Difficult Conversations Are Inevitable

It is natural to want to avoid difficult conversations. Pretend conflict is just temporary. Assume there is no discord in our team. If Difficult Conversations are inevitable, unavoidable, then why is it so hard for us to deal with them?

Difficult Conversation is a necessary evil, yet 66% feel stressed to deal with difficult conversations.

We avoid dealing with them because –

  1. We think they are confrontational in nature and we want to feel liked and supported by others.
  2. We lack the ability to convey the message correctly.
  3. We fear it will upset people and disrupt business.
  4. We are worried about how the other person will respond. Will they get angry?
  5. We think it will affect our relationship and impact future work.
Sometimes the most important conversations are the most difficult ones to engage in.
– Jeanne Phillips

As Leaders of teams, we dread certain conversations, especially the ones where there is contention, misalignment, disagreement, or sensitive issues at stake. In my 18 years in the Software Industry, I have dealt with many Difficult Conversations. Here are some examples from my experience …

⊗ Team Member, who is aware that his performance has been declining: “So when can I get a performance raise?”

⊗ Team Member who has missed several deadlines and is now adding churn to the team: “I promise, this time it will work. I only need 2 more days to complete this task. My design is better than theirs.”

⊗ New Member on the team: “I don’t like how you guys are doing things in this team. This is not how we did it in my old company.”

⊗ X complains about Y’s code: “Y has been writing overly complex code. It’s hard to read.”  Y complains about X’s code: “X is always in a rush. His code is short-sighted. It’s not robust, he has not covered failure use cases.”

⊗ Big Leader up the chain: “Your team’s charter is changing, get ready to give away all the applications you built.”

Be brave enough to start a conversation that matters. – Dau Voire

Why Is It Important To Have Difficult Conversations?

When we avoid difficult conversations, the issue never gets resolved. We lose an opportunity to have open discussions, generate new ideas, and correct something that’s not working for the team. Keeping it bottled up continues to play havoc on our minds. Ignored conversations lower team morale, lessen employee engagement, and impair productivity.
When we participate in difficult conversations, we build trust. We prove to the team that these are important matters that need to be addressed and as leaders we are not afraid to deal with them. When we value something deeply, we have to be brave to talk about it. In the long run, it creates rapport and builds better relationships.

Some Of My Favorite Books

When dealing with Difficult Conversations, I have found these 3 books to be a great reference. All 3 are extremely insightful and offer practical strategies. I find myself reaching out to them quite frequently.
  1. Getting to Yes, by Roger Fisher, William Ury & Bruce Patton [Link]
  2. Crucial Conversations by Joseph Grenny, Kerry Patterson, Ron McMillan, Al Switzler & Emily Gregory [Link]
  3. Difficult Conversations: How to Discuss What Matters Most by Bruce Patton, Sheila Heen, Roger Fisher [Link]

How To Take Control & Deal with Difficult Conversations

Your team looks to YOU to acknowledge, address and navigate difficult conversations. To help you get over the overwhelm, anxiety, and dread of tackling challenging conversations, here are some strategies to help you.


#1 Build A Culture That Encourages Safety & Candor

Your primary job as a Manager is to build psychological safety on the team. Make it Safe for your people to have difficult conversations.


One of the building blocks for a great performant team is a culture of Empathy. Embrace Empathy. Lead by example. Show your people they can rely on you to be heard.


Make mutual Respect a core foundation of your team. When you lead with respect and authenticity and not by attacking, you show your people that you value them and their feelings.


Address difficult conversations in a Timely way. Don’t sit on it for days. Don’t let it brew. Inaction with a difficult conversation builds resentment, anxiety, anger, and frustration.

#2 Prep For The Conversation

Ask yourself – Is the problem worth addressing? What impact is it having on the team? Is it something that will go away in due course of time? Are you over-reacting? Or does it warrant an immediate discussion?
Be clear about the reason for the conversation. What are your intentions with addressing the problem? Are you just using this to vent frustrations, flex your superiority or do you really care to find a mutually acceptable solution?
Are there any past experiences that are relevant to the current problem? Is there some history to this behavior? Has it happened before? Has it been addressed before?
Where do you plan to meet them? You will of course want to discuss these types of conversations behind closed doors. But ensure you are choosing a neutral location. Is your office the best place for it? Does your office give a subtle indication of power? Is power a contributor to the conversation? If not, choose a meeting room, instead.
  How will you inform them? Will it be a meeting on their calendar? Or are you just planning to grab them at their desk? You don’t want to spring a total surprise and catch them when they are least expecting it. It’s only fair to give them advance notice of a couple of hours so they don’t feel unprepared.    How will you approach the conversation? What will you say to them? Do not give mixed messages. Nobody likes a feedback sandwich. Be honest and candid about the problem you want to discuss. 
Be mindful of the after-effects. How do you want them to feel after the conversation? The next steps may not be entirely up to you but what actions are you hoping them to do?
Be sure to check my post on Strategies for Effective Communication.

#3 Get Clear On The Problem

What is the problem about? What happened? What was their intent? What was the impact – impact on themself, impact on the team, impact on the business? When faced with a problem, we have a tendency to make assumptions about behaviors and actions. Be intentional about removing bias when analyzing the situation. Get rid of any assumptions you may be using. Focus only on the facts. The goal of any difficult conversation is to address the problem, learn from it and get better.

#4 Two Sides of a Coin

During a Difficult Conversation, remember there are 2 sides to a coin. Share openly and candidly – What happened according to you. Use data to support your story. Then ask What happened according to them? What’s the data to support their story?
Without resorting to blame-game, determine how you got to the problem. How have their actions contributed to the situation? Acknowledge your contributions to the situation. How have your actions contributed to the situation?
Are they aware of the impact of this problem? The impact is measured at many levels. How does this situation impact their deliverable, their career growth? What impact does it have on the team dynamics, team morale? Is the business impacted? Are your customer affected? It’s your job as their manager to assess the right impact and make them aware of it. In doing so, the goal is not to make them feel worse, it’s, to be honest about how actions lead to consequences.
How is this situation making them feel? Most likely they feel frustrated, angry, and helpless. How are you feeling? Frustrated, angry, and helpless? Have an honest conversation about how makes you both feel.
Every good conversation starts with a good listener.
– Anonymous

#5 Listen Intently

Embrace the mindset of Listening to Understand v/s Listening to Respond. Sometimes we are so burned by the situation, we don’t really care to listen. We discard the other person’s comments as excuses. Hone your attitude to be of curiosity rather than accusations. Listen to really understand. There may be more to it than what’s showing up at the surface.
Ask follow-up questions to gain additional clarity. Lack of context makes it harder to understand the situation. So when you ask follow-up questions,  tell your people, the questions are not to doubt them but for you to gain context. 
Use Paraphrasing as a tool to get clear. This is such a vital step and yet many will skip it because it seems babyish. But in my experience, “saying it back” has really been insightful. I am surprised how many times we get each other wrong.  You paraphrase it back to them. Ask them if you understand their stance correctly? Ask them to paraphrase what you said. Did they understand your concerns correctly?

#6 No Need For Blame-Game

With Difficult Conversations, there is no need for Blame – make this amply clear to your team. People resort to blame-game when they feel threatened. When you build a culture where there is complete ownership (even for failures) and the focus is on learning from mistakes not avoiding mistakes, you take your team away from the nastiness of the Blame-Game.


You as their leader can set an example and move away from judgments. There is no need to judge who is good or bad, right or wrong. The goal is to fix the problem, learn from the mistakes, and move on.


At the same time, you should not ignore the root cause of the problem. Build mechanisms that allow your team to deep-dive in a collaborative manner and identify root causes using frameworks such as Root Cause Analysis (RCA) or the 5 Whys. It’s important to get to the bottom of the problem so that we don’t repeat it again. And it can be done in a systematic way without the need for blame.
The two riskiest times in crucial conversations are the beginning and the end.
– Excerpt from the book Crucial Conversations

#7 Workout A Solution 

OK, so far you have been a brave leader. You decided to have a Difficult Conversation. You worked out the details, you looked at both sides, you shared candidly, listened attentively and you had a constructive dialogue. What’s next?


Now, it’s time to decide how to get to a solution. 


All parties involved in the Difficult Conversation need to agree on 2 things –  The Decision Maker and The Solution.


  1. The Decision Maker can be you or the other person. Or it can be your team. Or it can be a Leader or Stakeholder. It’s for you and the other person to hash out who will be the decision maker.
  2. You may need to brainstorm collectively to determine the best solution. Bear in mind that working out a solution may be a longer process and that’s OK. In my experience, getting clarity, seeking alignment, and setting expectations can be done in one session. I usually need a separate session to hash out the solution, create milestones and action items. But it has to be a solution that’s fair and acceptable to both parties.

    Once you have decided on a solution, be sure to create action items. Every action item needs an owner, a date (ETA), and a mechanism for sharing updates. Also, be sure to perform periodic follow-ups. 

    Before an intimidating conversation, I always remind myself that I will be the same person before and after the conversation, no matter the outcome.
    – Olivia Fay

    Don’t Ignore Feelings

    Feelings allow us to experience situations. They also allow us to navigate difficult conversations. Feelings are complex and not easy to read.
    So, be prepared for heated tempers, arguments, denials. Acknowledge the feelings, both yours and theirs. Don’t shove them under the carpet. You will earn the trust of your team when you appreciate their feelings, not just their work.
    Difficult Conversations are hard – for every one.  Invest in some self-care for yourself. Follow up with your people. Check on them. How are they feeling after the conversation? Acknowledge that it was a difficult time for you as well.

    Difficult Conversations Are Hard, But They Don’t Have To Be

    Difficult Conversations are challenging for all involved. Here is a reminder of what not to do.
    1. Don’t ignore them
    2. Don’t get judgemental or defensive
    3. Don’t play the blame-game
    4. Don’t shy away from telling the truth
    5. Don’t forget to use data
    6. Don’t be closed to hearing the other person
    7. Don’t interrupt the other person
    8. Don’t use your power to gain control
    9. Don’t get upset, angry, or scared
    10. Don’t forget the goal is to resolve, learn and improve
    11. Don’t forget to follow up


    Difficult Conversations are hard, but they don’t have to be. Don’t put off conversations just because they are inconvenient or hard. If there is something that’s disrupting your team, it’s best to address it before it becomes a big mess. Don’t let your emotions run the show. Focus on problem-solving and learning. Think of how you would like to be treated during a Difficult Conversation. Use the same parameters for the other person. Apply the strategies from the post and make Difficult Conversations an important and successful mechanism on your team. 

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