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Think strategically — what does that mean?

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Seeing beyond the path while you’re walking

Think strategically — what does that mean?

I define strategic thinking as applying a predictive model (mental or otherwise) in order to understand the path to a desired outcome. This is how I keep a strategic mindset from ideation to iteration and beyond.

Thinking and doing happen apart and together

I keep a strategic mindset as I’m going through my day. Think of it as a framework of things that get me to a goal. I’m constantly playing out each decision and action against that framework. Then testing the framework (often in my head) against a larger model of the systems I’m attempting to influence.

I’m constantly running scenarios in my head against each decision I have to make and each action I take. I watch carefully as something I’ve decided to take a strategic approach to transitions between states to see if it’s moving in the direction I expect. Generally, I have two or three strategies I’m working at a time in the background.

Thinking three steps ahead

One of the things you’ll often hear me say is “I was thinking three steps past where we are.” It’s partly innate and partly that I’ve trained my brain to always be thinking three steps past where I am when I’m investigating a problem. Running scenarios backward and forward, then matching them to the strategic framework.

This is fantastic when I’m working a strategy to influence an organizational decision. This is because enacting a strategy to influence across an organization you have to constantly balance more factors than I care to list here. Basically, you’re balancing each of these:

Personal makeup

  • Open and easy-going, I can approach and pitch when comfortable
  • More closed, I need to give them a reason to care before pitching

Business outcome

  • More money — this is always the first and most effective influence tool
  • Better reputation — for the org, team, or person
  • Better team — better morale, attract new talent, increase team impact

Keeping all that in mind as you’re talking through an idea during a coffee with someone you’re trying to influence is tricky, nearly impossible. However, if you keep the framework of your strategic goal in your head you’ll see how that tiny conversation can tick a big box toward your goal.

It can be terrible when defining a problem, especially in the details. This is because I tend to think and do at the same time. So sometimes I shoot right past the detail of the problem because I’m too focused on the overall system and a set of goals. I’ve learned to stop and ask “is this the problem we’re solving?” More often than not it is but this helps put your focus where it is needed.

Systems of systems

To understand a holistic strategy I’ve learned to think and design beyond the system I’m comfortable with and instead think in systems of systems. Always looking for the points of connection, decision, action, and transition between phases that lead to the outcome. I’ll zero in on detail then back out and think:

  • Then what happens?
  • How does that affect the things around it?
  • What idea am I pushing forward or helping push forward?
  • What influence will this have over the person, team, organization?

These questions work whether I’m implementing a design strategy like creating an onboarding flow or trying to influence an organization to adopt a method or idea.

Strategic thinking isn’t the same thing as a strategy

A strategy informs a coherent plan to achieve the desired outcome. It guides the tactics and methods used to implement the plan. A strategy is written down and shared across an organization it is not something only one person keeps in their head, we all hope.

Setting strategic goals

Setting strategic goals means you’re going to risk missing them. If you’re setting serious strategic goals for your product, content, or design you’re at least in part trying to anticipate an outcome mired in uncertainty. When you’re setting strategic goals for yourself and your career you will have things you can affect and things you cannot. Any effective strategic mideset requires flexibility.

Stop, gather, assess, understand, redefine, and reimplement framework.

Intellectually strategic

My intellectual differences, like being ADD and Dyslexic, have become beneficial to me in this arena. It’s like having a system running scenarios in the background constantly. This enables me to, I think, have a tiny advantage. It’s also exhausting and sometimes troublesome but that’s a different blog.


Think strategically — what does that mean? was originally published in UX Planet on Medium, where people are continuing the conversation by highlighting and responding to this story.