Courageous conversations at work

Why "courageous" and not just "difficult"?

The word "difficult" puts the problem in the conversation itself. "Courageous" puts it where it belongs — in the person who chooses to raise it. Most of the exclusion that happens at work isn't deliberate. It accumulates in the silences: the remark nobody challenged, the feedback nobody gave, the pattern nobody named. Courage is the decision to break that silence — not because it's easy, but because staying quiet is costlier in the long run.

As I put it when speaking to the Security Awareness Special Interest Group: "It's not always easy. We know it's not easy. Having courageous conversations, calling out discrimination, calling out challenging conversations when someone's making remarks — sometimes you have to have the courage to stand up for what you believe." The alternative is a culture where people quietly disengage rather than raise what matters.

Calling in versus calling out

Both approaches have their place, and the choice matters.

• Calling out is public and immediate — naming the behaviour in front of others as it happens. It signals to everyone in the room that the culture does not tolerate this. It can feel harsh, which is sometimes exactly what is needed.
• Calling in is private and relational — taking the conversation aside, asking questions, inviting reflection. It prioritises learning and preserving the relationship over making a point. It assumes that most people, given a genuine opportunity to understand, will want to do better.

Neither replaces the other. Calling in is usually the better first move; calling out may be necessary when a pattern has persisted despite private challenge, or when others in the room need to see the behaviour named. The question to ask yourself is: what outcome do I actually want from this conversation?

Intent versus impact

One of the most common reasons courageous conversations stall is the intent defence: "I didn't mean it that way." Intent matters — it affects how you approach the conversation — but it doesn't change the impact. Someone can have entirely good intentions and still cause real harm.

The most useful frame is to treat intent and impact as separate, real things that both deserve attention. Start with impact: what happened, and what effect did it have? That's factual and observable. Then, with curiosity rather than accusation, explore the intent: what was the person trying to do? From there, you can agree a different path forward. Focusing on impact rather than character keeps the conversation productive rather than defensive.

Staying curious: the E + R = O principle

A framework I return to often is E + R = O: Encounter + Response = Outcome. When two people disagree or when harm has occurred, we tend to focus on the Outcome — the conflict, the hurt, the impasse. But the Outcome is shaped by the Response, and the Response is shaped by perspective.

Before reacting, pause and ask: why do I see this the way I do? Why might the other person see it differently? Their background, their experience, their identity — all of these shape how they've interpreted the same encounter. That's not an excuse for harm; it is, however, the most direct route to understanding and repair. Curiosity about perspective is what turns a stand-off into a conversation.

This connects to what forecaster Paul Saffo called strong opinions, weakly held — a phrase I find genuinely useful. Have your view. Hold it clearly. But hold it loosely enough that new information can actually change it. That's not weakness; that's how learning happens.

Repair over blame

The goal of a courageous conversation is not to win, or to establish who was wrong. It is to repair — to leave the relationship and the culture in a better state than you found them. That means:

• Naming what happened clearly, without catastrophising it.
• Sharing the impact honestly, without weaponising it.
• Staying present for the other person's response, even if it's defensive at first.
• Agreeing what changes — specifically — and following through.

Psychological safety is what makes this possible. If people know that raising something won't result in marginalisation or ridicule, they'll raise things earlier and more honestly. Creating that safety is a leadership responsibility — not a one-off gesture, but a pattern of behaviour over time.

How this connects to Smile · Engage · Educate

My approach to inclusion — Smile · Engage · Educate — applies directly here. How you approach a courageous conversation matters as much as what you say. A conversation that starts with warmth and genuine curiosity will land very differently from one that starts with a verdict. Smile: bring openness, not accusation. Engage: listen before you conclude. Educate: share your perspective and invite theirs, so both of you leave knowing something you didn't before.

This is also why I describe the best of these conversations as "calling in" — you are inviting someone into a better understanding, not ejecting them from the community for a mistake. As I often say: you can call something out or call it in. The choice reflects what you believe about people's capacity to change.

Practical starting points for leaders

• Name what you saw, not what you decided. "When you said X, the effect on the team was Y" is far more useful than "you're being exclusive."
• Choose your moment. Immediately after an incident, emotions are high. A short pause — an hour, not a week — often produces a better conversation.
• Ask before you tell. "I wanted to check in about what happened in that meeting — how do you think it went?" opens a door that a verdict slams shut.
• Be honest about your own discomfort. "This is a bit awkward to raise, and I'm raising it because I care about the team" is disarming rather than threatening.
• Agree what changes. The conversation isn't finished when it ends — it's finished when something is different. Make the agreement specific and check back in.

Take it further

Courageous conversations sit at the heart of The Inclusive Leader's Journey — the keynote that helps leaders move from good intentions to genuine inclusion. They're also explored throughout the Inclusion Bites podcast, where guests and I work through the real complexity of making workplaces better. For the broader picture of what inclusive leadership looks and feels like, read the companion guide What Is Inclusive Leadership?