Original article from the Flevy business blog can be found here: http://flevy.com/blog/teach-strategic-thinking-with-these-3-simple-questions/ When the Big Strategic Idea someone pitches you is blatantly boneheaded and un -strategic, you might remind yourself that strategic thinkers are made, not born. If this person is your friend or subordinate, then maybe it’s your job to help them learn the skill called “strategic thinking.” These three simple questions will get you off to a good start. First: “What’s the point here?” Like the guy who interrupts a meandering meeting with, “What are we trying to accomplish today?” you can awaken your mentee by probing for the point of a proposal. What result, end-point, outcome, or effect are they angling for? Imagine that a manager has come to her boss with a plan to merge two departments. “Boss,” she says, “I think we could capture some real synergies if we merged Madge’s department with Larry’s. I’ve got a plan for doing that, and I’d like to walk you through it and see what you think.” But her plan isn’t the first thing to care about. The first issue to tackle is: how will the world be different if the plan is successful? Or, simply, “What’s the point here?” For instance, can she identify the “synergies” she’s promising? We see friends’ calendars fill with speaking engagements. Occasionally we’ll ask, “Why are you talking to that particular group?” Often we’re told that it’s “good exposure,” or it’s an opportunity to “deliver a message.” If we’re feeling a little bold, we’ll press the point: Sure. But after the exposure, and after delivering the message, what do you hope your audience will say or do differently than before they heard your message? In other words, what’s the point here? This question benefits effort at all levels of the organization. In fact, we’ve found that the bigger and more expensive the undertaking, the more likely this niggling little question has been ignored, or not answered thoughtfully.

1. Teach Strategic Thinking with These
3 Simple Questions
Contributed by William Casey on July 14, 2015 in Management & Leadership , Strategy, Marketing, & Sales
When the Big Strategic Idea someone pitches you is blatantly boneheaded and un -strategic,
you might remind yourself that strategic thinkers are made, not born. If this person is your
friend or subordinate, then maybe it’s your job to help them learn the skill called “strategic
thinking.” These three simple questions will get you off to a good start.
First: “What’s the point here?”
Like the guy who interrupts a meandering meeting with, “What are we trying to accomplish
today?” you can awaken your mentee by probing for the point of a proposal. What result,
end-point, outcome, or effect are they angling for?
Imagine that a manager has come to her boss with a plan to merge two departments.

2. “Boss,” she says, “I think we could capture some real synergies if we merged Madge’s
department with Larry’s. I’ve got a plan for doing that, and I’d like to walk you through it
and see what you think.”
But her plan isn’t the first thing to care about. The first issue to tackle is: how will the world
be different if the plan is successful? Or, simply, “What’s the point here?” For instance, can
she identify the “synergies” she’s promising?
We see friends’ calendars fill with speaking engagements. Occasionally we’ll ask, “Why are
you talking to that particular group?” Often we’re told that it’s “good exposure,” or it’s an
opportunity to “deliver a message.” If we’re feeling a little bold, we’ll press the point: Sure.
But after the exposure, and after delivering the message, what do you hope your audience
will say or do differently than before they heard your message? In other words, what’s the
point here?
This question benefits effort at all levels of the organization. In fact, we’ve found that the
bigger and more expensive the undertaking, the more likely this niggling little question has
been ignored, or not answered thoughtfully.

3. Second: “What’s the point of the point?”
Now that we’re talking outcomes, not effort,
the student of strategic thinking needs to
examine how a proposed result fits into a
bigger picture. “Sometimes it’s better to climb
up than to drill down,” a wise admiral once
told us.
So if you’re the boss, it’s not unfair for you to
ask, “Okay, so how will this help me
accomplish my goals?” It may be the first time
they’ve pondered their contribution to your goals. And even better might be to ask, “How
will that help me accomplish my boss’ goals?” That question moves their thinking up two
levels, instead of just one.
Let’s say that the proposal to merge two departments could yield an interesting result: 25%
reduction in cycle time of a key transaction. Great. But is the overall organization prepared
to exploit faster transactions? Maybe the paperwork pileup would just drop down to another

4. bottleneck, helping nobody’s higher goal. Or maybe it’s exactly what’s needed to goose along
an important, higher-order achievement.
In any case, the so-what of the so-what is always a useful conversation, and helps people see
their work through more strategic eyes.
Third: “What could go wrong?”
This is the part where you help your mentee develop strategic peripheral vision: teach them
to anticipate negative side effects. Almost any strategic outcome risks negative side effects.
Sure, lots of side effects aren’t knowable in advance. But most forehead-slapping failures
stem from easily predictable side effects that weren’t predicted. And that’s because nobody
asked, “What could go wrong?”
In our little merger example, it would be easy to accidentally chase off talented employees.
Or, maybe that “more efficient” system is also a more fragile one, easily broken by the
absence of an employee or two. Or . . . lots of other things.

5. “What could go wrong” is the simple question that might have complex answers. But time
and again we’ve seen that question raise our clients’ strategic thinking as they broadened
their vision.
There are more than a few rocks to kick over in this conversation. The achievement itself
can have side effects, but so too can the effort to produce the achievement. Also, side effects
can occur immediately, and they can occur over time. Side effects can be second order, but
also third order, and up. And they can occur in many, many domains: safety, politics
(internal and external), costs, morale, and on and on.
There’s plenty to talk about. But the broader goal here is not to kill strategic ideas; it’s to
make sure the ideas are fully fleshed out. It’s about ensuring that victories aren’t Pyrrhic.
“Strategic thinking”–in fact, wisdom– occurs only in light of broad context. Understanding
the point of our intentions, and then the point of that, and then being alert to repercussions:
not a bad beginning down that path.

6. About William Casey
Wendi Peck and Bill Casey are CEO and President, respectively, of Executive Leadership Group, Inc. , a
management consultancy serving leaders in both business and government.

7. Flevy (www.flevy.com) is the
marketplace for premium documents.
These documents can range from
Business Frameworks to Financial
Models to PowerPoint Templates.
Flevy was founded under the principle
that companies waste a lot of time and
money recreating the same foundational
businessdocuments. Our vision is for
Flevy to become a comprehensive
knowledge base of business
documents. All rganizations, from
startups to large enterprises, can use
Flevy— whether it's to jumpstart
projects, to find reference or comparison
materials, or just to learn.
Contact Us
Please contact us with any questions you
may haveabout our company.
• General Inquiries
support@flevy.com
• Media/PR
press@flevy.com
• Billing
billing@flevy.com