Thursday, September 10, 2026
HomeLeadershipAdviceEveryone’s Holding a Different Flower: How Good Leaders Make Success More Likely

Everyone’s Holding a Different Flower: How Good Leaders Make Success More Likely

Rachael Hudson 

Ask someone to think of a flower. Any flower.

You probably won’t picture the same one. One person might see a dozen red roses. Another a loose, mossy woodland posy of primroses. Someone else something glorious and tropical, all birds of paradise and sculptural leaves. Ask for a car and the gap widens. Ask for a cat and, for reasons I’ve never entirely worked out, I always picture a black panther while most other people seem to imagine something domestic and asleep on a windowsill.

None of us is wrong. The word has done its job: it’s pointed us towards a category. But the picture itself has been assembled privately, from memory, association, preference and experience. Because the word feels familiar, we rarely stop to check whether the picture in my head bears much resemblance to the picture in yours.

This is fairly harmless when the word is flower. It becomes considerably less harmless when the word is ownership. Or integrity. Or urgency. Or respect. Or hard work.

Shared words can create the illusion of shared meaning.

One of the easiest mistakes in leadership is assuming that because everyone understands the vocabulary, everyone understands the expectation. We use familiar words and experience them as precise, even when they carry quite different meanings for different people.

“Take ownership.” “I need more urgency.” “Use your judgement.” “We need to raise the standard.” “I expect more commitment.”

Every one of those sentences can sound perfectly clear to the person saying it and mean something subtly, or significantly, different to the person hearing it. “Take ownership” might mean make the decision without checking with me. To someone else, it might mean keep me informed but don’t make me chase you. To another, it might mean solve the problem rather than simply reporting it.

Everyone can leave the same conversation believing they understood, while holding quite different interpretations of what was actually agreed.

The more abstract the word, the wider the gap can become. With a flower, there is at least a physical category containing the ambiguity. We may picture entirely different flowers, but we are at least somewhere in the same garden. With more philosophical words such as loyalty, fairness, professionalism, commitment, respect, integrity or trust, there’s no such neat perimeter. Their meanings are built from experience.

What did hard work mean in your first organisation? What did loyalty look like in the family or culture you grew up in? What behaviour taught you that somebody could or could not be trusted? What did respect look like when you were junior?

Two intelligent, capable and well-intentioned people can hold quite different definitions of the same word and both be entirely sincere.

This becomes particularly important in leadership because organisations depend heavily on abstraction. We write values on walls. We put behaviours into competency frameworks. We tell teams to be more commercial, show leadership, take accountability, move faster, be strategic. Then we’re surprised when people produce something different from what we had in mind.

We assume the meaning travelled with the word when, in many cases, only the word did.

Imagine for a second… A leader asks for urgency. The employee hears: prioritise this today. The leader meant: stop everything else and deal with this now. The employee completes the work by four o’clock. The leader sees a lack of urgency. The employee sees a successfully completed priority.

What began as a definition gap can quickly become a judgement about attitude. The judgement affects feedback, the feedback affects trust, the employee becomes more cautious and the leader more frustrated. A small ambiguity in language has now become a relational problem.

And this is where briefing becomes more than a communication skill. It becomes a leadership responsibility.

A good brief gives someone a genuine chance to succeed.

If I ask someone to produce something against a picture that exists only in my head, and then evaluate them against that unseen picture afterwards, I’ve created a rather unfair test.

They may have worked hard. They may have exercised perfectly reasonable judgement. They may even have delivered exactly what another competent person would have understood from my words. Yet they still experience the result as failure because the expectation against which they were judged was never fully available to them.

Repeated often enough, this can erode confidence and morale. People begin second-guessing. They check unnecessarily. They become more cautious about exercising judgement because previous attempts have apparently been wrong. Some conclude that pleasing the leader depends less on doing good work and more on learning to read their mind.

The extra minute or two spent defining a brief properly can feel inefficient when everyone is busy. In reality, it’s often one of the cheapest investments a leader can make. It reduces rework, protects time later, protects morale and communicates something important: I want you to succeed at this, and I’m prepared to do my part in making success possible.

Over time, that kind of clarity can build confidence, trust, loyalty and commitment because people know what’s expected of them and have a fair basis on which to use their own judgement.

Clarity need not become micromanagement.

The clearer a leader is about the outcome, the boundaries and what good looks like, the more freedom they can often give someone over how they achieve it. Vague expectations, by contrast, can make people more likely to seek reassurance, escalate decisions and hesitate over choices they might otherwise have made confidently.

A simple way to close the gap is to make the picture more visible. 

Before delegating something important, I think there are five useful questions to ask:

  • What exactly do I mean?
  • What do I not mean?
  • What does success actually look like? 
  • What does it not look like? 
  • What has the other person heard?

That last question is particularly useful because “Does that make sense?” will usually get you a yes. “What does that look like to you?” tells you far more. So does: “Talk me through what you think I’m asking for.”

Those questions give you access to the picture the other person has actually formed and give both of you a chance to correct any mismatch before it becomes expensive.

The same applies to organisational values. If a company says it values accountability, what does accountability actually mean there? Is it admitting mistakes quickly? Owning outcomes rather than activity? Raising risks early? Making decisions without unnecessary escalation? Keeping commitments?

Unless the behaviour is made visible, different people can enact different versions of the same value while believing they are aligned. The organisation may be using one vocabulary while operating with several different meanings underneath it.

So before diagnosing a performance problem, it can be worth inspecting the definition. Do we actually mean the same thing by the word I keep using? Have I made the expectation sufficiently visible? Have I explained the boundaries, or only named the category?

Sometimes the problem really is capability, judgement or commitment. At other times, the success criteria were never clear enough for the person to have a reasonable chance of meeting them.

The better we become at leadership, the more shorthand we tend to accumulate because so much of what we mean begins to feel obvious to us. It may be obvious to us. But that does not necessarily make it obvious to the person receiving the brief.

So the next time you ask for ownership, urgency, quality, judgement, leadership, commitment or respect, spend a little longer checking the picture. Ask yourself what you actually mean, what they might reasonably think you mean, what it looks like, and what it does not look like. If the distinction matters, ask them to tell you what they heard.

Otherwise, everyone may be nodding in agreement while holding a completely different flower.

Rachael Hudson
Rachael Hudsonhttp://www.rachaelhudson.com/
Rachael Hudson is an Executive Life & Leadership Coach, coaching confidante and trusted "secret weapon" to senior leaders, founders, partners and accomplished professionals who are carrying more than they can comfortably show. Her clients are often people others rely on for judgement, steadiness and direction, while privately wrestling with overthinking, self-doubt, over-responsibility, visibility, difficult decisions or the unsettling sense that they've lost some of their usual edge. The higher the stakes, the fewer places there can be to explore those things honestly. A concern shared with the wrong colleague can affect confidence in your leadership. A vulnerability exposed in the wrong room can have professional or reputational consequences. Friends and family may care deeply, but are often too close to the situation. Rachael gives clients somewhere outside that scrutiny. A place to say the unedited thing, test the thought they would not say aloud elsewhere, work out what is actually driving the pressure, and separate a genuine leadership issue from an old internal response that has been activated by it. Her particular interest is in the hidden adaptations behind high achievement: the ways responsibility can become over-responsibility, sensitivity can become hypervigilance, independence can become difficulty receiving support, and high standards can become something closer to compulsion. These qualities may have contributed enormously to someone’s success. The difficulty begins when they stop feeling entirely optional. Rachael’s work is not about making accomplished people into different people. It is about restoring choice, clarity and range so they can use their strengths more consciously, recover confidence in their own judgement and lead from what is true now rather than from patterns that once served them well. With more than 25 years’ experience in coaching and human development, she works privately with senior professionals as well as through leadership development, speaking and her signature programmes, including Foundations Rewritten™ and Imposter to Impact™. Clients often come to Rachael when nothing is visibly “wrong”, but something important is no longer working as well as it used to. Her role is to help them understand why, regain their edge and return to their work and lives with greater clarity, confidence and command.
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