How To Be More Comfortable With Having Uncomfortable Conversations

Today, more than ever, there are many polarizing topics away from which we steer because we are avoiding hurt feelings, defensive argumentation, and damaging relationships. Consequently, most of us stick to the “safe” conversations centered around sports, weather, and the latest Netflix series we’re binge-watching.

The problem is, we’re missing out on opportunities for growth if we don’t learn how to engage in deeper, uncomfortable conversations whether it’s negotiations, performance feedback, or broader social issues.

Being honest (in a graceful way) is one of the most loving and caring things we can do for one another. It builds trust and respect. The fact is, most people avoid being completely honest with others because they struggle with the mechanics of how to effectively communicate in uncomfortable situations.

How can leaders create a safe environment in which the involved parties feel it’s encouraged to speak candidly without negative repercussions?

How do we condition ourselves, as leaders, to be better listeners and move beyond our own tensions and discomfort with difficult conversations?

I reached out to several of my previous CWL guests and other respected leaders to gather their perspectives on jumping feet first into uncomfortable conversations. Their insights were instrumental in this presentation I gave on The Daily Huddle on this topic.

Recorded Conversation On The Daily Huddle [9:30]

Tracy Notte – HR Executive

One study showed that only 7 percent of communication is the words we use. Thirty-eight percent is our tone of voice, and 55 percent is body language. In face to face conversations, we are using all three. On the phone, we’ve lost the body language so we are down to two. When our communication is completely through email, texting, or social medial we’re down to one – and we have lost 93 percent of the tools that help us connect. When uncomfortable conversations are required they need to happen face to face. Face to face conversations provides a better opportunity to see the perspective of the other person accurately. 

When conversations get tough, we often respond by digging in our heels and fighting for our positions, hoping to convince the other person they are wrong. These kinds of conversations tend to escalate because we are focused on ourselves and what we want. The foundational skills for having an uncomfortable conversation are:

  1. Make it safe. Work together to solve the issue. Show respect for the other person even when we disagree. Don’t count on people changing. Challenge them to grow but they need to know we accept them and value them whether they change or not.
  2. Eliminate intimidation. Realize that different people communicate in different ways. It is not right or wrong just different.
  3. Practice power listening. Give the gift of genuine listening. It’s the fastest way to soften the strain of a tough conversation.
  4. Encourage honest feedback. Make it safe for others to share feedback. Listen to their input and resist being defensive. Input is their perspective, not necessarily the truth.
  5. Start with kindness. Kindness is a strength that builds relationships. If the conversation is not going well take a kindness break. Ask for five minutes to affirm something about the other person you value. 

The more uncomfortable the topic the more important it is to connect with someone. Often we try to avoid uncomfortable conversations by communicating electronically. Would you text someone “Last week I lost our life savings gambling”? 

David Bond – My Dad & Retired Insurance Executive

  1. A problem never gets better if it’s not addressed and resolved. Unresolved issues would cause me to feel tension, and I typically found those with whom I had such conversations also felt tense.  “Clearing the air” would at least start to make it better for everyone involved.
  2. Your people look to you, as a leader, to handle difficult conversations. If you delay or duck this responsibility, your leadership authority is weakened in the eyes of your staff, and perhaps even customers or other constituents. Conversely, dealing with difficult conversations/ problems/ issues effectively may enhance your leadership authority. 
  3. Frame and deal with reality, but leave them with hope. This can be as big as our President failing to square the reality of the pandemic with our nation, to helping an employee realize they are not right for the job for which they were hired based on x,y,z.
  4. Listen without judgment (from Mom). Similar to how Matthew McConaughey would respond with “heard” when talking with Emmanual Acho on “Uncomfortable Conversations With A Black Man”. Powerful!

This is from the perspective of business leadership, but I believe the same principals can be applied to any number of social, civic, and more personal relationships challenging conversations.

Rev. Dr. Jarrod Longbons – Senior Pastor

  1. Begin with empathy so that you can understand where people are coming from. Most anger and frustration exhibited is probably NOT all about you. What else is going on in their world to make them feel a certain way? 
  2. Assume the best. Most people do not wake up thinking of how to destroy you. Yet we often start with adversarial notions in mind (us v. them). When a baby cries, no one assumes that the baby is trying to do us harm. We assume that the baby is hungry, tired, or has a full diaper. Why can’t we assume the better of other adults? If we did, we would be more graceful in hard convos. 
  3. Take responsibility for yourself, words, and actions. Be willing to say I’m sorry. Be willing to acknowledge where the other person is correct. 
  4. L.U.V.
    • Listen – do not interrupt or do that thing where people can see you waiting to talk. 
    • Understand – Repeat back what you heard to make certain that you understand properly (this de-escalates things a lot).
    • Validate – You do not have to agree to validate. You are only validating the person’s feelings. (I can see why you feel that way, that makes sense, etc.). 

Karen Cramer – Chief Community Impact Officer

I’m a huge fan of Radical Candor and our former CEO James Franklin always said “clear and kind.” That has always resonated with me!

Beth Armknecht Miller, CMC – Talent Management Advisor, Leadership Coach & Trainer, and Contributing Writer on Chat With Leaders

I have two words of advice, the first is to practice being curious and concise. The second is that most leaders overthink the process and imagine the worst when going into a difficult conversation. Start with thinking about what would be the best result from the conversation (i.e. the person understands your perspective or the person has a plan to improve.)

Mark McKenzie – Owner of Docqmax Digital Printing

Therefore whatever you desire for men to do to you, you shall also do to them; for this is the law and the prophets.

Matthew 7:12

Basically treat others the way you would want to be treated. Open honest conversations as well as demonstrate empathy and compassion.

Also, LISTEN intently and on purpose. This is the most important part of any conversation. Something that is a work in progress for me but I am getting better at it.

Take a deep breath, pause, be in control of your emotions, and THINK before you reply!

Not always the easiest things to do but usually the only way I can sleep afterward.

Jeff Davis – Founder & President of Southern Data Solutions

The best advice I can give for this situation is to ALWAYS start the conversation with a positive note. Such as if you have to reprimand someone, tell them what they are doing that is good and then lead into what needs to be worked on.

Also, I would say that no matter what the topic is, always offer to be part of the solution, to help figure out a course of action (together) and cheer on the person to not only make the progress but as they make the progress. Helping someone should be our first goal as some people don’t know about their issues and just need guidance or mentoring.

Evan Knox – Founder & Chief Marketing Officer

Empathy and self awareness! 

Greg St. Jacques – Vice President, Talent Solutions

My rules of thumb are be prepared, be honest, be constructive.

Shaun St. Hill – CEO & “Helper In Chief” at Tech & Main LLC

  1. Go into the conversation seeking to understand
  2. Don’t get caught up in the wording being used to describe the situation (i.e. white privilege versus white blessing)
  3. Be the change you want to see (be sure to give Gandhi credit 🙂)
  4. Leaders are readers (do a little bit of research on the uncomfortable topic)
  5. Let people know you don’t have all the answers but that you care and want to be part of the solution.

Staci Ingram – SVP Corporate Communications & Development

The most important thing about a difficult conversation is to not think about how uncomfortable you are but to focus on how you would feel if you were receiving the information you are about to deliver and how would you want someone to tell you.  Focus on the other person.  Even if the news is that they have an attitude or are defensive (and even if you know that they will give you attitude or be defensive), understand why they might react that way and rise above it.  Be loving.  Be understanding.  Deliver the information because they deserve to hear it and always be concerned about what’s best for the person receiving the information.  Even if they don’t receive it well when you deliver the information, they will appreciate you in the long run and ultimately know that it was just as difficult for you.  But don’t make it about you – make it about them. 

Chris LaFay – Founder & President of Classic City Consulting & Co-Founder of Chat With Leaders

  1. Avoid being passive.  Surround yourself with people that are more proactive than you.  Passivity kills uncomfortable conversations because the longer you put it off, the worse the conversation will be.
  2. Make a quick decision:  This isn’t 100% good advice, but I was having to make a decision to let go of an employee.  I spoke with one of my business friends and he told me: “the longer you dither on that decision the more money you are wasting away.  You can always find another person to replace Person A with.  Just let the person go and let the chips fall.”  This was great advice for someone who sucks at making hard decisions (aka. I took 6 months on this decision and lost $10-20K because of it)

Eddie Thomason – Keynote Speaker & Author of “Unlock Yourself”

  1. HUMILITY: Accept the fact that YOU DON’T KNOW EVERYTHING – most of us are unwilling to have uncomfortable conversations because we’re afraid we may look “stupid” because of something we say or we should “already know” the answer – the truth is, we don’t know everything, therefore we need to get comfortable asking/learning about what we don’t know.
  2. Seek understanding/don’t push your own agenda – Enter the conversation truly wanting to listen and hear the other person’s perspective. Listen with the intent to understand instead of with the intent to (speak) rebuttal. The more common ground you identify in the beginning, the more impactful the conclusion/resolution of that conversation will be.
  3. Use, “Tell me more.” or “Elaborate on that.” – Take the pressure off of yourself to speak. When someone else is sharing a thought/idea, instead of trying to make a follow-up statement on incomplete information, ask the other person to elaborate so you can get to the root reason behind their statement.
  4. Agree to disagree – You can’t “win” an argument. Don’t make someone else look dumb or stupid to prove your point. Sometimes you’ll just have to agree to disagree.

Crucial Conversations is is an AMAZING book that will help you navigate uncomfortable conversation!

Dee Ann Turner – Author of “Bet On Talent” & 33-year veteran of Chick-fil-A’s Leadership Team

One of the most important is to get to the point. When we beat around the bush, we create anxiety in others that just makes it that much more uncomfortable. 

Jim Jarrells – Founder & CEO of J&D Consulting

  1. Take a deep breath.
  2. Be clear & concise about the topic/subject.
  3. Remember “uncomfortable” doesn’t mean “worst”.
  4. Consider using “we” or “us” (instead of “you”) to reflect team and compassion.
  5. Consider the other person’s point of you.
  6. Reserve any immediate response to feedback or criticism until you’ve thought it through.
  7. Summarize and restate any action items for follow-up.

Jay Shaffer – Board Member at Atlanta Technology Angels

  1. Ask yourself, why is this conversation uncomfortable?
    • You may be jumping to conclusions. The other person may be relieved you bring this topic up.
    • Or, the person may be unaware.
  2. Know your audience.
    • Who will you be addressing? What is important to that person?
  3. What do you want to accomplish with the conversation?
    • Any intermediate steps you could achieve on the way?
  4. Carefully determine what you want to say first, then listen. The person listening controls the conversation.
  5. During the conversation:
    • Be empathetic.
    • Keep your poise.
    • Criticize the behavior, not the person. “When you do this <behavior>…  not,  you are <noun, adjective >…  

Tim Smith – Co-Founder of Chat With Leaders

  1. If you don’t know the goal/objective of the conversation, don’t have it until you do.  But, don’t procrastinate. 
  2. If possible, have the conversation early in the day to remove mental distractions.
  3. Don’t let your tone/approach become the topic of the conversation- use the appropriate words in a genuine, thoughtful manner.  Always.  Don’t “overly preface”-  be direct, but be kind.  Focus on the issue and not the individual. 
  4. Look for opportunities in the conversation for you to learn and grow too- stay humble and care more about “doing right” vs. “being right”.
  5. Compliment in public, criticize in private.
  6. Summarize expectations (if appropriate) and follow-up.

Tony Robinson, CTO

The struggle one has to engage in a ‘real’ conversation is in direct proportion to the lack of care one has for the receiver of the conversation.  

Of course, you have to care for their whole career not just their tenure as your direct report.  Of particular note: if one can care for the individuals in their stewardship to this degree then there will be no potential for the false perception of care.  That should be avoided at all costs – no leader who is perceived as falsifying emotional care will ever be trusted sufficiently to inspire loyalty.  Sociopaths don’t inspire loyalty, but fear of failure.  Fear driven cultures are always less effective than loyalty driven cultures.

If you fire someone and they want to shake your hand and leave with respect for you, you did it right. 

Charlie Paparelli – Speaker, Writer, Angel Investor

Don’t own the outcome. Give the outcome to God and have the conversation.

Richard Hicks – CEO of inspiredu, formerly PowerMyLearning Greater Atlanta

  1. Don’t beat around the bush on the issue involving social equity, be brave, and talk about it.
  2. Leaders should encourage community engagement and assist in breaking down barriers.
  3. Leaders should never be afraid to show their humanistic side.

These are some of the issues I’ve observed with trying to have the uncomfortable conversations, especially in today’s time.  Self-reflecting and engaging in these conversations are important.  We as leaders have to grow and be better at have these kinds of uncomfortable talks.

At the core of Jeff's work is helping servant leaders use their influence as a force for good. As the Co-Founder of Chat With Leaders Media and Executive Partner at People First Elevation Team, he empowers organizational leaders with media solutions that spark collaboration and shared purpose with their teams and customers.

Together with his team, Jeff delivers event production, podcast production, content creation, cross-cultural training, and strategic advisory solutions. They are committed to unlocking the power of inclusive storytelling, shared experiences, leadership development, and feedback integration to ensure their media solutions meet the needs of their clients' stakeholder groups.

Their core values—Partnership, Inclusion, and Empowerment—guide everything they do. By fostering strong partnerships, embracing diverse perspectives, and equipping leaders with the tools to succeed, they aim to transform the way people engage while getting meaningful work done.

Outside of work, Jeff cherishes time with his wife and three kiddos, balancing his roles as a husband and father with his professional life in Atlanta, GA. Connect with Jeff to explore how impactful media solutions can drive success and engagement.

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