3: Effective Socratic Method Part I
Constant curiosity. Empathy that means understanding, not agreeing. Don't ever ask "why".
Socrates (470 BC - 399 BC) wrote the manual we need today for dealing with snap judgements and emotionally charged discussions. His mindset and tactical playbook are the most effective method ever developed for getting people to carefully consider their own beliefs. It is a technique built on empathy instead of argument.
The Socratic method is a structure of dialogue driven by a sequence of critical questions designed to bring all parties closer to the truth. Questions which can destabilize the underlying assumptions which have lead someone to a false belief. But it’s far more than just asking “why” or saying “you’re wrong”.
While Socrates often knows that someone’s belief is incorrect, he never ever says “you’re wrong.” Instead, he says “can we agree on this? And what about this?” He works with people’s beliefs and in doing so, helps them to find contradictions in their mental models. This is a critical mindset shift.
If someone is wrong, it feels natural for us to tell them our (correct) point of view. If you logically explain something to someone they’ll surely believe it, right? Of course not. We’ve seen this time and time again. People shut off or they get defensive. And that mindset is counterproductive to genuinely changing their view.
Instead, we need to talk a mile in their shoes. The foundation of the Socratic method, and effective dialogue as a whole, is the ability to speak from your counterpart’s point of view as closely as possible. The ability to explore a subject using their mental model of the situation, not your own. This is not easy. It takes constant effort on our part, but it eases the cognitive load needed for their side. It’s an entirely empathetic approach. And the empathy we express, while not a demonstration of agreement with the other side, is a demonstration of understanding the them. You simply will not get people to embrace ideas by telling them. You get them to embrace ideas by thinking about the ideas, helping them to frame it in their own mind and make connections between their neurons.
I’m going to start with an example. Then I’ll go into specific tactics to use and the science behind why they work.
Scenario: A missing product feature
This is a real-life scenario that has played out half a dozen times on demo calls. A potential customer is considering buying our software. They see that our competitor offers “A/B testing” and ask if we also have that feature. The short answer is no, we don’t offer A/B testing; we haven’t built it because most of our customers don’t want to deal with the hassle of running A/B tests. Furthermore, A/B testing is actually a red herring for our product and can lead to erroneous results. Instead of A/B testing, we have an internal tool for running something called “uplift modeling”, which will perform better than A/B testing. We manually run this every month and send customers the results and our recommendations.
Prospective buyer: I saw Acme, Inc’s product includes A/B testing, does your product have A/B testing?
Me: No, but I can manually run the tests for you each month and send a report with the results which we can look at together and use to iterate and optimize.
This is what I used to say, almost word for word. It’s true, we can and do manually run the tests, and it saves the customer time, but saying it in this way leaves the prospect with a feeling like we’re patch-working together solutions that aren’t built to last. Basically it looks like a big red ❌ on the prospect’s notes.
So, I started to ask why they wanted to run A/B tests to unfold one more layer of their thoughts.
Prospective buyer: Does your product have A/B testing?
Me: Why are you looking to run A/B tests?
Prospect: So that we can maximize our revenue with the discounts we’re offering.
Me: Sure. While A/B tests can be helpful, they will actually underperform compared to a technique called uplift modeling. Since the models for uplift modeling are more complex, we prefer to have our in-house data science team run those tests and report back to you with results so that you can optimize revenue.
This feels like a completely reasonable thing to say. But it’s all from a self-centered perspective. There’s far too much telling. The prospects would tune out. All they got from this is that we have something in place like A/B testing, but they’re not really sure what it is or if it will work.
Prospective buyer: Does your product have A/B testing?
Me: How would your team want to use A/B testing?
Prospect: Well, we would try out different discount amounts and see which ones were most likely to be accepted by our customers.
Me: I’m curious. How would your team strike the right balance between higher offer acceptance rates and the increased cost of needing to give out bigger discounts to achieve those higher acceptance rates?
Prospect: We would have our customer success team look at the data and make a decision based on what they see.
Me: Would your team also want to factor in future reactivation revenue from customers after they accept a discount?
Prospect: Yeah, I guess so.
Me: It sounds like you want to strike a careful balance of discount amount, acceptance rates, and reactivation rates. And ideally all in a data driven way. Would you be opposed to our in-house data science team running these tests for you?
Prospect: No, that sounds great!
Note that there isn’t any calling out A/B testing for being worse and suggesting “uplift modeling”. This would only increases confusion and prompt argument. Instead, this dialogue walks the prospect through what data needs to be taken into account - not just offer acceptance rates, but the amount of discount and reactivation rates.
By the time the prospect understands everything that needs to go into it, they are relieved to hear that we have an in-house team that can run those tests for them.
The last piece of dialogue from my side is a summary plus a “no-oriented question” (TM Chris Voss). It’s a great way of consolidating that you’re seeing things from their viewpoint and then making a suggestion in a collaborative way, instead of forcing it on them. It gives the prospect the sense that they are in control at all times, and don’t need to get defensive.
Why it works
We want to achieve two main things in any Socratic dialogue. First and foremost, we want the other person to be actively engaging with us. We don’t want them to tune out. Secondly, we want to make sure the person is thinking logically, not defensively or confrontationally.
Open-ended questions are critical for getting the other side to actively think on whatever you’re talking about. If you’re telling someone something, they can tune it out. They just nod their heads and move on with their days. By asking strategic, open-ended questions, you guarantee that they are actively thinking about the topic.
Once someone is actively engaged, we want to make sure they are afforded the opportunity to think logically. If we start throwing out accusations - “why’d you do it that way?” - they’ll get defensive and start looking for things to say instead of actively exploring the topic together. You want them to know you’re working together so that they can focus on the topic at hand instead of worrying about their side of the argument.
Tactics and Examples
Don’t ever ask “why?”
Why is a really easy question to ask from our point of view and often comes from a place of genuine curiosity instead of accusation - it feels like a completely reasonable thing to ask. But, like telling or explaining, it comes from a self-centered perspective. Why is the question any 5 year old asks on repeat; it’s inherently a selfish question meant to gain more information for our own mental model. It doesn’t help our counterpart think critically.
The other bad thing why does is that it almost always shifts the other person into a defensive mindset. Since we were children, why has served as an indication that someone is judging our beliefs or our actions. We start searching for answers that sound reasonable and will get us out of a sticky situation, instead of searching for solutions.
Instead of why, you can use how or what.
Your partner says, “Can we leave 30 minutes before we were planning to?”
✅ What makes you suggest that?
A potential sales prospect tells you “We decided not to go forward with your product?”
✅ What led you to that decision?
When you need to ask for favors, do it from their perspective
This is one of the simplest tactics to employ. Whenever you would say “could I”, replace it with a “would you mind if I”.
❌ Could I eat the last slice of pizza?
✅ Would you mind if I ate the last slice of pizza?
❌ Could I borrow your headphones?
✅ Would you mind if I borrowed your headphones for class?
This subtle change puts the person you’re talking to in control of the conversation. They don’t feel like you’re bullying them into a decision and they have space to make their own decision. If they say yes, that’s great. If they say no, your relationship is in a better spot because of how you phrased the question.
Similarly, if you have a suggestion to make, instead of phrasing it as “do you want to”, phrase it as “would you be opposed to”.
❌ Do you want to order-in Thai food?
✅ Would you be opposed to me ordering Thai food for us?
This is a similar tactic in that it puts them in control, but it also works toward relieving the other party of the mental responsibility of making a decision. Plausible deniability in a way. “Do you want to order-in Thai food” makes someone think about the other possibilities. We naturally get defensive when we hear a question like this, like we’re being forced into Thai food. “Would you be opposed to me ordering Thai for us” tells them they they have every right to say no, while giving them an option ripe for the taking.
✅ Would you be opposed to our team handling the A/B testing for you?
✅ Would you be opposed to scheduling a follow-up meeting where we could help you with implementation?
Make assumptions from their perspective
When ever you make assumptions about how someone is feeling or thinking, it’s a risk. You can minimize that risk by putting things in terms of their perspective. If you’re correct, great. If not, they’ll correct you. Either way, it shows that you’re thinking about their thoughts and you’re not worried about pushing an agenda right now.
❌ So far I’ve heard that you’re feeling overwhelmed at work and you don’t want to work on Fridays anymore.
✅ So far you’ve told me that you’re feeling overwhelmed at work and you don’t want to work on Fridays anymore.
“I’ve heard that” is commonly suggested as a way to engage with someone, but it can very easily make the other side feel attacked. “You’ve told me” is impartial - it summarizes without inserting an impression of your own feelings and bias into the matter.
Scenario: Not Getting a Response
In this situation, a prospective buyer has ghosted me after at least one good meeting between the two of us. This is typically the result of conflicting priorities.
Often our first reaction here (as a salesperson) is to throw out a deadline to try to get a decision. A more empathetic approach is to understand that they’re having trouble making up their mind, or with other priorities.
Fundamentally, we want to impose a deadline because we have a problem with them delaying. They don’t have a problem. We should express this concretely. This should actually be more intuitive, and should feel more honest. Making them feel like something is their fault is only counterproductive. Take the burden on yourself, and let them know the position you’re going to be in, and let them make the decision.
❌ Any update on this?
❌ Do you have time this week to talk through implementation?
❌ Is there anything I can do to help you get started?
These all leave the prospect feeling some mix of guilt and something else added to their plate. They want to put it out of their minds so they just close their email.
If you get set up by Friday, I can credit your account with $500.
This has the effect of urgency while seeming like you’re doing them a favor. It can work sometimes, but it’s still coming from our perspective.
✅ Is customer retention no longer a priority for you?
This combines a no-oriented question (giving the recipient control) with a provoking question to think about their priorities.
I recently started reading Chris Voss’s Never Split the Difference for the 3rd time. The first two times I read it, I noted the tactics but didn’t understand what they were doing at a deeper level, so found it hard to put the techniques into practice. This time through, armed with knowledge of the Socratic method, I’m understanding the influence behind each tactic, and it’s made it much more natural to implement in practice. I’ll report back in a months time with additional examples of where this dialogue has worked (and not worked) in practice.