Before the Numbers: How We Start the Conversation About Money and Retirement

Most people expect a first meeting with a financial advisor to start with account statements. Ours usually starts somewhere else. Before we look at a single number, we want to understand how you think about money, what worries you, and what you actually want your money to do for you, especially once you stop working. This article walks through why we start there and the kinds of questions we ask. It describes our general approach; every conversation is shaped by the person or couple in the room.

Why not start with the numbers?

Because the numbers only make sense once we know what they're for. Two households with the same savings can need completely different plans. One may care most about never running out of money. Another may want to travel while they're healthy, or help their children buy a home. A plan built without knowing that is a plan built on guesses.

Our process reflects this. The first two steps of working with us are an initial conversation to see whether we're a good fit, and a discussion of your circumstances: your objectives, time horizon, and comfort with risk. Portfolio decisions come later.

What kinds of questions do we ask?

We organize the conversation around three areas.

What worries you about money? This is about protection. Are you concerned about outliving your savings, a health event, a market decline right before retirement, or taking care of a spouse if something happens to you? Knowing what keeps you up at night tells us where the plan needs the most support.

What are you committed to? This is about the people and causes beyond yourself. Do you want to help children or grandchildren, support a parent, give to charity, or leave something behind? These commitments often shape decisions years before they happen.

What makes you happy? This is about the life you want. What does a good week in retirement look like? Travel, time with family, a second home, a new project, or simply not having to think about work? We ask people to be specific, because "a comfortable retirement" means something different to everyone.

Why does it matter for couples?

Two people who share a life don't always see money the same way, and some of these priorities may never have come up between them. One spouse may be focused on security while the other is focused on enjoying the years ahead. Neither is wrong. Asking each person separately, then talking through where they agree and where they differ, helps a couple settle on shared priorities before we build anything. It also makes sure both partners, not only the one who usually handles the finances, feel heard and understand the plan. Decisions like when each spouse claims Social Security are much easier once those priorities are clear.

What happens after that first conversation?

Once we understand what matters to you, we turn to the details: your accounts, income sources, taxes, and timeline. From there we discuss how a plan and a portfolio could support the priorities you described, along with the trade-offs involved. Priorities change over time, so we revisit these questions as life changes, not only at the start.

The bottom line

A good financial plan starts with understanding the people it is for. If you are interviewing advisors, pay attention to whether they ask about your life before they ask about your accounts. Our list of 7 questions to ask your financial advisor can help you compare. This article is educational and describes our general process; it is not a guarantee of any outcome, and every plan depends on your individual circumstances.