Readiness was never the destination

During a workshop a few years ago, I asked an executive group what their ‘ready for anything’ song was. The song you play when you know you need to bring your A-game. As you may expect, many gave songs like Eye of the Tiger by Survivor. Galvanize by The Chemical Brothers. Get Ready for This by 2 Unlimited. All conveying agency, action and forward momentum. (It’s a great playlist accumulated over a year, by the way, if you want a copy.)

One song choice was unexpected. Beethoven’s Moonlight Sonata. If you know it, you will hear it instantly. Slow, steady, a little haunting.

The executive told us in the year after COVID, they played it every morning on the drive to work deliberately. For them, readiness was not about generating more energy. It was about finding calm before entering the storm waiting inside the doors of their workplace, so they could make better decisions and convey the equanimity their people needed.

The song choice was not motivation. It was preparation.

Being ready for anything is a phrase used constantly and defined rarely. In 2023, Harvard Business Publishing Corporate Learning surveyed more than 1,300 leaders globally, and its report named being ‘truly ready for anything’ as the main development need. I started to ask people what it meant to them. The answers were always varied. Courage. Resilience. Competence. Agility. Adaptability. All fine, and all a little elusive, a mix of adjectives, verbs and nouns standing in for a definition. This is why the question has rattled around unsettled in my brain ever since.

Confidence is an unreliable measure

Many people treat readiness as a feeling. They connect it to a moment that is unfamiliar, important or outside the norm. There is no playbook to follow; they feel out of their depth, and they conclude they are not ready.

Many describe the resulting doubt as impostor syndrome. I prefer to read it as the brain doing its job, scanning for threat. It is why I love the expression "doubt means prepare". Searching for confidence is not the solution.

Confidence can feel reassuring, yet it is not always evidence of capability. We have all encountered people who speak with complete conviction while missing half the picture. Equally, highly capable leaders often question themselves because they understand the complexity of what they are facing.

When we associate readiness with feeling confident, we turn it into an emotional destination, and leaders wait for a feeling that may arrive too late, or not at all, when critical decisions are required.

A more useful question is not, am I ready for anything? It is, am I sufficiently clear about the context to take the next responsible action?

Our state matters, but state alone is not enough. The advantage is not certainty, but rather the mastery of leading in context when nothing is certain.

Readiness is a practice

Of the hundreds of people I have coached, those leading well rarely treat readiness as a destination they will eventually reach. For them, it is a practice that never ends.

I watched a senior leader at a critical juncture in his career. He was caught in a loss of confidence, the work volume was overwhelming, and the drama around him was wearing him down. The weight of high emotion meant he had lost sight of context. Rapid globalisation, operational strain and cultural challenges were contextual. They were not personal.

He started to change, beginning with the peer leaders he had never bothered with, and got curious about their read of the operational issues instead of passing on blame. When drama flared in a team, he paused and saw resistance as information rather than an attack. Before jumping in with solutions, or taking on accountability that was not his, he read who was capable of stretch and where the bigger priorities meant some things would have to wait.

To me, readiness is the practice of mastering contextual fluency. The moment you stop reading the context, readiness misfires.

It is also why old playbooks fail. A playbook can create false confidence by handing a leader an answer before they have understood the question. It may have worked in another role, organisation or market. That does not make it fit for this one. Experience gives us patterns, judgement and perspective. It also gives us assumptions that likely no longer serve us or others.

Under pressure, his defaults still return. Decisiveness becomes control. Curiosity can become a circular conversation that goes nowhere. Attempts to be a ‘calm leader’ become emotional suppression, rather than discerning action. But this is the point. Reading context has its own failure mode, and I see it as often as I see the opposite. The leader who has understood their situation for two quarters and still has not made the call. Contextual fluency is in service of action, not a substitute for it.

AI cannot read the room for you

I recently heard of a leader asking AI during a board meeting to generate a clever question about a board paper, so they would look sharp in the room. That should give us pause. It reveals something about the pressure leaders are facing, and the lengths some will go to hide their uncertainty.

Two leaders, the same feeling. One sat in their car with Beethoven, preparing herself to enter a context. The other sat in a room, seeking confidence from the quick cover of AI. Both were managing doubt, but only one was doing the work.

AI can support contextual thinking, but it cannot remove your responsibility to do the work, and unless you enter the context clearly, it will miss what matters. Just when you feel most discerning because an LLM has validated your reasoning, you may have missed the most important part of the picture.

Leadership is not demonstrated by producing the smartest-sounding question. It is demonstrated by paying attention closely enough to ask the question the context requires.

Stop waiting for the feeling

You may not feel ready for the difficult conversation, the unfamiliar role or the decision with no perfect answer. That feeling is not a verdict; rather, it is information telling you to prepare.

Readiness is demonstrated through the quality of your attention and the honesty of your assessment. It is built each time you locate yourself within the context, illuminate what needs to be understood and activate a considered response.

There is no final point at which leadership becomes predictable, and uncertainty disappears. Readiness was never the destination. As one of my clients once said, leadership is a conversation, not a course.

So, rather than asking whether you are ready, consider these more useful questions:

What is different in this context?

What does this context require from me now?