The art of asking the right question in life planning
By Steve Conley, founder of the Academy of Life Planning
“Can I afford to retire?”
It’s a good question. I can build a cash-flow forecast, show you the assumptions and give you an answer. Then you might look at the numbers, take a breath and say, “Actually, I’d like to leave this job, take six months off and then do some work I care about.”
Now we have a different future to plan for. Your income might change sooner. You may need to fund six months without work. You may earn something again after that. We’ll need to revisit the original question because we now know what you were hoping the money would make possible.
I’m happy to do that work twice. Sometimes seeing the first forecast gives you the peace of mind to think about what you really want. And sometimes one question gets us there before I open the software.
“Tell me more about what you mean by retire. What would you be retiring from?”
A good question can carry an unmade decision
Ask an adviser, a search engine or an AI, “How much should I save for retirement?” You may get a perfectly sensible answer. To produce it, someone has to assume how long you’ll work, what you’ll earn and when you’ll start drawing on your savings. Those are reasonable inputs for a forecast. They can also stand in for decisions you’ve never made.
I wish AI would sometimes ask a question first.
“Do you want to spend the next twenty years doing the work you do now?”
If you love your work and intend to keep going, we can get on with the sums. If the question makes you pause, you may have a more important decision in front of you. What would you like to do with those years? Could you spend some of them doing different work, caring for someone or using your talents in a way that matters more to you?
The first question asks for a number. The second lets you decide which future the number should describe.
Enough for what, exactly?
When people first encounter the GAME Plan, some find it odd that we get halfway through before we start talking seriously about money. I’ve heard versions of “I’ll plan my life. You tell me about the money. That’s what I’m paying you for.”
Fair enough. My answer these days is “I can help you work out whether you have enough. First I need to know enough for what, exactly.”
Tell me what you want to do and when. If you’ve already worked it out, we can get straight to checking the spending assumptions. How much will it cost to live the way you want to live? Which costs are one-offs? Which will continue, and for how long?
That’s what I mean by a lifetime liability forecast. It puts dates and amounts against your expected spending and commitments over your lifetime. If you want to work three days a week from 55, we’ll need to understand what your life will cost at 55 and what you might earn on three days a week. We can then look at what you already have and what you can earn, and work out what human and financial resources you’d need to put in place to support that life.
In the GAME Plan, Goals establishes what you want. Actions turns it into something you can do. Means tests what it will take. Execution puts your choice into practice. When I ask about your life, I’m checking what the financial plan needs to support. If you’d like help working out what that life could look like, we can do that together.
Ask one question about the question
Student planners often ask me, “What should I do when the client starts with a Means question?” I’d begin with the client’s own words.
If they ask, “Can I afford a bigger house?”, try “Tell me, what is it about a bigger house that you want?”
They may tell you they need a downstairs bedroom for a parent who can no longer manage the stairs. You now know what the space has to do. You can explore a move, an adaptation or another arrangement the family would consider. If the client has already considered those possibilities and wants to know what a move would cost, you can help them with that.
Here’s the rule of thumb I’d give a student planner.
Ask one question about the question, then listen. Ask one question about the answer, then listen. Repeat while it helps.
Reflect back what you’ve heard before going further. “You want your mum to be able to stay with you and have a bedroom she can get to easily. Have I got that right?” That gives the client a chance to correct you. Perhaps the arrangement is for visits. Perhaps their mum is considering moving in. The difference matters to everyone involved and to the financial plan.
The tone matters too. “Why do you want a bigger house?” can sound like a request to justify the purchase. “What would the extra space let you do?” invites the client to tell you what they’re hoping will change.
Give the ladder somewhere to go
I’ve long liked the idea behind Bill Bachrach’s Values Staircase. The planner starts by asking what’s important about money to the client, then uses each answer as the basis for the next question. Bachrach’s method describes levels of answers and a point at which the client reaches the top of the staircase. Bill Bachrach’s explanation of the Values Staircase · How Bachrach follows up on the client’s last answer
My question is what we’re trying to get to. If a client says “freedom”, I’d like to know what freedom would let them do on an ordinary Tuesday. If they say, “I want to be home when my daughter gets back from school,” we may already have an answer that can shape a real decision. Another question about what’s important could send us wandering into the desert while the client is trying to work out whether to ask for different hours.
Sometimes the ladder goes somewhere deeper because the client wants to follow it. It can help them see a path of purpose. In the GAME Plan, that means seeing where your talents, the work you love and the needs of others come together. In a career conversation, we can also ask where there’s paid work for those talents. Here’s how that might sound.
Client. Can I afford to retire?
Planner. Tell me more about what you mean by retire. What would you like to stop doing?
Client. Managing the team. I’d miss working with the apprentices, though.
Planner. What do you enjoy about working with them?
Client. I’m good at spotting where they’re stuck and explaining it in a way that clicks. I’d happily do that a day or two a week.
Planner. So you’d like to give up managing the team and keep helping apprentices. Have I got that right?
Client. Yes. I’d never thought of asking if I could do just that.
The client now has an option they can explore. They might propose a mentoring role to their employer or see whether a training provider needs someone with their experience. If they want to know whether a two-day week would work, we can put that into the forecast. We got to the numbers with a clearer idea of which life they might want to live.
Let the client decide when you have enough
A question can open up choices. It can also steer someone towards the answer the planner wants. “Wouldn’t you rather spend more time with your family?” tells the client what the planner thinks a good life looks like. “How would you like to spend the time you’d get back?” leaves the answer with the client.
That’s the agency test I’d use. Has the next question helped the client see a choice they can make? They may want to go deeper. They may want a provisional answer to the question they arrived with. If a first forecast gives them enough confidence to imagine a different future, we can make the assumptions explicit and use it as a starting point.
One way a conversation builds decision capital is by leaving the client with a question they can use again. The next time an adviser, a spreadsheet or an AI gives them an answer, they can ask “What did this answer assume I’d already decided?”
When I say “Bring me the problem, not the portfolio,” I’m asking what you’re trying to work out. Bring the question you have, even if it’s “Do I have enough?” That’s a perfectly good place to start.
Breakout exercise The question behind the question
Allow 12 minutes. Work in pairs or try it on your own. Choose a real question you’re comfortable discussing, or use “Can I afford to retire?” Leave out names, account numbers and anything you’d prefer to keep private.
- Write the question as you’d naturally ask it (2 minutes). Keep a copy so you can compare it with the question you end up with.
- Try the conversation in ChatGPT (6 minutes). Paste the prompt below and add your question. Answer one follow-up at a time. When ChatGPT reflects back what it heard, correct anything it’s assumed. Ask it to answer once you’re happy with the wording.
- Compare and discuss (4 minutes). Read the two questions aloud. What had the first one already assumed? What choice or option did the conversation bring into view? Which question would you now want answered, and why? If your original question still fits, say what the conversation confirmed.
Copy and paste this prompt into ChatGPT
Help me work out whether I’m asking the question I most need answered. Start with my question as I’ve written it. Hold off on answering while we explore it.Ask one short, open question about my question, then wait for my reply. Use my words. Start with a phrase that could mean different things to me. If I ask, “How can I cover my expenses?”, you might ask, “What would ‘cover my expenses’ look like for you over that period?”After each reply, briefly reflect what you heard and give me room to correct you. If another question would help, ask one about my answer, then wait. Let my reply guide where you go next.Explore what I want the answer to make possible, what I want to protect, what I’m assuming is fixed, and what I might be willing to change. If we’ve started down one route, ask what other routes I’d consider. For a money question, those might include changing spending, earning more from skills or relationships I already have, borrowing, or using capital in a home or business. Bring up a possibility when it fits what I’ve said, and let me decide whether it belongs in the conversation.When a number or deadline comes up, use it to understand the decision. If I have both an immediate concern and a longer-term goal, ask which I want the question to address.Once we know what I’m trying to decide and which choices I want to consider, suggest a question in my own words. In one sentence, explain what it would help me decide. If my original question already fits, say so. Ask which wording I want you to answer, and wait for me to confirm or revise it. If I ask you to stop exploring and answer directly, treat that as my choice.Then answer the question I’ve chosen. Build on the options, resources and constraints I’ve shared. If the answer depends on an assumption or missing information, say what it depends on.My question is [type your question here].
What decision are you trying to make?
Bring it to a 50-minute Zoom meeting with me. We’ll start with the question you have, work out what you want the answer to help you do, and see what you need to know next.
