Navigating Uncertainty, Handling Complexity – Leadership Skills Development (session recording)

Synopsis: Thanks to the popular “VUCA” acronym, the ability to manage enterprises and lead teams in volatile, uncertain, complex and ambiguous conditions is now recognized as an essential leadership skill earmarked for development. But what exactly is this skill and how do we develop it? The concept is understandable, yet beyond as a mindset, what does it entail? How do we act on this skill? In coaching and training on this topic, I (Coach Takeshi) have found it useful to distinguish this skillset across the spectrum of the Cynefin Framework; most notably considering uncertainty and complexity handling as intertwined yet somewhat independent concepts, and a renewed appreciation for classic management skills in balance. In the dōjō session I shared this insight and how to generally approach the topic for learning and development, along with practical examples of tools, frameworks and processes to apply in each area of navigating uncertainty, and complexity handling.

Post session note: During Q&A, one of the participants commented that today’s contents actually felt like an integration of a lot of different leadership skills, and they were wondering how to learn them all, as they all seemed essential to today’s topic of navigating uncertainty and handling complexity. Indeed, today’s session was literally a stack of mental models, one after another. Post session, I reflected further on this great question. Is it a prerequisite to have all these leadership skill components first to be able to navigate uncertainty and handle complexity? Absolutely not! Instead, the idea here is to apply learning on learning itself. “What are some tangible ways to navigate uncertainty? I don’t know. This itself is uncertain to me.” In the lecture I emphasize multiple times the importance to tap into the experience and wisdom of our forebearers. It’s the keyword “vicarious” in Charlie Munger’s famous saying, “You’ve got to have models in your head. And you’ve got to array your experience ‑ both vicarious and direct ‑ on this latticework of models.” The key visual I created for navigating uncertainty is a person holding a flashlight into the dark. You found this article because you were curious to learn about how to navigate uncertainty. You flashed the flashlight. And now you get to see a collation of the many wise teachings from the people who’ve been there done that. Learning is a choice. One thing at a time, pick up things that you find important to you, and try them yourself. It’s a process of weaving the learnings into your own latticework of mental models.

Enjoy the video. Slides and transcript are below.

Slides & Transcript

Navigating Uncertainty, Handling Complexity - Leadership Skills Development

As always, let me ease you into the space of learning, helping both your body and mind to be prepared. Everybody relax your neck, relax your shoulders. We’ll do one breathing exercise, and I’ll chant my usual mantra to go into the space of learning. Extend your arms in front of you, open your chest, take a deep breath all the way to the top. Hold it there. An exhale as slowly as you can. Suspend your assumptions. Suspend your judgment. Choose to be a learner.

Today we have some heavy contents, so it will be lecture and Q&A style. The real truth is that, actually, navigating uncertainty should be a 90 min session on it’s own, and complexity handling another 90 minutes too. And I even have a bonus section for core management skills in the middle. And I’m trying to do all of this in, what 53 minutes to go?, including Q&A and discussion.

So I’ll be doing a super condensed job of uploading knowledge into your brains today, so be prepared, it will be intense. Just to manage your expectations, the lecture will be about 40 minutes, and I’ll be talking a little bit fast to cover everything.

Before we start, one administrative announcement, this session will be recorded and shared on our website post-session. If there’s anyone that doesn’t consent, let me know.

Ok, ready? Let’s go.

First, check-in: Are you overwhelmed?

So today’s topic is leadership skills for navigating uncertainty and handling complexity.

You might later refer back to today’s learning, when you have a challenging situation in front of you.

Now when that happens, I’d first like you to check-in with your state of emotions.

If you are feeling overwhelmed with the situation, do yourself a favor and see if you can de-overwhelm yourself first. I have an article on how to do that here.

The reason why I say that is because, when we are overwhelmed, we get brain fog, and we make simple things complicated, complicated things complex, and complex things uncontrollable.

So first, check-in with yourself.

Cynefin framework

Okay, today we will be using the Cynefin framework a lot, so let’s do a refresher first.

Simple, complicated, complex, chaotic; the Cynefin framework, it’s from a Welsh word so it’s pronounced like this. It’s a decision making and sense-making tool created by Dave Snowden in 1999.

So simple things, nowadays it’s revised as “clear” by Snowden, but for the sake of simplicity I’ll stick to the original wording as I like to keep things simple, but anyway, simple things are things that are easy to duplicate results. Washing dishes, assembling IKEA furniture (although some people will disagree), submitting your expense reports, things like that.

Complicated things may require many expert steps and time, yet they still produce predictable results. A car engine has 10 to 30 thousand parts, and it takes skill to assemble one. Yet, a Corolla engine from one car to another is practically identical, at least when it leaves the factory. So it’s difficult stuff, but still completely replicable, so long as you follow the steps.

In complex things, you generally know what to do and how to do and you’re pretty confident that you’ll get a satisfactory outcome, yet at the point where you’re starting the job or project, you don’t have full and complete details of the “what” and “how” all along the way, and it’s difficult to predict the exact details of what the final outcome is going to look like. New product development is a classic example of a complex job as you’re pretty confident that you can ship out a final product by the target launch date, but what it will look like is hard to guess at this stage as it will depend on the development process where there’s new technology being incorporated and a lot of new customer feedback reflected.

Finally chaotic is an uncontrollable situation. Don’t know what’s happening, don’t know what things are going to look like in the end.

Simple Cynefin test:
Can you see the whole? Can you see the parts?

Today we’re also going to talk about Systems Thinking, so let me warm you up on that too.

Systems Thinking looks at the whole and the parts, and we can apply them to the Cynefin framework like this. In fact, we can use it as a test of which state the situation belongs in the Cynefin framework.

So, simple things you can see the whole and the parts quite easily.

With complicated things like the car engine, you can see the whole engine and although there are 10,000 parts, you can see all parts too if you want to.

With complex things, you can envision the whole new product launch mentally so you can see the whole. However, in the beginning of the product development process, likelihood is that you have awareness of the various chunks of work that need to be done, but not the full details of every single component of work that needs to go into the development. So, you have low resolution, almost like a coarse, pixelated image of the parts in the mental image of the whole picture that you have.

With Chaos, you can’t see the whole nor the parts. It’s just chaotic.

Difference between chaos and uncertainty

Now half of today’s topic is on uncertainty, and you may have noticed that it’s not in the Cynefin framework.

Let me put uncertainty into the whole picture of Cynefin.

So again, chaos is a situation of unpredictability, and (perceived) lack of patterns and therefore the sense of disorder. Now I say “perceived” because the universe is a funny place where mathematics rule, and apparently there are many patterns out there beyond human cognition, at least at our current level of intelligence. So I’m just being kind to the scientists and theorists out there.

And here comes uncertainty. Uncertainty refers to a situation of lack of or incomplete information, where you don’t have enough information or knowledge to predict future outcomes with certainty.

To summarize, a chaotic situation is difficult to manage, whereas an uncertain situation does not imply disorder, and if patterns or trends can be identified, the situation may become manageable.

How does this fit into the previous visual? At this moment you’re struggling to the see the whole and the parts. Yet at some point you’ll start being able to see them. That’s where uncertainty fits in.

Situations of uncertainty, situations of complexity

So we’ll now dive into how to handle uncertainty and complexity, but before we do that, to make the dive-in more relatable and tangible to each of you, can I ask a few people to share some situational examples of uncertainty and complexity?

What comes to your mind? Any past or current experiences of these situations?

Navigating uncertainty

Okay, navigating uncertainty.

We are blind in the dark.

We can use a flashlight to look around.

We can walk around and shine more light into the darkness.

Let me explain this analogy.

Initially in the state of uncertainty, we have little or no information. That doesn’t mean that there is no information; it may be there, except that we don’t know.

The proverbial flashlight is our ability to ask questions, and the proverbial leg to walk around is our ability to probe and explore.

See, navigating uncertainty is a cognitive game. It’s about finding patterns and making educated guesses, so that the situation is brought down to a more manageable level of predictability.

So our critical tools for navigating uncertainty is the power of inquiry, and probing and exploration.

What to do in the face of uncertainty: (2) Keep the cool

Okay, enough for the conceptual introduction. I’m facing uncertainty right now, right in front of me, what do I do?? Let’s look at practical steps on what to do in the face of uncertainty.

First, keep the cool. Know that all decisions are emotional.

These are clear learnings from MRI scans of the brain, psychology, behavioural economics and decision science. In my opinion, take it as a fact. All of our decisions are emotional.

So while we must strive to be level-headed and as rational as we can in our decision making, still be very aware that our emotions are at play.

And why is this important? For example, that instinctive choice to play safe, it’s coming from our survival instincts.

In most simplistic terms our brains are made of three layers. The inner most lizard brain is all about survival, and our middle brains largely prioritizes safety too.

So our default choice to seek certainty actually is an animalistic override of our lower brains over the more modern, intelligent layer of our brain.

Finally, most importantly, be aware that we are full of cognitive biases.

In the face of uncertainty, what do we most fear? Arguably, error in judgement, right?

And, what are the key contributing factors to error in judgement? Anyone?

  • Not enough information, pattern recognition (lack of experience)
  • Chance
  • And, our own biases. And there are so many of them.
  • Recency bias, availability heuristic, dunning-kruger effect
  • Anchoring bias, confirmation bias, self-serving bias (fundamental attribution error)
  • Sunk cost fallacy, survivorship bias, neglect of probability/base rate, gambler’s fallacy
  • Groupthink, bandwagon effect, authority bias, halo effect
  • Loss aversion, endowment effect, optimism bias, negativity bias

So be cool, be rational, keep your biases at bay.

What to do in the face of uncertainty: (2) Seek information, seek patterns

Next, seek information, seek patterns. Why? It’s for informed decision making. Let me explain.

Sooner or later, you’re going to have to act on the situation right in front of you, right? You will need to make a decision, a choice of action.

And you’d want to make a good decision. [pause] It would be wise to make decisions based on factual information in hand, and best guesses, as long it’s a guess of good quality, right?

These decisions are called “informed decisions” and there is good research proving that they are consistently better decisions compared to, for example, flipping the coin.

So, first, seek information.

Remember, you’re starting from a place where you’re in the dark. You have little or no information, yet. So just get started. Collect any information that you can. It’s quantity over quality. Soon pattern recognition will kick-in and you’ll be starting to look into the right place.

Next, take a look at the information you’ve collected and see if you can generate insights. Do you see patterns?

Humans are predictable, not everything, but on many things. You’d agree, right :-)?

Therefore, for things where people are involved, which is pretty much everything, many things we can generate pattern recognition. On certain things, we can often guess with relatively high accuracy what people we do. Let’s use that pattern recognition.

Meanwhile, history repeats, and it would be mad not to learn from our forebearers. People known as visionaries, actually don’t read the future – they have an acute sense of pattern recognition based on learnings from our past, and they play on probability. You can be a visionary yourself; it’s more science than magic. So research past similar events and tap into the wisdom of people with experience.

What to do in the face of uncertainty: (3) Scenario think and game plan

Third step is to scenario think and game plan.

“God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference.” The serenity prayer, many of you know.

First, what do we know and don’t know, things that are clearcut black and white.

Things we know and can keep under our control – great, be very aware of it and make best use of it.

And things we have absolutely no control over, especially adversity; while a sense of powerlessness and resentment may prevail, we actually may still have a choice – resign to fate, or risk manage the adversity. There’s still something we can do.

Now into the grey zone, which are most other things

People are predictable and many things repeat a pattern; that doesn’t mean things will happen as expected. The name of the game here is to play on probability. And here’s how you play it out.

Develop the skill of scenario thinking. It’s simple. Just be conscious of our tendency to do linear thinking; that is basically just thinking of one scenario. So lateral think or parallel think and think of many possible scenarios. Just imagine many possible paths of how things can unfold.

And from there, make an “informed decision.” Which of the scenarios are more likely to happen, and why? Use the information and your best guess to make a calculated bet on which scenarios you would like to play out.

Finally, “game plan” upfront. Once you’re in the game, new information and interactions among the players will emerge. These are called emergent properties, and I’ll explain more later. The original scenario may no longer hold because of these emergent properties and that’s expected. What’s important here is that it would make a big difference if you are mentally prepared to use the multiple scenarios you already thought ahead of. The game is shifting in a certain direction? No worries, I’ve thought about it and have a scenario in place, no panic. This preparedness will help you keep the cool all the way.

What to do in the face of uncertainty: (4) Cover the terrain, convert unknown territory to known, (5) Who over what, who over how

Cover the terrain, convert unknown territory to known. What’s the significance of this?

See, complexity is much more manageable than uncertainty. Therefore, in a way you can consider one target of navigating uncertainty is to try to downgrade the state of uncertainty to complexity, so that you can manage it better.

So probe and explore. Cover the terrain and convert unknown territory to known. Make those places no longer the land of unknown and instead just a land of complexity where you can flex your management muscles better.

Finally, a word of wisdom if I may share. It’s always, “who over what” and “who over how”. Figuring out what to do and how to do on your own? It’s always easier to tap into someone that already knows how to do what to do. So don’t try to do everything by yourself. Find great people, make people’s talent yours!

What to NOT DO in the face of uncertainty: Overly seeking certainty

Last slide for navigating uncertainty.

So we covered what to do in the face of uncertainty.

For what NOT TO do in the face of uncertainty, I have only one recommendation.

Don’t overly seek certainty.

Don’t get me wrong. Your safety is our utmost concern. So safety first, take cover.

Most likely you’re in a not so fun situation when uncertainty is hitting you. It may be adversity, a situation that you were involuntarily thrown into.

So take cover, make sure you protect yourself first.

However, once you’re in a safe space to think, assess your options.

Don’t fool yourself. Wishful thinking is another form of cognitive bias. You might be safe for now, but how long would that last? Inaction, may actually be a high-risk choice.

As demonstrated, there are known ways to address uncertainty. It’s uncomfortable and heavy cognitive work. But go ahead, tackle uncertainty head-on when you’re ready, and increase your chances of success.

Handling Complexity:
Applied Systems Thinking

Okay, topic number two for today, handling complexity.

I’ve got to say it; there is NO way one can learn complexity handling without learning Systems Thinking. In fact, complexity handling is a practice of systems thinking. It’s applied systems thinking.

Linear thinking gets us stuck. In academia it’s called “event oriented thinking”. Basically it’s our simplistic view of the world where we falsely believe that everything can be explained by a cause an effect relationship. Got a problem, no problem, just find that cause and fix it.

That works for simple and maybe complicated stuff, but definitely not for complex stuff.

Things are hard to predict in a complex situation because of emergent properties of the many variables inside it. We need a different set of lenses to be able to see what’s going on in a complex situation, and that is systems thinking.

What is Systems Thinking?

A quick primer of Systems Thinking

What is Systems Thinking? There’s a great 1990 book from Peter Senge and in it he describes Systems Thinking as the following. “Systems thinking is a discipline for seeing wholes. It is a framework for seeing interrelationships rather than things, for seeing patterns of change rather than static “snapshots.””

Key Concepts of Systems Thinking are, having a holistic perspective, seeing interconnected components, understanding feedback loops and emergent properties, accepting that systems are dynamic in nature and nothing is static, and being conscious of boundaries within and outside the system.

Now most importantly is, how can Systems Thinking be helpful in handling complexity?

When the situation becomes complex, non-linearity of events quickly kick-in and it starts to become difficult to track “what’s going on” and explain why things are happening as they are in the traditional cause and effect sense.

Systems Thinking helps us see and explain that by sense-making the whole, the parts and their interactions. Once we can see and understand what’s happening, we can then design and implement adaptive means of interventions; i.e. the situation becomes more manageable despite the complexity. This is why Systems Thinking is integral to complexity handling.

Grounded approach to complexity handling: (1) Sense-make the situation, (2) Identify the actors and factors

Number 1, sense make the situation.

What’s going on? Try to see things from a whole perspective. I recommend two ways:

First is what I call the map or picture approach. This is for people who find comfort in seeing the whole as one visual.

Or try the movie or story approach. For those that are comfortable to get a sense of the whole from a movie title or a book cover and are happy to jump to scenes or open a chapter to get whatever necessary information, this is the way.

Next, identify the actors and factors.

Who’s involved? What role do they play?

What are the assets and activities that people are interacting over for? Or in plain words, what are people fighting over for?

Grounded approach to complexity handling: (3) Visualize the interactions, (4) Find leverage points

Next, visualize the interactions.

Who speaks to who on what?

Is there power, influence, money etc. at play in these interactions?

What is each person’s what’s it in for me, that is, the benefit and motivation they feel in taking their actions.

Now take a step back and look at those interactions. Can you find leverage points?

Are there bottlenecks that could use help?

Are there key people or relationships that can benefit from influencing?

Are there efficient areas that can make use of investment, of attention, effort, or money?

Grounded approach to complexity handling: (5) Hypothesize, (6) Ideate, design

Now hypothesize.

Are you happy with the current state of affairs?

If not, what would be a better state?

How might we achieve that better state?

In other words, what do you want to go after?

Once you are clear on your target, now ideate and design.

From current state to target state, what can you do to instigate change?

Along the leverage points, think of few ideas of intervention.

Can those ideas become bite size experiments?

Design them into a few actions to try.

And design an implementation plan. What, how, who, where, when?

Grounded approach to complexity handling: (7) Experiment, (8) Learn

And now time to intervene. Run those experiments and see what happens.

Did it work? Did it not work? Or did it so-so work? Arguably the most important part of this loop is the learning from the experiment and feedbacking it into the next step.

Grounded approach to complexity handling: (9) Iterate

And rinse and repeat until you get what you want. Iterate.

Basically, what we’re doing here is Agile, Design Thinking and Lean Startup.

This is no coincidence. You might not have been aware, but Agile and so on are systemic tools that were developed for handling complexity.

Full circle, right? Good, now go do more Agile and Design Thinking, this time with consciousness of how these practices embrace Systems Thinking.

That’s all for part 2, complexity handling.

Coach Takeshi’s view of modern leadership skills

Okay, bonus contents for today.

In the teaser visual, you saw that in the center is this thing labeled “management discipline”.

As you know I am a big promotor of generalist management education as I feel there’s not enough attention given to it.

Consider these as the core muscle building equivalent in gym training; it’s about essential, fundamental skills that every leader and manager should have and continuously develop.

Meet the organic leader

And what are those core management skills, or disciplines as I like to call?

Humor me with my little creation. Meet, the organic leader.

The word organic is so integral to my work and keeps on popping up in all corners of my leadership education, and I’ve settled to use the word “organic” as an extract of all these values.

Let’s take a look. How I see great leadership and management is as following:

The organic leader sees people as people. They understand individual and team growth are organic by nature, and a mechanistic treatment of people stifles learning and collective performance. They are also patient and persistent, making them bold and resilient in times of challenges. Image plants and trees in nature, they may wither and shiver, but they stand strong and survive.

The organic leader is an organizer of people, teams, work, projects, processes. And what’s unique about them is that they never forget the need for fun and creativity in group and teamwork, helping people flow and flourish in working together.

And as individuals, they are very “organized”. They are consistent, focused, complete, concise, and they follow-through. Really the basics of a reliable individual, trustworthy in their actions.

The organic leader is “organismic”. What does that mean? It means they have a keen sense of belonging to a larger whole, an organism. They are holistic and inclusive in behavior, appreciating the diversity of people, and the blessings received from nature and the environment in a vibrant eco-system.

And finally, “organization”. The organic leader is versed in the organization. They understand people and other dynamics, have a healthy regard for rules, roles and responsibilities, and yet a sane awareness and the ability to handle the many funny things that happen in the organization. While they have these amazing traits of a decent human being, they are savvy and veteran enough to be great corporate operators too. So a good balance between living idealist values everyday, while being realist in accommodating the many humorous things we see in the workplace.

So, as you can see, around the word “organic”, we have a balanced leader. These areas are indeed my focus of leadership coaching, training and facilitation.


That concludes my knowledge sharing for today, as summarized here.

Let’s open the floor to questions, comments and discussion.

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