This is a transcript of episode 156 of the Troubleshooting Agile podcast with Jeffrey Fredrick and Douglas Squirrel.

We discover that we’ve given opposing advice about asking “Why” questions—including in our chapter on the Why Conversation! It turns out that a big factor in the success or failure of a “why” is your intent, and that (as usual) greater transparency can avoid misunderstandings and help you find new options.

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Listen to this section at 00:14

Squirrel: Welcome back to Troubleshooting Agile. Hi there, Jeffrey.

Jeffrey: Hi Squirrel.

Squirrel: So yesterday we were jointly coaching somebody, which is one of my favourite things to do. And you said something that really surprised me in the moment and I wanted to talk more about it. What you said was “why is always an attack?” And I thought we could talk more about using ‘why’ and how it’s useful, because, in fact, I use it all the time and maybe I’m attacking people and I don’t know it, help me out.

Jeffrey: Okay! So that was that was me slightly misquoting Chris Voss from a book, Never Split the Difference. And he has a section in there about calibrated questions. And he has this line and it’s slightly different than what I said. But it was it’s very easy because he’s talking about words to use that are reporter questions, the who, what, when, where, why and how. But then he gives the advice to cut that list down in the context of the negotiation. And in particular, he gives the advice that using ‘why’ can backfire. And he had a line that really stuck with me, although apparently not perfectly, which was “regardless of the language, the word ‘why’ is translated into it’s accusatory.” That was the thing that I was remembering. And the context here is when you’re talking back and forth, that then it’s the warning that when you ask why it can it can be very sound like an accusation and triggered defensiveness in the other person. And so often I coach people to use the word ‘how’ rather than ‘why’ when they’re in a difficult conversation and I think that it comes down to the issue that it’s a function of what you’re actually thinking in the conversation will come through. And so the word why can by its nature, it can have this element where if I’m thinking, ‘that’s really dumb. I can’t believe anyone thinks that.’ And I say, “well, why do you think that?” That’s going to come across in my tone of voice and I think it’s that situation where ‘why’ has this power to essentially derail collaboration. Does that make sense?

Squirrel: It certainly does. And what’s surprising is that we said the opposite in Agile Conversations, and that’s what really struck me. So what we were talking about, there was something I remember learning a long, long time ago when I was hanging out with a bunch of lawyers and they said, “well, one of the things that we’re trained very tightly to do and drilled on law school is never to ask why.” And the reason is that if you ask why in a cross-examination, you can get an answer that’s surprising.

Squirrel: So you have somebody on the stand who you’re wanting to paint as a guilty person. And if you say to them, “why were you in your car idling right outside the bank while the robbery was in progress?”, then they might say, “oh, yes, I was picking up my aunt and she’s at the care home nearby.” You get a whole bunch of stuff that you weren’t looking for. And that derails your narrative. What you want to do is box in the person you’re talking to and get them to follow your story. You were idling outside the bank, weren’t you? And then you had a gun in your car. And then when the police came, you told them, et cetera, you want to lead the witness and get them in a box following the story that you want to tell. And of course, in a difficult conversation, if I’m talking with someone about a new requirement or if I’m dealing with a request from my boss or something like that, any of the kinds of things our listeners run into, I want to do the opposite of that. I don’t want to be leading the witness. I want to be discovering more information that could help me. And I’ve often found way to be a very useful response. For example, when clients come to me and say, Squirrel, what I’d like you to do is coach this person and I’ll say, well, why? What’s the goal of doing that? And I often then discover that there’s some completely other purpose and the coaching that person would be a terrible idea or that there’s a much better option on the table. But I only discover that by being curious and why really helps me to do that. In fact, we titled a whole chapter of the book, the whole conversation, and we talked about how to get to the why of what you’re doing and align with your team. So we’ve said a lot of good things about ‘why’ and here you were saying why it doesn’t work, agreeing with Voss. So what’s the difference?

Curiosity is the Key

Listen to this section at 04:53

Jeffrey: I think it’s great and I think actually in from what you said, which is we talk about wanting to get to the ‘why’, and I think we do want to get to the why and in a sense that goal of understanding the other person and this might be kind of a test, which is when you genuinely want to know, if you’re very curious about whether the person believes and you’re open to it, and you see it as a potential to learn, if you see the answer to the question as being valuable, then I’m going to guess you’re going to ask ‘why’ in a way that’s going to be conducive to their interpreting it well. I think the challenge is the context where you’re less curious, in fact, I’ll say this, where you’re not curious, where you’re not open, then I think that ‘why’ is going to come through in a very different way, lands in a different way. So I think it’s this question of what you’re thinking now. I do think we were talking about this ahead of time in part, though, that actually there’s a funny element here, which is I talked before about the connection between what’s in your left hand column, what are your thoughts.

Jeffrey: And this is a reference, of course, to our two column format for doing a conversation analysis. The right hand column is where we put the actual dialogue in the left is what we’re thinking. And so we’ll talk about that difference, so it’s a question of if what you’re thinking is ‘Wow I think that’s really dumb’ and I ask them “well why do you think that?” That dissonance is going to come across that my sort of lack of curiosity will come across in the why. On the other hand you mentioned to me and I thought this is a great point, that if you actually are more transparent, if you rather than leaving the negative thoughts unsaid just implied in the ‘why’ you actually say, “I hear you saying that and I just find it really strange because it seems to me like going that way would be a disaster and I’m really surprised then that you are advocating this. And I’m and also really curious, would you be willing to explain to me why you think this is a good idea?”

Squirrel: And I might say something also, if this is true about my willingness to change my mind, I’m interested in hearing more because I might be willing to change my mind. I might learn something new that would change what I’m thinking. If that weren’t true, of course, I wouldn’t want to say that. I might just say “I’m pretty settled against this one. I’ve thought about it a lot. I’m willing to hear why you think that, we might discover something new that we could collaborate on. but, you know, setting up a Ponzi scheme to cheat people out of their money just really isn’t going to work for me. I’ve thought about that. Not a good scheme.”

Squirrel: So if you were dead opposed to something, you could share that as well and still ask why, if you were genuinely curious about it and if you thought it could enhance the conversation. But that transparency, I think, removes the venom, takes away the accusatory nature of the ‘why’ or makes it bare. At least it’s clear that I have this view, I’m settled on it. You and I are not going to come to agreement, but I’m still willing to hear why you think what you think.

Jeffrey: What’s interesting here is the accusatory nature, I think is it’s not actually laying it bare in the sense that the accusation would be, you know, you’re wrong for for thinking this. The accusation is about the other person. And I think what we’re being transparent here with is about our own feelings on it and I think that’s the difference, is that when the problem is in the accusatory ‘why’, is the feeling of judgement of the other person that when you ask that ‘why’, that you’re accusing them of being bad in some way, ill intended or illogical. And it’s that accusation is where the danger is. In what you’re describing, when I heard you talking, you were being transparent about your own feelings, your own thoughts about the situation. You weren’t saying, “I think a Ponzi scheme like this is immoral. And anyone who advocates it is a terrible person.” Instead, you were talking about yourself and saying, “I’ve given a lot of thought to this and it’s not right and I can’t see myself going along with it.”

Squirrel: And if you did want to share the information that you thought it was terrible and a person who does it is a terrible person, ‘why’ wouldn’t be a question that would actually be very useful because you’re kind of set on that view and that would be a valid view to share but it wouldn’t lead to a lot more conversation on that topic anyway.

Jeffrey: I think you could be right. And then I think actually, in that case, maybe the ‘why’ maybe is an accusation.

Squirrel: It is.

Jeffrey: And so I think it’s in that sense, that version of ‘why’ comes through.

Squirrel: Indeed.

Squirrel: And so news from us don’t set up Ponzi schemes, we’re going to have a negative view of that. That’s our advice for the day. No, I’m kidding. But if it is accusatory, if you are wanting to tell the other person that there’s a moral component to what you’re saying, that’s a valid thing but probably enquiring into it is not going to help you.

How vs Why

Listen to this section at 09:51 Jeffrey: One thing I would say too is if you look at the kind of substitution effect, if we could go back to the intent, as you said, the lawyers don’t want to ask why, because of all the things that might uncover.

Jeffrey: And so this is where the advice that I’ve often found that using the word “how” in many cases will be similarly open ended and will similarly have the dialogue, so we definitely want that two way dialogue. We want to get to what’s that picture in the other person’s mind. And I often find “how” will work very well for that, because I can ask something like, “how did you come to that conclusion?” Rather than “why do you think that? Or how do you see this working?” Rather than, “why do you think this would work?”

Jeffrey: And so I do think there’s a lot of cases where “how” is a good substitute that lacks the potential for accusation.

Squirrel: And the context we were in, as you were giving this coaching advice, was one where a product manager was hearing a series of ideas from somebody outside the team, ‘hey, why don’t we try this and let’s do that? And this is a great idea.’ Not that any product managers listening to this have ever heard that kind of thing. This is very common. And your advice was that if you ask “why” each time it can sound accusatory, whereas if you ask “how”, how would we do that? How would we adjust our plans? How would we drop something else in order to make room for that? It can lead to the sort of dialogue that you’re looking for. And I can absolutely see that. The other case that is happening more often with me is that I have someone who is coming to me discussing what sorts of consulting work I might do with them and there I really do want to get to the underlying cause. What is the motivation that lies behind this? Because I’m meeting the person building the relationship with them and I don’t know what their context is in their organisation. Is large or small? Is it an initiative coming from somebody else and I should be talking to that person. There can be lots of information that I’m missing and I value getting to that information efficiently. It helps the other person faster and it helps me be more efficient. And so I find that ‘why’ question there helps me more because a ‘how’ question tends to focus them on the method of achieving whatever it is, whereas the ‘why’ question gets them thinking about other options. But I’m thinking that it would help me probably to be more transparent about why I’m asking ‘why’. So I could say something like, giving the explanation I just did. I often find that understanding more about your context and what led you to that request for me to, I don’t know, lead your off site or coach. This person helps me help you more. “Is it okay if I ask why you did that? What is motivating you, where that idea comes from or what your goal would be?” I think that might be a way to diffuse some of this ‘why’ defensiveness.

Jeffrey: That’s a really good point. And I do think the contextual difference is important. I think, as you said, there’s no real tension between you and the client who is coming with the request to come do this thing. Whereas in the product manager difference, one of the elements was that there was tension between the existing plans and the new request. And this is a really great example of the ‘how’ question. It fits very well with Chris Voss’s idea of calibrated questions that you are in part trying to have the person be on the same side as you to see your dilemma. So the question of, “well, how would this work? How does this relate to our existing plans? How would we be able to accomplish this?” Positions each of you together, looking at the dilemma, you’re essentially you’re sharing the problem that you see, whereas conversely, when you’re in that situation, when you’re just saying “why” you’re not sharing the problem, you’re kind of pushing back on the person, “why would we do that, given all these great things we have planned? You’re actually setting up an opposition. And I think that’s where some of the energy and tension comes. So very interesting difference in context.

Squirrel: Indeed. And it reminds me of an episode we did a few months ago, a couple of months ago on. Yes And, it’s the same kind of notion when you’re getting these kinds of requests and something is coming in and you’d like to get the other person talking and you’d like to discover more. You’d also like to be transparent about your view that the overall outcome of that is you’d like to be on the same side as the other person. You want to be jointly designing a solution. And when there’s tension, when there’s a lot of demands, there’s a lot of input coming into your team for example, as a product manager, that can be difficult to do. Being more transparent about how you think about it and what things are important to you. That would be a ‘yes and’. “Yes, I’m on your side and there are some conflicts and tensions and difficulties and also avoiding why, but asking how could help you in that situation.” Whereas when you’re setting up from fresh where you don’t have a tension existing, a why can can be the anti-lawyer get you the additional information you need. Is that a fair summary?

Jeffrey: Yeah that sounds great! I really like that framing of the two different situations.

Squirrel: Excellent. Well, if listeners are finding that they are getting all those massive requests and they’re not sure whether to ask why or how or help, then perhaps they could get in touch with us and we’d like to talk about this topic even more and help you out so you can do that at, where you’ll find Twitter and email and mailing lists and dojos and events we’re doing and workshops I’m setting up and all kinds of other things that are going on, so have a look there. And of course, we’ll be back next week. So if you hit the subscribe button in whatever app you use to listen to us, then you’ll hear us again next Wednesday on some other interesting question word I’m sure.

Squirrel: Thanks, Jeffrey.

Jeffrey: Thanks Squirrel.