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Courageous Conversations at Work: A Guide To the Discussion You Are Scared Of

Courageous Conversations at Work: A Guide To the Discussion You Are Scared Of

You probably don’t want to have a tough conversation in your workplace. You’re very likely scared that you, or someone else, will say the wrong thing, mess it up or cause more pain. 

But avoiding the subject altogether can undermine employee trust, inclusion and belonging at work. And these experiences are crucial for things like employee well-being, innovation and productivity.

Courageous conversations in the workplace are about broaching complex and sensitive subjects like race and privilege with your team, boss or HR manager.

They are the sort of conversations that can stir strong emotions, which might feel out of place for work, and they require careful and mindful discussion.

Why is it important to have courageous conversations in the workplace?

“Courageous conversations in the workplace are part of developing a learning culture,” explains Tony Bond, EVP chief diversity & innovation officer, Great Place to Work®.

“These conversations lead to a better understanding of the needs of others, such as Black employees. They enable leaders and employees, both Black and non-Black to become more comfortable having dialogue around race.”

Worrying about adding salt to wounds or saying the wrong thing are reasonable concerns. Still, they are fears you need to take on if you, your team, and your company want to move forward in the middle of a crisis (such as that teeny global pandemic that is still going on.) 

So, here’s what to do: talk about it. Together. Now.

And guess what? It will help. A lot.

I know it will because we had this discussion twice since the murder of George Floyd, once with our management team and then with the entire company. The benefits reported by employees were huge. 

Folks shared their feelings of relief and said talking to their peers helped them feel less alone. One man learned that even people who look different from him shared the same fears. 

Another woman said her family discussions were so charged, it was a relief to get to share her feelings calmly. Many parents talked about the hopes and fears they have for their children and the tough dinner table discussions they’d been having.

Opening up the conversation validated people’s feelings, gave them a new and psychologically safe outlet and helped everyone feel cared for.

So, here’s a quick guide for setting up what might feel like a difficult discussion. It works best if the whole company participates, but even talking at the team level can help.

How to lead courageous office conversations

1. Set your intentions clearly

The goal is to provide a secure space for every person to share their experience, whatever it is, not to fix or solve anything. All feelings, concerns, hopes or anxieties are welcome. This is a time to share questions and concerns and to provide an opportunity for everyone to ask for support.

2. Create a container

Set up dedicated time to have this talk, at least 60 to 90 minutes,. Make sure everyone is expected to join and participate. If you're a leader, express how important this conversation is and support your team to clear their calendars. This works great on video conferencing technology to ensure everyone is physically safe.

3. Prepare facilitators & groups 

You should start together in a large group and then break into groups of about six to eight to for conversation, so prepare your breakout groups carefully.

If you have a high-trust environment where employees can have respectful conversations about tough topics, then less structure will be needed.

If your organization has low trust; if COVID, race or politics are charged topics for you; or if there is a wide variety of thought, feeling and opinion across your business, more facilitation and organization may be needed to create a positive experience.

The goal is to ensure that each person feels they can share freely without judgment or criticism, even when individuals may disagree. Designate a facilitator who can manage that kind of discussion for each group.

4. Set it up

Start your meeting together, with a senior leader sharing the intentions and ground rules with everyone. Focus on the company values that are appropriate to this discussion (for example Care and Be Curious are the two Great Place to Work values most appropriate to this experience.)

Ask everyone to keep the specifics of who said what confidential—we can share the discussion generally, but it’s better not to quote individuals, to avoid misrepresenting them.

Then split into your groups. Our Chief Diversity & Innovation Officer Tony Bond created these simple discussion questions to get us started:

  • Check in with each other
  • How are you experiencing what’s happening?
  • What are you confused about?
  • How can I support you?
  • How can we support each other?
  • How do you find hope to keep going?
5. Open with vulnerability

Each facilitator should set the tone by opening with some personal truth and vulnerability. Participants will take their lead, and determine how safe the space is, from the leader’s openness and honesty.

6. Have the discussion

Keep the focus on sharing personal stories and feelings. Ensure that each person gets an opportunity to speak at least once, if they want to. Help curb interruption and cross-talk to give open airtime to all.

And if folks hold differing opinions, that’s OK. But do not allow anyone to debate or negate another person’s personal experience.

When speaking about race, gender, religion, or any other demographic, do not ask a person to speak on behalf of a group they may belong to. For example, do not ask Black people or other people of color to explain racism, “tell me how I can help,” or share a list of resources to educate anyone else.

While strong feelings are welcome, including tears, there should never be an expectation that anyone in the group has to make another feel better.

7. Come back together and close

Bring the small groups back together and invite voluntary comments from anyone who wishes to share their experience. The senior leader should then close with gratitude for everyone’s participation and explain any personal resources available for folks that want them.

8. Support each other

If specific requests for support have been expressed, do whatever you can as an organization to deliver those. If a conversation went sideways in a breakout, the facilitator should call in your HR leaders and team leader(s) to help work it out or resolve it. Don’t ignore a messy problem: It’s better to get in there and at least try to make it right.

9. Keep it going

This is not a one-and-done situation. We will all need to keep having conversations about the state of the world for the time being. If this format works, great! If not, find or use whatever fits your company culture.

Moving forward

In my own personal experience, I did not want to have this conversation at the time. It felt hard and frustrating. But after having it, I feel clearer, calmer and more secure knowing it’s okay for me to be a real human and bring my whole self to work.

I know that my leaders and co-workers all care about me and my experience. And I got to tell them that I care about theirs, too. I built relationships with people I don’t know very well and was able to share some vulnerability and build trust.

Plus—if those valuable outcomes aren’t enough for you—productivity is a cherry on the top. After our courageous conversation, I could get back to work and focus in a way that certainly wouldn’t have happened without the discussion.

So be brave and go for it.

Tell us how your discussions went and what other resources you need. Great Place to Work® is here to help you create a great workplace For All


Julie Musilek