Meaningful conversations in business rarely begin with a statement. They begin with a question someone actually thought about.
Success means different things to different people — and for business owners, most versions of it depend on relationships. Very little of consequence gets built alone. Building those relationships starts with understanding the people around you: their experiences, priorities, and concerns. Two simple tools may help more than almost anything else — open-ended questions and probes.
Why the Question Shapes the Answer
Questions do two jobs at once. They teach you about the other person, and they tell the other person something about you — whether you arrived prepared, curious, and genuinely interested.
But how a question is framed changes what comes back. A question answerable with a quick yes or no usually produces exactly that. A broader question makes room for reasoning, priorities, and experience. The goal is never to interrogate; it is to create the conditions for a more thoughtful exchange.
Open the Door with What, Why, and How
Open-ended questions cannot be answered in one word, which is the point. Compare: “Are you satisfied with the project?” against “What parts of the project are working well, and which areas remain challenging?” The second invites a real answer.
They are especially useful when you want to:
- Understand someone's priorities, or how a decision was made
- Explore the reasoning behind an opinion
- Surface concerns that haven't been said out loud
- Clarify what the other person actually hopes to accomplish
An open question doesn't guarantee an open answer — some people need time, and some subjects stay private. The setting and the relationship matter as much as the phrasing.
Temper the Sensitive Ones
Some questions touch personal or financial ground. When you're unsure how one will land, soften it with a brief preface: “I'm not sure how to ask this, but…” or “This might be a sensitive subject — may I ask about…” The preface acknowledges the question is personal and gives the other person a graceful way not to answer. If they decline, respect it and move on. And a preface doesn't make every subject fair game — ask only what's genuinely relevant.
Turn Statements into Questions
Confident, experienced people default to declarative statements — useful when direction is needed, limiting when discussion is. Three small conversions open things up:
- Direct conversion: "This is a difficult project" becomes "What makes this project particularly difficult?"
- Invite their reasoning: "I don't see how your idea would work" becomes "How do you see it working, given what we've discussed?"
- Attach a question: "I'm going to change the company structure" becomes "I'm considering a structural change - what approach would you suggest?"
Not every statement should become a question; leaders still have to decide and say so. The skill is recognizing the moments when another perspective would genuinely help.
Then Probe, Gently
Once a good question opens the conversation, probes keep it going. A nod, steady eye contact, an interested pause — or a simple “Tell me more about that” or “What happened next?”—signals that you're listening and invites the fuller version of the story. These approaches may encourage people to share more.
At our firm, we aim to put this approach into practice. The first conversation in the SWM Wealth Navigator, the Exploratory Call, is built on exactly this idea: twenty minutes, one good question at a time.
This article is provided for general educational purposes and is not a substitute for individualized investment, legal, tax, accounting, or business advice. Business owners should consult appropriately qualified professionals regarding their specific circumstances.
Advisory services are offered through Lee Johnson Capital Management, LLC d/b/a Sorensen Wealth Management (“SWM”), an SEC-registered investment adviser. Registration as an investment adviser does not imply a certain level of skill or training. The opinions expressed herein are those of the author as of the date of publication and are subject to change without notice. No client or prospective client should assume that any discussion contained herein serves as the receipt of, or a substitute for, personalized advice from SWM or any other professional.
A copy of SWM’s current written disclosure Brochure discussing its business operations, services, and fees is available upon request.