How to help your team think more strategically

As your company and teams mature, it is critical to help leaders think strategically (and carve out time for it).

Strategic thinking isn’t just about setting goals or following a plan—it’s about navigating through uncertainty, understanding complex situations, and making informed decisions to drive long-term success.

Gartner CMO Journal (*) provides valuable insights into how CMOs can cultivate this essential skill within their teams. Here is a recap and personal examples.

Embrace ambiguity

Planning is an art of dealing with ambiguity and complexity: How will the environment evolve? The macroeconomics? The competition? What will our resources look like? Will our product bets pay off?

To prepare your team to handle complexity, Gartner suggests three steps:

1. Evaluate tasks individually: Break down tasks and assess them on their own merits. This granular approach helps identify unique challenges and opportunities within each task, rather than overwhelming the team with the big picture all at once.

As an example, strategic thinking about a Go-To-Market strategy involves deeply understanding the market landscape, defining a unique value proposition, and refining product-market fit. It further includes building a repeatable sales playbook, creating demand and optimizing the customer experience, all supported by clear metrics and KPIs. Depending on the market maturity a company may consider one of the 4 GTM playbooks below.

2. Understand the context in micro-details: Encourage your team to dive deep into the specifics of their tasks, the environment, and the potential implications of their decisions. This detailed knowledge will provide a solid foundation for making informed choices in uncertain situations.

Understanding regulatory changes is critical. As an example, Apple quickly adapted to the European Union's Right to Repair regulations, which required companies to make products easier to repair and provide access to spare parts and repair manuals. In 2022, Apple launched in Europe its Self Service Repair program, allowing customers to access genuine parts, tools, and detailed repair manuals to fix their devices at home.

3. Recognize potential decision biases: Decision-making can be clouded by biases, whether they’re based on past experiences, personal preferences, or external pressures. Training your team to identify and mitigate these biases will lead to more rational and objective decisions.

Founders who have been successful with specific channels to acquire their first customers may be tempted to apply the same playbook. As the below table shows, some tactics may be more efficient depending on the ease of reach of a target audience.

Source: Lenny's Newsletter. 

See the bigger picture

Business acumen is critical for leaders. They don’t just have a functional hat, but first and foremost a leadership hat with the ability to connect the dots and see the big picture. Here are some practical ways to practice.

Draw parallels to analogous situations: Encourage your team to look beyond their immediate tasks and find similarities with other situations. This practice can help them draw on past experiences and insights, applying lessons learned to current challenges.

Breathe Series A announcement draws a parallel to how Apple revolutionized the tech industry in 2007 by integrating software and hardware to create a superior user experience, ultimately making Blackberry irrelevant. Similarly, in the battery industry, there has been a long-standing focus on improving hardware components, but the opportunity now lies in leveraging software to enhance battery performance, longevity, and affordability.

A past industry shift can provide a relevant parallel for a new situation, here featuring the software-led transition from Blackberry to iPhone.

Think broadly about connections: Help your team connect the dots between different challenges and insights. By seeing how various elements interact, they can strengthen their strategic point of view and make more informed decisions.

As an example, challenges in converting trial users to paying customers might not be solely due to the product's features or pricing but could be influenced by factors, such as poor customer onboarding processes or lack of trust in the brand.

By examining the broader customer journey, including a behavioral journey, and considering insights from other areas like customer support interactions, marketing messages, and user feedback, your team can identify overlooked pain points or gaps in communication that may impact conversions.

One the the step of a behavioral journey from Irrational Lab, full template available here bit.ly/4dVl7wU

Apply systems thinking: Systems thinking is about understanding how different parts of a system interact and influence one another. Encourage your team to think in terms of systems, which will help them anticipate the potential ripple effects of their decisions and actions.

In a circular economy, systems thinking involves recognizing how product design, material use, and business models are interlinked. By redesigning products for longevity and recyclability, businesses can reduce waste, create new economic opportunities, and contribute to a regenerative system that benefits both the environment and society.

Source: Ellen MacArthur Foundation, capturing the essence of the circular economy

Enhance strategic thinking with mental models

To further support your team’s development of strategic thinking, consider introducing them to a comprehensive set of mental models—frameworks that can help simplify complex situations and improve decision-making. Here are some key models:

Common mental models.

These mental models, along with the principles outlined here can be powerful tools in helping your team think more strategically.

Conclusion

While many companies focus on execution, leaders must make time to practice strategic thinking. By using tools and models, they can better analyze scenarios and develop strategies that align with their goals, navigate change and uncertainty and build smarter and more agile organizations.

(*) Check out the CMO Gartner Q32023 Report here.