How to Have Vulnerable Conversations at Work

The year 2020 will forever be remembered as a year of change in business. Both the medical and social levels demand a necessary shift in the way we function as businesses.

The lines between work and home have vanished for everyone. Under quarantine, we went from a separate home and work life to everything happening under the same roof. There is no longer any illusion of what life is like outside of work. We’ve gotten a glimpse into the reality of life for so many other people. Now, more than ever, leaning into love seems to be the only viable step forward.

Whatever the conversation at hand in your workplace, it is important to begin with self-education. Beyond that, start having transparent conversations. But those conversations only come in an atmosphere of vulnerability.

But, especially in the political climate of the summer, the question often comes down to how? How do we even begin to talk to one another? And how do we facilitate these conversations in offices and digital meeting spaces across the country and around the world?

You create an atmosphere of vulnerability.

Why vulnerability?

Being vulnerable involves feeling safe because when you don’t feel safe, you would rather protect yourself than risk opening up. Rather than transparency, unsafe environments create conversations that devolve into defensive stances and accusations. You’ve probably seen a conversation escalate once or twice, especially on social media.

Safety generally happens in circles of people you trust. That’s part of the disconnect right now in so many organizations. On any team, you hopefully have different groups of people from different backgrounds and all walks of life. The problem is that there is a real lack of trust between backgrounds, races, and lifestyles. Because there is no trust, many companies speak in platitudes or try and fail to make politically correct statements.

We can often misinterpret our own closed-off nature as safety and think of vulnerability as a risk—one many leaders might think of as unnecessary.

The insidious undertone of questions is: Why take the risk of a vulnerable conversation when you can just be silent and let “political” issues pass in time? Why speak up and “rock the boat” when you can go on about your day? Why not leave everyone safe in their isolated thoughts? But that line of thinking is why systemic inequality and racism still exist.

Aesop said, “Our insignificance is often the cause of our safety.”

Food for thought…

If you are playing it safe, you are more than likely insignificant in the conversation at hand. If you want to have a significant impact, you have to be willing to take a few risks.

The truth is, you cannot actually build trust and thereby a safe environment without vulnerability. A proverb says, “faithful are the wounds of a friend” (Prov 27:6). It is better when someone hurts you in an open conversation than if they flattered you through lies.

Tough conversations tend to go best when you don’t think of them as difficult conversations. Having an open dialogue is a normal and healthy thing but to some, vulnerable conversation may be new.

Facilitating Candid Conversations

The best, most productive teams, are happy teams. And happy teams only truly happen when team members feel safe and acknowledged in their work environment. And that only comes about in an atmosphere where vulnerability is accepted and valued.

The one thing we can all recognize is the difficulty of understanding what it means to create a vulnerable space where candid conversation can happen organically if you’re new to the idea. This idea is bigger than “watercooler” talk about the game on Sunday or the latest episode of the team’s favorite show. I am talking about conversations that impact the atmosphere of your office and change the dynamics of your team for the better.

So I pulled together a few of the thoughts that have helped me facilitate possibly vulnerable conversations over the years. I hope these tips help you navigate difficult or tough conversations with your team.

How to have vulnerable conversations at work:

  1. Listen first. 
    People are used to being told what to do at work, but that doesn’t work well with candid conversations. Those are a two-way street. 
  2. Ask how you can help
    Don’t assume you know what to do, or how to help someone. Before speaking, take a moment and think through what you want to say. 

    People will understand your “what” easier once they understand your “why.” Be real, be human, and share who you are. Asking how you can help should develop naturally out of the conversation. As people see your why, they’ll understand your motivation for wanting to help and appreciate you more because of it.
  3. Reflect
    Sometimes the best insights will happen later, as you reflect on yourself and those around you. You may never fully understand what someone else is experiencing, but it’s often enough to admit that you don’t fully understand, but you are trying.
  4. Support employees and allow them to be themselves
    Provide a safe environment and encourage questions and open dialogue. When the national atmosphere is thick with emotion, then it might, understandably, lead to some emotional responses at work. Be careful to not belittle or patronize teammates if they get emotional.
  5. Talk candidly, even about difficult topics. 
    If you know your team has areas where you’ve failed, don’t hide from it. Call it out those areas with transparency and share the steps you are taking to improve it. Many team members feel like they cannot criticize a company for fear of being ostracized. When leadership shares constructive criticism of their own company, then it creates an environment conducive to feedback. In one conversation, you open the door to a candid conversation.
  6. Confront your own bias. 
    We all have lenses we view life through. For many leaders and company owners, it’s an unintentional lens of white or even male privilege. How do you cure this? Try not to hire, promote, and fire based on your own personality or who you get along with. This mindset creates homogenous teams and echo chambers. If no one on your team is challenging you, you and your team will never grow past a certain point.
  7. Don’t force it. 
    Some employees may not like discussing personal or difficult issues at work because some personal topics are often rooted in trauma. Be careful to never put anyone on the spot or force the conversation. Just make sure you are doing what you can to make the environment safe.
  8. Set realistic goals. 
    If you don’t have an open and transparent culture, change should not be your goal overnight. Set actionable steps to get there by starting with identifying the root issues preventing a positive and safe culture. 

The point is to show your employees that you and your company are comfortable with and open to change. Maybe it is certain leaders or even the organizational structure that keeps your team from having a candid conversation. Take measured steps to change your organization from the top down. That action shows your team members that you are not only aware that change needs to happen, you’re willing to do something about it. 

That willingness speaks volumes about how much you care about your team. It tells your people how much you want to see them and your company grow through tough conversations.

How To Rescue Vulnerable Conversations

Here’s the thing… The best, most productive teams, are teams that are happy to be around their co-workers, happy to come into work, and happy working for you… Those kinds of happy teams only occur when team members feel safe and acknowledged in their work environment. The only way that happens is when vulnerability is not only accepted but when it is valued.

Now, let’s be real, we’re all human. Sometimes, our mouths run away with our words before our minds have a chance to catch up and a vulnerable conversation turns heated before it’s too late. In a heated discussion, it can be easy to forget we are talking to people with feelings, wounds, and trauma of their own.

So, let’s set the scene… your goal was to create an atmosphere that supports vulnerable conversations within your team but in the process, a conversation quickly got out of hand. Maybe someone misheard something. Maybe someone said something else without regard for another person’s perspective. Or, maybe the conversation was ugly from the start? Don’t worry, there are ways to save a conversation that’s already gone south and reestablish an atmosphere of safety and vulnerability with your team.

What to do if a tough conversation goes (or has already gone) south:

  1. Take a moment to pause. Like we already talked about, sometimes, there are moments in national history that are more emotional for some than others. Regardless of what has come before or what comes after such a moment, people are bound to get emotional. If or when that happens, be willing to take a step back from a conversation.
  2. Level up your thinking. If you need to, walk away gracefully for a moment and gather your thoughts, examine any bias, and calm down. If you sense any team members getting emotional, you may also gracefully encourage them to do the same and you can return to the conversation when they are ready. The point is to not get defensive and to see the bigger picture. If you are the leader, you are responsible for diplomacy and de-escalating the situation rather than escalating it.
    What this sounds like: “Let’s take a breather…” “I need a moment to gather my thoughts…” “Let’s come back to this in a few minutes…”
  3. Listen more than you talk. As the conversation progresses, focus on actively listening in the moment and not just listening to make a good argument. A well-articulated opinion might sound great, but it is not always the most important issue on the table, nor is it always helpful.
  4. Be willing to forgive. Maybe a conversation went south before you could course correct. Maybe you’ve been a silent witness to inequalities and/or systemic bias in your workplace and waited too long to say anything at all. Forgive yourself. Forgive anyone who might hold that against you with grace. The path forward through where we are now to where we could be in a decade is paved with forgiveness.
  5. Focus on the future and hope. Your team might, understandably, be concerned with the history of how certain things have been handled. If you know their concerns are both true and valid, listen, acknowledge, and ask for forgiveness. Then, turn the conversation to how those things can be addressed and fixed in the future. The conversation is a good start, but actions will always speak volumes about your willingness to change your organization for the safety and wellbeing of your team.

The most important thing in deescalating a conversation is being aware of when a situation requires intervention before it becomes untenable. Learn to recognize the signs of an escalating conversation (power stances, clenching fists or jaws, sudden changes of body language or tone, and disruptive behavior) even in yourself. Be ready to measure your response and stay calm, listen to concerns, and shift the conversation to the future and to hope. 

As a leader in your organization, it is critical that you remember you set the tone for the future. Every tough conversation is an opportunity to further establish what that future looks like. You can freeze and watch a conversation escalate, or you can recognize your position is one that the future of your company hinges on and encourage growth, candid conversation, and vulnerability in your team. 

No matter what the world is facing, I believe one thing we can all do is start having candid conversations. First with ourselves, and then with others. No matter how hard they are, where we stand on political lines, or what our race or gender is, we can have those hard conversations, and then maybe we’ll start to heal our nation. 

Facilitating Vulnerable Conversations with Remote Teams

The past few days we’ve been talking about facilitating vulnerable and candid conversations in the workplace. I wanted to have this conversation in this space as an evergreen conversation but the context is too relevant now. The conversation is too poignant. We’ve been talking about having candid conversations with respect to the Black Lives Matter movement and its importance this year but the tips we’ve been discussion are absolutely transferrable to any topic. 

We talked about how to set the atmosphere for these conversations and facilitate them. We even talked about how to rescue them when they go south.

But the truth of the moment is that COVID-19 has most of us still safe at home even as summer breaks over the world. So how do you take those tips and translate them into the remote model most people are still working from?

While we’ve been safe at home, the national political climate has imploded multiple times this year alone, mostly for the better. Necessary conversations are happening on social media, across phone lines, through screens and glass windows, across balconies and over yard fences. 

But somehow the conversation hasn’t happened on your team yet… Everyone is keeping their thoughts to themselves, but you can feel the tension rising…

Address it now.

Not via email. That’s appropriate for your customers or clients who might be too numerous to all bring together though that’s certainly an option.

If you’ve avoided it until now, share why. Open your heart and set the stage and an example for the rest of the team’s vulnerability.

Leverage tools for transparency.

Unlike office environments, remote teams can no longer rely on those watercooler moments to facilitate candid, organic conversation. Rather, because we are all at home, leaders must be direct and intentional about creating the opportunities for these moments. 

Make a plan for a conversation with your team and put it on the schedule. As you prepare, make sure your company’s vision and culture are clear and communicated. This can be handled in private conversations between leadership, then communicated to the larger team. 

Pull your team together for a round table discussion on Zoom or Google Hangouts or Microsoft Teams or Messenger Rooms on Facebook—whatever application you use, make sure it is face to face. The most important thing in candid conversations that require vulnerability on the part of any person or group of people is that face-to-face connection.

As wonderful as the English language is, so much is lost in translation when communicating with just words. The nuance of emotion cannot be properly expressed with text so an email communication, text conversation, or Slack thread won’t do the conversation justice.

Set expectations for the future. 

Recognize that the moment we’re in right now won’t last forever. Eventually, we will get back to the office and those water cooler conversations can resume.

Until then, it’s important to set the stage for where your team goes from here. If the product of the conversation is that the culture of the company needs to change, be upfront about that and willing to listen to suggestions from your team. Then, again, after a private conversation within leadership, communicate those changes with clarity.

Be the light on your team and set an example for those around you. Because from this moment forward, it is up to each of us, leadership and teams alike to spark change in our own ways. In a leadership role, it is your greatest responsibility to create an atmosphere of hope and change. Do that well and your team will follow—even from their own homes.


If you enjoyed the post, I am so glad! This is an adaptation of what we discussed in this month’s edition of The Inner Circle, a monthly newsletter I send.

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