How to build situational awareness for your digital team

A way to deal with that 'WTF?' feeling that anyone can apply

The term "situational awareness" comes to us from the military world.

It's defined as 'understanding an environment, the elements within it, and how both are changing in space and time'.

You may have heard of the 'OODA loop', developed by USA Air Force Colonel John Boyd. OODA stands for Observe, Orient, Decide, and Act. It was developed to train fighter pilots to be more agile than their opponent.

Situational Awareness is the outcome we get when we run the first half of this loop; Observing and Orienting.

Ok — so you're probably not a fighter pilot. How is this relevant?

In today's fast-moving, ever-changing world of digital work, we encounter complex issues and opportunities all the time. Often, the stakes can be high, or the situation can be totally new to us.

Being able to orient yourself and the people around you — with speed and accuracy — is a crucial skill!

What does this skill unlock?

  • Map out facts, opinions, assumptions, causes, and relationships and quickly.

  • Socialise your perceptions and understanding with anyone, which enables delegation and collaboration.

  • Stop wasting time playing 'broken telephone'.

  • Make better decisions!

Over time, the benefits build up

  • Cognitive load reduces, even as your capacity increases.

  • Learn from each and every encounter. Grow as individuals, and as a team.

  • Less fear, uncertainty and doubt for your team and your ecosystem.

  • Build trust and autonomy for you and your team — become the experts!

It's a fast-track to expertise in the 'responding to things' part of the work, which, let's face it, is a large proportion of the work!

Intentionally building skills and habits in this area levels you up in all the work you do.

Complexity is unavoidable

Every day, the digital world of knowledge work moves faster and becomes more complex.

Constraints change. We encounter new opportunities. We lose or gain resources — whether it’s time, access to people, tools, or you-name-it.

The most recent tsunami: ChatGPT.

We have to adjust, adjust, adjust as the world happens to us, all while we are trying to happen to it in some meaningful, productive way.

To be nimble as a team in this world, we need an intentional practice for establishing situational awareness.

After all, it doesn’t matter how efficient you are, if you’re efficiently doing the wrong thing. To know what the right thing to do is, you need to track your reality clearly.

In complex knowledge work, we need to accumulate information (Observe) and we need to form a coherent understanding (Orient). And, as we Decide and Act, we need to reference both of these parts continuously, and, update them as we go, as we create change and receive feedback.

Generic principle

If you’re feeling like I’m saying things here that are patently obvious, there’s a good reason for that!

Each of us already has some degree of practice with SA, even if we've never heard the term before. For most of us, it's implicit and hidden in the work.

We each learn to do just enough of this for ourselves to be competent in our roles. From simple sticky notes on our desk, all the way up to fine-tuned personal wiki databases, we have our own way of 'keeping track of our world', of being aware.

Similarly, many of our 'normal work' processes are designed to produce SA in some formal way. Work systems like Kanban and Scrum include rules and processes for producing and maintaining SA for their particular categories of effort. Team retrospectives and incident reports are a technique for looking back at the recent past to add additional kinds of SA that weren't available as events unfolded.

As good and as necessary as both of these are, they have disadvantages. They are either unconscious or intuitive (and therefore inconsistent) or too formalised and specific (and therefore applicable only to parts of the work).

There's a generic pattern, a principle, that we can lift out and apply to just about anything, and derive immediate and long-lasting benefit.

Situational awareness is a mindset, a state of being. You can tell when you have it (because you're clear and ready to act) and you can tell when you don't (because you feel uncertainty and doubt... you have that 'fog of war' WTF?! feeling).


The other thing to recognise is that we deal with many situations in parallel. An intentional practice allows us to manage many situations at once with less strain. Good SA helps us load in context when context switching.

And, it's recursive. For example, a software bug report is a situation, but so is a collection of related bugs, and the current capacity and capability of the team dealing with those bugs, and the principles and practices that this team follows, and the strategic imperatives and goals that this team is obligated to accomplish.

These are all situations, operating at different levels of abstraction, all interrelated and interdependent on each other. And that big picture is itself a situation.

They all need someone to be aware of them, so that they can be managed, guided, nudged, or intervened with, as appropriate.

Having an intentional 'build and socialise a coherent understanding' practice allows us to work within and across these levels with greater clarity.


To provide our team, business, or ecosystem with leadership to reduce pain and increase value with the time and energy we have.

To make sense of things today, as they are today.

With time and practice, it allows us to scale our attention, both horizontally (e.g. lots of bugs at once) and vertically (up and down the abstraction 'ladder' I describe above).

I've received feedback from lots of different people over the years, that I'm calm and dependable, and I'm someone you want to call when things are 'going pear-shaped'.

I truly believe that my situational awareness skill is the core superpower that people are actually reaching for, and interacting with me is just the shortcut to accessing it!

I also truly believe that anyone can learn this skill and become just as valuable.

The fundamental process

Ok. Sermon over!

What does it look like in practice?

At least one person on your team (congratulations, that's you!) needs to take the responsibility to take the right steps, and to repeatedly check whether you're on track with it.

Next, I’ll provide a generic set of steps that any digital team could follow. My only assumption is that you're working together via online tools — team chat, video calls, real-time collaboration documents (e.g. Google Docs, Notion, Miro).

Then, we’ll look at how this process applies to a couple different scenarios, to demonstrate the principles in action.


  1. Make a dedicated workspace to contain the situation. Label it so that the goal is clear.

  2. Share access to everyone who needs it. Grant them permission, and provide them with the link.

Both steps in setup are crucial.

The dedicated space with a clear label is important to avoid confusing the situation with anything that’s unrelated. Using a tool with a good search capability means you can handle lots of situations in parallel.

And, sharing access is important as we want to remove all friction for collaborators to do the right thing.

Without these, we end up with conversations and information spread out across multiple systems, channels, emails, and so on. It’s simply not possible for anyone to see what’s happening. Total fog of war.

This requires real discipline. For some situations, the decision to take this step and insist that people participate correctly can make all the difference, especially when the stakes are high, and 'fight or flight' mode is kicking in.


  1. Every question, answer, fact, observation, opinion, assumption relating to this situation goes into that workspace. Screenshots, links, pastes from emails… everything that’s relevant. This is the ‘situation’.

  2. As information accrues, organise it to build a coherent understanding. With iteration, this produces the ‘awareness’.

  3. Everyone uses this shared space as their source of truth. They do not work elsewhere.

Which questions you're asking, and how you're organising that information is, of course, situational (I'm not even sorry), and is a topic for another time.

How do we know we’re doing this correctly?

Early and often, we ask ourselves “Is the situation clear to everyone?”

Questions and responses should be squarely aimed at getting to “YES” for that question.


So, to recap, the skill of building situational awareness is to:

  1. Recognise the need to establish clarity.

  2. Create a shared space, and make everyone use it.

  3. Accrue information and build coherence in that space.

  4. Relentlessly pursue the "are we clear now?" question.

That's it. If you're doing that, you're doing it correctly. It doesn't matter what tools you use, or what capital-letter work management framework you're using.

"But Robert," you cry, "this is so basic and obvious?" I agree.

It's deceptively simple. Obvious, even. You may even actually say ‘duh, but I knew that!’ as you were reading this.

The thing is, knowing it isn’t enough. You actually have to do it, and, you have to be relentless with your focus as you do it.

Exercise and making good food choices are basic and obvious, too, but if you don't do them, you won't benefit.

What confusion is your team dealing with today, that you could practice this skill on?

Roll up your sleeves and get stuck in!

In case this was forwarded to you:

Hi. I’m Robert Stuttaford.

In this Knowledge Worker's Toolkit newsletter, I introduce, explain, tell stories, share past experiences, and explore the connections and intersections of all the various systems thinking & knowledge work concepts & models I've encountered during my tenure as CTO at Cognician, over the past 13 years (and counting!)

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