A few months ago (the November 2023 edition), the Strategy Toolkit explored further the intricate relationship between strategy & philosophy, and (amongst many others) the philosopher Socrates’ guidance regarding the importance of living the “examined” life. A life open to questioning. A life of curiousity. A life full of learning.

Wonderfully, I caught up with a New York-based researcher and practitioner in the field of human learning, Jeff Wetzler. Jeff embodies the Socratic ideal and is bringing what he has learned to the world through his book, Ask. Below is my interview with him. I believe you will also find the story fascinating. Feel free to follow up with him directly if interested in learning more.

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TST) The use of questions (inquiry) in communications is timeless:

• the Oracle of Delphi,

• Osiris’ afterlife questions in ancient Egypt,

• the Socratic method,

• the importance of questions in faiths such as Judaism,

• the Heavenly Questions (Tianwen) of poet Qu Yuan,

• psychoanalytic therapy,

• Einstein’s “question everything”,

• appreciative inquiry,

• even arguably the whole prompt engineering aspect of generative AI

To name just a few.

Can you situate for us your research and the Ask Approach within this evolution and landscape of methodologies?

JW) The idea of asking questions is one that has been prevalent throughout human history. It's also been one that I think has had in some ways a bad reputation throughout human history. If we look back at Socrates, who asked a lot of questions, they killed him for asking too many questions. And question asking can be seen as subversive and discouraged. And there's all kinds of expressions like curiosity killed the cat and things like that. And there's even things in our own society that send the message: if you're a strong leader, you should appear certain and you should have the answers and you shouldn't be asking questions. And there's the old stereotype of men don't ask for directions when they're out or whatever, because somehow that's going to make them look weak. And so there's all these messages that society sends one way or the other, that there's something wrong with asking questions. Either it's too subversive or it's too weak, or different things like that.

I draw from the tradition that you and I share from our background at the Monitor Group of organisational behavior, of which Chris Argyris was one of the pioneers, who also said that people can switch into this mode where especially when things feel stressful, that they just need to drive forward and answer and push for action and things like that. And in those modes, questions go to the wayside. And so this is, in some ways, I would say, countercultural to a lot of the strands of our society that say there's something wrong with asking questions, and also counterintuitive when we are under situations of threat and potential embarrassment, potential stress. And it draws, I would say, directly from the field that Chris Argyris pioneered, called action science, which basically says if we want to get better results, especially under tough conditions, we need to act in this other way, which he called Model Two. I avoid using that term because I think it's a little too academic, but basically it's a much more curious, much more inquiry-based way of acting. That doesn't mean we don't share our own opinions as well, but it does mean that we really consider what we can learn from other people.

TST) How does Chris Argyris’ Model Two map onto Daniel Kahneman's two ways of communicating (System one and System two)? I couldn't tell if System two mapped onto Model two or not. Do you have a point of view on that?

That's a good question. I don't think it's a direct mapping, but I do think that both of them are onto the idea that the human mind can operate in different modes, and that one of those two modes is more conducive to learning than the other. There's the ‘thinking fast’ mode (System One), which we need for action and whatever else. But there's also the ‘thinking slow’ mode (System Two), which gives us the chance to take in new information. And then there's Model One, which I think can be appropriate in certain situations, like when there's a crisis or an emergency and we just need someone to take charge and drive us all forward, but under ambiguous conditions, which more and more are the conditions that we're in, it gets us into trouble. So I think I hadn't made that connection to these two modes in the past. They're not a perfect match, but I think they have a lot of correlation.

TST) From my lens as a strategist, you make this very interesting comment in the introduction of your book that, when you were young, you had a survival strategy to be quiet. Because you were the outlier in a cultural setting, right?

There are a lot of instinctive things that all humans do that are strategic. And yet - if humans have been naturally selected to do some things, which in this case means ‘don’t ask questions’, then I keep wondering why is it that we find value in doing the things that are not instinctive, that we intentionally learn some skills, that we take different actions? From your perspective, if there are natural reasons to stay quiet, what's your argument to overcome that?

I'm trying to make the argument not that we should speak up and overcome the quietness that I had, but rather that we should recognise that other people might be silencing themselves in the same way that I silenced myself or for other different reasons, and we should make it easier for them to self-express. That's the value of the Ask Approach.

TST) The Ask Approach has 5 steps. A tradecraft question: tell us more about why you chose these steps (rather than simply asking questions iteratively in a proverbial “double click”.

As every strategist knows, every model is incomplete and every model is false in certain ways and conditions. So to me the design question is: is the model more useful than anything else? The core of the Ask Approach, which is step three, is the posing of the questions and the taxonomy of different questions and things like that. But I realised if we just advise someone to ask a question, but they're doing it because it's a technique and they're not genuinely curious, it's not going to come across as authentic.

Firstly, if someone is genuinely curious, it's going to be a lot easier for them to access those questions in the taxonomy as well. And so that's why curiosity is step one. It does start with this internal state, this internal mindset of what can I learn from this other person. And if we don't have that, the questions will only take you so far. You can get probably some value from them, but not really. So that's why I really felt the need to start with curiosity.

And then I realised, even if I'm curious to learn from you, if you don't feel safe telling me your answer, it doesn't matter what questions that I'm going to ask you. And so that's what got me to number two, which is make it safe. And I learned this the hard way myself coming out of Monitor. I was equipped with all the questions. I was equipped with all the curiosity. And then I walked into a very diverse work environment, far more diverse than at Monitor, far more diverse than at any of our clients. And I was in a position of power as an operating leader. And my curiosity, my questions were not enough because people didn't feel safe telling me the truth. They told me what they thought I wanted to hear. And this was in addition to the kind of Argyris stuff that I just felt was particularly important in today's workforce, where people are operating across all kinds of lines of difference, whether that's power, hierarchical differences, gender differences, racial differences, and other identity markers. So I felt that before we could actually get to the question piece, we needed to have curiosity and make it safe.

Then we come to the heart of the Ask Approach, which is to ask quality questions.

Then I realised that once we asked the questions, that's not enough, because at that point we have to listen to the answers. I think (back in the Monitor days) in the feedback training and productive reasoning stuff, we didn't really drill down as much into how do you listen. So I wanted to give that some attention because I felt that if we just had people ask questions, but they were listening in their old ways of listening, they weren't going to get nearly as much out of the questions.

Then the last piece, which is reflect and reconnect, is an attempt to say, once you have listened, it all comes down to, how do you process what you hear? How do you make meaning of it? And you probably remember the Argyris ideas of single loop, double loop learning that we had. I tried to translate that into a little bit more accessible language, to say: now go through that process of looping, through the learning, to make sure you've got the right takeaways. Overall, I felt that the questions were only one piece of what was important to convey to people, hence a five-step Ask Approach.

TST) Is there a particular source for the second step of making things safe? From where did you draw your inspiration? Or was it from your own research and experience?

The biggest source is the body of work by Amy Edmondson on psychological safety. She's done just phenomenal work about how powerful that is. What I've tried to do in that second step is apply it. Her work usually lives at the organisational and cultural level, and I'm trying to apply it to the interpersonal level. I’ve had the opportunity to spend some time with her, honing that step, and it was really powerful.

TST) Now let’s dive deep into your book for an example of application: in chapter 9, you talk about the importance of asking questions at an organisational level. Share with us the “Oreo cookie” case study and what more is needed when using the Ask Approach beyond individual interpersonal relationships.

You could look at organisations as the aggregation of individual interactions. And when you do that, you start to realise that there are certain patterns that begin to emerge. And if there is silencing that's happening at the individual level between two people, you start to add that up, and you realise organisations are missing out on key aspects of the collective intelligence that they have.

And so the Oreo cookie story was told to me by Irene Rosenfeld, who was the CEO of Kraft, as one of those examples where collective intelligence failed. Literally, people on the front lines could see the cookies were being shipped out all crumbly, but they were not discussing that. Irene ends up finding it out in a very embarrassing way in her board meeting. But if the people in her organisation had been having these kinds of conversations where they were saying: what do you see going on? What's working, what's not working, what ideas do you have? All that kind of thing, then chances are they would have been able to catch the problem much sooner and not only avoid those kinds of errors, but ultimately would have tapped into the ideas and innovation potential that's also present in organisations and teams, too.

This Oreo Cookie manufacturing example was a retrospective story. Irene told me about it afterwards. They ended up asking: what's going on? How's it going? All that kind of thing. They found the root cause of the problem, and they did discover that people knew about it and weren't saying something about it. So they had a technical fix to the problem, which was that they fixed the machine that was crumbling the cookies. But then they also started working on this question of how do we get people speaking up more in our organisation?

I didn't get all those details from her, but what she told me is that it raised her consciousness in her interactions with her leadership team, which is where she felt like it needed to start, that people on her own leadership team were more able to tell her bad news and give her different ideas and feedback and stuff like that.

TST) Stepping away from the book for a moment and into your day to day practice: tell us about a situation (professional or personal) where your use of the Ask Approach made a memorable difference.

One example comes immediately to mind, from back in our Monitor days. When I was first going through the Argyris training myself, one of the questions that we taught people to ask is to invite people to share their reactions. I was a brand new module leader, and I had a case team member on my case, and I had just given him a whole bunch of feedback and guidance and direction for what to do. I thought we were in good shape. Then I remembered that I just got trained to ask this question: What's your reaction to this? So I said, hey, what's your reaction to what I just said to you? And he paused for a minute and he looked at me and he said, if you really want to know the truth, it's completely demoralising to me. And I was shocked. I mean, I thought we were good and whatever. And by finding out that he was demoralised, I could then dig in. And I realised I had different data than he had about what we were supposed to do for this client. And that, based on the data that he had, it made no sense what I was asking him to do. And so it gave us a chance to dig back into this and get back on the same page. We probably would have wasted days or weeks, and I would have had a very demoralised team member on my hands, had I not asked that simple question.

I use the Ask Approach all the time. For example, I run an organisation now, and I have a lot of investors. When I'm with an investor, the first thing that I will do is to think to myself, what can I learn from them? What might they be thinking, what might they be seeing that they're not telling me that could be valuable for me to know?

Here’s a specific situation. I was having breakfast with a high net worth individual who was contemplating making an investment in our organisation. And I was thinking to myself, what could I ask her? What could I learn from her? What new information could I know? What occurred to me is she might have some critiques of my organisation that could be holding her back from making an investment, or that could be holding her back from making as high a level of investment as I would want her to make. So that was the first step of getting curious.

Then I thought to myself, how do I make it safe for her to tell me this exactly? She may think that she doesn't want to criticise me. I'm going to get upset. I'm going to be defensive. I basically just said to her, look, you see a lot of organisations because you invest in a lot of different organisations. I don't have that same vantage point. And I'm always trying to make my organisation, Transcend, better. And so I'm now trying to open up what I call radiate resilience and say, is there anything you see that could help me make Transcend an even stronger organisation? In this way, I'm letting her know that I'm not going to take this as a critique.

I then asked “Is there anything that you think we could be doing better as an organisation?” And her answer was “I think you're doing too many things, and you could focus more, that you're spread too thin.”

I tried to listen very hard to that, and then I tried to let her know that I heard what she had to say and used a sort of paraphrase and test: “I think what I'm hearing you saying is that you might be worried that we're actually making too many different bets as opposed to going deeper, and that that could be harming our impact. Tell me more about that.”

And so we got into a conversation where she would elaborate on that and tell me more. Then I said, “When you look at what we're doing, are there certain things that you see us doing that you think are some candidates that we could shave off, that we could prioritise less,” basically inviting her help in doing that. And so that got us through steps one through four of the Ask Approach in our conversation.

Then, after the conversation, I reflected on it and asked myself the implications. I actually took it back to our team and I said, “Here’s what we’re hearing from a potential investor, what meaning do we want to make of this, etc.?” And we kind of thought it through. Then I went back and I closed the loop with the potential investor and I said, “Here’s what we're going to take into consideration as we make our next budget decisions, based on what you're saying,” in this way closing the loop from her, taking step five of the Ask Approach.

TST) To round things out a bit, who can benefit from the Ask Approach and why?

Leaders who are facing a range of different problems can make use of it. One category of applications that I'm seeing people do is coaching and feedback. How do I have a better developmental conversation with someone? By not just telling them what to do or withholding telling them what to do because I'm afraid to tell them what to do. It's so much easier to give somebody tough feedback. If you then say, what's your reaction to that? What might I be missing? You can almost communicate anything to someone with that level of transparency. If you're genuinely curious to know how it's landing for them and what you could be learning from them as well.

There's also been a lot of application around organisational collaboration. Working across traditional fault lines in the organisation. Literally this morning, I was talking to an organisation that was basically saying that their HR people are trying to maximise retention, but the field doesn't want to implement their initiatives. They want to use the Ask Approach to have better conversations on cross organisational initiatives.

And then there's a whole bunch of applications around innovation, essentially asking, what is the collective genius that is lying dormant in teams, and how do we use questions to elicit it?

So those are some of the places that I'm seeing the Ask Approach starting to have traction.

TST) Lastly, subscribers to the Strategy Toolkit want to ‘get smarter about strategy’. If anyone wants to follow up on what they’ve learned here and want to become more proficient in the Ask Approach, what can they do, practically (besides buying and reading your book)? Do you offer training? YouTube videos? Etc.

I would encourage them to subscribe to my newsletter because I'm constantly putting out ideas, applications, things like that. They can get that at my website.

There's a whole bunch of podcasts and other articles and things like that which you can also find at the website. There's a diagnostic assessment that they can get on the website for free that shows them the five steps of the Ask Approach. Which ones come easy to them, which ones might they need to get better at as well? So a whole bunch of fun tools and resources and things like that.

I'm constantly posting new ideas and tools and resources on LinkedIn as well. So if people connect with me on LinkedIn, that's another good resource.

We’re also offering a series of experiences that range from brief things like keynotes or book talks, to more medium length things like two hour workshops. And the workshops are organised by different use cases, e.g. if you want to ask for innovation or ask for honest feedback or different things like that. For those who want to really go deep, there's the masterclass, which is more of those kinds of things that you and I did at Monitor, where people will actually bring their cases and we'll do follow ups and different things like that.