In General

In my executive coaching work, I come across a lot of “”wishes” that most of us do nothing about.  We wish the boss would give us more space to make decisions. We wish our co-worker would stop sabotaging us behind our back. We wish our direct report would have a better work attitude.

Many of these situations call for conversations to be had, conversations that often don’t happen, because they are difficult and frankly we’d rather go get a root canal. My goal is for us to all have the personal power to have difficult conversations.  So here is a step-by-step checklist for making these difficult conversations easier so that they actually happen.

Step 1 – Are You Seeing the Situation Clearly?

Conversations become difficult when our feelings and emotions are involved. Emotions cloud our judgment and ability to see the situation clearly. We often have filters or stories that impact how we see a situation. The first step in a difficult conversation is to look within.

Leadership Practice

  • Look inside yourself to see how your emotions could be distorting how you view the situation.
  • Take the time to calm yourself down and get some perspective.
  • What are personal beliefs you have about yourself and the other person involved that make the situation charged for you? How would you view the situation differently if these beliefs were not true?

Step 2 – Identify your Intent

It’s important that we are specific about both our short-term goals (the specific asks we want to make) as well as our long-term goals (the importance of the relationships involved).

Leadership Practice

  • Ask yourself what are your desired short term and long term outcomes (e.g. I would like to get more autonomy in making decisions, and I want to make sure I preserve the relationship with my boss).
  • What specifically are you asking for? (e.g. I would like to be able to make decisions that involve $10,000 or less in my budget).

Step 3 – Put yourself in the Other Person’s Shoes

Putting yourself in the other person’s shoes helps us realize that there are many ways to look at the same situation. We often have a lot invested in “being right” about a given situation or that there is only “one way” to interpret a situation and that is never the case. We need to remind ourselves of our intent (Step #2 above) vs. our unconscious need to be right and to get our way.

Leadership Practice

  • Ask yourself what the other person’s goals are.
  • How could they be viewing the situation differently than you? What are their emotional needs? What filters could they have?
  • Determine what would be the best way to influence them. There are multiple influencing strategies you can employ. Which would work best in this situation?
  • What would be some common goals you both have?
  • What’s in it for them to give you what you want?

Step 4 – Have the Pre-Conversation(s)

Depending on the level of trust in the relationship you may need to have a “pre-conversation” to get more objective perspective on the situation.  The objective of the pre-conversation is to get answers on the questions from above that you are uncertain about without before making your request.

Leadership Practice

  • During the pre-conversation bring a curious and learning attitude. Be willing listen without judgment and without an investment in you being right and them being wrong.
  • Keep your goal in mind but don’t necessarily make the ask. For example you can say, I would like to have greater autonomy in making decisions and I would like to hear your thoughts on that. What can I do to help us get there?
  • Gather input from others on the context/situation. These are people who you can trust will keep the situation confidential and will have good objective perspective on the situation. Be careful you’re not picking people who will just agree with your point of view. You’re looking for objectivity.
  • Revisit your goals (from Step #2) and see if based on the new information you want to adjust the ask you are making.

Step 5 – Pick the Right Time and Place

When planning a “difficult conversation,” the time and place can make a difference in your outcome.

Leadership Practice

  • Make sure the other person is in the right frame of mind (hopefully a time when they have a positive view of you and the relationship is positive or at least neutral).
  • Pick the right environment (when noise and disruptions could be minimized and you have enough time to have a quality conversation).

Step 6 – Bring Empathy To The Difficult Conversation

Bringing a learning attitude and empathy lowers the defenses of others and helps you have a more productive conversation. Latest neuroscience research shows the power of limbic resonance.  This research shows that all mammals (including human beings) adapt our emotional states to those around us. If we bring an attitude of empathy to a situation, the likely response from another will be to match this attitude.  So, our first work is within ourselves.

While it may be counter-intuitive, being able to be vulnerable (see tools below) is an excellent leadership practice. It shows courage and strength. It’s where we share with an open heart our own truth about a situation without blaming another person or having any specific expectation about how they will respond.

I was able to witness a difficult conversation between a client and her boss where the client shared with great vulnerability how she felt “the need to prove herself” when she first took on her large role. It caused her boss to open up and share how he had felt the same way earlier in his career. This one conversation forged a deeper bond between the two which she credits as the turning point in their relationship.

Leadership Practice

  • Start by putting them at ease (if the situation is difficult for you, it is likely difficult for them).
  • Start with the common objectives you both have.  Ask them what their objectives are in this situation.
  • Clearly state your desired outcome (from #2). Instead of asking for their agreement or disagreement, keep your questions open. Ask them for their thoughts and feeling on this subject.
  • Listen to both their words but more importantly listen for the feelings underneath (see tools below). Neuroscience research shows people make decisions more from their feelings (unconscious) than their rational mind.
  • Help them feel heard by repeating what you’ve heard them say and clarifying it. When people feel heard their resistance lowers. If there are questions you have, ask them with open curiosity rather than blame.
  • Be willing and open to finding a different solution than what you identified in # 2 above. When you are willing to “give up” on your agenda in search of a better solution for everyone, the other person is often likely to reciprocate.
  • Summarize the agreements and thank them for being open to listening to you in the conversation. This may or may not be the last conversation on this topic, so leaving it in a way that keeps the door open for a productive future conversation and relationship is important.

Step 7 – Focus on Your Successes

Regardless of outcome of the conversation, your goal in this step is to reflect on what you learned and what you did well. A significant success is your willingness to have a conversation. Another success is developing stronger skills in having a difficult conversation. Yet another may be getting more information during this conversation that will allow you to have a better conversation the next time.

Leadership Practice

  • Write down what worked well. What did you do to create that success? How did the other person contribute to creating that success?
  • What did you learn that was new in this conversation?
  • How will you be more empowered to have a difficult conversation in the future?
  • What is your plan and next steps?
  • Our goal is to practice having difficult conversations so they become easier over time. I would also highly recommend a book called “Difficult Conversations – How to Discuss What Matters Most” for in-depth reading and skill building on this topic.

If this resonated with you, please comment, subscribe and share with others.

Additional Resources:

Why Vulnerability can be your Biggest Strength

Listen to how You Listen

Showing 9 comments
  • Edmond Smeal

    Awesome read. I just passed this onto a friend who was doing a little research on that. He just bought me lunch because I found it for him! So let me rephrase: Thanx for lunch!

  • Ruth

    I read 2 articles about making a difficult conversation easier and managing office politics. These 2 have given me a step ahead on how to manage the situations b’se these are my 2 greatest challenges now. I feel better after reading the articles and I am more energised because I now know i have a way to start on the solution.

    • Henna

      Thanks for your comment. I am glad that the articles resonated with you. Good luck with everything you’ve got going on.

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