Building the Muscles for Critical Thinking

Transcript

Shane Hastie: Good day, folks. This is Shane Hastie for the InfoQ Engineering Culture Podcast. Today I'm sitting down with Dannielle Pearson. Dannielle, welcome. Thank you for taking the time to talk to us.

Dannielle Pearson: Thanks for having me, Shane.

Shane Hastie: We met at the LAST Conference in Melbourne a little while ago, and you were talking about strategy and critical thinking, but I suppose before we go there, who's Dannielle?

Introductions [01:14]

Dannielle Pearson: Who is Dannielle? That's a great question. Like all people, Dannielle is many things. In the professional realm, which we'll talk mostly about today, ultimately, I'm a commercial strategist. Now, what does that mean? To understand that, you have to understand a little bit about my background. So I've had a varied career. I started my career in the United States Air Force. I'm an ex-intelligence officer. I actually committed myself to the Air Force on the 10th of September 2001, so one day before 9/11. And I spent about nine years in total in the US intelligence community, mainly working alongside it, so many three-lettered acronym organizations I can attest to working with.

And then from there, about 2011, I moved from the US to Australia, so I'm a dual citizen, and I started working in the world of software. So I entered Salesforce and was an account executive and got about three years into that and went, "Man, we don't ask a lot of questions." People are very confused in the realm of software and yet, we just have to meet this monthly quota and we're not really thinking about what we're actually doing within the organization. And that started the strategy piece, particularly underpinned by the intelligence background.

And so over the last probably 10 years or so, I've worked with predominantly software companies and some implementation consultancies really on commercial strategies. So everything from go-to market, to strategic planning, to revenue operations, sales strategy and international expansion strategies. And this is where I've learned there's a gap in critical thinking, less so on strategic thinking but really the basis of critical thinking.

Shane Hastie: So let's delve into that one. What is critical thinking?

What is critical thinking? [02:47]

Dannielle Pearson: Great question. It's funny. When I was prepping for LAST conference, I had to delve into some details for content, and I started, myself, looking up, what is critical thinking? And I came to realize very, very quickly that there's lot of misconceptions by a lot of well-intentioned data but almost too much data available. And so what often gets typecasted as critical thinking is this very stoic, logical, analytical, occupationally driven, "I'm a doctor. I'm a lawyer. Here are my critical thinking skills."

And actually, when you really look at what critical thinking is, one, I always say this, it's a choice. It's a metacognitive process. You do not have an IQ level that determines whether you can critically think. You can have an IQ that's below average and critically think, and you can have mental level intelligence and not critically think. It is a choice that you make. So that's number one.

The second bit is it's really the pathway to independent thought. The minute you decide I'm not going to take the set face value and I'm going to start to question it, you then become thought independent, and independent thought is the pathway to self-actualization. And so I actually say that critical thinking is a metacognitive process that leads to self-actualization.

Shane Hastie: Cognitive process that leads to self-actualization. Why does it matter?

Dannielle Pearson: Everybody wants self-actualization. Whether they say it or not, you can see it at an individual level. I've met a lot of people, particularly in the tech sphere, of not feeling heard, not feeling seen, are intelligent. They're seeing what's happening in front of them and they feel powerless to do anything. Well, that's self-actualization, and you see it at a global level. You see it in international conflicts at national levels. I'm not going to name any because I don't want to go in that direction, but you can see a lot of countries and people that are frustrated with not being heard and not being seen. So self-actualization is something we all strive for.

Shane Hastie: And for you stepping into the space of communicating this, asking those questions, why did you bother?

Dannielle Pearson: Frustration, actually. I've always been wired this way and not really realizing that it was a skillset. It wasn't until I got maybe 15 years into my career that I went, "Hang on. Wait a minute. I seem to be one of the few people here questioning things or at least articulating the notion to question. Everyone seems to be questioning stuff but not really bringing it up." And I genuinely believe, and this is a bit altruistic but I believe it, which is you have to be the change that you want to see in the world. So if I see something that goes, "Well, hang on. I've got the skill in critical thinking. I see that I can put the pieces together and other people aren't necessarily getting this message," then it's incumbent upon me to say something.

Shane Hastie: So what does critical thinking look like in practice for a technologist?

Critical thinking in action as a technologist [05:30]

Dannielle Pearson: Look, that's a lot, right? If I think of a regular technology scenario, it's the business saying, "Hey, I've got a request." So the technologist is probably dealing with some type of tech debt. There's BAU to keep the system up and running, and that's assuming you're not going through some type of transformation project, which you probably are because that's always happening. The business is saying, "I need this and I need this now." And there's a series of decisions that have to be made in that do you inform the business on why that might not be a priority or the impacts of that should the business push? What are the impacts to the other pieces that the technologist is actually weighing up? And how to educate the people around the technologist as well as themselves to determine and prioritize what they actually need to focus on?

So I think technologists, whether they realize it or not, are in a constant state of the need to critically think just with the multiple customers they have to serve and all the varying things they need to balance.

Shane Hastie: I want to delve into the critical thinking or communicating my critical thinking. How do I come across that, hey, I've got some questions. I'm not sure about this. Here's what I'm seeing. And not be the, oh, you're always being negative.

Communicating the message so people will listen [06:44]

Dannielle Pearson: Yes, that's a great one. I get that often. The minute you set up a block, right? Hey, I've got a question. Immediately, it's deemed as negative. And I think that's actually the starting point and that's a great point. There's an awareness and an acknowledgement that not necessarily agreeing with things and asking questions is deemed contentious. I think out of the gate, having awareness on that is number one.And how you phrase things is also critically important. So the person across from you, whoever you're speaking with, might take it as contentious. And the first thing you want to do is say, "Look, I don't mean this in a contentious way, but I have a few questions. This is the purpose of the questions. And actually if I don't get the questions answered, there are outcomes to that." And so it's really taking that person on the journey of understanding your thinking. So that's number one.

And the second thing is pick and choose your battles. And I remember being asked this at LAST conference, how do you think critically a hundred percent of the time? And the answer is you don't. And my response would be, "Please don't. It's not a good use of time, and you can get into overthinking and analysis paralysis, but it's about picking and choosing the moments and determining what's going to be the biggest impact." If someone is coming in with a major transformation project and that's going to thwart key initiatives that you've been working on that align to the strategic direction of the business and you know that they're disconnected, well then, it's incumbent upon you to educate the business or the owner or whoever is asking you that question what the implications are in a conscientious manner.

Shane Hastie: Stereotypically, technologists are accused of not being good communicators. How do we break that stereotype? How do I get that message across in a way that people will listen?

Dannielle Pearson: So if I was in front of a whiteboard and you look at critical thinking, one, I'd have critical thinking in a bubble and then I'd have, for the Venn diagram, I'd have communication and complex problem solving skills running through that. And then it would be encapsulated in a box marked confidence. You need confidence to speak up. You can be the best critical thinker and analyzer, but if you don't say anything, it doesn't matter.

And so I think the first thing is, one, picking and choosing your battles, but having the confidence to say something, being very clear in your thinking on why, what's the impact? Noting it's an education piece for the person that's observing or on the receiving end of the information.

But I think initially, it's just being cognizant of you have a voice, use your voice, your voice matters, and being confident. And once you start engaging with that, not all the times are going to go well. You're going to have people that don't receive the message well, but you just need to continue to back yourself and have that confidence.

Shane Hastie: Tell me some stories. What are some situations you found yourself in where bringing this message across has worked and when hasn't it worked?

Examples of communicating critical thinking [09:34]

Dannielle Pearson: I'll give you one where it was both. So I was at Salesforce, and I was probably three, four years into my journey there and was getting bored in the sales role. I had a really good leader who said, "Hey, we're verticalizing as a means of a growth strategy and Australia is behind America in the verticalization strategies. We're going to establish a healthcare and life sciences vertical." And I had had a previous year, I'd been in sales around healthcare and I understood the industry. I had analyzed the industry, understood how it was structured, where we played and where we didn't play.

And I looked at this territory that I was given because basically, what they were going to do is fuel the need for a vertical off of one territory. And I looked at it and went, "There is no way this is going to happen. We don't have product market fit across all of these segments. We don't actually have a view of a lot of the segments. So who's engaging with us are more commercial players, which isn't actually indicative of the entire vertical." You've got hospitals. They don't know who you are. They have no idea who you are, and your product doesn't actually fit, and we don't know how to talk to those people or types of clients.

So initially, when I had raised this, immediately I got a stereotype. This salesperson is whinging. How many people think salespeople whinge? A ton of people think salespeople whinge, and some salespeople do whinge, but sometimes they have a lot of value and insight that they can add. So realizing that, I said, "Oh, stuff it." It happened to be summer and we had a handful of interns, and I said, "Great. You guys aren't doing anything. Come with me." And we ended up doing a complete bottom-up analysis of the market. And so what I did was I showed my key stakeholders why they were wrong and why it wasn't going to work, but I did it via data and I broke down the market. I educated them on the segments. I educated them on product market fit, where things were going to work, what the core pain points were, and then got into the investment of really standing up a vertical and what they needed to do.

But that mind shift of showing them, going on the journey, one I had to go on the journey to understand, I had an inkling that what they were trying to do wasn't going to be accurate. But once I actually validated that with data and information, that gave me insight and empowered me to say, "No, I know a hundred percent this isn't going to work." But once I was in that position, I had run the scenarios, I had done the analysis, I was clear, I had an army of interns behind me that would also validate this. Once I showed up with that message and I could show them, physically show them, it became very different. Their attitude towards me wasn't, "Oh, you're no longer a whinging AE. You're actually trying to fix a problem we didn't even realize we had." That's probably one of the better examples I can give but there are numerous.

Shane Hastie: So as a technologist struggling with, "They're not listening to me," you mentioned the confidence, the communication, that complex problem solving skills. What does that look like?

Understanding resistance [12:25]

Dannielle Pearson: Well, let's go back to the first bit, right? They're not listening to me. "They're not listening to me" is fueled by one of two things in general. Either, one, they're operating in fear. I've got to get this done. I've got people breathing down my neck. I just need you to do it. So that's number one. I'm feeling kicked, so I need to kick you because I just need an outcome. I need a result.

The other bit is they're not listening to me as they don't understand. They don't actually know what your world looks like. And I see this often with tech. I was working with a tech lead recently, and he was talking about an experience he had with a startup where a CEO would ask for a series of things for this product, this piece of software that we're building and just thought it was easy. Here's 20 things. Go get it done. It needs to be done by next Friday. And those 20 things could take six months and massive amounts of investment.

So going back to your point of they're not listening to me, they often don't know what they're asking for, and that's why tech, whether you're a developer or you are a tech lead or a solutions architect or a tech architect, you've got to understand that they don't understand your world. They don't understand oftentimes how difficult things are, and if you don't get it right, the cost of the business is going to be massive. And so that's where communication comes into play. You can actualize the critical thinking and complex problem skills, any framework can walk you through that, but the communication of the why is really critically important. I hope that makes sense.

Shane Hastie: It does indeed. Communicate the why. Dannielle, some great advice in there. What is one or two actionable skills that I can take that I can go and learn to do this well?

Actionable skills to improve critical thinking [14:04]

Dannielle Pearson: So the first is one stop ... And this seems like a no-brainer and it seems pretty easy until you go out in the world and actually try doing this. So number one is ask the question, do I just carry on with what's being requested or do I question it? That's number one. Do I make the internal choice that I'm going to take everything at face value or am I going to begin to question it? That doesn't sound like a skill. It is absolutely a skill, particularly given the world as abstract as it is these days with generative AI. There's many, many, many opportunities to take things at face value and pass it off and it doesn't necessarily make it right. So the very first thing you can do is start to question things.

The next thing and really, really critically important to critical thinking is scenario planning. Okay, I've got these options. None of them apparently look very good or all of them look fantastic. It'll be somewhere in between. It's not about being perfect. It's about getting the best that you have at the time. And so once you make that decision of skillset number one, "I'm going to start questioning things. I'm not going to take things at face value. Even though I might be time poor, I'm still not going to do it. I'm going to take that Copilot extract that Microsoft gave me, and I'm going to start reviewing it to make sure it aligns with my thinking and adapt it where I need to." So that's number one.

And then the second piece is more complex issues. Start forcing yourself to do scenario planning. If I go with A, what happens? Pros and cons. Okay, great. If I go with letter B, what happens? And be very clear on that. So when you make your decision, and critical thinking is all about decisive decision-making, not iterative cycles, at least you can back that decision up. It's not perfect. I know that. Here's the pros and cons, but I'm confident that this is the right thing to do going forward.

Shane Hastie: And what if I'm wrong?

It has to be safe to make mistakes [15:50]

Dannielle Pearson: Then you're wrong, but at least you backed it up with information. At least you did it coming from a position of you knew what you were walking into. It might go pear-shaped. Life does that sometimes. But if that happens and you're wrong, and I've been wrong numerous times in my life, you're coming from a higher baseline. You can pivot much quicker than you were wrong and you didn't actually do your due diligence.

And actually, Shane, on that point, I think, and this is just me sharing my view, but I think we're too afraid of being wrong. I think we're afraid to fail, and I think that's a real problem, particularly in tech. The other day, I was speaking to a CTO at a government organization, and he was really refreshing because he said, "This organization needs to be okay to fail. Fail quickly, fix it, but you can fail. And that's the positive thing."

Shane Hastie: Fast feedback. Fail early. Fail fast.

Dannielle Pearson: Yes.

Shane Hastie: Now we come to culture. In many organizations, that's hard.

Dannielle Pearson: Yes, it is. Remember what I said when you said, "Why are you doing this?" And I said, "You have to be the change that you want to see in the world." It doesn't start from the top down. Change starts from the bottom up. Same with culture. You can do these things. First of all, the organization should have some level of critical thinking. Even though we're not universally taught how to think critically, we do think critically. We don't do it nearly as much as we should, but it's happening on some base.

If you're in an organization where you call something out that you don't agree with and you're doing it in a respectful manner and you've laid out the options and you've been very thought-provoking and you've done your best and they don't value that, there's a decision point of, is this the right organization for me? Because I get that question all the time, and that's the answer I commonly give, is sometimes you're not in the right place.

Shane Hastie: Change your organization or change your organization.

Dannielle Pearson: Yes. It doesn't mean give up. Sometimes things are difficult, but if you repeatedly hit a wall and you don't see things moving and evolving forward, it might not be you. It might be the place that you're in.

Shane Hastie: Dannielle, lots of food for thought there. Lots of hard questions and things for people to explore. If our listeners want to continue the conversation, where do they find you?

Dannielle Pearson: I have a website, I've got a reach out tab there. Also I'm active on LinkedIn, Dannielle K. Pearson, and I have a site on LinkedIn as well where you can list various things on critical thinking. I'll unpack topics. I just did one on trauma in the workplace, how to overcome that. So there's a wide variety of everything from critical thinking to strategy insight through to more coaching materials. So I'm readily found.

Shane Hastie: Thank you so much.

Dannielle Pearson: Thank you, Shane.

Mentioned:

• Dannielle Pearson’s website
• Dannielle K. Pearson on LinkedIn