Mastering Difficult Conversations: Strategies that Work

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Mastering Difficult Conversations: A Guide for Growth Oriented Leaders

Mastering Difficult Conversations: Strategies that Work

business culture creation leadership mindset personal performance self mastery Jun 02, 2023

Disagreement at home? Asking for a raise? Negotiating a sale? Receiving feedback? Discussing differing political positions? Difficult conversations are an inevitable part of life, affecting us both personally and professionally. As leaders who are dedicated to personal and professional growth, it's crucial to equip ourselves with the necessary skills to navigate these challenging interactions. By mastering the art of courageous conversations, we can foster positive outcomes and mutually beneficial solutions.

Whether it is on the home front or in the professional space avoidance tends to lead to more problems.  We will explore the key aspects of difficult conversations, highlight the top 10 challenging scenarios, and provide practical strategies to communicate effectively in such situations.

Most people find the following topics challenging. I, personally, can think of real life examples for each of the top 10 that made my mouth dry, my hands clench and my words scramble. We are human. Each of these difficult situations can be easy for many who have practiced communication and near impossible for those who haven’t.  In other words, the label “DIFFICULT” is very subjective.

Which of these top 10 conversations do you find most difficult?

  1. Delivering bad news: Telling someone about a death, illness, or job loss can be emotionally challenging for both the person delivering the news and the person receiving it.
  2. Ending a relationship: Breaking up with a romantic partner, ending a friendship, or severing a business partnership can be emotionally difficult and may involve difficult conversations.
  3. Addressing conflicts: When there are disagreements or conflicts between two people, it can be difficult to address them in a constructive manner, without causing further hurt or tension.
  4. Giving feedback: Providing constructive feedback can be difficult, as it often involves pointing out areas where improvement is needed.
  5. Addressing personal shortcomings: Acknowledging one's own faults, mistakes, or weaknesses can be difficult, especially if it requires admitting to past wrongdoings.
  6. Discussing sensitive topics: Topics like religion, politics, or personal beliefs can be sensitive and may lead to disagreements or conflict in some situations.
  7. Asking for forgiveness: Offering a genuine apology can be difficult, as it involves acknowledging wrongdoing and taking responsibility for one's actions.
  8. Asking for help: Seeking assistance or support can be challenging for some people, as it may require admitting vulnerability or a need for assistance.
  9. Negotiating: Negotiating for better pay or conditions, or negotiating a business deal can be challenging as it often involves advocating for oneself and may create tension between parties.
  10. Challenging authority: Having to speak up to a superior or challenge authority figures can be difficult, especially in a hierarchical workplace or society.


So how on earth do we practice or prepare for all of these scenarios?  Make it simple.  Every one of these difficult conversations can fit into 1 of 3 buckets.

  1. Truth Telling: Something  to be shared that is challenging, upsetting or uncomfortable for either party.
  2. Truth Receiving: Something to be received that is challenging, upsetting or uncomfortable for either party.
  3. Worthy Request: Something to be requested that is important. Rejection of the request is challenging, upsetting or uncomfortable for the requester and sometimes confrontational to the requestee.

The most important thing to remember is that each is subjective to the individual. 

Their truth is different from yours.

Their “worthy request” is different from what you find worthy.

You likely have different objectives and finding common ground will be key… and much easier when you can categorize into 1 of the 3 buckets.

You have simplified the conversation into a category… Now what?  

Stew about it and panic?  Avoid it because you know it will be painful?  Absolutely not!  You are a leader and you are growth minded.  You know that this is a skill and it can be learned and practiced.

The most effective actions in difficult conversations are the following communication practices:

  1. Be clear and direct: When delivering difficult news or having challenging conversations, it's important to be clear and direct with your words. Avoid beating around the bush or using euphemisms, as this can lead to confusion or misunderstandings.

  2. Show empathy: While being clear and direct, it's also important to show empathy and understanding towards the other person's feelings. This can help to make the conversation less confrontational and more constructive.

  3. Use "I" statements: When expressing your thoughts or feelings, try to use "I" statements instead of "you" statements. This will help you avoid sounding accusatory or blaming the other person, and instead, focus on your own feelings and experiences.
  4. Listen actively: Listening actively and attentively is key to having effective conversations, especially when delivering difficult news. Pay attention to the other person's reactions and respond in a way that shows you understand their feelings.
  5. Offer solutions: If the conversation is about a problem or challenge, try to offer solutions or alternatives to help move the conversation forward in a constructive way.

  6. Be respectful: No matter how difficult the conversation may be, it's important to maintain a respectful tone and attitude towards the other person. This will help to create an environment where both parties can communicate effectively and find a mutually beneficial solution.
  7. Prepare beforehand: If you anticipate having a difficult conversation, it may be helpful to prepare beforehand by thinking about what you want to say and how you want to say it. This can help to reduce anxiety and increase confidence when it comes time to have the conversation.

Ok... let's be real.  I realize that when you are challenged you aren’t going to remember all of that!

So, here is all of it in an acronym that can prompt you to remember… 


P: Prepare beforehand (and prepare them too by letting them know)

R: Remember "I" - use I statements not “you” statements

E: Empathize with the other person's feelings

P: Be Pointed (clear and direct)

A: Actively listen

R: Respect the other person's perspective

E: Explore solutions together

This acronym is not something to magically create communication perfection.  It is a tool that is to be practiced.  It is worth practicing in every conversation, not just the difficult ones.  It is key to aim for 1-2 of the points initially and as you practice you will find that it is easier and easier to incorporate more.  Do not expect that things will go wonderfully just because you show up with better communication skills, yet you can expect that they will prevent things from getting worse!

Remember,  as humans we are very influenced by the people we interact with.  If they got upset, you likely felt something too.  If they accused you, you likely wanted to defend yourself.   If your news was painful for them, you were likely uncomfortable or pained too.  In these heightened emotional states you will not be as clear as you are right now reading the handy acronym that I have created for you.  In other words you may not remember any of the tips and skills that I have shared.  Therefore, I share these final words to get you through anything.  If all else fails and you are at a complete loss... stay calm and be empathetic

Now go forth and create greater trust, solutions, growth and connection in your leadership!

For more support on this topic... listen in to the Empowered Team Podcast Episode 236 The number 1 solution for the 3 most Courageous Conversations

and Episode 239 Grounding Communication

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