Could you describe a scenario where your coaching helped an executive enhance their strategic thinking abilities?

The key word here is “thinking.” Strategic thinking means you have the ability to assess your current reality, look ahead, take in a large amount of information, and make connections with that data to face the current challenges with innovative and creative solutions. It’s about looking at things differently and being able to anticipate and address change, moving from reactive leadership style to a more proactive leadership approach. Strategic thinking enables leaders to see things from a new perspective and anticipate and plan for what they might be wanting. Too often, leaders stay busy with their daily activities, and this is often where I begin in coaching clients who want to be more strategic. Strategic thinking requires space to reflect and consider alternatives, zooming out from the daily events to see more of what is possible, and then determining the best course of action. Clients often have to learn to let go of control of the daily activities in order to take a broader perspective and consider alternate ways of functioning to be able to see the larger picture and anticipate what might be coming.

Once when working with a client who was new to a senior executive role, I had the opportunity to help him transition to managing his peers in a way that helped them see the vision of the organization so they could get on boad with methods to stay in alignment. This also required him to be more open with the way he thought about strategy, the people executing the plans and the consumers impacted by what they wanted to accomplish. He had to learn to have a broader view in order to then laser focus on what was most important and designing the most cost and time effective ways to get there.

First, we had to address their growth mindset. Strategic thinking is challenging without a growth mindset, confidence in making decisions, and resilience to risks and failures. Mindset and the ability to see the bigger picture are foundations of strategic thinking. The next step was to analyse their previous decisions to understand the thought processes that led to existing outcomes and how they might be improved. Finally, we moved into practising scenario planning and engaging with the executive team to gain feedback and challenge assumptions. At the end of the coaching engagement, we looked at how strategic thinking and planning could become part of their organisational culture and not a one-off exercise.

I work with a lot of Silicon Valley executives. I was introduced to the CEO of a promising tech startup who felt overwhelmed by the rapid growth of his company and was struggling to prioritize and foresee the long-term implications of his decisions. Through our coaching sessions, we embarked on a journey to sharpen his strategic thinking skills. We looked over some of the complex business decisions he had to make, analyzing not just the immediate outcomes but the ripple effects of each decision. As a result, the CEO learned to navigate the complexities of his industry with a more nuanced approach, considering multiple perspectives and potential futures. This transformation didn't just elevate his leadership; it propelled his company forward, securing a leading position in a competitive market. The change was remarkable—the CEO's newfound ability to think strategically enhanced his decision-making process, leading to innovative solutions that had a profound impact on his company's success.

The first step of being strategic is imagining and creating. The second is looking ahead at the horizon to see what's coming (AI and automation, just to name two), and anticipating. Most of us benefit from some prompting when we're trying to think outside of the box. The more time an executive has spent in an industry, the more they may tend to be focused on the micro, the implementation, efficiencies, and on project or departmental delivery. A coach can prompt them with questions to help them think about what's not there, and ask why not. We can help them engage their imagination and creativity, which comes from a wholly different part of their brain than the logical, linear, reasoning part. Some executives can find it hard to be untethered in their thinking, grounded by logic and reason. We help people understand how to productively brainstorm, by storytelling, probing, prompting, and even bringing our own experiences to bear. Then, we can prompt them to think about where their industry and their company will need to be in 5 or 10 years, and how to start preparing today, in order to hit that goal. And then, how to make sure that this kind of thinking is supported and sustained in their company or department, and to think through embedding some permanence to it, so that it remains in constant focus. Two heads are always better than one, so a coach can be a sounding board, as well as a catalyst for the executive. Saying all of this makes me wonder why anyone would attempt to do this by themselves.

I coached this manager on strategy through an ongoing series of problem-solving exercises in which I served as a ‘drill sergeant’, presenting him with live business issues in which he role-played a real-world industry leader who had to think strategically about a market disruption and craft strategic responses that effectively positioned his company for future growth. This approach proved to be highly effective in helping executives develop ‘muscle memory’ for strategic concepts and their application and to become better decision-makers. What was gratifying was to find that they were now using the concepts successfully in their own leadership decisions.

As the CEO of Startup House, I once had an executive who was struggling to see the bigger picture when it came to our company's growth strategy. Through coaching, I encouraged them to step back and analyze the market trends, competition, and customer needs. By asking thought-provoking questions and challenging their assumptions, they were able to develop a more strategic mindset. Eventually, they were able to make more informed decisions that positively impacted our business's trajectory. Remember, strategic thinking is not just about making plans, but about understanding the why behind them.