How to Be Strategic

Roman Helmet “You should be more strategic.” “Product Management needs to focus on the strategic.” “I’d love to be more strategic, if only I wasn’t stuck doing all of these tactical things!”

Do any of the above sound familiar to you? Being asked to be more strategic, or wishing to become more strategic has been around as long as someone called themselves a Product Manager, but what does it really mean? How can you become more strategic when everyone is vying for your time - all the time?

Strategic is a term that has lost meaning since it became part of the Executive lexicon. Everyone wants to “be strategic,” because in the information economy we associate the most value with the people who come up with the best thoughts. Being tactical is, amazingly, viewed as a negative. You can hear the connotation drip from people’s mouths when they say it: “Oh, he’s a good candidate, but I think he’s too tactical.” Everyone wants to be the chef, no one the waiter…as if the food will cook itself and walk out to our customer’s tables.

Wikipedia defines strategy as:

“…a long term plan of action designed to achieve a particular goal, most often “winning.” Strategy is differentiated from tactics or immediate actions with resources at hand by its nature of being extensively premeditated, and often practically rehearsed. Strategies are used to make the problem easier to understand and solve.”

You can boil that down to strategy is about having the best plan. Whenever I hear people talk about not being strategic enough (or I catch myself doing it), three thoughts immediately pop into my head:

Being strategic is not binary; you don’t wake up one day and say “today I am strategic!” It is a journey and a destination.
If your goal for being strategic is to be well regarded, to be a leader, and to “win,” remember that people follow leaders that inspire not only by their words but by their actions. Even great strategic thinkers have to get into the tactical muck and implement their grand plans.
You can control how strategic you are by your own actions. If being strategic is about having the best plan, and by extension the best/smartest/most agile thoughts, you can train your brain to be a step ahead of your competition and your peers. Here are some thoughts on how.

I’ve been fortunate to work with some really bright thinkers so far in my career and picked up a few tips on how to be a more agile thinker. Everyone has their own processing style, for instance I like to digest and think on a topic for awhile before coming up with a plan of action, but you might be a snap thinker who can do all of this on the fly - if so you’re ahead of me! Note that some of these questions overlap in scope.

Ways to be a Strategic Thinker

If we take the current action, what will be the downstream results to X, Y, Z? How will they likely react? How will we counter-react? You can’t get through a strategy discussion without a chess analogy, so here you go. These questions help you anticipate the moves of your competition, channel, etc, and decide beforehand how you want to react, so you’re not caught flat footed.
Who and what else are connected to this decision? How will this affect them? I like this question because it forces you to think through the implications of your decisions early. It’s easy to sit back and say “let’s change our distribution model” or “let’s move to SaaS!,” but being able to accurately predict and describe the challenges of plan of action will help guide you to the best choice.
Ask the Five Why’s; This sounds like a something out of a kung fu movie, but the Five Why’s are real. Five Why’s is a B-school/consulting method that says if you ask “why” at least 5 times you can get to the root of the problem. It’s all about digging deeper. Observe:

“I hate your company.”

“Why?”

“Because I have to wait for tech support for 3 hours to get someone on the phone!”

“Why?”

“Because your product didn’t work right when I plugged it in!”

“Why?”

“Because when I went to training they didn’t tell me I needed to hold the reset button while I plugged it in to load the factory settings!”

“Why?”

“Because your training is a joke, it’s all sales and no technical!”

“Why?”

“I only went because I couldn’t get a sales guy to call me back!”

In this example what appeared to be a product problem may actually be a sales, training, and support problem..

What external influences will affect me in the future? If your competition introduced a product tomorrow with the same features as yours at half the price, how would you react?
What internal influences will affect me in the future? If your company downsized and you lost half of your development staff, how would you react? What if you faced mega sales and had to quickly scale up?
Where is “good enough” okay, and where do we really need to invest to provide an out-of-this world experience? You can’t do everything perfect all of the time.
If I had unlimited funds, what one product development would move the revenue/profit/customer satisfaction needle more than all others? Which needle is more important to move?
If I had only one development dollar, where would I put it and why? This is closely related to the question above it.
Why are we winning today? Why are we losing? You need to understand your current stance if you want to build a solid future plan.
What do we do better than everyone else? Do you understand your core competency?
What problem do we need to solve for the customer? If you don’t know this…find out fast because it’s probably different than your assumption.
What barriers exist to prevent us from winning? Is it better to smash through those barriers, or route around them? Sometimes the only road to winning is to go through a competitor. But it’s 3-5x more difficult/expensive to gain a new customer than to recruit business from existing customers. Is there a way to win business without a head on confrontation?
What can we do that’s never been done before? I love this question because it’s challenging. It doesn’t just apply to engineering either, you can apply it to Marketing and Sales as well.

What other ways do you use to be a better strategic thinker?