06/12/19 | Career, Menu-Homepage

Strategic Thinking, We Meet Again

I’ve come to consider the concept of Strategic Thinking as an old friend. It alongside its buddy, Big Picture Thinking (BPT if you’re hip), can be seemingly elusive. These concepts repeatedly showed up during my annual performance reviews as an “Area for Development.” The path, however to acquiring these skills was unclear. I was supposed to understand these concepts intuitively, and once understood, I would then be SENIOR and capable of MORE. In other words, I needed this skill to be promoted. Ooh, let the games begin!

It’s not that my managers didn’t try to explain what I needed to do, but it was a “we know it when we see it” kind of thing. If you’re told to plan for the future, you will. But is this to the satisfaction of others? Well, that depends. Are they more senior than you? Can they see further out in their crystal ball than you can? Can they see things you can’t see because they know things you don’t? I was working with a lot of people who could think bigger than me, and I needed to embiggen fast.

“Leveraged for the Greater Good”

Over the years I would continue to receive feedback about this area. Why? Strategic Thinking is a friend that keeps evolving.

1st time: Strategic Thinking: Alana sets aside time to think big picture about the direction of the team and how it should be expanded to meet these needs. As the number of products and markets continue to grow, it will become even more important to focus strategically on the role of our team and how we need to adapt to meet the growing needs on the horizon.

2nd time: More Big Picture Thinking: In the past six months, Alana has taken a step back and applied her extraordinary problem solving skills to higher level problems. I encourage her to continue to apply this talent to many of the larger scale problems we face…As one of her teammates put it, “I know that her leadership and operational aptitude can be leveraged for the greater good of other teams as well.”

3rd time: Continued Strategic Planning: Alana is good at big picture thinking and strategic planning. As she delegates more of her work…, she will have more time to focus on the big picture. It will be great for the team and Alana to stretch herself further in this area.

As I did better, the finish line moved a little further out. There was always a bigger, better way I could be thinking strategically. Fun!

What IS this skill?

In short, it’s the ability to see further and then even further down the road. My management wanted me to be looking ahead, past the curve in the road, predicting where we were going, and planning for that point. They knew I was good at executing, but they wanted me to be thinking about 3 months from the present. When I improved at that, they wanted 6 months, then a year, then 3 years… The more senior I got, the further ahead I needed to be able to plan. This required practicing a few different sub-skills that I found comprised Strategic Thinking/BPT.

But first, a story

In 2011, I joined Google Fiber to run customer service and installs. I had not done this before — running customer support for start-up Internet provider — but I had gathered various theories and beliefs from internal and external experience and observations. So I talked my way into this job, and then I started planning how we would launch customer support for a still-being-built product. I remember sitting at my desk, having just been lectured by a colleague who knew way more about the industry than me (he drew whiteboard pictures), and I pulled up a blank document and started typing.

My brain basically did a jigsaw puzzle, mixing and matching years of exposure to tools, talent and training to come up with a plan. I sold others on it and improved it with feedback. We committed to it. We executed it. We won awards. I’m truncating the story, but you get the picture. It starts with a blank page.

How do you figure out what’s next?

I’m going to tee up some big skills all in a row, but these are developed over time. All of these skills and habits together helped me see further down that road. But it took time and practice. Here are some actionable tips and advice that I’ve learned in the process:

1) Stop Thinking about Now: The first step is always the hardest. As long as I was looking at my inbox or having meetings, I was never going to see beyond the here and now. I needed to see way more forest, and pay way less attention to trees. I started to put specific time aside to do Strategic Thinking; I would book it on my calendar. The goal is to clear brain space — turn off alerts, close the inbox, and imagine the future.

An important corollary — I learned over time to imagine a future with fewer problems. As an operations person at heart, I can foresee the issues with any potential plan and immediately begin to mitigate problems. Unfortunately, mitigation also can reduce big ideas into smaller, less impressive ones. Now, when I’m in brainstorming mode, I explicitly turn off my inner naysayer. She can come back when we start planning the execution of a project where she’s more helpful. Remember that this is the creative stage. Exercises like this help.

2) Question Asking: In my opinion, the easiest way to start Strategic Thinking is to ask questions. The classic example: SWOT analysis. What are our Strengths? What are our Weaknesses? What are our Opportunities? What our are Threats? Answer the questions and see whether it helps you form an initial game plan. If we have X strength, can we address Y opportunity?

Another corollary: If you’re part of a collaborative culture where involving others in strategic thinking is welcome or expected, this is a great stage to do it. Having people ask and answer these questions together helps with aligning around the problems, opportunities, and solutions. Simple activity here.

3) Reuse, Recycle: Whenever I sit down to work on a slide deck, I think about the best slides I’ve seen. I’ll mine a library of slides I’ve already made to reuse templates that worked. You also can do this for strategy work. Take a look at how others have approached similar problems. Why did they do it? Are there common outcomes to their approaches? Use these as foundations to craft your idea.

Do you like corollaries? This is a time to remember, however, that perfect can be the enemy of good. My least favorite meeting is one where we’re discussing and re-discussing the exact wording in a mission statement. Get to a good 80% mark and agree to revisit tabled items as you go.

4) Decision Making: When it comes down to it, decision making is the heart of a strategy. When I first proposed a strategy, I began by teeing up a recommendation for a path forward. At first I presented this information to someone more senior, and they made the decision. Since they were actually responsible, this was like having training wheels. I could see what questions they had and how they made the call. As I got more senior, I became responsible for the decision.

Last corollary: I’ll probably write a whole article about this one day, but if I could recommend one skill to hone it would be the big D. Being able to make decisions, especially when you have limited data, has helped me in all the roles I’ve had. Start practicing on smaller decisions like the hiring decision for 1 person. Then build up to staffing a whole team. Taking smaller risks will help prep you for when you have to make larger strategic decisions and also build your confidence.


During the years I managed policy, I practiced these skills. Those poor teams were my guinea pigs as I worked to hone and develop what a strategy looks like. And I received a promotion to Director along the way, a sure sign I had embraced and demonstrated Big Picture Thinking! By the time I got to Fiber, I had the confidence to develop a strategy even though I was new to the space.

“Courage, My Dear” – C.S. Lewis

I would be remiss if I didn’t note that Strategic Thinking requires COURAGE. The courage to present your ideas to others. The courage to ask hard questions. The courage to guess. The courage to decide. Strategic Thinking is a good thing that can feel initially bad. It gets better.

And that’s normal. Remember that you are looking far down a road, beyond your immediate sight. Will there be deer? Will it be raining? Will your car work? Be brave. Strategic Thinking may be the first place where you’re asked to go out on a limb, make a plan, and lead. Don’t shy away from it, but bring a raincoat just in case.

This piece is selected from an ongoing series, chronicling my 17 years at Google and the performance feedback that has helped to shape my career. People often wonder what has motivated me to stay so long at one company. I usually tell them it’s the people and career opportunities that Google affords; it’s also the ability to level up my personal growth. I consistently ask myself: what have I learned along the way and how am I continuing to improve? As you may know, we love data at Google. In this vein, I dug back into past performance reviews and cataloged the feedback I’ve received. This has been a humbling journey, but also one where I can appreciate just how much I’ve grown over the years and help others with feedback they may be receiving today.

For more pieces in this series, please see Ambition, a Foreign Land, It’s Delegation Time, Accepting Emotions and Change, Dealing with Frustration on the Job, and Prioritization – the Visible Invisible Skill.

Alana Karen

Alana Karen

Alana Karen has spent 17+ years at Google in various customer service and operational roles. She's committed to growing people-focused leaders at Google and beyond, most recently with her LinkedIn series "Still Learning: 17 Years of Lessons Learned at Google". Alana raises her 3 kids and dog in California with her husband.

Straight to your inbox.

The best content on the future faces of tech and startups.

This field is for validation purposes and should be left unchanged.


Join the Angel Sessions

Develop strategic relationships, build skills, and increase your deal flow through our global angel group and investing course.