Everything I know about strategy
“What is strategy, anyway?” I asked this exact question to a senior leader in my first job post-grad school. It was my first role that was not direct service, and I was still getting my footing - learning about what work looked like when young people weren’t in the room every day. I consider myself to be a natural strategist, and yet no one had ever broken down what strategy is before. Mind you - I was 31 at this point. The senior leader said, “Strategy is choosing a path among many paths.” She went on to share that it’s not only about what you do do - it’s what you don’t do that defines strategic choices. If you’re choosing to do it all, you’re not being strategic. Period.
Seems straightforward, right? Nope.
The way she laid it out made sense to me, and I was glad to have such a simple way to describe a thinking style that, generally, comes naturally to me. But was it straightforward? Not so much. Strategy isn’t easy, because it doesn’t happen in a vacuum. As an Executive Director, I often felt bombarded by the often varying (and often disparate) interests of my board, team, larger organization, boss, and myself. It felt complex, and in a very on-brand way, I often overcomplicated it. Further mucking things up were my own personal beliefs, conditioning, and intuition (which I often accidentally ignored). Missteps in the strategy process impact not only whether you hit your goals but also the culture of your team, the health of your resources, and the system within which you operate. It took a lot of time and practice to realize that good strategy usually means slowing down, involving the right people, and listening to my gut while being open to challenge. Good strategy is the alchemy between what the hard data tells us and what we already know intuitively. Check out below for some common mistakes, and the antidotes that make strategic work - and the people that create and execute it - better and more inspired.
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Common mistakes:
Skipping the goal-setting and visioning + alignment.
Over-estimating resources and under-resourcing strategies.
Trying to do too much or do it all.
Over-emphasizing quantitative data.
Power-hoarding on strategic decisions.
Antidotes:
Choose a goal and setting a vision for impact. This is a skip that often gets skipped - or doesn’t get fully completed before moving into the next step. It’s critical to get clear on where you’re headed first, and then land on the path you think is most likely to get you there. Then, test the viability of that path through the lens of people, capacity, values, and capabilities - and align resources to make it happen.
Examine the conditions. Often, there are “below the surface” pieces that need to be shifted to allow for change to take place. Listen to people, look for cultural patterns, and identify mindsets that might boost - or hinder - your strategy to ensure real systems change.
Ensure your strategy is values-aligned. Leave it on the cutting room floor if doing it would compromise your integrity or the integrity of the team, or if you’d need to do anything outside your values.
Get clear on what you won’t do. There are lots of different ways to get to a goal, and many leaders feel pressure - either self-imposed or imposed by funders or other forces - to do way too much. The consequences of this go without saying - there are cultural ones (people feel scattered, under resourced, confused, or operate with a false sense of urgency) and there are impact ones (it’s harder to meet a goal when resources are spread too thin, and the most valuable ways of spending time aren’t clear). You have to choose. You just do.
Align resources appropriately. Really listen to the people executing the strategic priorities to understand what is needed to truly do them justice. This means often resourcing more than feels comfortable to ensure that folks have what they need, are compensated appropriately, and don’t burn out. A strategy is only viable if the people doing it are able to do it in a way that is sustainable, and it’s only equitable if it doesn’t tax some folks (with less power, agency, or proximity) disproportionately.
Look beyond the numerical data. Strategy comes from qualitative data - but also hunches, intuition, qualitative data, and connective stories. While it’s obviously smart to look at quantitative data, if you just look at that, you’re losing out on a critical piece of the picture — and a lot of the context in which you operate.
Allow for flexibility and what emerges. That means building in spaces and opportunities to review and change direction as needed or consider additional information as it becomes available. It also means leaving some empty space in a plan so your team isn’t overtaxed and folks have some spaciousness.
Share power, be transparent, and include diverse perspectives. Strategic planning must be inclusive of diverse perspectives across your team, organization, and external organizations (depending on the size of the project). It will make it better - and make sure it actually comes to fruition. More importantly, perhaps, it’s critical that folks across all levels of the organization feel a genuine sense of ownership and investment, which starts with involvement. Strategic direction, if done right, will have a very real impact on people’s day to day lives - and often, the biggest impact on those doing the direct service work. While you’re not trying to reach consensus, you are ensuring all voices are heard, centering those with the least decision-making power.
While it’s not as simple as “a path among many paths,” it doesn’t need to be complicated either. Every leader has areas of strength when it comes to strategy - and areas for growth. Putting the time and energy into interrogating your approach and what’s working (and what isn’t) will lead to stronger strategy, more motivated teams, and better outcomes.
