Want your team to be more strategic? Ask these three questions

rosie-yeo-go-for-bold

Rosie Yeo, author of Go for Bold. Source: supplied.

It’s an uncertain world we live in, perpetuated even more by the past two years of living through COVID-19. For businesses, uncertainty is hard to navigate — but not impossible.

In Go For Bold, leading strategist Rosie Yeo shares how to you can come up with the fresh ideas necessary for business success, as well as how to bring them to life. In this exclusive extract, Yeo looks into the three questions you can ask your team in order to help them think more strategically, too.

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. However, we can all learn how to become more strategic.

Umit Subasi, who I’ve mentioned before, has created and implemented bold, successful strategies in some tough circumstances throughout his career. He’s been responsible for up to 5000 staff and $2 billion businesses. He’s developed and implemented new operating models and delivered growth across Latin America, India, Africa, Europe and the Middle East. He’s dealt with murky security in post-recession Russia and successfully turned around a German operation which had churned through 40 general managers in 55 years. Yet Umit confessed to me that in one of his earliest roles, he was daunted when he was invited to attend his first strategy offsite:

‘That was such a steep learning curve for me as a young person in the business. Going in, I had no idea. I had seen the general manager’s bullet points saying, “This is what we’re going to achieve”. I thought… “How are we going to do that exactly?” I just didn’t know, but after those two or three days I said, “Okay, I get it now. This is how you do it, there’s lots of things we can improve and build on”.’

Taking part in those strategic planning sessions was an important learning opportunity in his early days.

Sometimes people think that strategy is something other, more senior people do in the organisation. That’s not enough to fuel boldness! All of your people need to feel that they are contributing to achieving a shared ambition for your organisation. So, here are some simple ways to encourage a strategic focus within your organisation, by encouraging the following three behaviours and three repeated questions:

  1. Look up and wonder, ‘What if…?’
  2. Look around and consider, ‘What about…?’
  3. Lock in and commit to ‘What matters most?’

Breaking down the questions

  1. 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 that daydreaming state I mentioned earlier called ‘abstraction’, and we begin to think in a different, more complex way. Think about the last time you looked up at the stars, or out beyond the horizon. It can lead to magical moments of contemplation in which your mind expands and you feel a sense of possibility.

    As we explored in chapter 3, you can’t be strategic without being creative — since strategic thinking is about planning for a future that doesn’t yet exist, we have to imagine what’s possible. So, we need to collectively spend more time looking up. The best way to do that is spend more time together inspiring our collective imagination, by 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?’; and
    • ‘What if we gave away our core product for free?’
  2. 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. Earlier I mentioned X’s focus on finding team members who were ‘T-shaped’: who had deep expertise but were willing and able to collaborate across a wider field. This is ‘looking around’.

    In my 20s, I spent a few years working as a political adviser, and I learnt very quickly the importance of understanding all points of view before a decision was made. In politics, that’s mainly so you can assess the level of community and stakeholder support and opposition. In strategy, using a wider lens ensures that you identify all potential opportunities and hurdles, including those that are not immediately obvious.

    Many geniuses demonstrate a commitment to ‘looking around’. Leonardo da Vinci used a series of notebooks to pose a wide range of questions and his potential answers:

    ‘Why is the sky blue? How does the heart function? What are the differences in air pressure above and beneath a bird’s wing, and how might this knowledge enable man to make a flying machine? Music, military engineering, astronomy. Fossils and the doubt they cast on the Biblical story of creation.’

    We are so focused on our own patch of grass and on what we know best that we often forget to try and see things from other perspectives, but as strategic thinkers in organisations, we must widen our range of questions, too. It’s a given that you will be asking:

    • ‘How are our customers’ needs changing?’;
    • ‘What are our competitors up to?’; and
    • ‘What government policy changes will impact our operations?’

    The challenge is how you can broaden your questions to look beyond your immediate sphere. For example:

    • ‘Where are our customers looking next? What are they excited about that we don’t offer?’;
    • ‘Where are new competitors or substitutes for what we do likely to emerge?’;
    • ‘What can we learn from other industries about new ways of operating?’; and
    • ‘What government policy changes should we be advocating for that will help us succeed over time?’

    So, we look up and we wonder, ‘What if…?’ We look around and we consider, ‘What about…?’ The third behaviour that underpins bold strategic thought is to lock in and commit to what matters most.

  3. Lock in and commit to ‘What matters most?’

    Strategists open their minds, consider all perspectives and then make decisions. This requires a laser-like focus on what’s most important. The reality is that we can’t do everything, so we need to choose. This is just as important in the everyday decisions as in the big strategic discussions.

    You can encourage people in your own organisation to 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 objectives, and whether it’s really necessary).

    Henry Mintzberg described strategy as being ‘a pattern in a stream of decisions’.82 Imagine a canal, with water flowing in one direction towards the ocean. The pace and flow of the water is like the momentum created when an organisation is committed to a shared ambition and united in how to achieve it. There might be some rocks below the surface that disrupt the flow, but momentum still carries the water forward. Similarly, when people in organisations have a clear sense of purpose, challenges don’t throw them off course, because their shared ambition provides enough momentum.

    Now imagine that same body of water with a series of openings along its flow, allowing small rivulets to branch away. You can still see most of the water flowing in the same direction, but the loss of water means that the hurdles under the surface disrupt the flow more than they used to. When organisations don’t have that united commitment, momentum towards their ultimate objectives is more easily slowed or interrupted when circumstances change.

    Once a commitment has been made, there will always be a series of ongoing decisions and actions that contribute to bringing the strategy to life. We tend to forget that each time we make a decision or take an action, we are effectively choosing either to stay on the path (keeping the water flowing at full momentum in the canal) or to poke holes in the canal walls.

    Sometimes, of course, when the unexpected happens a significant strategic shift is needed. Much as if you were building a new canal, you need to invest time and effort in making the waterway deep and wide enough to build momentum in the new direction. Your organisation’s ongoing strategic conversations are key to maintaining momentum and achieving bold ambitions.


This is an edited extract from Go For Bold: How to Create Powerful Strategy in Uncertain Times by Rosie Yeo, available now at Booktopia.

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