Better Conversations™ · Advisor Training
Go beyond “Can you afford to retire?”
Help your advisors uncover what clients are retiring to—and connect that understanding to the financial plan.
Practical, interactive training on identity, purpose, relationships, and life after work.
Discuss Training for Your TeamThe opportunity
A retirement decision involves more than money.
Work provides structure, connection, recognition, and a sense of contribution. Leaving it can raise questions clients haven’t yet found the words to ask.
Your advisors don’t need every answer. They need the confidence to ask thoughtful questions, listen carefully, and recognize how the answers affect the plan.
What your team will learn
Skills for the moments that matter.
01 / ASK
Uncover what matters.
Move beyond dates and dollar amounts to explore identity, priorities, expectations, and concerns about life after work.
02 / LISTEN
Go beyond the first answer.
Recognize hesitation, assumptions, and differences between partners. Use follow-up questions that invite deeper understanding.
03 / CONNECT
Bring it back to the plan.
Connect client insights to retirement timing, spending priorities, and planning conversations. Identify when additional coaching could help.
See the approach
One question. A more useful conversation.
“What will you miss most about working?”
Recognition. Daily structure. Colleagues. The feeling of being needed.
“Where else could you find that sense of contribution?”
Discuss how the client’s answers may shape their preferred retirement timing, phased work, or priorities for the next chapter.
How the training works
Less lecture. More conversation.
Advisors work with recognizable retirement situations and practice an approach they can bring into their next client meeting.
Topics and exercises are tailored to your team’s experience, clients, and goals.
- Explore real situations A financially ready client who keeps postponing. Partners with different expectations. An unexpected career ending.
- Practice the conversation Work through questions, listening cues, and follow-ups with colleagues.
- Leave with practical tools Conversation guides and reflection prompts to support application in client meetings.
Ways to bring this to your team
Choose the right depth.
Introductory Session
A focused introduction to the personal side of retirement, with practical questions advisors can begin using.
Interactive Workshop
More time for discussion, client scenarios, and guided practice with conversation frameworks.
Multi-Session Program
Build skills over time with opportunities to apply the tools, reflect on experience, and deepen practice.
Format, scope, and investment are discussed based on your team’s needs. Virtual and in-person options.
Your facilitator
Finance. Leadership. Lived experience.
Diane Wilbur
Founder, Retirement Fitness™
Diane brings more than 20 years of experience coaching senior leaders through change, along with a background as a CPA and financial advisor.
As the former Head of Leadership Development at Fidelity Investments and a Certified Professional Retirement Coach, she connects advisor development with the realities of life after work.
Her own unexpected career ending adds a personal understanding of what it means to lose the structure and identity work provides.
Former CPA & financial advisor · Former Head of Leadership Development, Fidelity Investments · Certified Professional Retirement Coach
Common questions
Before we connect.
Who is this training for?
Financial advisors and wealth management teams who want to deepen retirement discovery and support clients preparing for life after work.
Can it fit our existing planning process?
Yes. We’ll discuss your current approach and identify where the questions and tools can support discovery, retirement planning, and review conversations.
Does this train advisors to become retirement coaches?
The focus is developing conversation skills within the advisory relationship. Advisors also learn to recognize when a client may benefit from specialized retirement transition coaching.
Is continuing education credit available?
Please ask about the status of CE eligibility for your proposed session. Credit is not guaranteed.
Let’s talk about your team
Better questions. A clearer picture of retirement.
Tell us about your advisors, the clients they serve, and the conversations you want to strengthen. We’ll recommend a format and scope for your team.
Inquire About Team Training