At the Uncertainty Project, we highlight tools and techniques for strategic decision making that are either thought-provoking, applicable, or both!

Every other week we package up our learnings and share them with this newsletter as we build the Uncertainty Project!

In case you missed it, last week we covered part 2 of ‘from data-driven to decision driven’ with a post on how the 'data-driven' mindset feeds our dangerous craving for certainty

This week:

• 🔮 Topic: 360° Strategies: Integrating inclusive, exclusive, proven, and aspirational strategies

• 🎙️ Upcoming Talk: Next week we’re sitting down with Melissa Ushakov, Group Product Manager at GitLab to talk about GitLab’s explicit, systematic approach to decision making. If you want to see it before we mention it in the 9/6 Newsletter, then give us a follow on LinkedIn 🙂 - we provide more regular updates/content there.

• 🎯 A milestone is right around the corner! We have almost 1,000 subscribers! A huge thanks to all of you for following this project and engaging every week! 🙏 - We’d love to hear more about what has been and would be valuable moving forward. If you have a minute, feel free to give us feedback! It can be completely anonymous (name is optional)

This week’s post is by:

360° Strategies: Integrating inclusive, exclusive, proven, and aspirational strategies

“Strategy” as a term has been so abused that it almost doesn’t mean anything. The reason it is so different in each org is that people only focus on a particular part of the full picture, usually the one that is most problematic for them.

What ends up happening is that the “strategy document” is a listing of competitive analysis, plans, team charters, etc. But what is the ideal formulation? If we don’t get this right we will end up confusing the team in the worst case and not aligning anything in the best case.

If you only take one thing away from this post it is that we need to consider what is in, what is out, what is known to work, and what points to bigger aspirations to build a complete strategy. In this post, I want to talk about a new 360° view of strategy that takes the various angles I’ve found to work within strategies into one view.

The first step of all strategies: comprehensive coverage

When most teams get started with strategy they simply compile all of the projects they are currently doing (or plan to do) and say that is the strategy. These are things we can have high confidence in but may just be what the group has settled on with little evidence.

By looking at a higher level of abstraction that ties these things together can we start to assemble the decisions that were made to get us to this point:

• What are the hard questions we have chosen one way or another that have accepted these plans into our current workload?

• What types of signals have we seen already that show these projects are “working” and providing “success” toward our end goals or vision?

• Even if we don’t know the answers to these questions we can start to back into them by asking “What are the themes of these projects?”

This is a lot like when people first start to use OKRs: they tend to just create an OKR set that covers every team’s work across the org. No one should be left out!

Aspirational bets with less evidence

While people build these comprehensive lists of things that are happening and working, right now, they will also start to consider what bets they think they should make toward the future. These can be considered as aspirational strategies. Things that we don’t have much evidence of today but the leadership team has made abductive leaps towards.

What happens with aspirational strategies is that they are generally not tested later. They are left as aspirational and rotated out the next strategy cycle because they didn’t really do anything. This is mostly a problem with linking strategy to execution but it is one worth mentioning.

These strategies are important because we'll always have a hypothesis of what we need to do in the future that will give us access to new opportunities.

Negative (or bizzaro) strategies

When we need to choose between two good things that means there is some possible organization out there that is the “opposite” of what your org is. They will choose the reasonable opposite and could be successful. I call these “bizzaro” strategies after the Bizzaro Superman who is the opposite of the good Superman.

The opposite of what your organization would do is key to understanding your own strategy. This is because: 1) if they are fluff if the opposite is not valid and 2) they help outline what we won’t do as an organization to limit (or govern) how the team makes choices.

There are benefits to both positive (“we will do this”) and negative (“we will not do this”) strategies. They create a possible shape or cone to the future of what we can consider.

In a talk by Sonja Blignaut titled “Becoming Modern Day Way(s)finders” she includes positive and negative strategies. But what I had originally missed with bizzaro strategies specifically were constraints that could be regulations, limited budget, etc. They are constraints that are as immovable as gravity for our concerns and we wouldn’t choose but try to acknowledge in our framing.

Pulling it all together

When we think about these current and aspirational, “will do” and “won’t do” strategies we start to build a full view of our strategies. I’ve started to think of it as this 2x2:

Placing all of the strategies or decisions you are making into this framing requires you to create a whole picture rather than focusing on one or two of the sections like we usually would.

These strategies then start to form “even over” statements by taking the corresponding positive and negative statements. Balancing the strategies we know work today with those that might work in the future we can start to build out a balance that allows for learning and resiliency.

With all decision making the strategy (or principles or values) should help frame the decision itself. This goes for OKRs as a goal-setting framework or roadmaps as a listing of things we will do now/next with that lens.

Building a full 360° view of your strategy is what everyone should be looking to achieve. Without it, you will make short-sighted or less-aligned decisions across your organization. Try it today!

✨ Highlights (Interesting reads):

• Throwing an Exception: 3 types of decision and what to do in each case, Simon Cross - “There’s lots of reasons why orgs end up with bad decision-making cultures (e.g. fear of failure) but one problem I’ve observed is that often people don’t know what decisions they can make, and what decisions they can’t — so they default to the safest option: not making a decision.”

• How to Prepare for Strategy; Less is More, Roger Martin - “I think of strategy as a thinking process that results in either the reaffirmation of the choices you have already made, or the making of new set of choices that are different than the choices that inform and guide what you are doing today.”

• A Wonderfully Simple Heuristic to Recognize Charlatans, Farnam Street - “Taleb argues that the greatest ‘and most robust contribution to knowledge consists in removing what we think is wrong—subtractive epistemology.’ He continues that ‘we know a lot more about what is wrong than what is right.’ What does not work, that is negative knowledge, is more robust than positive knowledge. This is because it’s a lot easier for something we know to fail than it is for something we know that isn’t so to succeed.”

• Becoming Modern Day Way(s)finders, Sonja Blignaut - “Wayfinding is dynamic response-ability. This dynamic strategy is at its most powerful when people, whether on the board or front line, are reading signals, even weak ones and feeding them back to others”

We hope this post was valuable and interesting! Have feedback? Just reply to this email! It would be great to get in touch!