Reader situation
Someone experienced has agreed to talk with you. You have 30 minutes. Without preparation, it is easy to spend half of it explaining background and the rest on questions that drift, and to leave without knowing what to do next.
Central idea
An expert conversation becomes more useful when you arrive with a clear situation and focused questions. Prepare the context, explain your constraints and distinguish what the person has observed from what they recommend. That respects their time and makes the advice easier to use.
Practical steps
- Brief the situation. Send a short summary before the conversation, ideally a day or two ahead. Cover what you are trying to do, the decision in front of you, the relevant context and anything you’ve already tried. Keep it to half a page. A brief lets the other person think ahead and lets you start the conversation at the point that matters.
- Writing the brief also tests your own understanding. If you can’t summarize the situation in half a page, the conversation is likely to spend its time on background. Leave out history that doesn’t affect the decision, however interesting it is to you.
- Choose three questions. Pick the three questions that matter most and put them in order. Three is enough to fill a short conversation without rushing. Good questions are specific and open: “What would you look at first in deciding between these options?” invites more than “Is option A better?” Hold back further questions in case there’s time.
- Put the question you most need answered first. Conversations often run in unexpected directions, and if the first question opens a useful discussion, it’s better to follow it than to rush through the list.
- Disclose constraints. Tell the person what you can’t change: budget, deadlines, team size, regulations, commitments already made. Advice that ignores real constraints is hard to use. If there is something you can’t share, say that there is a confidential factor rather than leaving it out silently. That way, the other person knows their advice may need adjusting, and they can frame it with that uncertainty in mind.
- Separate advice from evidence. During the conversation, notice whether the person is describing what they have seen happen or what they think you should do. Both are useful, but they carry different weight. You can ask directly: “Is that something you’ve seen work, or your instinct about our situation?” Note the conditions in which their experience happened, so you can judge how far it applies to you.
- Confirm takeaways. In the last few minutes, summarize what you heard: “So the two things I’m taking away are…” This gives the person a chance to correct you. If they offered a resource or introduction, confirm it. Afterwards, send a short thank-you, and later let them know what you decided. People who give advice rarely hear what happened next, and an update is often the most welcome thanks. It also makes them more willing to help again.
Worked example
Fictional example
Jonah is deciding whether to build an internal data team or work with an outside firm. He has a call with Rita, who has done both.
His brief
We’re a 120-person retailer. We need regular reporting on sales and stock, plus occasional deeper analysis. Our budget allows either two hires or a firm on retainer, not both. We’ve tried a freelancer for six months, with mixed results. I’d like your view on three questions: (1) What would make you choose one approach over the other? (2) What goes wrong most often in the first year? (3) What should I ask an outside firm before signing?
During the call, Rita says outside firms “usually” become expensive after a year. Jonah asks whether that’s from her own experience. She says it happened at one of the two companies she worked with, and explains why. He notes the condition: the cost rose because the company kept adding requests without changing the contract. At the end, he summarizes her two main points and confirms she’ll send him a list of questions she used with firms. Rita corrects one detail in his summary, and he updates his notes before they finish.
Boundaries
- Don’t ask for more time than agreed. If the conversation runs out, ask whether you can send one follow-up question in writing.
- Don’t share confidential details from your employer or clients beyond what the conversation needs.
- An expert’s advice is one input. You remain responsible for the decision.
- Paid professional advice, such as legal or financial advice, should come from a qualified professional engaged for that purpose.
One action to try with a professional peer
Before your next advice conversation, write a half-page brief and three ordered questions, and send them ahead.
Discussion prompt
What is the best question anyone asked you when they came to you for advice?
