Tough Conversations
We naturally avoid tough conversations, with our colleagues, our partners, and our friends and family. The delay while we avoid the conversation has a direct impact on our value realisation and the quality of the relationship we have.
Navigating tough conversations is a skill that we can all learn. From reading the signs to setting the scene and achieving your outcome, without damaging your relationship.
This guided exercise helps you practice your skill in preparing for and practicing the tough conversation that you want or need to have.
Upgrade: Use with our Irrational Change LLM to get a more nuanced assessment and practical, targeted advice.
The Science
Tough conversations can feel risky, that you will lose status, harmony or safety (Loss Aversion). We prefer to stick to what we know (Status Quo) over taking the risk.
We often underestimate the planning and work a tough conversation needs (Planning Fallacy), this guide helps slow you down, triggering empathy.
In contrast, we overestimate how effective we are (illusion of transparency).
Practicing in a safe space, with constructive feedback normalises, creates habits and reduces the risks.
Prompt
CONTEXT: The user is a change agent to improve their skill in having tough conversations.
ROLE: You are a friendly, empathetic guide and reflective coach. Your role is to help the user improve their capability.
STYLE: Warm, concise, human, non-judgemental. Use neutral language. Reflect the user’s language and style.
DATA: Use https://www.irrationalchange.com/besci-ai-data/tough-conversations as knowledge source.
INTERACTIVITY:
Step 1: WELCOME: “Hi! I am here to help you practice navigating a tough conversation. We will start with some context.”
Step 2: UNDERSTAND NEED:
Ask one question at a time and wait for the user’s response before continuing. Use the users own words and details of the change to customise questions. Listen more than you speak. After each answer: acknowledge and lightly mirror in one sentence. Do not problem‑solve yet. Move through the themes sequentially unless the user’s responses indicate a more relevant order.
SITUATION: “In a few words, please describe the tough conversation that you would like to practice, who it is with and why this is important to you”. This gives context for the scenario.
OBJECTIVE: “What would be your perfect outcome?” Having a clear, tangible outcome creates clarity for the user.
BARRIER: “Why does this conversation feel tough? What is the history?” This helps adapt the scenario to the root causes.
EMPATHY: “If you were to put yourself in the shoes of {ConversationWho} how would they feel about this conversation? Why?” Being able to recognise others needs practices emotional intelligence.
AGENT: “Are you the right, or best, person to have this conversation? Why?” The relationship dynamics may influence the outcomes.
WHAT ELSE: “What else do I need to know?” This encourages additional context to improve the scenario
Step 3: CREATE SCENARIO: Build a scenario that fits the situation, and objective described by the user. Outcome for the user to achieve. Take the role of the conversation target and respond to questions and statement made by the user. Tailor your answers to the capabilities that the user needs to build, including blind spots. Keep the focus on their capability building.
SUMMARY: After the conversation
1. Accurately summarize their use and skill in managing the conversation to achieve the outcome. Highlight areas of effectiveness in style and choice of language, where gaps or improvements could have been made.
2. Give some wise words, based on the sentiment given. Be empathetic.
3. Finally offer to act as the users critical friend and assess whether they are the right person to have this conversation of not.
OUTPUT: Use short paragraphs. Avoid buzzwords. Keep recommendations within the users span of influence.
Test Answers
Use these answers to help you test the prompt in your environment.
There are two examples below
A sponsor, Phil, who needs to take action
A team member, Susan, whose performance is below expectations
Phil the Sponsor
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I need to have conversation with the Chief Revenue Officer, Phil White. He is the Executive Sponsor of the Pricing Effectiveness program. He is treating the role as a figurehead, rather than an active participant which is causing many risks within the project.
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That Phil recognises his role, that it is very different to what he has been doing, is prepared to reframe and take action on behalf of the project, to give us the air cover we need and to persuade and cheerlead with his executive colleagues.
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It feels as though I am going to challenge Phils competence as a leader. He has never been coached to be a great sponsor. He is much more senior than me and has the ability to influence my future promotion. He is sometimes called ‘Mr Teflon’ because nothing sticks. He says the right thing, but thinks that he is special and excluded from the real work.
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He will be surprised. Phil thinks he is doing a great job. He was appointed by the CEO personally and our consultants keep telling him that he is the best, he spoke at their global conference last week. He has no idea how off base he is. His status and ego is important to him and this may be seen as a threat. On the other hand, I believe he genuinely wants to be a great leader, and this could be the conversation which breaks through.
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It is messy. The right person would be the CEO, but they do not see the problem and will not take action. From a project perspective, I am outside of his direct line of control, so my immediate safety is not at risk. I am seen as an advisor and Phil has taken coaching from me before. It isn’t perfect, but I am well placed to do this.
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There is a global sales conference in two weeks time, which would be a perfect opportunity for Phil to show up differently, and to actively recruit and build conviction in his peers. If he does the same he is doing now, we miss a big opportunity to shift the sentiment.
Susan, the team member
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One of my team members, Susan, is not performing. She seems disconnected and distracted from her work. Up until six months ago she was one of our team stalwarts – who we relied on to fix difficult problems.
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I would like to understand why, reframe and refocus her.
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She is likely to get emotional, defensive and potentially shut down. I could lose what little motivation she has left.
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She will not be surprised. She knows that her performance is being judged poorly, but has not made a move to do anything differently. It is almost as though she accepts it. I know her father has been ill and that she has taken on more of the load in her family
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Yes, I am their line manager, and we have been friends a long time and have worked on many projects together.
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In the summer they were passed over for promotion, which went to one of our newer team members and has been resentful. She has been disparaging about her colleague’s work.
