slowing down long enough to choose well. In 2025, that wasn’t a philosophical stance. It was an operational necessity.

Decisions were no longer isolated. One call affected ten others. One compressed timeline created risk somewhere else. One “we’ll sort that out later” quietly became someone else’s problem to manage under pressure.

Humility showed up in unglamorous ways:

  • Asking questions earlier than felt comfortable
  • Letting experts complicate the plan instead of simplifying it for convenience
  • Admitting when an assumption didn’t hold up once it met reality

It also showed up in resisting the urge to appear certain when certainty wasn’t warranted. Saying “I don’t know yet” isn’t weakness when the alternative is false confidence.

When the work gets real, humility stops being a value you talk about and becomes a discipline you practice often privately, often under time pressure, and usually without recognition.

That’s the shift 2025 demanded.

Restraint Is Not Hesitation

Momentum is real. And it’s dangerous if you don’t respect it.

When alignment builds and timelines lock, the pressure is to keep moving. Faster decisions. Tighter windows. Fewer pauses. At that point, speed starts to get confused with progress.

That’s where restraint matters.

In 2025, restraint wasn’t about slowing things down for the sake of caution. It was about being honest about where the work actually was, not where we wanted it to be.

Restraint showed up as:

  • Not presenting the work as “ready” when readiness was uneven
  • Allowing subject-matter experts to challenge direction without reframing that input as resistance
  • Saying “not yet” when the conditions to move simply weren’t there

None of that felt comfortable. It would have been easier to keep momentum going and deal with the consequences later.

But restraint is what protected the work from avoidable rework.

Rework is one of the most expensive failures in leadership. It costs time, trust, and energy, and it almost always lands on people who had no role in creating it. Preventing rework rarely looks decisive in the moment, but it’s one of the clearest signs of sound judgment over time.

Restraint isn’t hesitation. It’s choosing not to trade short-term confidence for long-term problems.

Listening as Risk Management

Listening is often framed as a courtesy. In complex work, it’s something else entirely.

It’s risk management.

In 2025, the most useful information rarely came packaged as certainty. It came as hesitation, concern, or a quiet “this might be an issue later” from people close to the work. Those signals are easy to dismiss when timelines are tight and pressure is rising.

They’re also the ones that matter most.

Humility required treating those inputs as data, not disruption.

That meant listening to people who weren’t responsible for the final decision, but who would live with the outcome. It meant paying attention to friction early, when it was still cheap to address, instead of waiting until it showed up as something that needed to be managed under pressure.

It also meant resisting the urge to immediately fix things.

Not every concern needs a solution on the spot. Some need space to be understood properly. Jumping too quickly to resolution can be just as risky as ignoring the issue altogether.

Listening, done well, didn’t slow the work down. It made the risks visible while there was still time to do something about them.

Ignoring those signals doesn’t make risk disappear. It just defers it—and usually hands it to someone else to deal with later.

That’s not efficiency. That’s avoidance.

Preparation Has No Applause

Preparation is where leadership gets quiet.

There’s no recognition for validating assumptions, pressure-testing timelines, or building contingencies that may never be used. Most of that work is invisible by design. If it’s done well, it disappears into the background.

In 2025, that was the work that mattered most.

Preparation meant being honest about how systems behave under strain, not how we wish they would behave on paper. It meant planning for fatigue, turnover, weather, delays, and imperfect information—because those aren’t edge cases. They’re the operating conditions.

It also meant acknowledging limits. No matter how experienced the team, no one can hold the entire operation in their head. When preparation relies on individual knowledge instead of shared systems, it becomes fragile. When it’s embedded in clear roles, repeatable processes, and decision pathways that work under pressure, it becomes resilient.

This kind of work rarely feels urgent in the moment. It’s easy to deprioritize because the payoff isn’t immediate. But the absence of preparation always shows up later—usually as rework, last-minute fixes, or stress that lands on people who had no role in creating the gap.

Preparation isn’t about controlling every outcome. It’s about reducing the number of things that can surprise you at the worst possible time.

There’s nothing flashy about this work. It doesn’t create visible wins or easy stories. But it’s where humility becomes discipline: doing the unremarkable work early so others aren’t forced into heroics later.

That’s not cautious leadership. That’s leadership that respects the people doing the work.

Looking Ahead to 2026

If 2025 was about building the system, 2026 will be about running it under sustained pressure.

The work itself won’t suddenly become harder, but the conditions will be less forgiving. Time will compress. Decisions will stack. And the space to recover from a wrong call will narrow.

Leadership in 2026 won’t just be about making good decisions. It will be about making enough good decisions in sequence, without the luxury of pause. Issues won’t arrive one at a time. They’ll overlap, compete for attention, and often demand action before the full picture is clear.

That changes the nature of the work.

Decision density will increase. Context-switching will become constant. The mental load of holding multiple moving parts at once will grow heavier, not lighter. Leaders who treat each decision as a standalone problem will struggle. The work will demand an awareness of cumulative impact—how one choice limits or enables the next, and how today’s decision shapes tomorrow’s options.

This is also where fatigue becomes operational risk.

When there’s no space between decisions, small errors compound quickly. Judgment erodes faster than people realize, especially when urgency becomes the default setting. Pretending that people can operate indefinitely at that level isn’t resilient leadership—it’s wishful thinking.

Humility here means respecting those limits. Building space where possible. Designing decision pathways that don’t rely on heroics. And being disciplined about which decisions truly require senior attention, and which are better handled closer to the work.

The challenge won’t be speed alone. It will be sustainability under speed.

In that context, leadership won’t be tested by how well plans read on paper. It will be tested by how those plans behave when assumptions are stressed and time is limited. The value of the groundwork laid in 2025 will be revealed quickly, and without much sympathy.

This is where judgment matters more than intent.

There will be moments where there is no perfect answer—only trade-offs. Moments where the information is incomplete, timelines are fixed, and consequences are real. In those moments, leadership isn’t about finding certainty. It’s about making a call, standing behind it, and adjusting quickly when reality provides new information.

One of the real risks in 2026 will be overcorrection.

As pressure increases, the instinct is to pull decisions closer, add approvals, and centralize control. Sometimes that’s necessary. Often, it isn’t. Systems designed to distribute responsibility don’t suddenly perform better when trust is withdrawn.

The work ahead will require decisiveness without theatrics. Calm without detachment. Visibility without interference.

It will also require leaders to be deliberate about what they choose to react to, and just as deliberate about what they don’t. Not every issue needs escalation. Not every problem benefits from being solved at the highest level.

Part of the work will be creating the conditions for people closest to the ground to make sound decisions—and then standing behind those decisions when they’re made. That support doesn’t mean second-guessing in real time or pulling control upward. It means being present, available, and clear about where authority sits.

Another reality of 2026 is cumulative fatigue—not just physical, but cognitive. Decision density wears people down. Leaders who ignore that reality tend to create more risk, not less. Protecting capacity—your own and your team’s—isn’t a nice-to-have. It’s an operational requirement.

What will matter most is consistency. Doing the right things repeatedly, even when they’re no longer novel or energizing. Holding standards when shortcuts are tempting. Keeping communication clear when time is short.

2026 won’t reward noise, urgency for its own sake, or visible busyness. It will reward clarity, trust, and systems that were built to hold when conditions tighten.

This is where humility shows up again—not as caution, but as steadiness. The ability to remain grounded when others feel compressed, and to lead in a way that makes the work feel possible, not overwhelming.

A Personal Line in the Sand

As the pace increases, I’ve been clear with myself about how I need to show up.

Not with slogans or resolutions, but with a few non-negotiables that matter most when time is short and pressure is high.

I intend to stay curious longer than is comfortable. To listen past my first reaction, especially when the instinct is to move quickly. To name uncertainty early, without transferring anxiety or creating unnecessary noise.

I will correct course when needed and do it visibly. Not defensively. Not quietly. And not by shifting responsibility. Course correction isn’t a failure of leadership. It’s part of doing the work honestly.

I will be deliberate about protecting capacity—my own and the team’s. Not everything needs urgency. Not everything improves under pressure. Creating space where it’s possible to think clearly is part of the job.

And I will work to be calm in ways that are useful, not passive. Calm that steadies the work. Calm that allows others to do theirs. Calm that holds when things are compressed.

These aren’t aspirational statements. They’re practical commitments. The kind that only matter when conditions are less forgiving and the margin for error is thin.

That’s the standard I’m setting for myself as the work moves forward.