3 Tips For Being More Strategic, Starting Now

In the last post about strategic thinking skills, no places have been more important for strategy than in chess and war. In those contexts, strategy intended to render opponents useless. Somehow, that made its way into corporations, where also through strategy, we wage a different battle with products and services.

Just as humility, integrity and vision earn their rightful top spots in the leadership tool box, so should strategic thinking. But, it doesn’t get as much focus and that’s probably because of two things: we’ve accepted it as a process versus a skill, and thus haven’t invested the time to define, assess and encourage strategic skills in leaders. Several experts will say we are entering the age of the Strategist (and somewhat leaving strategic planning), shown in this excerpt from Wikipedia:

Strategic thinking

Photo credit: quinn.anya

“While there is no generally accepted definition for strategic thinking, no common agreement as to its role or importance, and no standardised list of key competencies of strategic thinkers; most agree that traditional models of strategy making, which are primarily based on strategic planning, are not working. Strategy in today’s competitive business landscape is moving away from the basic ‘strategic planning’ to more of ‘strategic thinking’ in order to remain competitive. However, both thought processes must work hand-in-hand in order to reap maximum benefit. It has been argued that the real heart of strategy is the ‘strategist’; and for a better strategy execution requires a strategic thinker who can discover novel, imaginative strategies which can re-write the rules of the competitive game; and set in motion the chain of events that will shape and ‘define the future.'”

What if you’re someone who wants or needs to become more strategic because of what your current role demands, or to set yourself apart from peers, or you wish to advance to senior leadership?

You can find a planning process anywhere, that’s the easy part. Below are three simple strategic thinking actions for any leader at any level:

See the Big Picture:

WordPress flagged my section title for being cliché. Indeed it is, but clichés are clichés for a reason: they’re true! Strategic thinking starts by being able to see and appreciate from end-to-end an entire process and related dependencies. Hand in hand with collaboration, a strategic planning approach will involve people from many areas to ensure that a diverse, comprehensive view drives decision making. A person can, and needs to get in the habit of thinking like this all the time.

Put more specifically, you need knowledge and other perspectives. Start by casually spending time with leaders in other disciplines and learn their processes, challenges and opportunities. Even consider shadowing such people.

Reality check: At this point, let’s be candid about the inevitable reality that some people are “naturally” big-picture thinkers (you know who you are) and some people are more detailed thinkers (you also know who you are). If you’re the latter, it’s very important for you to understand your unique gap, not just try to do a bunch of things to become more strategic. Once you give the tips in this post some thought, run it by a trusted colleague and come up with some ideas for “stretch roles” to close the gap (not a training class!). Trying out strategic skills only in your current role probably won’t work if it’s a role that has you “in the weeds” all day.

OK, next point.

“Look Beyond the End of Your Nose:”

Apologies for the crude analogy, I actually got that feedback from a boss at my first “real” job out of college. It had immediate and lasting effect, because it was obvious what needed to happen: Look up and forward instead of down at the immediate tasks and crises at hand today. I spent a lot of time with this director picking her brain about how she approaches things, and it become even more obvious what I needed to do differently.

This looks different for everyone, but some examples might include:

  • Establish a habit of jotting down observations about threats, changes in the marketplace, etc. that can affect your business or area of work. Share them regularly with those that have the power to act on them.
  • Like with my above boss example, talk to someone who you consider strategic about their thought process. Brainstorm with her/him how to think through specific issues.
  • Anticipate and imagine the future through scenario planning. I love scenario planning. It’s such a great process for bringing about ideas, so long as you remember the future is mostly unknown. It’s just a tool and must be accompanied by, sorry, looking beyond the end of your nose. In this case, being open to changes and opportunities.
  • Maybe it’s as simple as a mindset change: instead of “putting out fires” or drowning in a perpetual problem-solving loop, or the “what,” start asking “why.” Initiate a monthly, “Why Instead of What” group (out of the office) to brainstorm on those critical issues.

Speaking of asking “why” more often, that is a good segue to something called out in Fast Company’s6 Habits of True Strategic Thinkers.”

Challenge Conventional Thinking:

The article said, “‘Conventional wisdom’ opens you to fewer raised eyebrows and second guessing. But if you swallow every management fad, herdlike belief, and safe opinion at face value, your company loses all competitive advantage. Critical thinkers question everything. To master this skill you must force yourself to:

  • Reframe problems to get to the bottom of things, in terms of root causes
  • Challenge current beliefs and mindsets, including your own
  • Uncover hypocrisy, manipulation, and bias in organizational decisions.”

Do not fear becoming the devil’s advocate or being perceived as negative! This is the problem with so many organizations: everybody sees and avoids the most obvious problems because it’s uncomfortable to address them. You want respect, and if you have valid questions that challenge conventional thinking, you will gain respect and strategic thinking skills. You may have to repeat yourself several times because people generally don’t like to be challenged…but that’s what leaders do.

While there are probably at least 10 more attributes to strategic thinking, these are a good start. The important thing is to know your valuable skills and strengths and decide what strategic skills will complement those and how. Then, have some fun doing a couple of things here and there to develop.

To summarize:

  1. See the big picture: what are your industry or organization knowledge gaps? Add diverse input into your day-to-day activities.
  2. Look beyond the end of your nose: what does that mean for you?
  3. Challenge conventional thinking, those things that matter.

“There is nothing so useless as doing efficiently that which should not be done at all.”
— Peter Drucker

  1. Another aspect of scenario planning which may be helpful is planning for risk mitigation. Thinking through what can go wrong helps you think about all of the key dependencies end to end. Of course it can also help protect you against derailing issues which can also make you more effective.


  2. Thanks for the comment, that’s a great point!


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