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Strategic thinking is a prized skill in organizations, but people often get feedback that they don’t think strategically enough or that they need to think more strategically, with no specific guidance on what that means or how to develop it. Over the years, I’ve had several clients ask me to help them learn to think more strategically. Fortunately, developing this skillset is entirely doable.

Here are some specific ways you can train your brain to think more strategically:

1. Challenge your Assumptions.

We all live in our own unique version of the world, built by the paradigms we’ve developed over the years that shape how we perceive and interpret the situations we find ourselves in. One of the most powerful ways to uplevel your thinking is to realize that your perception and experience of the world is not the only way of seeing or experiencing the world. Consider this: you are one of several people standing around a huge elephant, and all you can see is one leg. From here, there is no way to guess the full scope of what you are seeing if you don’t realize you only have one view.

In organizations, people who insist that their way of seeing things is the only truth, miss out on opportunities they are blind to, and often make poor decisions. A good question to ask yourself in business situations is, “who are the all the players in this situation, and what do things look like from each person’s perspective?” Just asking this one question can help you get a better view of a situation and uncover important and strategic insights that others cannot see.

2. Put Boundaries on your Resources.

In every business case study on excellent strategy, the organization in question made clear and specific tradeoffs that allowed it to take advantage of a unique position that competitors couldn’t easily replicate. Southwest Airlines always comes up as a great example of a low-cost business model that could not have existed unless it was willing to give up something important that was commonplace in the industry to that point. Southwest made three key tradeoffs that would not have sounded like good ideas when they were originated: (1) it would not use the traditional hub and spokes model, and instead do point-to-point travel, mostly short distances; (2) it would not assign seats or provide first class seating; and (3) it would not provide meal services.  Eliminating these three key benefits that, up until that point, everyone had assumed were best practices in the industry, allowed Southwest to drastically reduce the time planes spent on the ground.

The company also decided to use only one model of plane, which reduced many additional costs associated with training and airplane maintenance. With that extra margin, Southwest was able to pass on cost savings and higher value (such as no baggage fees) to customers, and thus rapidly take market share away from well-established competitors. When those same large competitors tried to jump in with low-price models of their own, it didn’t work as well because they couldn’t replicate the operating margin. They had not changed their underlying method of utilizing resources.

It’s important to note that while the trade-off story for Southwest ended up with a positive outcome that landed the company in the business case study hall of fame, there are hundreds of equally brilliant trade-off ideas that don’t take off. When it comes to strategic thinking, the point is to always look for opportunities to manage things differently. Ask yourself, “where are we assuming we have to do things in certain ways?” or “where is our biggest drag on resources?” and play with different ideas and scenarios. The more you think about different approaches to doing what you are doing, the more you are developing your strategic thinking muscle.

3. Practice Scenario Analysis.

When you are just trying to get through your to do list and manage crises each day, you often miss the opportunity to think about other ways of doing things. Thinking strategically is intangible, and it doesn’t give you an immediate burst of satisfaction related to a job completed or well-done. So sometimes despite your best intentions, you won’t allocate time to it. The “What-If Analysis” is a practical way to work strategic thinking into your day because it’s a tangible exercise you can add to your to do list. One example of this might be to take every decision you feel is important enough to benefit from strategic thinking and set aside 20 minutes to do a what-if analysis before making the decision. This can even be done collaboratively as a team activity to develop everyone’s thinking skills.

The what-if analysis can take several forms, but the general idea is to consider one decision and list 2-3 three choices or options. For each option, identify best case, worst case, and probable outcomes. For each outcome, think about what you would do next and how you could make the most out of that scenario.

For example, a typical scenario that happens in job transition is when you are in the interview process for more than one job. You get an offer from your second or third favorite option, and you have to respond before you know the outcome of your favorite option. Here is what the what-if analysis for that scenario might look like:

Situation: I have been offered Job B, and I need to respond by Friday. I want Job A more, but I’m not through the interview process and might not hear from them for three more weeks.

Option / Choice Best Case Outcome Worst Case Outcome Probable Outcome Contingency Plan
Accept Offer B I end up loving Job B and find out later that Job A wouldn’t have been offered to me anyway. I get offered Job A when I have already started at Job B. I will either burn bridges at Job B by quitting shortly after I start, or I will decide to stay, and maybe I will like it. It depends on how much more I prefer Job A over Job B. If I love Job A a lot more, then I will burn that bridge!
Reject Offer B I’ll be offered Job A and love it. I will not get offered Job A, and Job B will also be filled. I might get offered Job A, but even if don’t, I’ll be continuing to interview and will likely discover something else I like. I’ll keep interviewing and trust that something new will come along that might be better than Job A.
Be honest with Company B and request more time to respond Company B appreciates my honestly and will hold my offer for three weeks, while also working on their own backup plan. Company B doesn’t hold my offer and gives the job to someone else. Meanwhile I do not get Job A. Company B will likely respect my integrity and may even sweeten the deal. They might be willing to give me one more week. Same as above.

Working through the table above takes about 15 to 20 minutes and provides additional clarity and confidence when it comes to making a decision. As a regular practice, it builds your ability to quickly consider multiple scenarios and make better decisions consistently. Working through a table like this also forces you to write your thoughts down, which improves your ability to articulate your thought process.

The more you talk about different options you considered and why you chose a particular option, the more others will respect your thinking and view you as strategic.

If you would like to work on developing your strategic thinking with customized mentoring, don’t hesitate to reach out for a coaching consultation by filling out our contact form.



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