Succession Conversation Cards
Navigate the conversations that matter most
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These 12 conversation cards cover the most critical topics in succession planning. Tap any card to flip it and reveal discussion frameworks from both the senior leader and next generation perspectives. Use these prompts to facilitate productive conversations that bridge generational divides and align expectations.
"When will I be ready to lead and who gets to decide that?"
Framework for Discussion
What specific milestones demonstrate readiness? Are you holding on due to legitimate concerns or fear of losing relevance? Have you clearly communicated your criteria?
What evidence can you provide of readiness? Are you seeking responsibility or just authority? How can you demonstrate leadership without the title?
"What is the real price tag and can I actually afford to buy in?"
Framework for Discussion
Is your valuation based on retirement needs or actual worth? Are you willing to finance the transition? What is your plan if they cannot afford your price?
Do you understand the full financial picture? Have you calculated what you can realistically afford? Are you prepared for ownership risk?
"Whose way of leading wins and what happens when we disagree?"
Framework for Discussion
Can you accept different approaches that still achieve results? Which decisions require your input versus full autonomy? How will you handle disagreements publicly?
Have you studied what made their approach successful? Where do you want to innovate versus preserve? How will you honor legacy while driving change?
"Will this business consume my life the way it consumed yours?"
Framework for Discussion
Were your sacrifices necessary or habit? Can the business succeed with different boundaries? What do you wish you had done differently?
Are your expectations realistic for a leadership role? How will you set boundaries while earning credibility? What systems could create better balance?
"Do we even agree on where this business should go?"
Framework for Discussion
Are you open to strategic pivots? What parts of the current model are sacred versus adaptable? Can you support a vision different from yours?
Have you articulated a clear vision? Do you understand why current strategies exist? How will you balance innovation with proven approaches?
"These clients trust me. How do we make them trust you?"
Framework for Discussion
Are you introducing successors early? Do you have a systematic handoff process? Are you prepared to let clients see the successor as the expert?
How are you building your own relationships? What unique value can you bring? Are you learning client preferences before taking over?
"Am I being paid for what I contribute or what you think I am worth?"
Framework for Discussion
Is compensation tied to clear metrics? Are you paying based on potential or proven results? How does compensation evolve as responsibilities increase?
Do you know the full compensation picture including benefits? What benchmarks justify your desired compensation? How will you prove return on investment?
"What exactly is my job and when does yours end?"
Framework for Discussion
Have you documented all your responsibilities? Are you creating overlap time for knowledge transfer? What role do you want after the transition?
Do you understand all the informal duties? Where do you need shadowing time? How will you handle being undermined or second guessed?
"Are we making business decisions or family decisions dressed as business?"
Framework for Discussion
How do you separate family roles from business roles? Are non working family members influencing decisions? What is the forum for business versus family discussions?
Are you being evaluated as family or as a professional? How do you handle disagreements without damaging relationships? Where do you need boundaries?
"What from your legacy must I keep and what can I change?"
Framework for Discussion
What values are non negotiable? Can you articulate why these matter? How will you feel if things change after you leave?
Which values do you genuinely share? How will you honor legacy while evolving? What is your plan to preserve institutional memory?
"How much training should I expect and how long should it take?"
Framework for Discussion
Do you have a structured development plan? Are you willing to invest in external training? How will you measure progress?
What skills do you need to develop? Are you actively seeking learning opportunities? How do you handle feedback constructively?
"When exactly are you leaving and will you actually go?"
Framework for Discussion
Do you have a concrete exit date? What will you do after leaving? Are you financially and emotionally prepared to let go?
Can you be patient with a reasonable timeline? How will you support their transition out? What happens if they keep delaying?