How to Get Comfortable with Uncomfortable Conversations

What breathes dread into more managers and leaders than almost any other responsibility? Facilitating uncomfortable conversations.  

No matter how many years experience someone has, when you walk into that conversation, it can be nerve-racking. Why do they want to talk to me? How will they react? Will it stay civil? Am I wasting my breath? What if they hate me afterward? 

Just last week, a friend asked me what they should do about their husband. Um, talk to them, not me, and get comfortable with uncomfortable conversations. I’d listen to them vent, but to change things for the better, they were talking to the wrong person.  

How often does that happen at work? Every day. People whine and complain about their team members, colleagues, and bosses. They also have great ideas that they’re unwilling to share because they’d rather be angry and frustrated than uncomfortable.  

Uncomfortable Conversation Styles – What’s Yours?

Years ago, I led workshops for managers who needed to give developmental feedback to their team members. More often than not, the managers were not only nervous about how the feedback would be received but also how they’d be judged in the process. They wanted to be liked, not perceived as an adversary.  

Let’s get clear from the start: Having a difficult or uncomfortable conversation with someone does not mean you’re working against them. It means that you value them enough to have a respectful and honest dialogue. That is what most of us want from our boss or peer –  not avoidance or fear or attacks.  

The majority of the workshop participants aligned into three distinct camps: 

Camp 1:  Soften the feedback to the point where it’s nothing but mush – like quicksand for tough messages; the key points lost below the surface.  

Camp 2: Their direct and distant tone and words came off as aggressive and unsupportive. People left conversations with them wondering if they did anything right at all.  

Camp 3: Sandwich method enthusiasts who struggled to have enough stuffing to make the conversation meaningful or leave a taste of anything beyond the rah-rah.  

On the flip side, there’s a lot less advice for people who are the ones invited into uncomfortable conversations. Last week, I told someone the truth about some self-destructive and self-sabotaging behaviors I’ve observed. They came to me for support and advice, but still had strong resistance to the message. In fact, they left instead of talking it through. 

There are two sides to an uncomfortable conversation: Instigator and Invitee. Both sides need to get comfortable with discomfort, and instead of treating the conversation like it’s one side against the other, with a winner and a loser, embrace a better way forward.  

From my many years working in change management, HR, and coaching, here are some best practices for uncomfortable conversations you can implement immediately.  

Uncomfortable Conversations – Tips for the Instigator:

  1. Be clear why you’re having the conversation and why it matters. Is it a regularly scheduled feedback session? An intervention? Tough love? Bad news? Positive changes? Provide information? Agree on next steps?
  2. Give examples, but avoid making your point 72,000 different ways. 
  3. Stop talking and ask for input. It’s a conversation, not a monologue or an attack.
  4. Don’t defend your perspective but instead be open that there are pieces of information you’re missing. Remain curious. You are do not wear their shoes no matter how much you’ve tried to walk in them.
  5. Practice or share your key messages with a trusted mentor or friend to get comfortable being clear, concise, and supportive too. 
  6. Remember, any message, hard or soft, can be delivered with a heart at peace or a heart at war. If your heart is waring walking in, it’s not the right time for a confrontation. Choose a heart at peace, and if you need help to do that, ask for it. 

Uncomfortable Conversations – Tips for the Invitee:

  1. Don’t freak out in advance because you know it’s going to get uncomfortable. In fact, do not freak out at all.
  2. Keep an open mind. 
  3. Stay. Listen. Respond. When someone is willing to tell you things that feel uncomfortable, it’s not a signal to leave or cut things off. 
  4. Share your perspective even if it’s contrarian. It’s ok to disagree, and learning to share your thoughts is imperative to your success. 
  5. Turn down the self-talk. We all know what it’s like to be in an uncomfortable conversation while listening to your internal dialog instead of the other person: “They’re a jerk. What do they know? Seriously? Whatever…”
  6. After the conversation, ask yourself: What could be true that I’ve been ignoring, dismissing, or accepting as unchangeable?

Whether you’re a leader who is facilitating uncomfortable conversations with your team as a whole or with individuals, start with respect, an open mind, and a heart at peace.  

We need to be able to have uncomfortable conversations as parents, partners, teammates, and friends. If we put all of our energy into avoiding the discomfort, we’re missing out on opportunities for growth, compassion, and collaboration.  

Whether virtual or in-person, be someone who uses uncomfortable conversations as springboards for success.   

What if?

The next time someone initiates an uncomfortable conversation with you, thank them for having the courage to care and the commitment to you and your success.  

The next time you consider backing away from instigating an uncomfortable conversation, instead commit to leading with confidence, competence, and creativity instead of avoidance, aggression, and allegations.  

What do you do when faced with an uncomfortable conversation?