Understanding your clients’ needs and challenges is non-negotiable.

It’s “table-stakes” in business.

And it it never hurts to talk with prospective clients.

That’s why I recommend having exploratory conversations with prospective clients at every opportunity, asking open-ended questions about the challenges they are facing.

You will learn how they perceive problems, and the language they use to describe the pains and the transformation they’re seeking.

Strengthen your relationship, and uncover valuable insights at the same time.

One way to do this is to use Socratic Questioning – aka “The Socratic Method”.

What is the Socratic Method?

The Socratic method was developed by the Greek philosopher Socrates.

It involves asking a series of probing questions to get to the core of an issue, uncover assumptions, analyze concepts, and generate ideas.

The goal is to promote critical thinking and draw out knowledge through thoughtful dialogue.

In the Socratic method, you ask questions that prompt the other person to think deeply, challenging their own ideas. You need to ask good questions, actively listen, and think critically about the answers.

Why use Socratic Questioning?

  1. Get a deeper understanding of your clients’ problems (and how they perceive them)
  2. Uncovers assumptions and biases (yours and theirs)
  3. It encourages knowledge discovery vs. knowledge delivery (which makes for a more effective sales call, by the way!)
  4. It gives them ownership over ideas (this is powerful in a sales or team building environment)
  5. Reveals complexity and nuance in issues (there’s usually nuance – this helps cut to it)

Real-World Applications

I use Socratic questioning in initial discover calls, strategy and coaching sessions. I’ve also used it in podcast interviews and on research calls where I want to learn more about a particular topic.

Here are some examples of how you could apply the Socratic method:

  • Client discovery: probing questions help you deeply understand a client’s problems and goals. Get beyond surface issues and learn the language they’re using to describe the issues.
  • Strategy & coaching sessions: use questioning dialogue to analyse and uncover blindspots, prompt self-reflection and new insights vs. directives.
  • Podcast interviews: ask interesting questions that dig deep into a topic to provide insights for the audience
  • Negotiation: Socratic questioning can help you to understand the other party’s position and needs (this is crucial in getting beneficial outcomes)

Downsides of using Socratic Questioning

I’ll be straight up with you: it can be difficult, frustrating and time-consuming.

It can be time-intensive, which makes it awkward for shorter calls – I try not to use it on calls where we have less than an hour scheduled.

There’s potential for frustration, because the constant questions can be irritating, particularly if they are looking for quick, direct answers to straightforward questions, and you risk it feeling like an interrogation.

It can also be tiring – the human brain uses a lot of calories when thinking and concentrating deeply. That can compound with the frustration, so be careful with how you use this technique.

How to Implement the Socratic Method Effectively

  • Prepare open-ended, thought-provoking questions ahead of time. Avoid yes/no questions. (I use a question sheet prepared in advance for sales calls as a starting point for this)
  • Ask for reasons, evidence, and concrete examples to back up claims. Don’t accept speculation.
  • Probe the origin and implications of ideas. Ask “what led you to this belief?” and “what effect would that have?”
  • Play devil’s advocate to get different viewpoints. “How might someone with an opposing view respond to this idea?”
  • Periodically summarise key points. (This is also great for the listener, if it’s a podcast episode).
  • Give ample time for respondents to think and respond (at least 30 seconds – yes, this is hard to do)
  • Maintain a curious, inquisitive and non-judgmental tone.

Example Questions

Clarification questions:

  • What exactly do you mean by that?
  • Could you provide an example to illustrate that point?
  • Can you rephrase that in another way?

Probing questions:

  • What makes you think that?
  • Why do you feel that way?
  • What led you to that conclusion?

Assumption questions:

  • What assumptions are you making with that viewpoint?
  • Why would someone make that assumption?
  • Is that necessarily a valid assumption?

Evidence questions:

  • What evidence do you have to support that?
  • Could you walk me through your reasoning?
  • What additional data would help back up your point?

Implication questions:

  • What effect would that approach have?
  • What might be some unintended consequences?
  • How could that play out in the real world?

Viewpoint questions:

  • How would someone with an opposing viewpoint respond?
  • What perspectives haven’t we considered yet?
  • Why might reasonable people disagree on this?


The Socratic method can be a fantastic tool for digging deeper, uncovering hidden insights, and delivering more value to your clients. If you do it right, it can help you build relationships and get invaluable insights.

Would you like to experience it from the other side of the table? I use Socrating Questioning in my strategic coaching – you can see some examples on that page, and book a call if you’re interested in working with me.

Get the Sales Questions sheet that I use here