Is everyone capable of being strategic?
A client recently shared with me that she’s worried that one of her senior leaders is not particularly strategic. While this person is a content expert, they aren’t great at thinking ahead, backward designing, planning for the future, or leveraging resources to have impact.
This client asked me: “Is everyone capable of being strategic?”
The research suggests that most people do, in fact, have the capacity to learn to become strategic. I fundamentally believe that leadership, management, communication, leadership, and entrepreneurship are teachable skills.
For instance, at MIT, we figured out how to train engineers to communicate effectively. It required having just the right “guide,” an authentic motivation to learn, and breaking down key concepts and skills into bite-size experiential learning opportunities.
And at Harvard, we designed an experiential learning model to train first time entrepreneurs how to build effective startups. “Operation Impact” was essentially a programmatic “obstacle course” that provided tiny amounts of money that got unlocked when effective practices were deployed - like conducting unbiased customer discovery and running MVP pilots.
But in tough tech startup life, we don’t have the luxury of time to invest in bringing someone from being a novice strategic thinker to becoming an expert. We need to hire leaders who already think several months ahead and know how to backwards design getting from here to there.
So, how do you assess whether or not someone has strong strategic instincts?
If you want a quick strategic thinking test, ask folks how they prepare to go grocery shopping and have them walk you through their process.
I love asking this question. I get answers like “My wife and I make a list on the white board during the week of things we need and I take a photo of it to the grocery store with me.” Or, “I have a “to list” app on my phone and I create a list of things I need and I check off items as I walk around the store.” I think it’s really interesting to see how people think about the menu for the week and come up with a strategy to execute.
How do I prepare to go grocery shopping? I thought you’d never ask. First I look at a few cookbooks and pick out some recipes I want to make for the week. Then I go to the “Food” page in my personal Notion board and I have a grid that I’ve set up to help me organize dinners by day, starting with Sunday, which is grocery shopping day. I usually pick one breakfast item for the week (omlettes) and one lunch meal for the week (avocado toast). After I have the big picture, I create a shopping list based on how Whole Foods categorizes each item and then I organize my list by its location in the store (i.e. produce first, then dairy, then grains, then meats, etc.). Is this a little overkill? Perhaps. I literally can’t turn off this part of my brain. I’m constantly thinking about the most efficient and effective way to do everything - from laundry to leadership training.
Another way to assess strategic thinking is to give someone an assignment as part of their interview process. Scope out a 1-hour project for them to do and ask them to solve an open-ended project. I find this is more telling than spending a whole day with someone because it shows you the kind of work they are likely to produce on your team.
Here are a few examples of good strategic-thinking assignments:
Walk me through how you’d spend the first three months on the job.
We need to get to this particular milestone [fill in the blank] by [specific date], with these resources [details]. How would you organize the team to get there?
We are facing a challenge in this area of the organization [provide details], what questions would you ask to try to improve outcomes? What would you want to better understand as you build a new strategy moving forward?
Anyone on your team who is going to manage other people needs to be a fairly strong strategic thinker. They need to be able to help their team assess where they are, where they need to be, and then come up with an effective game plan to get there. They need to be able to leverage other people and delegate to produce an optimal outcome. It’s better to find this out right up front than to hire someone with a lot of experience, who is taking up a big salary and a key role, and later on realize that they don’t have the ability to create a product roadmap or design effective OKRs.
Again, I do think that everyone could probably become strategic eventually with enough training and support - but in all likelihood you don’t have the resources and time to invest in someone building this skill over time if you may not exist in two years if you don’t reach your milestones.
