Tough Conversations
Assess the Situation
Preparation is essential. Take time to review and assess the situation.
Clarity
Pause and Assess before the Conversation
Action: Understand the desired outcome, what good and bad look like, the current perceptions of the person you’re persuading, likely objections, and the minimum viable position.
Who
Start With Who, Not What
Decide who is the right person to hold the conversation, is there someone they trust more, who should be the messenger. Consider leveraging leaders to create social proof.
Action: Identify the most appropriate person, and layer social proof.
Assess the Dynamics in Play
Within any conversation there are dynamics in play. Take time to assess the context that you are working with.
Human Dynamic
Work With Cognitive Overload, Not Against It
Traditional rational persuasion fails when people are stressed or overloaded.
Action: Assess cognitive capacity, use a BeSci informed approach that factors emotion, threat responses, and cognitive bandwidth.
Trust
Gauge Trust & Disconnect
Assess the level of trust and disconnect in beliefs to predict how difficult the conversation will be. Low trust + high disconnect = high danger and conflict risk.
Action: Assess trust levels, invest ahead and proactively build trust. Match your persuasion tactics to the available trust.
Tribes and groups
Groups can be hard to persuade, they often lack the trust or common goal, vision or understanding to bring them to a common outcome. Different people have different needs and experiences.
Group persuasion is harder; success depends on understanding influence structures, trust levels, and tribal loyalties. Often individual persuasion is required first.
Action: Map Tribes, Influence Networks & Competing Priorities. Assess levels of trust, and whether a group strategy can be effective.
Start with Discovery
During this phase your objective is to understand the positions of others, so that you can craft a tailored response.
Pull
Pull, Don’t Push
Begin with pull tactics to understand their reality and to uncover their position before you attempt to shape it.:
Action: Build trust, Show empathy, Be open to being influenced and Find common goals
Ask Questions
Use the Discovery Process: Questions, Not Answers
The most powerful persuasion tool is curiosity expressed through questions. Enables insight into beliefs, stress levels, tribal influences, and emotional context.
Effective persuasion comes from open questions, asked with positive intent:
Exploring Questions: “Tell me more…”, “What else?”, “Can you expand?” [I
Vision & Change Questions: “What do you want to see change?”
Perspective Questions: “What are we missing?”, “Why do you think that is?”
Emotion Questions: “How did that make you feel?”
Reflection Questions: “What would you do differently?”
Permission‑led Questions: Ask consent to reduce threat and build agency.
Challenge Questions: Respectfully disrupt limiting assumptions.
Action: Ask great questions, they are your superpower.
Listen
Actively Listen and Balance the Conversation
Let the other person talk more. People feel more positive and connected when they speak more than the other party. This increases persuasion effectiveness.
Action: Listen actively.
Dig Deeper
Spot and Navigate Distractions
People use socially acceptable answers or diversions. These are data probe with follow‑up questions rather than accepting surface responses.
Action: Probe to dig deeper
The Conversation
Pivot
Pivot Only After Trust, Insight & Openness Exist
Once rapport, safety and openness to alternatives are clear, shift gently from pull to push, if you need to
Small Steps
Stay Below the Threat Threshold
Avoid triggering defensive walls—no hard sells, pressure, or speed. Once entrenched, the other person closes down, ending influence.
Action: Create an environment of openness and trust, monitor the signs of distress and the risk of a defensive reaction
Self Discovery
Leverage Self‑Discovery
People trust insights they arrive at themselves more than ones they’re told. Design questions that help them reframe their thinking internally.
Pace
Use Time as a Tool
When things feel pressured, slow the pace: “Think about this over the weekend…”
Time reduces threat and increases rational consideration.
Emotions
Validate don’t dismiss
Be comfortable responding to emotions. Validate feelings while still listening with openness and empathy. Be careful in validating beliefs if they are false. If there are tears, give a moment to allow the self soothing effect. Do not rush in too quickly.
Heard
Summarize what you heard
Include your interpretation, this helps others feel valued. Ask others to summarize what they have heard, to check understanding.
Move to Action
Validate
Validate and Reinforce
Provide positive reinforcement on contributions, thinking, and progress. Makes the experience rewarding and repeatable.
Tentative Steps
Use the Small‑Step Approach
Test “temperature” with soft, future‑focused language: “How would you feel about…?” “Have you considered…?” Gradually firm up only when evidence indicates readiness.
Small Sign
Ask for a Small Action to Test Conviction
A small, measurable ask validates movement, builds momentum, and increases ownership.
