Eight to Late

Sensemaking and Analytics for Organizations

Making sense of entrepreneurship – a conversation with Craig Brown

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KA: My guest for this instalment of my “sensemaker” series of interviews is Craig Brown. I have known Craig since about 2009 when he was a project and program manager. He has since transitioned to running his own software development company, Everest Engineering. So, welcome Craig, let me begin by asking you to introduce yourself and talk a little bit about your journey that got you to where you are now.

CB: Thanks Kailash. How far back do you want me to go? Would you like me to start right at the beginning or just the last few years?

KA: Mostly the transition from project and program management to entrepreneurship. What made you do it? What drove it?

CB: OK. Well, early in my career I worked at different companies and corporations, as many of us do. I even did a very small stint in consulting.  These experiences were interesting because I learned a lot about how things happen in organisations – what works and what doesn’t.  Early last decade, I started working at a SaaS company in a general management role. That was interesting because the culture in those places, the way they operate, is very different from the established corporate world. You’re much closer to “life or death” issues on a month-to-month basis. As a result, you’re much more invested in delivering customer outcomes and value than in compliance, rules and process. That was refreshing and super interesting because I had never been in that situation before.

Anyway, then the day came when it was time to leave that organisation. One of the guys that I worked with, Ranganathan, used to manage part of the team in India while I managed the team in Australia. The two of us decided we would start a software product development agency together, and so began Everest Engineering.

The switch from working for someone to working on your own business is a big one.   Many of the differences are well-known, entrepreneurs have talked about them: it’s a lot of work, it can be very stressful, you’ve got to be multifaceted, you’ve got to be wherever the business needs you at any particular time. So, being able to switch modes and roles is really important.

As the company has gotten bigger, we’ve hired other people to help manage the business, grow it, support it. Ironically, this next stage is about breaking our old habits of being everywhere all at once, its about learning to delegate authority, share responsibility and all that sort of stuff.  What I think is particularly interesting about what’s happening to us now is that it’s kind of the opposite journey to what large companies are trying to do: i.e. they try to reduce bureaucracy and increase entrepreneurship by giving people autonomy and responsibility. We’re headed the other way, not towards bureaucracy (I hope!), but towards more structure and order from what can be described as chaotic, freewheeling entrepreneurship. Yeah, it’s stressful but a lot of fun.

KA: OK, before we get deeper into the conversation, what does Everest Engineering do and where are you located?

CB: We are a software product development agency. Capability wise, we have software engineers, platform engineers, product people, designers, testers, business analysts etc. Our team members live in about half-half on the east coast of Australia (mostly Melbourne) and India. We also have a few team members in North America and have just started building a development team in Malaysia as well. So, we’re kind of distributed across the globe. At the moment, most of our customers are in Australia but we’re growing the customer base around the world as well.

KA: Hmm, there are a lot of companies in the software product development business. It must have been difficult to get traction. How did you do it?

CB: The traditional story (in software development) is that you either a) find a niche that no one is addressing well and zero in on that or, b) you come in cheap and claw your way to the top. When we started our business, we didn’t want to do either of those things. We also wanted to build a generalist software product company, not focusing on a particular domain or particular skill set as many small outfits do. Our vision is that we become a big global company that can engage with lots of different problems. At the same time, we knew that if we swaggered in to client discussions saying that, no one was going to be interested.

So, what did we do?

We started by focusing on the Melbourne market, primarily because that’s where I live. To get traction we decided that we would be compelling in terms of the match between price and quality. In the world of software, you can rent services from agencies which are poor or average quality on the cheap, or you can pay a lot of money for top shelf quality. What we wanted to do is not be the cheapest in the world, but be reasonably inexpensive while also really focusing on quality. Interestingly, over time the price-quality trade off has become less important, which has enabled us to focus on quality. I’m not sure why this happened but I guess it has to do with a common experience in life: when a piece of work is completed, what’s remembered is the good outcome, not the cost to get there.

There’s a kind of irony about day rates versus outcomes. It’s a weird one. For example, the price of some of our India software development teams might be double or even more than what some of our competitors provide. But the deal is that we’ll get it right the first time, within the timeframe and the budget that you’re asking for. Compare this to having an expensive rework nightmare, which often happens when the upfront focus is on cost. I’m aware that this could be sounding like an ad, but it’s really that focus on delivering a quality, delivering an outcome the first time that is the key. Our customers don’t necessarily understand this upfront because quality is hard to talk about, but it is easy to understand when you see it.  So the deal is that after our customers have worked with us, they begin to appreciate the quality aspect we bring.

Another aspect of our strategy is maintaining relationships and sticking together over the long haul.  It’s really simple to state: win over customers through doing good work and keep them through being compelling in our value proposition. However, it is not easy to do. Indeed, it is work in progress, we’re not perfect. These are aspirational goals, and we’re working our way towards them.

KA: I understand the price-value proposition. However, because it is such a crowded market, your first few gigs must have been hard to get. How did you go about doing that?

CB: Yeah, I think it’s a trust-based decision making process when buying expensive, large services. The customer will not know upfront what the quality is going to be like. Fortunately, over the last two decades, I’ve built good strong relationships with lots of people across our industry. So, a lot of people know me, and I’ve had interactions with them through my work or contributions to our professional community (Kailash’s note: For example, Craig is the founder of Last Conferences). That’s gotten me access to a lot of people.  To add to that, in the early days of Everest, we would straight up give people a money-back guarantee. We could do this with confidence because we knew our team members – we knew they were smart people with a lot of enthusiasm for doing right by everyone around them. That enabled us to say to our customers, “if you don’t like the work, you don’t have to pay for it.”  That combined with my personal connections meant that we were able to cut through and get that first round of trust that enabled us to build the company.

KA: It must be doubly challenging to maintain quality and align expectations with a distributed team. Can you talk us through some of the challenges that you have faced?

CB: Yes, and there some nuances around this. One is that the software labour market in Australia is older, on average, than in India. So, there’s an asynchronicity of experience, and with that comes a misalignment of expectations. A really important aspect of this is that we try to be explicit about expectations from different teams, and this is mostly about managing people’s expectations of what’s going to happen and when. Another aspect is for us to develop a shared understanding of what Agile means to us: things like  transparency, focus on throughput, customer value, responding to feedback etc. Once we agree on what they mean, we have to do those things on a day-to-day basis.

It gets even more complicated when you bring the customer in. As you know, every organization has got its own version of what Agile looks like, and different understanding of what “good” means. So, we try very hard to moderate our version and meet the customers where they’re at. In other words, we co-develop shared Agile practices. A phrase that I think really resonates with the customers we work with is let’s improve together.  When there are cultural differences, we don’t see them as barriers. Instead, we reframe them as strengths. It is like, “right, we see things differently, and that is interesting because I hadn’t thought of it that way.”  These differences aren’t necessarily country to country, they can also be industry to industry or organisation to organisation. Of course, there are things that are cultural too. For example, if we’re doing retail websites, the online retail experience in India is different from one in Australia and, therefore, so are expectations of how things should work. You have to step back and go to first principles of user experience design and product management; you have to slow down and talk about what good looks like, and how we’re going to get there.  

Lastly, there’s the issue of managing timezone differences. To be honest,  we don’t find this a problem. The overlap between Australia and India is sufficient, and can lead to some good patterns where there’s like a half a day of focus time and a half a day of collaboration time. But again, this requires planning and preparation. You can’t just turn up to work and go; you have to be thinking ahead about what you are going to do.  As long as you’re able to level up your planning you can take advantage of this.  This also has general positive downstream effects: if everyone’s more organised, there’s less waste, better decisions are made better, and so on. However, it does take effort to get there.

KA: You used a phrase, “let’s improve together with our customers.” Can yougive me some sense of how this works in practice?

CB: The examples are quite mundane to be honest.  When a bunch of people come together to work on a new project, there is some learning required on how you are going to work together. As I had mentioned before, patterns and practices will differ between organisations.   For example, should you focus on Continuous Delivery and DevOps stuff. or should you focus on better product management or sensemaking and design work? The answer is: it depends. We (the customer and us) bring different strengths to the table, so we look at the situation in front of us and decide how to work together.

First of all, we agree on how we communicate, how our day and week runs – all that kind of normal sprint cycle stuff. Then we can get into specifics such as, how do we optimize (our ways of working) around the product that we’re working on?  What is a good outcome? What are the constraints?  In addition, we will have patterns and practices that we can kind of share with each other and learn together.  This is not about telling people about your practices like you have some special access to the truth. Instead, we slow down and go, “Alright, cool. I see this problem here. Do you see it too?” And then you might go, “Yes, I do.” Or you might go, “huh, I see a slightly different problem.” Or you might even go, “I don’t see a problem.”  That opens a dialogue and, before you know it, we’re solving the problem together instead of telling each other what to do. How that manifests could be as simple as changing how you run stand-ups, or set up sprint plans, good coding standards, or the emphasis you put on product design versus shipping a product. These are mundane, well-known things but the trick lies in how you customize them to the context of a specific relationship.

KA: Interesting. So, when you actually hire and get people in, you’d be hiring for technical smarts on the one hand, but you’d also be looking for, a kind of propensity to collaborate. Is that right?

CB: I hire certain kind of certain roles but the bulk of the workforce hiring is done by other people so I’m not actually close to the details. However, I do know that the notion of culture fit is taken pretty seriously in the recruiting process. From this perspective it is mainly about managing the tension between being an individual contributor and a team member. On a team, you will be an individual contributor so you do need to master your craft, be good at the job and all that sort of stuff. However, you also have to think about where your ego is. Do you have this deep need to be the hero, telling everyone what to do and being the master programmer.  Or do you deploy value through a collective effort?  By doing good work, but also looking around, seeing your teammates, recognizing their work and supporting them when needed. We draw these kinds of things out in interviews through storytelling, by asking for examples.

KA: When I look at what you’ve done, it seems like, such a simple idea: to not go on price or quality alone, but somehow marry the two. It’s like you saw a gap in the market, an anomaly that nobody else noticed – or if they did, they did not think it worth pursuing. I find that really interesting.

CB: Yeah, it is kind of like that. There  are a bunch of software agencies that I used to work with, here in Melbourne, they are full of great people. They are also what you would call the premium software agencies in Melbourne or in Australia – quality is top shelf but so is price.  Then at the other end, you’ve got these big factory warehouses of people who are lowly paid and not well supported.  And then there’s this place in the middle that’s almost unseen. What we thought we should do is compete on the one hand, at the quality end, and then also come in cheaper by leveraging the cost differential between the two countries.

You might say we are reinventing the outsourcing experience by maintaining the connections and relationships like small agencies but being able to do things at scale by having the staff, skills and experience commonly found only in much larger outsourcers.

KA: Right, and the interesting thing is that you grew the business in some pretty challenging times. Could you tell us about how you handled the challenges thrown at you by Covid, for example?

CB: Yes, there’s been a few things right, there’s been the COVID pandemic and now we’re on the cusp of another economic crisis. Indeed, the pandemic hit right after we got started. One of the things that I think enabled us to be resilient has been spreading our bets. So rather than chasing after a handful of big customers, what we’ve done is pursue a relatively even spread of customers in different segments, sizes and organisations types. So, as these crises ripple through different parts of the world economy, it hits us at different times rather than all at once. Don’t get me wrong, the middle of 2020 was really tough, but the fact that we had our spread was what got us what got us through that. I’m not sure if I’m using the term antifragile, properly, but it kind of leans into that. By spreading your bets, you discover all these new people, markets and domains that can grow into opportunities.

KA: That makes good sense. So, what next for Everest?

CB: We’ve been fortunate to have attracted these really interesting and diverse bunch of people to work for us. Equally, we’ve attracted an interesting and diverse bunch of companies that work with us as customers.  We’re only a few years old – four years this November – so we’re still focusing on our core business which is software development. I think in a year or two ahead, I think we will start to see that antifragility or diversity blossom into new opportunities. For example, we definitely want to work in the data space.  We’ve got data engineers and some people who have done projects, with machine learning and so forth, but we don’t actually have it as a practice. It’s kind of ad hoc at the moment. So, maturing these things into proper business units that have got sustained impact on the world will be something for us to do. And then there are other things we’re looking at – for example how product management works in the industry. Specifically, the patterns and the strengths and weaknesses in the product management industry and whether there are ways in which we can contribute to that community.

At heart we are a bunch of explorers and experimenters still…and hope we will remain so. We are on a journey through adjacent possibles. It is the only way to stay fresh and ensure that we don’t get pigeonholed.

KA: So, you’re continually scanning the periphery and horizon to see what new things you can do by adapting what you have. That’s brilliant!

CB: A lot of it comes through the diverse talents and interests of the people we work with, right? We’ve ended up attracting quite interesting people to work with us. Interesting people have – well –  interesting interests! So, for sure, the key thing is to get work done and ship products in time. But another important thing is to make the mental space so that you can actually invest time and energy into the things that you’re curious about. Ultimately that’s what spawns new ideas and new opportunities.

KA: That’s a nice place to close our conversation. But, before we do that I want to ask you one final question: what advice would you give someone who wants to start doing their own software development (or any other) business?

CB: The advice you hear from people that study new businesses is generally something along the lines of: it’s going to be harder than you think; it’s going to take longer than you think; you’re going to get very stressed and have these moments where you wonder why you’re doing it. But at the end of it, you’ll look back and love the fact that you’re doing it. And I think that’s actually true, right.  That said, I think that embracing the chaos and uncertainty isn’t for everyone. Like, here I am, I grew up poor, in a single parent family in regional New South Wales. In my late 20s, early 30s, I started working in corporate Australia in tech. All along I have been burdened by the usual mortgages and lifestyle costs and all that sort of stuff. And I haven’t climbed out of that yet: I’ve still got a mortgage I can’t afford. But yeah, it took me a while to get started on the entrepreneurship thing.  I was 48 when we started Everest, and it was driven partly by events outside my control. As I said at the start, the company I was working for got acquired and that gave me the push I needed to do my own thing. So, there you go. It’s not for everyone and, yes, the right circumstances have to be in place for you. But once you start, I think you’ll embrace it.

KA: That’s an inspiring story and some great advice Craig, particularly for older people who want to start doing their own thing.  You were driven to entrepreneurship in a way but you stuck to it and made it your own. Brilliant stuff, thanks so much for making the time to have a chat.

CB: Thanks Kailash, always a pleasure.

Written by K

November 1, 2022 at 3:42 am

The ethical dimension of complex decision making – a metalogue

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Salviati: Hello Simplicio, it is good to see you again, my friend. What are you up to these days?

Simplicio: Good to see you too, Salviati.  I have been doing a class on decision making as part of my MBA degree. It is nice to go over something one already knows well…and even nicer that I was able to convince my employer to pay for the course.

Saliviati: Well done!  What is the most important thing you have learnt so far?

Simplicio: Let me see…um, I think it is that decisions should be based on hard facts and evidence.

Salviati: Hmm. It is true that most decision-making approaches will tell you to focus on facts and evidence – that is, what you know or can find out about the problem. However, it is often difficult to find hard facts and evidence, particularly in situations where facts are scarce or contested. In such situations, you have no choice but to pay attention to what you don’t know, the uncertainties.

Simplicio: That does not make sense. How can you pay attention to something you don’t know?

Salviati: Let me give you an example. You have done projects before, haven’t you?

Simplicio: Of course, you know from our earlier conversation that I’m a project manager by profession.

Salviati: OK, so what are the key variables in a project?

Simplicio: Time and cost, two apexes of the iron triangle.

Salviati: That’s right. Whatever the project might be, you know that time and cost are key variables. However, you do not know their values upfront. Your job as a project manager, is to come up with good estimates for these. Is that right?

Simplicio: Uh huh.

Salviati:  OK, so you need to understand this uncertainty and to do so you must pay attention to it. The interesting thing about uncertainty associated with time and cost is that it is quantifiable. That is, you can develop numerical estimates for these variables using a range of techniques like, say, Monte Carlo simulation. The point I want to make is that regardless of the technique used, quantifying uncertainty involving known variables is a rational and logical process. Would you agree?

Simplicio: Yes, that makes sense.

Salviati: Now consider another problem, that of formulating a business strategy. What are the key variables in this case?

Simplicio: Hmmm…that’s a difficult one. It depends on several factors, the financial position of the organization, market share, the environment, business forecasts…oh, so many things.

Salviati: What information would you need in order to figure out which of these factors is important?

Simplicio: Oh, that’s impossible to tell without knowing more about the situation. There are so many things that could be important. You need to know a lot more about the business and its operating context before you can figure that out.

Salviati: Yes, that’s true, and I should also point out that no amount of data, number crunching or logical analysis is going to get you anywhere until you figure out what is important. Would you agree?

Simplicio: Yes.

Salviati: So, let me ask you: what do people in your organization do when they develop their business strategy?

Simplicio: Ah, they ask the experts of course – they engage Big 4 consultancies.

Salviati: Right…who better than a rank outsider to tell you what to do? At an inflated billing rate too! Surely there is a better way.

Simplicio: Like what?

Salviati: I’ll get to that in a bit, but I first want to make another point. A few minutes ago, I said that dealing with project estimation is essentially a rational and logical process. Let me ask you now: what kind of process do you think strategy formulation is?

Simplicio: What do you mean?

Salviati: Well, it isn’t logical…but it obviously isn’t arbitrary either. So, what is it?

Simplicio: I’m not sure I understand what you are getting at.

Salviati:  This is a difficult question so let me approach it in another way. We agreed that the difficult part in strategy formulation is to figure out what is important, right?

[Simplicio nods]

Salviati: So, let me ask you: important to whom?

Simplicio: to management, of course!

Salviati: Do employees not matter?

Simplicio: They do…but their job is to do as they are told.

Salviati: Really? You think it as Lord Tennyson noted: “theirs not to reason why, theirs but to do and die.”

Simplicio: That is over the top, Salviati. The situation of an employee in a modern-day organization is not comparable to the poor soldiers in the Charge of the Light Brigade. Nobody dies.

Salviati: May be not, but I think the analogy is justified. There are so many cases of ill-fated strategies that could have, should have, been questioned before implementation, but weren’t.  The consequences for employees, though admittedly not fatal, are disastrous…and the point is, employees are rarely given a voice in the decision. It is akin to the Charge of the Light Brigade.

Simplicio: OK, maybe it is, but what is your point?

Salviati: Strategy development and implementation ought to be treated as ethical matters rather than a logical ones.

Simplicio: Yes, I suppose they are. But that begs the question: how does one develop a strategy in an ethical manner?

Salviati: That, my friend, is the key question and it is a difficult one. The difficulty arises from the fact that ethics is hard to talk about meaningfully. Indeed, the philosopher Ludwig Wittgenstein went so far as to state that ethics cannot be articulated. His point is that the term “ethics” is meaningful only in the context of actions, not words. (Editor’s note: see this lecture by Heinz von Foerster for more on Wittgenstein’s take on ethics)

Simplicio: So how does one act ethically in this context?

Salviati: To answer that question, I will turn to Heinz von Foerster’s ethical imperative: act always to increase choices. (Editor’s note: see this lecture for more on von Foerster’s ethical imperative)

Simplicio: Umm…please explain.

Salviati: It is simple: if you do things that increase everyone’s choices then you are behaving ethically.

Simplicio: OK…but how do you “increase everyone’s choices” in practice?

Salviati: By involving them in the decision of course, and there are ways to do that. However, let me be clear, the aim is not to make a decision that satisfies everyone. That is impossible. It is to get as many different perspectives on the problem before making a decision. If you think about it, this is the only way to ensure that you do not miss important factors that could cause your decision to fall apart later.

Simplicio: That sounds idealistic and impractical.

Salviati: It might be idealistic, but it is not impractical. The basic idea is to make the different perspectives on the problem explicit.  This can be done by eliciting the preferred options of the different stakeholder groups and documenting arguments for and against them. There is a visual notation called IBIS (Issue Based Information System) that facilitates this. With IBIS, we can visualize the informal logic of conversation using three types of nodes: questions (or issues), which capture the problem being discussed; ideas, which are options offered by the different stakeholders; and arguments for and against those options (pros and cons).  By making the different viewpoints and the arguments explicit, you set the stage for making an ethical decision. Of course, one must also have in place the conditions that allow for open dialogue, and there are ways to do that as well.

Simplicio: So, the choices are matters of opinion, not fact? That does not sound right.

Salviati: Of course not. If someone makes a claim that needs to be validated or is factually incorrect, it can be challenged by others, even after the debate.

Simplicio: Ah, I see.  This is interesting, I’d love to see how it works.

Salviati: I’ll send you some books, papers and articles on IBIS (Editor’s note: here are some articles and a couple of books.). 

Simplicio: But I still don’t see how this makes the decision ethical.

Salviati: If you think about it, ethics is about doing what is good. The problem is if you try to define what is good and what is not good, you will tie yourself up in knots. It is impossible to come up with a meaningful universal definition of “goodness.” Wittgenstein was right when he claimed that it is impossible to talk about ethics.  If one cannot speak about ethics meaningfully, the only possibility is to do it… and that is what von Foerster’s dictum is about.  It tells us that ethical action is about doing things that increase choices for everyone. By eliciting multiple perspectives, you are increasing choices for the group. If the environment is one in which open dialogue can occur, then the choices can be freely debated by all and a decision reached. Even if the final decision does not make everyone happy – which it won’t, of course – everyone will agree that the process followed was inherently ethical.

Simplicio: OK, I think I see now. Since complex problems are multifaceted, one has to elicit diverse viewpoints on the problem to ensure one has not missed something important…and by doing so, one is also acting ethically.

Salviati: That’s exactly right! Incidentally, such complex, multifaceted problems are often called wicked problems. Much of the literature on wicked problems focuses on the surfacing and debating diverse perspectives, but very few writers (if any) comment on the inherently ethical nature of this process.

Simplicio: This is fascinating Salviati, thank you for broadening my perspective on complex decisions.

Salviati: My pleasure…but you should keep in mind that the process discussed will ensure that you surface and debate options comprehensively. The decision itself is yet to be made.

Simplicio: Oh! So, how does one make the decision.

Salviati: Unfortunately, there is no formula for that Simplicio. As you will appreciate, this is not simply a matter of picking the best option because different stakeholder groups may have different opinions on which one is best.

Simplicio: Hmmm, so what does the decision maker do if the group cannot settle on an option?

Salviati: Well then, the decision maker must make the call.

Simplicio: On what basis?

Salviati: I think I have already answered that. He must choose so as to maximise the number of future choices for all.

Simplicio: Hmm, we have already gone through that…

Salviati: There is no algorithm I can give you for this, if there were it would be a calculation not a decision – a matter of logic rather than ethics. All I can say is that, you, the decision maker must decide how you must act…and that should be in a way that increases choices for the greatest number of stakeholders. It may be further discussion or something else, it depends on the specifics of the situation. Regardless, it is a call you must make…and the choice you make says more about you anything else.

Simplicio: That is an unsatisfying answer.

Salviati: I’m sorry, but its as simple as that…and that is what makes it so hard.



metalogue is a real or imaginary conversation whose structure resembles the topic being discussed. This piece is inspired by Gregory Bateson’s metalogues in Part 1 of his book, Steps To an Ecology of Mind.

The characters in this metalogue are borrowed from Galileo’s  Dialogue Concerning The Two Chief World Systems in which the character Salviati is a proponent of the Copernican “heresy” that the Earth is not at the centre of the universe whereas Simplicio favours the Geocentric view proposed by the Greek philosopher Ptolemy.

Written by K

October 17, 2022 at 8:23 pm

From ambiguity to action – a paper preview

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The powerful documentary The Social Dilemma highlights the polarizing effect of social media, and how it hinders our collective ability to address problems that impact communities, societies and even nations. Towards the end of the documentary, the technology ethicist, Tristan Harris, makes the following statement:

“If we don’t agree on what is true or that there’s such a thing as truth, we’re toast. This is the problem beneath all other problems because if we can’t agree on what is true, then we can’t navigate out of any of our problems.”

The central point the documentary makes is that the strategies social media platforms use to enhance engagement also tend to encourage the polarization of perspectives. A consequence is that people on two sides of a contentious issue become less likely to find common ground and build a shared understanding of a complex problem.

A similar dynamic plays out in organisations, albeit on a smaller and less consequential scale. For example, two departments – say, sales and marketing – may have completely different perspectives on why sales are falling.  Since their perspectives are different, the mitigating actions they advocate may be completely different, even contradictory. In a classic paper, published half a century ago, Horst Rittel and Melvin Webber coined the term wicked problem to describe such ambiguous dilemmas.

In contrast, problems such as choosing the cheapest product from a range of options are unambiguous because the decision criteria are clear. Such problems are sometimes referred to as tame problems.  As an aside, it should be noted that organisations often tend to treat wicked problems as tame, with less-than-optimal consequences down the line. For example, choosing the cheapest product might lead to larger long-term costs due to increased maintenance, repair and replacement costs.

The problem with wicked problems is that they cannot be solved using rational approaches to decision making. The reason is that rational approaches assume that a) the decision options can be unambiguously determined upfront, and b) that they can be objectively rated.  This implicitly assumes that all those who are impacted by the decision will agree on the options and the rating criteria. Anyone who has been involved in making a contentious decision will know that these are poor assumptions. Consider, for example, management and employee perspectives on an organizational restructuring.

In a book published in 2016, Paul Culmsee and I argued that the difference between tame and wicked problems lies in the nature of uncertainty associated with the two. In brief, tame problems are characterized by uncertainties that can be easily quantified (e.g., cost or time in projects) whereas wicked problems are characterized by uncertainties that are hard to quantify (e.g., the uncertainties associated with a business strategy).  One can think of these as lying at the opposite ends of an ambiguity spectrum, as shown below:

Figure 1: The Ambiguity Spectrum

It is important to note that most real-world problems have both quantifiable and unquantifiable uncertainties and the first thing that one needs to do when one is confronted with a decision making situation is to figure out, qualitatively, where the problem lies on the ambiguity spectrum:

Figure 2: Where does your problem lie on the ambiguity spectrum?

The key insight is that problems that have quantifiable uncertainties can be tackled using rational decision making techniques whereas those with unquantifiable uncertainties cannot. Problems of the latter kind are wicked, and require a different approach – one that focuses on framing the problem collectively (i.e., involving all impacted stakeholders) prior to using rational decision making approaches to address it. This is the domain of sensemaking, which I like to think of as the art of extracting or framing a problem from a messy situation.

Sensemaking is something we all do instinctively when we encounter the unfamiliar – we try to make sense of the situation by framing it in familiar terms. However, in an unfamiliar situation, it is unlikely that a single perspective on a problem will be an appropriate one. What is needed in such situations is for people with different perspectives to debate their views openly and build a shared understanding of the problem that synthesizes the diverse viewpoints. This is sometimes called collective sensemaking.

Collective sensemaking is challenging because it involves exactly the kind of cooperation that Tristan Harris calls for in the quote at the start of this piece.

But when people hold conflicting views on a contentious topic, how can they ever hope to build common ground? It turns out there are ways to build common ground, and although they aren’t perfect (and require diplomacy and doggedness) they do work, at least in many situations if not always. A technique I use is dialogue mapping which I have described in several articles and a book co-written with Paul Culmsee.

Figure 3: An example dialogue (or issue) map

Regardless of the technique used, the point I’m making is that when dealing with ambiguous problems one needs to use collective sensemaking to frame the problem before using rational decision making methods to solve it. When dealing with an ambiguous problem, the viability of a decision hinges on the ability of the decision maker to: a) help stakeholders distinguish facts from opinions, b) take necessary sensemaking actions to find common ground between holders of conflicting opinions, and c) build a base of shared understanding from which a commonly agreed set of “facts” emerge. These “facts” will not be absolute truths but contingent ones. This is often true even of so-called facts used in rational decision making: a cost quotation does not point to a true cost, rather it is an estimate that depends critically on the assumptions made in its calculation. Such decisions, therefore, cannot be framed based on facts alone but ought to be co-constructed with those affected by the decision.  This approach is the basis of a course on decision making under uncertainty that I designed and have been teaching across two faculties at the University of Technology Sydney for the last five years.

In a paper, soon to be published in Management Decision, a leading journal on decision making in organisations, Natalia Nikolova and I describe the principles and pedagogy behind the course in detail. We also highlight the complementary nature of collective sensemaking and rational decision making, showing how the former helps in extracting (or framing) a problem from a situation while the latter solves the framed problem. We also make the point that decision makers in organisations tend to jump into “solutioning” without spending adequate time framing the problem appropriately.  

Finally, it is worth pointing out that the hard sciences have long recognized complementarity to be an important feature of physical theories such as quantum mechanics. Indeed, the physicist Niels Bohr was so taken by this notion that he inscribed the following on his coat of arms: contraria sunt complementa (opposites are complementary). The integration of apparently incompatible elements into a single theory or model can lead to a more complete view of the world and hence, how to act in it. Summarizing the utility of our approach in a phrase: it can help decision makers learn how to move from ambiguity to action.

For copyright reasons, I cannot post the paper publicly. However, I’d be happy to share it with anyone interested in reading / commenting on it – just let me know via a comment below.

Note added on 13 May 2022:

The permalink to the published online version is: https://www.emerald.com/insight/content/doi/10.1108/MD-06-2021-0804/full/html

Written by K

May 3, 2022 at 7:59 am

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