Moments that matter for teams

Evidence shows that teams are capable of making much more accurate predictions than individuals, especially when they have the right mindset and principles — Harness the full potential of your team with a 3-step process to co-create the moments that matter most and design ways stay on track to your goals.

Robin Wong
11 min readJan 17, 2021
Photo by Jack Anstey on Unsplash

In October 2002, based on assessments and predictions supplied by the National Intelligence Council (NIC), George “Dubya” Bush told the world that Saddam Hussein was building a “massive stockpile” of deadly chemical weapons that he was planning to unleash on his neighbouring Gulf states. The infamous “WMD” — Weapons of Mass Destruction.

In 2003, despite a lack of credible evidence supporting these claims, America and a handful of allies entered into the Iraq war and unleashed genuinely deadly weapons on the people of Iraq on the pretext of finding and eradicating their alleged stockpile of deadly weapons, only for none to be found.

In the end, it was revealed that the assessments supplied by the NIC were based on unreliable evidence supplied by individual intelligence analysts that lacked proper scrutiny before being cobbled together and supplied as an “intelligence product”.

The (now declassified) reports claimed that there was “high confidence” that “Iraq is continuing, and in some areas expanding, its chemical, biological, nuclear and missile programs contrary to UN resolutions”. This assertion was then followed by “We are not detecting portions of these weapons programs”.

In fact, the individuals who had created the assessment had detected precisely 0% of the weapons programs they claimed to have found, and the key moments that mattered in waging the Iraq war, from the pretext of stockpiling WMDs to the eventual lack of WMD, were sorely lacking in evidence, preparation and results.

Subsequent research that stemmed directly from this failure found that individuals generally perform poorly when making predictions, but teams, especially when they understand cognitive biases and receive training in ways of making better decisions, massively outperform on predictions.

In this article, I will look at what makes teams better at forecasting the future and how this can be applied to planning and roadmaps by following a 3-step process that helps you map the road ahead of you in just a couple of hours

Note: For people who want to take this to the next level, I’ve also provided some extra recommendations into how you can break those key moments down into more manageable steps that you can feed into discovery and delivery activities.

What makes a Superforecaster?

In an effort to avoid the kind of poor assessments and predictions that led to the Iraq war, the NIC set up an annual competition to pit their intelligence analysts against individuals and teams of forecasters from around the world to answer a series of very specific questions about the future, to see what they could learn about improving their own capabilities and methods.

This competition captured the interest of Phillip Tetlock (@PTetlock), who founded the Good Judgement Project to test a number of different approaches to addressing this challenge.

He set up a control group that made completely random guesses to a series of questions about the future and then observed the practices of various crowdsourced individuals and teams.

He found that people with a certain mindset and approach to making decisions had a step-change increase in the accuracy of their forecasts. That level of accuracy improved further when they were put into groups.

When those groups had a chance to train together, to become “Elite teams” as Tetlock calls them, that’s when the biggest increases in accuracy were achieved, with level almost double that of people who did not have this mindset and approach.

image courtesy of hbr.org

As you can see from the graph above, Elite forecasting teams were 66% more accurate in their predictions than the control group of random guessers.

Compare this to people who did not have the same mindset and values who were only more accurate 36% of the time, and it’s a sizeable advantage that these types of teams have over the competition.

Mindset and principles for better prediction

Tetlock had found that when it came to making predictions on questions that had to factor in evidence, insight and subjective judgement that 4 factors led to more accurate predictions.

  • Appreciation of cognitive biases and how they lead to bad decisions
  • Working knowledge of probability and statistics
  • Hypothesis-driven experimentation using data from multiple sources
  • Keeping an open mind and making small adjustments based on data

In essence, teams made up of individuals who accepted they could be subject to biases (see image below for how many biases can affect our decisions) and who were open to making small mental course-corrections based on a stream of cross-referenced data points were able to chart the future with a much higher degree of accuracy.

A map of every single cognitive bias — link to high resolution version — courtesy of designhacks.co

Much like the people he studies, Tetlock is continuously learning about and challenging teams of superforecasters to make better predictions on complex, multi-dimensional and timebound questions like the one below which seeks to understand when half the UK population will be immunised against the coronavirus.

Planning the future as a team

I spend a lot of my time coaching leadership teams and product squads, especially to help them connect what they do for their customers and colleagues to near-term priorities and longer-term business strategy.

To help adopt more of a superforecaster’s approach and map out this view of the future, I always recommend working as a team to avoid individual opinions swaying decision and to apply a rich set of perspectives to identifying worthy outcomes and mapping moments that matter in the journey to those outcomes into a roadmap.

Moments that matter are short experiences in life that carry meaning and elicit the kind of strong emotional response that helps you remember them long after they happen. It could be the moment you had a great insight that “pulled back the curtains” to reveal a hidden truth or the moment you made your first sale or when you broke-even and made a profit with your business.

In the journey towards achieving your team’s objectives, there will be lots of different types of moments that matter depending on who you’re talking to.

I like to get teams to collect these up, work out the most important ones, and at each of these key moments, I ask people to explore their senses around what Simon Wardley, the inventor of the Wardley Map calls “Situational awareness”.

He has this great quote from Mao about situational awareness where Mao talks about “Crossing the river by feeling the stones” - The idea that to overcome a complex challenge you need to be able to assess the situation at every step to understand which stones to step on to reach your objective.

To help teams develop this shared situational awareness and build a roadmap that explores where to step and where not to step, I recommend the following activities -

  • Define where you are now and later once your objectives are achieved
  • Individually list the moments that matter to you on this journey
  • Collectively group, prioritise and sequence key moments as a roadmap

As I mentioned at the start of the article, I’ve added a bonus section for people who want to go into more detail on each moment, set expectations of what each moment means, and how to fully realise each moment.

Note that this is often an iterative process, so like our superforecasters, be prepared to go backwards and forwards as new information comes to light.

Let’s explore each step in a little more detail…

Now and Later

I’m a big fan of Jeff Patton’s approach to building a strong shared understanding of what’s happening now and what you believe should happen later. If you haven’t read it already then I highly recommend Read this first to understand what I’m talking about right now, you’ll thank me for it later.

Example of what’s happening now and the outcomes we want later

Start by setting out the current situation that you find yourselves in now. It’s useful to describe who your end-customer is, what they’re trying to achieve, the challenges they face and the impact this has on you and your organisation. Always base this on evidence that everyone agrees on.

Then flip this on its head to describe what the future holds once you’ve helped your customer overcome their challenges, and you’re enabling them to do something they couldn’t do before without you.

How will you be able to tell this is happening?

What will this mean for your organisation?

If you have an organisational strategy, make sure your view of what you intend to happen later works towards this strategy.

Set these up as the start and end of your roadmap.

List the moments that matter

Assuming that you’re working as part of a cross-functional team, with people representing the customer, your colleagues, the business, operations and technology, spend 5 minutes working individually to list out all the moments that are important to you.

Examples of moments that matter — still to be organised

It’s good to do this individually because with all the different perspectives people bring to the table, you end up with a wide of array of moments that matter that collectively helps ensure that you’ve considered moments that matter from a desirability (customer & colleagues), viability (business) and feasibility (operations & technology) perspective.

In fact, as a prompt for this exercise, I recommend flashing these types of “lenses” up to the team to help spark off their thinking.

Group and sequence key moments

Once you’ve captured all the key moments, run through them each one by one and group them into common themes, removing duplicates as you go. I find it’s useful to give each theme a title.

Moments that matter grouped, themed and sequenced into a roadmap

Once you’ve got your themes, work as a team to sequence them into a logical order, making sure you discuss any dependencies between the themes to stress-test the sequencing.

Bonus steps

To take your roadmap to the next level and set out some really actionable steps to achieve each moment, it can be useful to break down moments that matter further.

To reach a common understanding of these moments, I find it’s useful to understand

  • How it feels in the moment
  • Why the moment matters
  • What the primary measure of success is for the moment
  • Who the moment matters for
  • What needs to be true (hypotheses, measures of success)
  • Capabilities required ( people, process, information, technology)
  • Management systems (decision-makers, risks, governance)

Here’s an example…

The dimensions of a moment that matters

Understanding why

For each moment I like to understand why it matters because this helps us work out whether the moment has been realised — in this case because the team reports that they feel united — and how we might measure that — everyone gives an average confidence score of more than 3 out of 5.

Who this matters to

Not every moment matters to everyone, so it’s important to understand who this moment matters for so you know who your primary audience is. In this example, you might be doing something for customers, business owners, designers, developers or colleagues in service.

What needs to be true

For each moment that matters, and for each type of person the moment matters to, a number of factors need to be true in order for that moment to be realised.

  • How will you determine the moment has happened?
  • How will that be measured?
  • What are your hypotheses and options to make it happen?
  • What do you need to do to test each hypothesis?
  • What are the risks and mitigations?

Think of each hypothesis as a small bet. How can you achieve each moment by placing a number of small bets — small tests that indicate the best way to achieve that outcome — and then doubling down on the test that drives the strongest desired outcome.

Capabilities

In determining what needs to be true, it’s like you’ll have implicitly or explicitly worked out what people, processes, information or technology you’ll have to put in place to enable something to start happening or to fully test your hypotheses.

For example measures of success will likely need some sort of analytics capture and reporting platform or measurement system, and a process to assess metrics over time.

Analysing what you need will help you further ascertain the feasibility of realising the moments that matter and assessing what needs to be true.

Management systems

Finally, once you have a clear idea of capabilities, you’ll need to think about how best to manage them to achieve the moments that matter.

In the case of something like managing analytics and reporting, we might need to assess who checks the analytics and how often, perhaps through an automated daily report like we have in our example above.

Charting your course

By mapping these moments that matter in this way, you have in effect created a prioritised list of outcomes, a range of target state behaviours, non-functional requirements and acceptance criteria to ascertain when a key moment has been realised along your team’s roadmap

For Agile officionados reading this, you’ll recognise a number of the key components of Epics, User stories and Behaviour-Driven Development (BDD) in here, although in this case of course, the focus is more on creating successful outcomes for your team and your ways of working.

Regardless of your style of working though, as a team, you have now charted a course to your goals and hopefully you’ve managed to acheve this in just a couple of hours, all without actually getting into the nitty gritty of exactly how you will get to your goal.

If you’ve followed the bonus steps, you should also have set out a number of ways to measure whether the steps you are taking are the right ones, or whether you need to course-correct and find new ways to achieve your strategy and realise your moments that matter.

So, if you’re reading this and you’re not satisfied that your team is aligned, have a go at mapping out the moments that matter to you and let me know how it works out!

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Robin Wong
Robin Wong

Written by Robin Wong

I help people turn ideas into human- and humanity-centric ventures. Global Head of Service Design at BT.

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