Most think building great stakeholder relationships means saying ‘yes’—but the real value comes from knowing when to challenge their thinking.
In this article, I’ll walk you through a workshop to help participants get stakeholder buy-in by challenging assumptions, reframing problems, and guiding decision-making—without damaging trust or relationships.
It leverages key insights from two bestselling books:
- The Challenger Sale: How to Take Control of the Customer Conversation by Neil Rackham
- Enchantment: The Art of Changing Hearts, Minds, and Actions by Guy Kawasaki
You’ll learn how to move beyond being a service provider and become a true strategic advisor.
Clients/customers/business partners often come to professionals with a fixed idea of what they need.
If you simply take their requests at face value, you miss opportunities to create deeper impact.
The best professionals don’t just respond—they lead, educate, and influence.
Most professionals either:
- Avoid challenging customers for fear of damaging relationships.
- Give answers too quickly instead of guiding business partners to better insights.
- Fail to engage the right people—convincing decision-makers instead of the real influencers inside the organisation.
“Your value isn’t in delivering what the client asks for—it’s in revealing what they truly need.”
What participants gain from this workshop:
- Master the Reframe Technique – Shift client mindsets by introducing unexpected insights.
- Develop Confidence in Difficult Conversations – Learn to challenge clients while strengthening trust.
- Identify and Engage Mobilisers – Focus on the people who actually drive change.
- Balance Challenge with Enchantment – Push back effectively while keeping clients engaged.
- Move from Service Provider to Trusted Advisor – Influence client decisions at a deeper level.
This workshop helps participants master the art of challenging stakeholder thinking while building trust and influencing decision-making.
Let’s get into it…
Challenging & Enchanting Client Conversations
Duration: 3 hours
Workshop Objectives
- Challenge Stakeholder Assumptions – Learn how to introduce new perspectives that shift stakeholder thinking.
- Improve Influence – Move beyond being a service provider to becoming a trusted advisor.
- Reframe Problems Effectively – Help stakeholders see the real issues behind their stated challenges.
- Handle Difficult Conversations with Confidence – Push back on stakeholder assumptions while maintaining trust.
- Engage the Right Stakeholders – Identify and work with Mobilisers who drive real change.
Workshop Agenda
1. Introduction: Influence vs. Enchantment (15 min)
Why this matters: Professionals need to both challenge and enchant their stakeholders (customers/clients/business partners) and push them toward better decisions while building trust and engagement.
Discussion:
- What’s the difference between persuading, selling, and enchanting?
- When have you successfully challenged a stakeholder without losing goodwill?
Key Challenger Element: Move beyond relationship-building – Stakeholders don’t just need friends; they need advisors who push their thinking. Set the tone early – Establish yourself as someone who brings valuable, sometimes uncomfortable, insights.
Key Enchantment Element: First impressions matter – Make warm connections before delivering hard truths. Show likeability and trustworthiness to create openness to challenge.
Tip: Prepare a strong introduction that positions you as helpful, knowledgeable, and confident from the start.
2. Five Professional Profiles (30 min)
Activity: Breakout discussions – Which profile best describes you?
Using insights from The Challenger Sale, discuss how professionals take different approaches:
- The Hard Worker – Executes well but may struggle to influence.
- The Relationship Builder – Gains trust but avoids tough conversations.
- The Lone Wolf – Operates independently but may lack collaboration.
- The Problem Solver – Fixes issues reactively rather than proactively.
- The Challenger – Teaches, tailors, and takes control.
Key Challenger Element: Challengers win in complex environments – They aren’t afraid to push stakeholders beyond their comfort zones. Challengers also tailor their approach – They adjust their message based on the stakeholder’s priorities and personality.
Key Enchantment Element: Build trust before challenging – People listen more when they feel understood. Give before you take – Share valuable insights first before making recommendations.
Tip: Use open-ended questions to uncover how your stakeholders think before introducing new ideas.
3. Mastering the ‘Reframe’ (45 min)
Objective: Learn to shift stakeholder mindsets by introducing new perspectives.
Activity:
1. Case Study: Present a common stakeholder problem.
- Example: A customer insists they need a new IT system, but the real issue is poor internal adoption of existing tools.
2. Pairs Exercise:
- Identify the customer’s stated assumption.
- Develop a reframe statement that shifts their perspective.
- Role-play the conversation.
Key Challenger Element: Teach stakeholders something new – The best professionals don’t just solve problems; they show stakeholders opportunities they hadn’t considered. Use insight-led conversations – Instead of asking “What do you need?” say, “Here’s what we’ve seen work well in similar situations.”
Key Enchantment Element: Use compelling storytelling to frame insights in an engaging way. Reframe challenges as opportunities to create a more positive response.
Tip: Use specific data or case studies to support your reframing—facts make insights more credible.
4. Challenging Without Alienating (45 min)
Objective: Develop confidence in pushing back on stakeholders while maintaining trust.
Activity: Difficult Conversations Role-play
- Scenario 1: A stakeholder insists on a flawed strategy.
- Scenario 2: A senior stakeholder resists change.
- Scenario 3: A stakeholder focuses too much on cost, ignoring value.
Participants practice:
- Using facts & insights to support their position.
- Asking provocative questions to encourage reflection.
- Handling resistance without damaging the relationship.
Key Challenger Element: Create constructive tension – Don’t avoid difficult conversations; lean into them with confidence. Take control of the conversation – Redirect discussions when stakeholders are stuck on the wrong issues.
Key Enchantment Element: Be likeable even in disagreement—listen, smile, and show empathy. Default to “Yes, and...” instead of outright rejection.
Tip: Instead of telling stakeholders they are wrong, ask thought-provoking questions that help them rethink their assumptions.
5. The Mobiliser Strategy (30 min)
Objective: Learn how to identify and engage internal Mobilisers—stakeholders who drive change.
Activity: Stakeholder Mapping Exercise
- Identify key stakeholders from past projects.
- Categorise them as:
- Mobilisers (drive change)
- Talkers (agree but don’t act)
- Blockers (resist change)
- Discuss strategies to influence each type.
Key Challenger Element: Focus on change-makers, not just decision-makers – Mobilisers drive internal change, so winning them over is key. Talkers won’t help you – Just because a stakeholder agrees with you doesn’t mean they’ll advocate for action.
Key Enchantment Element: Identify the people most likely to spread your ideas—make them your allies. Show them social proof of success to build momentum.
Tip: Find Mobilisers early in a project and equip them with powerful arguments to persuade their organisation.
6. Action Planning & Wrap-Up (15 min)
Participants commit to:
- One behaviour change they will implement in their next stakeholder interaction.
- A peer accountability check-in (e.g., after one month).
Key Challenger Element: Practice challenging stakeholders with confidence – Push yourself to introduce at least one new insight in every stakeholder meeting.
Key Enchantment Element: Stay authentic – Stakeholders respond best when you challenge them in a way that aligns with your personality.
Tip: Set a personal goal for integrating both Challenger and Enchantment principles in your work.
Conclusion
By using this workshop, you’ll never have to struggle to get stakeholder to see the real problem.
Instead, it becomes a simple process of guiding their thinking, reframing their challenges, and positioning yourself as a trusted advisor who drives real change.
Well, that’s it for today. I hope you enjoyed it.
See you next week.