Three Simple Questions To Make You A Better Strategist

Three Simple Questions To Make You A Better Strategist

Rosie Yeo (lead image) is a strategist and facilitator and author of Go For Bold: How to create powerful strategy in uncertain times. In this guest post, Yeo offers three expert tips for anyone wanting to improve their strategy outcomes…

In Douglas Adams’ The Hitchhiker’s Guide to the Galaxy, the philosopher Vroomfondel, representative of the Amalgamated Union of Philosophers, Sages, Luminaries and Other Professional Thinking Persons, sums up what we all secretly wish for:

‘We demand rigidly defined areas of doubt and uncertainty!’

The past two years have reminded us that uncertainty is ever-present in our life and work. Whether it’s the COVID-19 pandemic, digital disruption, economic upheaval or the kids’ refusal to put on their socks, we can’t control everything and we can’t always predict how things will change.

In a fast-moving, uncertain and highly competitive world, we need to be clear about our ambitions, and creative in how we achieve them. In other words, we need to be powerful strategists. So, how do we help ourselves and the people in our organisations to become more strategic in the way we work and plan? How do we stay focused on winning the long game?

I’ve worked with many people at all levels of organisations over the past two decades, and I’ve noticed that some people are instinctively strategic. They scan the horizon, think laterally and imaginatively, and map out several steps ahead and around. These abilities aren’t confined to a certain level of education, or years of experience, or even which field people work in. Some people just seem to have an innate ability to blend information, imagination and ambition and create great strategy. Others struggle to make the connections.

We can all learn how to become more strategic. It starts with three behaviours and three simple questions:

Look up and wonder, ‘What if…?’

There’s a school of thought in psychology focused on encouraging people to look up. When we look up and out, we enter a daydreaming state called ‘abstraction’, and we begin to think in a different, more complex way.  Strategic thinking is about planning for a future that doesn’t yet exist, so we have to imagine what’s possible, and that requires creativity.

We need to spend more time wondering “what if?” For example:

  • ‘What if we could expand our footprint?’
  • ‘What if we could communicate with our clients in an entirely new way?’
  • ‘What if we gave away our core product for free?’
  1. Look around and consider, ‘What about…?’

The second behaviour we should be doing more of is looking around. A strategic thinker ‘looks around’ – by that I mean they view situations through a wider lens. In strategy, using a wider lens ensures that you identify all potential opportunities and hurdles, including those that are not immediately obvious.

Leonardo da Vinci used a series of notebooks to pose a wide range of questions and potential answers across seemingly un-related disciplines. We are so focused on what we know that we often forget to try and see things from other perspectives or widen our questioning beyond the obvious. For example:

  • ‘What about where are our customers looking next? What are they excited about that we don’t offer?’
  • ‘What about new competitors or substitutes for what we do – where are they likely to emerge?’
  • ‘What can we learn from other industries about new ways of operating?’
  1. Lock in and commit to ‘What matters most?’

The third behaviour that underpins bold strategic thought is to lock in and commit to what matters most. Planning for the future never comes with an ironclad guarantee or a promise that things will never change. That’s why it’s so hard, and why we hesitate to make big decisions. The reality is that we can’t do everything, so we need to choose. This requires a laser-like focus on what’s most important, and a willingness to make and communicate those choices.

Clarity about “what matters most” is an ongoing discipline. You can ask this question more often by:

  • linking regular meeting agenda items to key elements of your strategy
  • finishing each work-in-progress meeting with a summary of ‘what matters most’ for the week ahead
  • challenging people to identify ‘what matters least’ on the work program (that is, what will have the smallest impact on the organisation’s ambitions, and whether it’s really necessary).

In times of uncertainty we need to spend more time focusing on our shared ambitions and mapping out new pathways to achieve them. We have the capability within ourselves and our organisations to become powerful strategists – to unleash more creativity, to become clearer about what’s most important and to build momentum for change by reaching powerful agreements to act. It can start with these three questions.




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Rosie Yeo

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