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Managing Difficult Conversations

Whether it is in your personal or professional life, there is a high probability that you will need to have a difficult conversation.  Because relationships are such an integral part of both, understanding how to pursue peace amidst conflict is crucial.  In this article, we hope to help you learn some valuable facets of managing difficult conversations, both at home and in the workplace.  These tools will help you to navigate difficult conversations at work by understanding a little more about why they are important in the first place.

Why are difficult conversations important?


Difficult conversations are important for a number of reasons.  For one, they can bring clarity and resolution to situations that may have occurred due to a misunderstanding or disagreement.  There is always room for improvement in our relationships, so opening the lines of communication to prevent future conflict are reasons that should encourage you to seek out these conversations.  Navigating difficult conversations in the workplace will allow for personal growth, help you improve at conflict resolution, and also build stronger relationships with co-workers.

Learning to openly, honestly, and confidently handle challenging conversations will foster personal and professional growth, helping you to understand how to set boundaries, and gain valuable experience in problem-solving and effective communication.

Why do we avoid difficult conversations?

Reasons for avoiding difficult conversations vary from person to person as well as from situation to situation.  For some, fear might be at the top of the list: fear of conflict, fear of creating further damage in already strained relationships, fear of rejection or of criticism.  Concern for the other person’s feelings is another reason people avoid difficult conversations, trying to protect the individual from feeling uncomfortable or hurt.

If a lack of communication skills and emotional vulnerability are two things holding you back from pursuing a difficult conversation, consider reaching out for help from a mentor, colleague, or professional to gain some experience before trying to handle things on your own.  Then, try practicing some group exercises on difficult conversations with family or friends. Once you start building your confidence, you will see how a well-thought-out conversation can truly improve your relationships.


It’s important to remember that the discomfort of addressing an issue by having a challenging conversation is only temporary and has far fewer consequences than avoiding it altogether.

Despite these common reasons, it’s important to recognize the harm caused by avoiding difficult conflict.  Unresolved conflict can cause irreversible damage to already strained relationships, having long-term effects.  By learning how to effectively communicate while practicing openness, honesty, and empathy, you’ll soon begin to navigate these discussions confidently and successfully.

What are the main points of difficult conversations?

There are a number of components that define the nature of a difficult conversation. Taking each of these into consideration will help you better understand how to navigate these challenging situations when they arise.

Emotional Charge: Difficult conversations often evoke anger, frustration, anxiety, defensiveness, and even sadness, in some cases.  As emotions run high, so may the volume of the conversation. Careful preparation will help you keep your emotions in check.
Competing Narratives: Obviously, we all don’t have the same opinions on everything.  In these situations, it’s often that not only is the perspective different but the stories might be as well.
Vulnerability: Open, honest communication where either or both people are expressing their feelings, insecurities or fears requires vulnerability.
Underlying Issues: We see only the surface level when, in fact, the symptoms might go much deeper than the issues being addressed.
High Stakes: Progress or lack thereof can have an adverse effect on the other party involved, which means the stakes are high, leading to significant changes in relationships, decisions, and positions.

Female coworker arguing with male coworker

What are good questions for difficult conversations?

two business people working out conflict

Developing a list of open-ended questions to refer to in a difficult conversation is another way to prepare ahead of time. These questions should be a crucial part of your conversation toolkit, helping deter from defensiveness and also reel things back in should emotions come into play.  They will promote understanding, facilitate a dialogue that will be productive, and uncover any underlying issues.  Here are some examples:

  • Can you help me understand your perspective?
  • What made you feel this way?
  • What would you like to see come from this conversation?
  • How can we work together to come up with a solution?
  • How can I help you to address these concerns?
  • What are some examples of instances that can help me to understand your concerns?
  • Do you have any other topics you’d like to discuss or concerns you’d like to address? 

Remember that the effectiveness of these questions depends on the context and the specific dynamics of the conversation. Tailoring your questions to the situation and actively listening to the responses will help guide the discussion toward a more constructive outcome.

What are the 7 principles of difficult conversations?

Engaging in difficult conversations effectively requires an understanding of what you can do in order to prepare. Here are 7 key principles to consider when building your framework for a difficult conversation:

  • Begin with the end in mind.  Think about your goals, which should involve mutual understanding and coming up with a solution to a problem rather than a competition to prove who’s right and who’s wrong.
  • Right time and place.  If either party isn’t comfortable or feels rushed, you have already set a poor tone for the conversation.  Find a mutually agreeable time and a private place in which to have your discussion.
  • Practice active listening.  This means giving your full attention, without distractions and without interrupting.  Do your best to try to understand the other person’s perspective.
  • Manage your emotions.  You already know emotions run high in challenging situations so be sure to keep your own emotions in check.  Having a good plan in place will help.
  • Use “I” statements.  This is how you express your feelings without assuming the feelings of the other person.  It helps them to gain insight into your perspective.
  • Ask open-ended questions.  Responses that involve more than a simple “yes” or “no” will help you to see their point of view, it will show that you are engaged and validate their feelings and concerns.
  • Seek a mutual solution.  There has to be some common ground here. Find it and use it as the basis for a collaborative solution.  Compromise as necessary.

By keeping these main points and principles in mind, you can approach difficult conversations with a structured and effective strategy to navigate them successfully and maintain positive relationships.

Boss shouting at employees

What steps should you take in managing a difficult conversation?


Managing difficult conversations isn’t easy.  However, a well-thought-out discussion can give relationships the boost they need, open the lines of communication and build trust.

So how exactly can you manage these conversations effectively?  By coming prepared with discussion points, facts about the issue(s) at hand, and ideas for a solution that will work for you both.  Here are a few steps to help you get headed in the right direction.


  1. Don’t avoid it.  Avoidance is the worst thing you can do when it comes to these crucial conversations.  As we mentioned earlier, the effects can be detrimental to your team and ultimately your business if you brush them under the rug or save them for discussion another time.
  2. Be prepared.  Think about your discussion points and goals.  What would you like to achieve from this discussion? If you know ahead of time what you’re planning to discuss, know how you’ll discuss it, and with the ultimate goal of resolving the issue at hand, then you’ll have little to throw you off course.
  3. Set a positive tone.  Clarifying your intention for the conversation and sharing your desired outcome is important.  Let the other person know that, although you may be conveying important information, you are seeking understanding from them as well.
  4. Be confident and direct.  Because you should have already come prepared with facts to back up your reason behind the meeting in the first place, the next thing you need to do is stick to the facts.  One thing people cannot argue with are the facts.
  5. Empathize and validate.  Even if you disagree with the other person, hear them out and try to understand their perspective. This validates their feelings which makes them feel valued and heard, as we mentioned earlier.
  6. Share your thoughts.  Of course, sticking to the facts is best, but as a leader, this has had some effect on you and potentially your team. Share with the other person openly, honestly, and respectfully about how this matter has made you feel.
  7. Stay calm and respectful.  This goes without saying….especially if you’re in a professional, workplace environment.
  8. Seek solutions. It’s important that you come prepared with ideas in which to solve the problem or goals moving forward.  But seeking a solution together will engage the other person and give them some input which will, in turn, motivate them to make necessary changes.
Handsome young man demonstrating his sketch while talking about his new project

What are the principles for handling difficult conversations?


There are a number of principles to keep in mind when handling difficult conversations.  Once you have a better understanding of these principles, you’ll be able to communicate more effectively in challenging situations, offering empathy and a willingness to collaborate on a resolution.

  • Prioritize relationships.  Your ultimate goal is building better relationships which means saving the relationship is more important than being right.  Focus on building trust and mutual respect.
  • Maintain privacy.  Confidentiality is important.  Unless this is something that needs to be discussed with another member of leadership, respect the privacy and confidentiality with which the conversation was held.
  • Avoid assuming.  You know what they say about assuming…If you go into this discussion already believing you know what the other person is thinking, will say, or do, it’s inevitable that you’ll start off on the wrong foot.  Give them the benefit of the doubt and allow them to speak for themselves.
  • Remain flexible.  Although you should come to this meeting prepared, be flexible, and read the dynamics of the room as the conversation unfolds.  Take breaks as necessary with sensitive topics.
  • Be patient.  These things take time but they are worth it.  While it may seem easier to monopolize the conversation, it’s not ideal.  Give the person time to think and time to respond. Don’t rush to a conclusion before giving them a chance to speak.
  • Be self-aware.  You will naturally have your own biases, emotional responses, and triggers.  Be aware of these things so that you are better able to manage your emotions and effectively communicate.
  • Encourage ownership.  Holding yourself accountable and teaching the other person to do the same will encourage the other person to take ownership of their feelings and actions.
  • Practice non-verbal communication.  Sometimes our bodies or our facial expressions say more than our words do.  Make sure your tone, body language, and facial expressions don’t give non-verbal cues as to the emotions you’re trying to keep in check!
  • Focus on problem-solving.  Rather than dwelling on what happened, talk more about what you both can do to move forward.

Every conversation will be unique.  However, these principles will help you build a solid foundation when navigating challenging situations.  Giving grace, and showing empathy and kindness will ensure a more successful outcome.


How to end a difficult conversation.


Chances are, if you made it to the end both of you are ready to get on with your day.  However, it’s important to clarify what you’ve discussed along with any measurable goals set in the meeting.  Summarize key points that you can go back to at a follow-up meeting.  Thank the person for their time, honesty, and vulnerability, leaving things on a positive note.

In closing, we would like to leave you with the answer to one more important question: What are three techniques for approaching difficult conversations in the workplace?  These three takeaways are of utmost importance when in the midst of a difficult conversation.  Commit these to memory and the other stuff will soon follow!

  • Practice active listening.
  • Ask open-ended questions.
  • Use “I” statements.

Although we cannot avoid difficult conversations, we can help control the outcome.  Understanding the principles, applying the techniques, and having a good set of questions in your crucial conversations toolkit will help you manage these talks while encouraging active participation.