How confident should you really be? A January reflection for transformation leaders

January is an interesting month.

There is energy again. Conversations feel constructive. Plans are signed off, and teams are back in motion. After the disruption of the previous year’s closing down, January brings a sense of control and possibility.

It’s also the point when we leaders feel most confident about the year ahead.

What I have learned over time is that this confidence leaders feel is not a bad thing. It is necessary. But it can also be misleading if it goes untested.

Many of the programmes I have seen struggle in later months of the year did not start badly. In fact, most of them started with the same optimism, intent and commitment we all recognise in January. What caused them to struggle was not a lack of effort or capability. It was a lack of understanding of, and a lack of challenging of, that early sense of confidence.

Confidence feels good, but it is not the same as resilience

Early progress is easy to evidence, and it generates positivity just as easily.

Plans exist, milestones are met, people are engaged; reporting looks reassuring.

But at early stages, delivery has not yet been asked to operate under sustained pressure. Dependencies have not tightened, operational teams have not yet absorbed the full impact of change, and governance has not yet had to navigate difficult trade-offs.

Confidence at this point is often real, generating vital positive energy. But it’s important to realise that it’s also unproven.

How confident a programme feels in January is far less important than how resilient it will be when conditions become less forgiving. That resilience rarely comes from pace alone. It requires clarity.

Where over confidence goes unchecked

Across years of working with transformation leaders, delivery teams and boards, I’ve noticed that over confidence tends to go unchecked in similar places.

Delivery readiness is often assumed rather than examined. Plans look coherent, but ownership of dependencies and decision points is not always clear enough to withstand pressure.

Assurance is frequently interpreted as activity. Testing is happening, but there is limited shared understanding of what has genuinely been validated versus what is being relied upon through assumption or supplier confidence.

Operational impact is acknowledged, but not fully felt yet. Teams know change is coming, but readiness to absorb it is often deferred until later, even though time is likely to be shorter and options fewer then.

Governance, meanwhile, can look structured and calm while still failing to surface emerging risk early enough. In January, escalation can feel disproportionate. Later in the year, it feels overdue.

None of the gaps I’ve just described are unusual. But it’s important they are recognised early so they can be dealt with more easily.

The question I find most insightful

There is one question I ask again and again in January conversations:

‘If delivery pressure doubled tomorrow, what would break first?’

It might not be an easy question to answer, but then, it’s not a question designed to elicit a feeling of comfort.

The value of the question is not in what the answer is, but in how easily that answer is given. When teams and leaders can respond clearly and consistently, it usually indicates that confidence is grounded in understanding.

When the answer is vague, inconsistent or avoided, it tells us something important. Not that the programme is failing, but that confidence may be resting on assumptions that have not yet been tested.

January is the right time to ask this question, when there is still time and space to act on what the answer reveals.

Why timing matters more than intensity

One of the biggest mistakes I see leaders make is waiting for certainty before intervening.

By the time certainty arrives, options are limited. Decisions become harder, more visible and more costly. What could have been addressed calmly in January becomes urgent in June.

Early in the year, there is still space to adjust scope thoughtfully, strengthen assurance without disruption, bring operations into the conversation meaningfully and ensure governance is genuinely supporting decision making rather than simply reporting status.

Sorting these issues early doesn’t slow delivery. It protects it.

Confidence is a leadership responsibility

Confidence is usually defined as a feeling. But for delivery leaders, it is also a responsibility.

As leaders, our role is not to remove optimism, but to balance it with clarity. To create environments where uncomfortable truths surface early, when they can still be dealt with constructively.

The strongest programmes I have seen are not the ones that start the year most confidently. They are the ones most willing to test the confidence they have before pressure tests it for them.

That willingness is what turns good intentions into sustainable outcomes.

Our actions in January matter more than most leaders realise. But it’s not what we perfect on the surface in January that has the most effect: it’s the deeper questions we choose to answer or avoid that quietly set the tone of the whole year ahead.

Confidence is important, yes. But clarity is essential.