Great strategy means picking a path.

Prioritize until it hurts. Then prioritize more, you’re almost there.

I had the pleasure of taking in a Cubs baseball game the other evening with a strategy leader for a global, multibillion-dollar industrial firm. In running strategy for the business, his career has sent him all over the world, working with teams in Asia, Europe, and the Americas. I asked him, from his experience, what was the one pattern he kept seeing that separated great business strategy from good business strategy, his response: the degree of focus. It didn’t matter what continent he was on or how smart the management team was, what consistently separated great business strategy from good or bad business strategy was how narrowly the strategy focused. A more focused strategy enables a business to martial resources in the best way to create and defend the best winning position in the market. However, teams most often want to keep more options open, pursue more ideas, and never say no to a potential opportunity (unaware they’re creating a real distraction).

A couple weeks ago, I had the privilege of attending a lecture from Harvard’s Boris Groysberg at Shore’s executive leadership academy, an event we put on to bring together and train all of the management teams across our portfolio. Boris shared the story of two team’s race to be the first to make it to the south pole. One team had tremendous resources and pursued multiple strategies with those resources. Another team had much more limited resources and focused on making just one strategy work very well. The team with all the resources died, the team that focused succeeded.

At Apply, Jony Ive described that one of Steve Jobs’ superpowers was making himself and others say no to opportunities – not just opportunities they weren’t very interested in, but opportunities they loved that it hurt to say no to in the moment. If it didn’t really hurt to say no, like it did when they shelved the iPad’s development to build the iPhone, then it wasn’t really meaningful prioritization.

At the Entrepreneur Center, we used to have a saying for early stage entrepreneurs: they don’t know what their business does until they can explain what it doesn’t do. Early stage entrepreneurs were particularly open to a world of possibilities (this was their strength) but when deciding what to do, frequently struggled to explain how they would use their scarce resources in a consistent manner long enough to maximize their chances of breaking through the noise in any single market.

So if everyone keeps saying prioritization matters so much, why is nearly everyone so bad at actually doing it? 

In my experience, it’s one truth and two drivers:

One Truth: No one believes they are failing to prioritize effectively.

Driver One: Fear – People (smart, talented people) are afraid of missing out on something because they focused somewhere else. Even though those same people would tell a different leader of another business to focus more.

Driver Two: Discomfort – It feels bad to say no to things, especially things like potential opportunities. And if you are doing this with a team, there will be conflict and difficult conversations – things that are, for most people, tiring and uncomfortable, so we want to avoid them (and usually don’t realize that’s what we’re doing).

So, what can you do? There’s a ton you can do, but I’d start with 4 steps:

1. Make sure you and your team align on the importance of prioritization before diving into strategy conversations. It’s hard to build this ethos in the moment when tensions are high. It is easier to build this reserve of strength outside of the debates, so that it can survive in and then grow from the debates.

2. Have an informed, objective outsider in the session – Someone who isn’t emotionally invested in the outcome needs to be in charge of pushing the team, appropriately with smart questions, to evaluate if they have truly prioritized and focused enough.

3. Be aware and push through: When discomfort is happening, teams have a better chance of succeeding when the leader acknowledges the discomfort, pushes through it, and models success. These tough conversations can happen in the middle of lots of other conversations, and leaders may be tired, distracted, or simply not at their best when these moments arise.

4. Realistically assess: Get as detailed and quantitative as possible. If you pursue two paths, what will that actually mean for resource allocation to each effort and its expected outcome? What’t that look like if you pursued just each one individually? There’s a ton of assumption and cognitive dissonance that comes out in this analysis, and often provides a LOT of clarity.

Prioritization is not easy: it’s about saying no to possibilities you love to maximize your team’s possibilities to win. Winning though, that’s pretty fun.

I talk about what I’ve learned from two decades studying and practicing strategy at the intersection of Boards, investors, and management teams of high growth businesses. Any identifying details of companies I’ve worked with have been changed to protect their identities, but the experiences and insights (when that’s what they are) are true. I’m always looking to hear and learn from others, so please ping me directly or leave a comment to keep the conversation going.