Better questions help your Financial Readiness Plan
Hi,
Welcome to this week’s Get Ready Newsletter.
This week, I’ve been thinking about the role questions play in helping people learn, prepare, and make better decisions.
When we are curious, we ask questions.
Those questions help us understand what matters, who needs to be involved, what information is missing, and what decisions need to be made.
That is the heart of financial readiness.
Before we can guide people with their money, we need to encourage curiosity and asking questions.
The Question to Ask Before Life Happens
Do you encourage questions when explaining a concept to someone or when a decision is being made?
Featured Conversation: People Changing the Way We Get Ready
Colleen Bowler on Better Financial Planning Conversations
This week on Get Ready: Before Life Happens, I spoke with Colleen Bowler, entrepreneur, speaker, and creator of The Passport Package, about the human side of financial planning.
What she’s changing:
Colleen is helping advisors and families create planning conversations where everyone’s voice is heard.
That starts with listening before offering solutions.
Why it matters:
Better questions help uncover what truly matters, bring quieter voices into the conversation, and prepare families for future transitions.
Planning becomes stronger when the people affected by the decisions are invited into the conversation.
Listening is one of the most powerful tools advisors and families have. , how planning conversations can bring out quieter voices, and why meaningful financial decisions begin with understanding what truly matters to the people involved.
Tony’s Take:
Financial readiness begins with understanding people. When advisors and families create space for every voice, planning becomes a conversation about the life people want to build.
🎙️What Happens When Financial Planning Starts With Better Questions? With Colleen Bowler and Tony Steuer on the Get Ready Before Life Happens Podcast (watch or listen)
How This Fits Your Financial Readiness Plan
This conversation connects to Your Support Team.
Your support team may include family members, powers of attorney, advisors, caregivers, professional contacts, and trusted partners.
Readiness improves when the people around you understand your wishes, know their roles, and feel comfortable asking questions before decisions become urgent.
A strong support team is built through conversations. The more clearly people understand what matters to you, the easier it becomes for them to step in when life happens.
Also This Week: Mark Crowley on How Emotions Shape Financial Decisions and Readiness
In my second conversation this week, I spoke with Mark Crowley, author and advocate for heart-based leadership, about how emotions shape the way we make decisions, build relationships, and respond to uncertainty.
Readiness connection:
Financial decisions often feel logical in the moment, but emotions shape how we respond.
Understanding that connection can help us make better decisions and build stronger financial readiness.
💭 Tony’s Take: Financial readiness involves understanding how emotions influence our decisions, relationships, and responses to uncertainty.
When we build self-awareness, strengthen our connections, and approach decisions with intention, we create a stronger foundation for navigating life’s unexpected moments.
🎙️ Mark Crowley and Tony Steuer on the Get Ready Before Life Happens Podcast (watch or listen)
Related Resource
Resource: What Is the Human Side of Money?
Best for: Advisors and professionals who want to build stronger financial conversations.
Why it matters:
This conversation unpacks why "behavioral finance" was only ever the gateway, not the destination. They walk through the many dimensions that make up being human (individual, relational, cultural, societal) and how money layers on top of all of them.
They draw a distinction that most advisors have never had named for them: the difference between the human side of money (what's happening inside your client) and the human side of advice (how you actually do this work).
That distinction matters because financial planning is not only about technical knowledge. It is also about how people think, feel, communicate, make decisions, and picture the life they want to fund.
How it helps you get ready:
Better conversations help people connect money to security, freedom, connection, legacy, health, and growth.
That makes this a strong companion to this week’s theme of asking better questions before life happens.
🎙️ Brendan Frazier and Ashley Quamme on the Planning & Beyond Podcast (Apple Podcasts)
From the Get Ready Archive
Michael Ervolini on Slowing Down for Better Money Decisions
In this conversation, I spoke with Michael Ervolini, author and active management thought leader, about how behavior and emotions shape financial decision-making and why having a simple, intentional process matters more than chasing perfect outcomes.
Why this conversation still matters: Slowing down creates space for better questions.
It helps us notice what may be driving a decision, understand the tradeoffs, and make choices with more intention.
🎙️ Michael Ervolini and Tony Steuer on the Get Ready Before Life Happens Podcast (watch or listen)
Worth Knowing This Week
🎙️ The Hidden Cost of Caregiving and Why Families Need a Plan: Lina Supnet-Zapata and Eric Blake discuss the realities families face when caregiving begins without a plan. And, how women often step into caregiving roles unexpectedly, the risks of leaving family members out of financial conversations, and why care planning must be integrated with financial and legal strategies to avoid costly, reactive decisions. On The Simply Retirement Podcast (listen)
📖 Retirement Planning Has a Decision-Making Problem: Chris Heye highlights decision risk, the risk that retirement outcomes are adversely affected by limitations in an individual's ability to make sound financial decisions.This highlights the need to ask questions with those you care for whether they are your aging parents or your clients (LinkedIn).
📓 Managing Retirement Spending With Better Withdrawal Decisions: Shifting from saving to spending is hard for many retirees. Morningstar research looks at why many retirees rely on simple withdrawal rules and how deeper goal-setting can support more confident retirement spending decisions (here).
This Week’s Readiness Step
Have one conversation with a member of your support team.
That could be a family member, advisor, power of attorney, caregiver, professional contact, or trusted friend.
Ask:
What would you need to know if you had to step in for me?
If you are an advisor, encourage one client to have a conversation with an aging parent, spouse, adult child, or power of attorney.
The goal is to create room for questions before decisions become urgent.
Start Your Financial Readiness Plan
A Financial Readiness Plan is a practical framework to help you move from insight to action, organize what matters, and prepare before life happens.
Use it to:
• Organize what matters across key areas
• Prepare for life’s financial what-ifs
• Clarify roles and responsibilities
• Guide meaningful conversations
• Make confident, values-aligned decisions
• Stay prepared as life changes
Start Your Financial Readiness Plan (here).
Final Thought
Better questions help people feel seen, heard, and prepared.
They help families understand what matters, advisors serve with more care, and support teams know how to step in when needed.
Financial readiness starts with curiosity.
Because when life happens, the way you think about money matters.
Tony
P.S. Have a new podcast episode, book, article, research report, tool, or project that helps people think differently about money or prepare before life happens? Send it my way. I’m always looking for thoughtful resources to consider sharing in a future Get Ready Newsletter.
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