Three Keys to Long Term Planning in Uncertainty

Mar 31, 2022 1 Min Read
Uncertainty in deciding which route to take
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How to Manage Uncertainty in Your Business?

Ask an executive which game is closest to the way we play corporate strategy, and you could expect to hear a range of responses: Monopoly, because it’s all about making smarter investment decisions than other players. Chess, because you need to be two moves ahead of the other player.  Perhaps Twister!
During the past two years, strategy might have felt more like a frustrating game of Snakes and Ladders. It didn’t matter how carefully you planned or how clever your strategy, every roll of the dice seemed to land you on a snake – with supply chain disruptions, lockdowns and constant rule changes sliding you further away from your objectives.

Infographic by Leaderonomics: Executing any strategy during the pandemic felt like a frustrating game of Snakes and Ladders

We talk about uncertainty being the only certainty during the COVID-19 pandemic. But the reality is, uncertainty is ever-present in our life and work. Whether it’s digital disruption, economic fluctuations or the kids’ refusal to put on their socks, we can’t control everything and we can’t always predict how things will change.

Infographic by Leaderonomics: Uncertainty is the only Certainty 

In the 18th century the French philosopher Voltaire wrote: “Le doute n'est pas un état bien agréable, mais l'assurance est un état ridicule.” Loosely translated, it means:
“It’s not comfortable to be unsure, but it’s absurd to be certain.”
Most of the time, particularly in strategy, we don’t always face up to how many things are out of our control.
So how do we keep moving forward and making bold decisions with confidence? Here are three keys to long-term planning in uncertainty, and one option you can take right now if you’re really stuck on where to go next.
1. Adapt your mindset: Approach uncertainty with curiosity
Strategic thinking doesn’t start from certainty. It starts with curiosity. INSEAD’s Associate Professor Spencer Harrison, writing with research partners from a large-scale 2018 Survey Monkey project on curiosity, notes that "successful organisations are rooted in curiosity”, with employees enabled to seek and absorb new information and make new connections.
There’s a myth that to be considered strategic, you need to know everything: you need to be the smartest person in the room. I’ve worked with many Boards and executive teams over the years, and while there is one attribute that differentiates high-performing teams from the others, it’s not IQ. Nor is it net worth, or their level of commitment to a cause.
High-performers walk in with curiosity. They are brave enough to say they don’t know, and open-minded enough to consider other perspectives and possibilities. Research by Harvard Business School’s Francesca Gino found that natural curiosity demonstrated by employees was associated with better job performance, as evaluated by their direct bosses. Another of her studies found that a twice-weekly text message encouraging people to be curious increased their innovative behaviours at work.
‘Not knowing’ can be a powerful source of innovation, because we’re not locked into familiar pathways. Encouraging ‘not knowing’ could be as simple as:
·      As leader, be honest with your team about something you are not certain of;
·      During meeting introductions, ask everyone to state one thing they’re interested in learning from others in the room (rather than what they are expert in) ;
·      List knowns and unknowns as part of your conversations about the future (and be imaginative with it).
2. Rethink risk: start with shared ambition
Bold strategic moves involve a decision to do things differently or a decision to do different things.  The more resourcing you invest in big strategic decisions, the higher the stakes. Not everything is within your control, however, so even the best-planned strategies carry some risk.
Too often we focus on risk first, rather than starting from genuine consensus about our shared long-term ambitions. With a clear long-term vision, teams can make braver decisions, because the risks can be viewed in the context of what matters most. We can understand the stakes, ameliorate the risks and be confident that what we’re about to do is worth it.


Infographic by Leaderonomics: Three Keys to Long-term Planning in Uncertainty

3. Don’t do it alone: Creative collaboration powers bold ideas
We have understandably been distracted by all the things we couldn’t control over the past two years. But on the upside, how good have we become at on-the-spot creative adaptation?
Now is the perfect time to harness that collective creativity and apply it to planning bolder strategies for your long game.
We need to give ourselves and our teams the chance to wonder and the time to explore new ideas together. You don’t have to move too far out of your comfort zone to encourage a more creative approach. One simple step is changing the way you set up your meeting room. IDEO Founder David Kelley refers to space as “an instrument for innovation and collaboration”. The traditional boardroom set-up with a huge table in the centre of a room can separate, rather than connect people, particularly if there is an ingrained hierarchy of seating. Changing the layout of the space, and the visual cues within it, can encourage more open conversation.
Space is more than physical: time is also needed. Writing in Harvard Business Review recently, Pronita Mehrotra, Anu Arora and Sandeep Krishnamurthy warned of “the Productivity Illusion”. When groups try to solve complex problems too quickly, innovation is inhibited because the participants jump to premature closure rather than allowing the space and time to work through all options. Creativity, like all exploration, takes time.
Trust is another key enabler to creative collaboration. In 2015 Google released the results of a two year study to identify the components of high performing teams, and the most important attribute they identified was psychological safety – being able to take risks without feeling insecure or embarrassed. When people are comfortable to wonder out loud and offer up alternate perspectives, creativity can flourish.
One exercise for when you’re uncertain about everything:
When you feel completely paralysed by uncertainty about the long-term, use this scenario planning exercise to help you make constructive short-term strategic decisions:
·     map out a best case and worst case scenario
·     identify hurdles and enablers to success in each scenario
·     highlight the top 3 hurdles and enablers common to both scenarios, and for each, identify and implement strategies to address them.


Infographic by Leaderonomics: How to Make Constructive Short-term Strategic Decisions

Related: Three Dimensions of Leadership Agility

In times of uncertainty, we need more bold ideas, not less. The way we collaborate is key to building the confidence needed to make strategic choices and move ahead. is an advertisement free website. Your continuous support and trust in us allows us to curate, deliver and upkeep the maintenance of our website. When you support us, you allow millions to continue reading for free on our website. Will you give today? Click here to support us.

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Rosie Yeo, author of Go For Bold: How to create powerful strategy in uncertain times, is a strategist and facilitator. She designs and leads strategic planning in boardrooms and executive offsites and injects energy and focus into larger meetings and complex policy consultations. She is known as a strategy alchemist because of her skill in helping leaders and teams collectively imagine and achieve a better future. Visit

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