We try to avoid having difficult conversations and find ways to live with the problem because our “inner gut” is scared that a confrontation could lead to a bigger problem. Truth is, how do we know how the other party will react? This uncertainty is the reason many of us never even try addressing issues in our jobs, business deals, or relationships.
Definitely, we do not know how others will react to confrontations but we sure can manage the situation. This guide will help you have difficult conversations in the most efficient and seamless way leading to a Win-Win outcome. But first, let’s understand what a difficult conversation is and why it is important.
What is a difficult conversation?
A difficult conversation is any situation where the subject matter is of
high stake or where opinions are strongly opposing which can lead to strong emotions.
Emotions are usually high during these conversations due to the fear of possible outcomes such as disputes or conflicts. This could be a discussion about the quality of work with a team member, situations in your relationship with your partner, or asking a friend to repay a loan. Even tiny issues.
An Interact survey conducted online by Harris Poll showed that over two-thirds (69%) of managers found it difficult communicating with their employees. This survey shows that you are not alone.
Over two-third (69%) of managers found it difficult communicating with their employees. — Interact survey
Why is this conversation important?
Difficult conversations are important because they always pop up when the stakes are high and we are in pursuit of something important. To attain a quality life we cannot avoid having difficult conversations. Most of the time, If you do not talk it out, you will act it out. Which explains why silence is not really silence.
“Our lives begin to end the day we become silent about things that matter.“ — Martin Luther King Jr.

A difficult conversation is not only self-serving. It is actually heroic because although it’s initially hard for you, it is intended to serve the greater good of everyone involved. The quality of a Team/Organisation/Relationship can be measured by the average time between identifying and discussing an issue.
The quality of a Team/Organisation/Relationship can be measured by the average time between identifying and discussing an issue.
A simple guide to having a difficult conversation
1. Make it Safe
The first step to having a difficult conversation is to ensure the other person feels safe. Safety is an element we should always look out for at every point during the conversation. How is the other person feeling? Are they feeling attacked or defensive?
With enough safety, everything is discussable. It might not be what they like but they will definitely listen to you. Mutual respect and mutual purpose are the fundamentals to creating safety in a conversation.
Some good techniques for keeping the other person safe throughout the conversation are…
I. Start with the Fact
In every situation, there are two realities. One is what actually happened which is the fact, while the second is what you tell yourself about what actually happened which is your story. Always state the fact before you share your story and avoid sharing your story as a fact. Sharing your story as the fact will immediately create an uproar leading to a threat to safety.
II. Contrasting(Don’t/Do)
Contrasting can be used to avoid misunderstanding by initially communicating what you DON’T want the other person to think and then laying out what you DO want, which is the purpose of the conversation. This method helps to de-escalate and reduce the tension in the conversation.
III. Be Accountable
Always acknowledge your shortcomings first in the whole situation. This sets a level playing ground in the conversation and also helps create ease to the roller coaster of emotions.
IV. Listen and Validate
Genuinely listening to the other person after communicating how you feel, then validating their opinions by acknowledging their point of view helps both parties understand each other’s purpose and create a pool of shared meaning. When people feel heard, they are less defensive and it is easier to reach your outcome for the conversation.
2. Set an Outcome:
During a difficult conversation, there is usually a roller coaster of emotions that defeats the purpose of the conversation and sometimes takes us back to the same position we were before we had the conversion.
Hence, we have to answer four questions before getting into the conversation. The answers to these questions will act as a compass and guide on how we should act at every point of the conversation regardless of the overflowing emotions.
1. What do I want for myself?
2. What do I want for the other person?
3. What do I want for the relationship?
4. How would I behave if I really wanted these results?
Restate the goal:
Keep talking till you hit the outcome of your goal. Ensure to clearly communicate what your underlining issues/thoughts/feelings are.
No one enjoys difficult conversations, at least initially but a great hack to igniting that difficult conversation is to separate the emotions you feel about having this conversation and focus on the outcome you want from the conversation.
3. PRACTICE
Take a deep breath, untangle your emotions from the subject matter, and lastly change your mindset, go into the conversation like every normal conversation.
It can also help to plan what you want to say by jotting and taking key points down before your conversation.
CALL TO ACTION
Now go ahead and practice with situations in your life, it is best to start around close friends and people you trust. Practice with people you’re comfortable with first.
Don’t worry about having the best conversation now, just make sure you make the best from your current knowledge.
Finally, don’t hesitate to share lessons you learned from having difficult conversations in the comment section.
Thank You!
Additional Resources
· Crucial Conversations: Tools for Talking When Stakes Are High by K. Patterson, J. Grenny, R. McMillan, A. Switzler
· Difficult Conversations By Douglas Stone, Bruce Patton, and Sheila Heen