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What does it take to have courageous conversations at work?

November 4, 2021 - 11 min read


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What are courageous conversations?

Why are courageous conversations so important?

What are the agreements of courageous conversations?

How to have courageous conversations about race – and other triggers – at work

What are courageous conversations?

Courageous conversations involve intentionally giving space to complex issues of social justice, race, and privilege with people at work. These conversations are courageous because they require being bold, openness to sharing your own experiences, and to hearing the experience of others.

Having these difficult conversations means being open to having your viewpoints challenged, as well as directly confronting topics that many of us have been taught to sidestep in polite conversation. 

Why are courageous conversations so important?

Some may think that they’re doing the right thing by asserting that they don't see color, gender, or other identities at work, but it’s a problematic stance to take. After all, nobody wants to be overlooked. In fact, pretending that these characteristics don't exist allows prejudice and systemic racism to continue to exist.

However, when social and racial justice issues are prevalent — both in the news and in every facet of day-to-day life — being able to ignore them is a privilege. However, doing so undermines trust — both the trust that your employees have in your organization and in society.


Being a person of color, non-binary, disabled, the “token” employee, or standing out at work for any other characteristic can be an uncomfortable experience. Having courageous conversations allows everyone to share in this discomfort in the very best way. When people are willing to do the work of challenging and uprooting their assumptions, it brings awareness to and validates these difficult experiences. This in turn creates partnership in the learning experience and in having all employees feel more connected and understood. 

Everyone has a unique experience, no matter who they are or where they come from. Courageous conversations give you the opportunity to share your experiences, have them validated, and be vulnerable. These conversations can be difficult and should be had with intentionality and care. But they are ultimately worth the discomfort if you value creating belonging in the workplace.


What are the agreements of courageous conversations?

The Denver Foundation outlines several Agreements for Courageous Conversations and Active Learning on their website. These guidelines are excellent tools to develop a space for uncomfortable discussions, whether about issues of race, privilege, social justice, or any other topic.

Stay engaged 

It can be tempting to check out an uncomfortable conversation, but this is typically just a defense mechanism. Being able to disengage is a privilege and leaves the weight of the conversation on others. Staying present, even if you don't say anything, provides space for others who do want to share.

Experience discomfort

Being triggered is part of having uncomfortable conversations, and that's okay. The point of a courageous conversation is not to isolate or ostracize anyone. It's to say the unsaid — to call attention to the fallacies in our thinking. These conversations are challenging, but ultimately safe spaces. 

Speak your truth

The Denver Foundation says “We are experts in defining our own experiences and personal realities.” It is healing to have a space where you can show up and be fully, authentically yourself. 

Be willing to say the hard things. When you’re brave and speak up, you empower others to do the same.

Expect and accept non-closure

There is no quick solution for social justice. The real work doesn't always happen in protests, marches, and policy change. Some of the most valuable work is done between people in small settings who are willing to understand and learn from one another.

Maintain confidentiality

Honor the space that you're creating by keeping everything that is said in confidence. Workplaces are unusual settings for conversations about inequities, and people need to be able to share openly without fear of retaliation.

Listen with the intent to learn

Even if you don't want to talk, you can participate in the conversation. Listen with openness and the intent to just take away something new, whether that's about racial consciousness or about your colleagues' experiences.

Signing up for a courageous conversation doesn't mean committing to have your mind changed or admitting to any wrongdoing; it means that you're open to hearing the experiences of another. 

Suspend judgement

Understanding privilege and implicit bias means that first, you have to suspend your judgment. It’s hard for each of us to release our certainty that the way that we see things is the right way. But the fact is that none of us have all the answers. 

Remember that everyone is the expert on their own experience. Assume that whatever someone is saying is valid. It's not your job to prove whether or not it's true. It is true for them, and that makes it real.


How to have courageous conversations about race – and other triggers – at work

Carrying conversations about these topics can be challenging at work. It can be hard enough for employees to talk about other aspects of their lives, especially when they  may be emotionally triggering. 

It's important, though, to understand that courageous conversations are necessary to have, because people only do their best work when they’re able to bring their whole selves to their workplace — and are welcomed and encouraged to do so.

Authenticity leads to creativity and collaboration, and trust builds belonging and retention. Without courageous conversations, there is no authenticity or trust.

Here are some tips to open space for courageous conversations:

Acknowledge what's in the room 

What is the trigger for this conversation? Usually, courageous conversations happen when they can't not happen — when something, whether inside or outside the workplace, triggers the need to have the conversation. Unfortunately, that means people may already have strong feelings about the topic. 

Tell your employees that you are providing a space for them to address any feelings that they have. It can help if you name some feelings, like disgust, anger, fear, or frustration. Naming these feelings in advance actually validates them, and avoids putting the first person to speak on the spot.

You may choose to offer a panel or seminar, but small group discussion should be part of the format.

Set aside time

Let everyone know that this conversation will be happening, and set aside a dedicated time for as many people to participate in it. Don't just drop it into a meeting that's already on the calendar, because people may feel blindsided or too nervous to participate. 

A good practice is to set intentions for the time in an email (in advance), restate them at the beginning of the call, and provide space for every person who wants to speak to have the floor. This can be done in small groups so that people have ample time to talk.

Model what you hope to see

Have the meeting start with everyone in one space, and then break out into smaller groups. This way, leaders can talk about their feelings and set the stage for authentic communication. 

Believe it or not, people do need permission from their leadership to share how they're feeling without fear of repercussions. If you can model this kind of open and direct conversation at the highest levels and tie it into company values, people will feel less at risk when sharing what they really think.

To ensure that people feel safe, avoid having managers in breakout rooms with their direct reports.

Keep the focus on individual experiences

The purpose of these conversations is to allow each person to share their own lived experience and develop cultural competence. No one, including the facilitators, needs to coach or correct anyone else's experience. 

Allow people to share, thank them for sharing, and move on to the next person. Avoid getting caught up in crosstalk (where people speak directly to one another). If issues arise, invite them to share their concerns at another time with a facilitator — and follow up by setting time with them.

When back together, allow people to share if they’d like. Remind them not to share anyone else's experience and to keep the conversations confidential. Thank them for their participation, their bravery, and their authenticity.

Open up the path to move forward

Give people a way to continue the conversation. Direct them to employee access programs (EAPs), coaching, or employee resource groups. Remind them of your commitment to allyship and positive change, and follow through on it. 

That will most likely mean that this is the first of many conversations. This initial dialog is meant to relieve the pressure and open up a sense of psychological safety in the workplace. Remind them that even you know that nothing is fixed, but you hope they feel seen, and that you know the work is still ahead of you.

Bottom line

Safety at work is a key part of the employee experience. People want to be acknowledged as whole people, and understanding that they can't show up at their best at work unless they feel safe is important in building that.

If you want people to continue to show up for you, you have to show up for them. You can model how to do hard things by having these courageous conversations at work and letting them know that they are not the only ones committed to learning and growth.

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Published November 4, 2021

Allaya Cooks-Campbell

BetterUp Associate Learning Experience Designer

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