top of page

5 steps to strategic thinking

September 5, 2023 Newsletter

A few months ago, a client mentioned that he’s having trouble getting a manager on his team to step up.

When I pressed him to explain the gap, he gave the following analogy: “This person’s a checkers player. I need a chess player in the role.”

I have to admit that I was rather intimidated by his analogy, as the few attempts I made in my life to learn how to play chess were… slow going.

  • But I understood his point: the higher one rises in an org chart, the more skilled they should be in reading a whole board, understanding everyone’s positions, and advancing accordingly to achieve their goals.

  • [West Wing sidebar here… anyone else think immediately of the artful episode where President Bartlet is playing multiple chess games at once?]

As a leader, would you define yourself as a checkers or a chess player? In other words, how many moves out can you anticipate and plan?

However you currently define yourself, strategic planning and execution may be a skillset you’re interested in developing. Here are a few things I’ve seen work as clients take steps in this direction:

  1. Make time for thinking, writing, processing, and planning. Block it off and guard it vigilantly. There isn’t a one-size-fits-all solution – some people like end of the week, some first thing Monday morning, some need long chunks, some short, some use their computers and some shut it. Figure out what works and communicate its importance to your team so they help you stick to it.

  2. Understand the motivations of other players. I don’t mean this cynically. Everyone is motivated by something (in many cases, multiple somethings), so the clearer you can be about their drivers, the easier it is to expect their next steps.

  3. Don’t go it alone. Recruit a colleague to be your thought partner and set aside dedicated time for talking through a thorny question. If others need to be pulled in, invite them to join the fun.

  4. Ask the hard questions. Sometimes the toughest questions are the most critical to explore. If it feels daunting to say them out loud, start by writing them down. Write out a few variations on the same question and circle/highlight/hold/star the most accurate version.

  5. Stay up to date on your field. There is always something new to learn in one’s space. If you’re not yet subscribed to podcasts, newsletters, magazines, or other media outlets that are specific to your industry and/or profession, find three this week.

Eventually you will learn to see further ahead and plan your next steps accordingly. It’s almost impossible to do so while feeling depleted, so the more you can proactively create the conditions for processing and planning, the faster you’ll accelerate this crucial skillset.


The Coaching Corner Reflect back long-term progress When someone is struggling on a task or project, they may lose sight of just how far they’ve already come. It’s a great opportunity to put on your coaching hat and give them some perspective on their growth, so far. The purpose isn’t to belittle the momentary struggle, but to help them summon the strength to keep going.



2023 Summer Reading Guide, compiled by McKinsey. We can still enjoy summer reading after Labor Day, can’t we?

Send me your recommendations! What have you read, listened to, or watched recently that inspired you?


Stay informed and never miss a beat! Subscribe to our newsletter for more coaching tips and weekly insights.


bottom of page