The question behind the question
In the final session of a coaching engagement, a client said something that captured much of the work we had done together: “I don’t need encouragement to speak anymore. I know how.” It was not dramatic. But it represented a significant change. When we first started working together, he was capable, thoughtful and commercially minded. He could see issues clearly. He had views about decisions, leadership and his own career. Yet in certain situations, he did not always express those views.
Sometimes he waited. Sometimes he softened the message. Sometimes he carried the frustration away with him instead of placing the issue on the table. This is not unusual. Many capable professionals do not struggle because they lack an opinion. They struggle because something happens between having an opinion and expressing it. Hierarchy matters. Relationships matter. The possibility of rejection matters. Family history can matter even more.
So the coaching question gradually changed. It was no longer simply: How can I communicate more confidently? It became: What would change if I trusted my own voice enough to use it consistently? That is a much deeper question.
When capable people hold back
Holding back can look deceptively professional. We call it patience. Diplomacy. Respect. Choosing our battles. And sometimes that is exactly what it is. Good judgement includes knowing when not to speak. But there is another version. We know what we want to say. We believe the issue matters. We leave the conversation without saying it. Then we continue having the conversation privately, sometimes for hours.
We replay what happened. We construct the response we should have given. We become frustrated that other people have not understood something we never actually made clear. The distinction is important: Silence can be a deliberate leadership choice. Or it can be avoidance wearing the clothes of diplomacy. The work is learning to tell the difference.
The promotion was not the real story
During the coaching engagement, the client began experimenting with speaking more clearly about his work, aspirations and expectations. Eventually, he received a promotion and greater responsibility. That mattered. Recognition matters, particularly when someone has worked hard and wants to know that the organisation sees their contribution. But from a coaching perspective, the promotion was not the most interesting result. The more useful development was the change in how he advocated for himself. The promotion alone could not establish what had caused it.
He had begun to advocate for himself. He was becoming more visible. He was communicating his expectations rather than assuming others should infer them. He was learning that speaking up did not automatically damage relationships. That learning can be more valuable than any single promotion. Because the promotion belongs to one moment. The voice can travel with you for the rest of your career. The promotion was an outcome. Finding his voice was the development.
Assertiveness is not aggression
At another point, a senior leader gave him feedback that he needed to become “more aggressive.” That language deserved examination. Aggressive in what sense? Speak louder? Push harder? Become more confrontational? Or was the leader asking for something else entirely? As we explored the examples, a different interpretation emerged. What appeared to be missing was not aggression. It was assertiveness. The American Psychological Association defines assertiveness as an adaptive communication style in which people express feelings and needs directly while maintaining respect for others.
That distinction became useful. We developed an informal communication spectrum: Submissive → Passive → Assertive → Aggressive → Domineering Assertiveness sat in the centre. Not soft. Not forceful. Clear. A clear yes. A clear no. A clearly stated expectation. A disagreement that does not require disrespect. A commitment that means something. A deadline that either will be met or will be renegotiated before it is missed.
This sounds simple. It is not. Because assertiveness is easiest when the emotional stakes are low. The real test comes when something important is at risk.
Why your voice changes with the room
One of the more useful discoveries during our work was that the client did not have a single “assertiveness level.” Context changed it. In a business discussion, particularly where the relationship was relatively neutral, he could be direct. In emotionally loaded family situations, he could become considerably less assertive. This raises a useful leadership question: Why can the same person speak confidently in one room and hesitate in another?
Because we never enter important conversations as blank sheets of paper. We bring history. Status. Loyalty. Expectations. Fear of disappointing someone. Fear of appearing ungrateful. Sometimes an identity that was formed long before our professional one. An executive may command a large team during the day and then walk into a family conversation where the relational hierarchy was established when they were eight years old.
The title changes. The nervous system may take longer. This is why I find simplistic advice such as “just speak up” inadequate. The real work is understanding what becomes activated in a particular context and then deciding how you want to respond.
From self-awareness to choice
Daniel Goleman’s work on emotional intelligence has long emphasised self-awareness and self-regulation as important leadership capabilities. Susan David and Christina Congleton approach a related issue through emotional agility. Their model begins not by eliminating difficult internal experiences, but by recognising them. They describe practices that include recognising patterns, labelling thoughts and emotions, accepting them, and then acting according to values. That last step is particularly important for assertiveness.
Imagine entering a difficult conversation and noticing: “I am uncomfortable.” That is data. It is not yet an instruction. You can also notice: “I do not want to disappoint this person.” Again, data. Then comes the leadership question: What action is consistent with the person I want to be? Perhaps it is speaking. Perhaps it is asking a question. Perhaps it is setting a boundary.
Perhaps it is postponing the conversation until you can handle it more constructively. The emotion remains present. But it no longer gets the deciding vote.
Calm, clear and assertive
By the final session, I asked the client to describe the leader he wanted to become. He chose three words: Calm. Clear. Assertive. There is something important in that sequence. Calm comes before assertive. Because assertiveness without self-regulation can easily drift into aggression. Clarity comes next. Because confidence without clarity can become noise. Then assertiveness. The willingness to put the thought into the room. This combination is useful because it rejects two common misconceptions.
The first is that strong leaders must dominate. They do not. The second is that respectful leaders should minimise disagreement. They should not. Respect and firmness can coexist. So can empathy and boundaries. So can listening and conviction. In fact, mature leadership often requires holding both sides of those tensions simultaneously.
The difference between a feeling and a conviction
One distinction that emerged in our conversations was between having a reaction and holding a considered conviction. A feeling may tell you: “I don’t like this.” Useful information. But a conviction asks for more. Why? What principle is involved? What evidence supports your position? What would change your mind? Being assertive does not mean stubbornly defending every instinct. It means being willing to articulate what you believe while remaining open to better information.
That creates a powerful standard: If I have a view, I should be able to explain it. If someone offers a stronger argument, I should be able to change it. This is not weakness. It is intellectual discipline.
A practical assertiveness test
I sometimes use a simple ten-point spectrum with clients. The labels matter less than the conversation they create. At one end is excessive submission. At the other is excessive domination. In the middle sits effective assertiveness. For one client, we called the middle Level 5. The exercise is not designed to produce a scientifically precise score. It is a coaching mirror.
1. Where am I right now?
Am I withdrawing? Am I over-accommodating? Am I preparing to push too hard?
2. What would Level 5 look like?
What would I say if I were calm, clear and respectful?
3. What exactly do I want the other person to understand?
One sentence. Not ten.
4. What boundary or value matters here?
What are you protecting?
5. What am I prepared to hear in return?
Assertiveness requires two voices. Not one.
Leadership test
Think of one person with whom your voice becomes noticeably smaller or louder. What happens to your Level 5 when that person enters the room?
Trusting your voice does not mean using it constantly
There is another trap here. Once people discover assertiveness, they can begin to believe every thought must be expressed. That is not the goal. Leadership requires judgement. There are times to challenge. Times to ask. Times to listen. Times to wait. Times to say no. And times to let something go. The objective is not maximum expression. It is congruence. Your internal position and your external behaviour should not routinely contradict each other.
If you disagree but choose not to challenge, let that be a conscious decision. If you say yes, let it be a real yes. If you need more time, say so. If you do not know, say that too. Congruence reduces an enormous amount of unnecessary internal friction.
The role of identity
Near the end of the coaching engagement, the client was also entering an important new stage of his personal life. That raised a different kind of question. Not: What kind of executive do you want to become? But: What behaviour would you want the people closest to you to learn by watching you? His answers included calmness, respect and focus. The question matters because leadership identity is not restricted to work.
We carry ourselves across systems. Executive. Colleague. Parent. Partner. Son or daughter. Friend. The contexts differ. The values should still recognize one another. And perhaps that is the deeper version of finding your voice. It is not simply learning how to advocate for yourself. It is becoming increasingly consistent about who is doing the speaking.
Leadership reflection
Consider these questions slowly.
- In which environments does your voice come naturally?
- Around whom do you become less clear?
- Where do you become more forceful than necessary?
- What are you protecting when you hold back?
- What might you be sacrificing by remaining silent?
- What does calm, clear and assertive sound like in your own language?
- When you say yes, how often do you genuinely mean yes?
- What conversation are you continuing in your head because you have not yet had it with the person involved?
Then choose one conversation. Not five. Enter it deliberately. Notice your state. Decide what Level 5 means. And speak from there.
What changes when you finally trust your own voice?
Perhaps fewer things change externally than we imagine. People may still disagree. A senior leader may still say no. A family member may still be uncomfortable. A difficult conversation may remain difficult. But internally, something changes. You stop outsourcing responsibility for whether your perspective enters the room. You become less dependent on encouragement. You spend less energy rehearsing conversations you did not have. And slowly, clarity becomes part of how you lead.
That is why the sentence from our final coaching session stayed with me: “I don’t need encouragement to speak anymore. I know how.” The goal was never to create a louder leader. It was to help a capable person trust that his voice could be calm, thoughtful and still strong enough to be heard.