Making Time For Strategic Thinking

Posted by
October 30, 2020

Topic: Strategic Thinking

Written by Karin Blair


Time to think — in a world driven by goals, metrics and milestones it can be hard to make time to think.

In the corporate world, we live by the mantra “what matters gets measured.” Results can feel like everything. Executive reviews include a list of accomplishments since we were last together. Teams have endless lists of “priorities” and results they’re chasing for that next review.

Because let’s face it, a leader without results has no credibility. Yet, results leaders without a sense of direction will be limited in how far they can go. They’ll likely be subject to dreaded, and often intangible, feedback “You need to be more strategic,” which basically means, “I don’t know what all of this activity sums up to. What’s the bigger picture here? Where exactly are you trying to go, and WHY?”

Making time to think strategically is a tangible step you can take toward being more strategic. You can do it at any time, regardless of whether it is “strategic planning season” or whether you are directly involved in that process.

Many of my coaching clients have committed to carving out that “time to think” in their calendar. And two weeks later when we check in on how the experiment went, well …. It went a little like New Year’s resolutions and good intentions that never quite manifest into the committed action we envisioned. 

Obstacles to strategic thinking time

In theory, carving out time to think should be quite simple. Add a two‑hour block of time on your calendar each week labeled “strategic thinking.” Simple enough.

Now notice, anything happen as you read that? Did your stomach tighten? Did your mind come up with objections to blocking the time? Just notice whatever resistance might be arising for you. Or what resistance might arise when it comes to actually spending those two hours thinking.

I encourage you to take a minute to write down your objections so you can see them and have more choice. For me, the list looks something like this:

  • What if this ends up being a complete waste of time?
  • What if I never have anything to show for this time invested? I have too much to do to waste a single minute that isn’t productive.
  • Two hours, that is a lot of time.
  • What exactly am I supposed to be thinking about right now?
  • How about I just knock out these emails quickly first? 

Let’s take a look at some of the common obstacles to help you break through them. 

Why is strategic thinking hard?

Making time to think requires us to take a leap of faith into the uncertainty of what might emerge.  Which becomes a huge obstacle for my accomplishment junkie self. There is so much more certainty in the value of time spent knocking something off my to‑do list than in this amorphous “thinking time.” We often can’t see the immediate benefit of the time spent. Delayed gratification is required, much like trusting that planted seeds will bear fruit. 

Strategic thinking is a creative process. And creativity is neither linear nor predictable. The emergent magic of creativity is undeniable. Surrender is required. And disciplined practice. Finding the courage to take that leap into what is beyond our control and navigate through our resistance to that uncertainty, is the work. What can you control?

  • Show up. Commit to the practice of strategic thinking and the time carved out.
  • Sit in the discomfort of not knowing if what you are doing will “bear fruit,” and do it anyway.
  • Connect to a situation where it is easy for you to commit to short‑term actions that generally only pay off in the long term—anything to leverage here?
  • Shift your evaluation horizon beyond the couple hours spent thinking.
  • Commit to the discovery process. Stay curious about what emerges: connections, implications, possibilities.
  • Trust that the jigsaw pieces will fit together at some point.

What do strategic thinkers do?

You've carved out the time, kept your commitment, but how do you use it in a way that results in greater strategic clarity and insight? What exactly are you supposed to be thinking about? Strategic thinking is the logic and the “why” behind key decisions—decisions on where to focus and where to invest to create long-term value and sustainability. It is future‑oriented. It is time to envision, to anticipate, to derive insight, to create competitive advantage—on a continual basis. Remember, this is a creative and reflective process. Without time for reflection, decision-making is often based on past experiences or competitive benchmarking, rather than on a clear perspective on the current situation and potential opportunities to shape and create a distinct future. You are not trying to solve a problem. Decision‑making is for another time. Use this time to lay the foundation for the strategic logic and rationale for future recommendations.  Maybe shift your focus from WHAT you want to do to WHY you want to do it. 

Strategic thinking starts with questions. Questions about the market, customers, competitors, sources of value and key capabilities. It ultimately results in decisions. Strategic decisions about how the business (or your function) needs to adapt and change. The questions most relevant to your situation will vary. There's no formula, but here are some questions that might get you started:

  • What is the most pressing opportunity or challenge before the business right now?
  • How could ______ (market trend) impact the business?
  • How might the market, customers, competitors change over the next three years?
    • What are potential options for our response to this changing landscape?
  • For a particular investment or initiative that you are recommending, what is the strategic rationale behind it?
    • Instead of using the “5 Whymethod to drive down to the root cause of a problem, use it in reverse to strengthen your strategic rationale.
    • What am I trying to accomplish? And why? For what impact? What is the desired future state you are moving toward?
  • If my team only accomplished one thing this quarter, what would it be? 
    • What makes this the most important area of focus for our future?

Or download a broader range of questions to help you improve the thought process and rationale behind business decisions with long‑term impact.

What really is your job? 

This last obstacle often requires a shift in mindset and a sense of your value proposition as a leader. You need to know what only you can do in your role. As one client said, “I realized if I wasn’t spending my time thinking about how to change the business, no one was. That this thinking time really is my job.” As a senior leader, more and more of your time should be charting new paths for the business rather than continuing to operate within and execute on the status quo. Your value shifts as you focus more and more of your time:

  • Anticipating and envisioning the future direction of your business, function, or department
  • Providing broader context and perspective to your team’s specific tasks and goals
  • Building relationships across the organization, to drive collaboration and alignment toward shared results
  • Coaching and developing direct reports
  • Challenging the status quo to spark innovation

You are now the architect of the future.  Making the foundational and direction setting decisions.  It is exciting, and potentially challenging as your impact becomes less tangible in the day‑to‑day. Resist the temptation to demonstrate your value through immediate and tangible results.  Remember, “what got you here, won’t get you there.” Notice if you are spending more time thinking about HOW to get this done than thinking about WHAT should be done and WHY. Then identify even one of those projects or priorities that you could delegate and develop a team member to own more fully, so you have 'time to think'.

Are you ready to commit to some strategic thinking time this week? Give it a try. Stay curious to what resistance might emerge. Changing your mindset and redefining your value can be hard—and painful—as you shift from the comfortable and familiar. But those moments of strategic clarity and insight, to create a new future, will be worth it.  Experiment with some of these practices and see how you can begin to amplify your strategic leadership impact.


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