(2025-01-26) Gilad Embracing Uncertainty A Modern Take On Strategy Goals And Roadmaps

Itamar Gilad: Embracing Uncertainty: A Modern Take On Strategy, Goals, and Roadmaps. We all strive for certainty � if we do X, Y will happen. Certainty is comforting; it allows us to operate without fear, doubt, or having to think too much. Many of the processes your company employs, especially strategy, roadmap, and project planning, are meant to create certainty

But developing tech products is anything but certain. There are many moving parts in the market, technology, product, and org; many assumptions, dependencies, friction points, and potential snafus.

The time we waste on false-certainty planning is just the tip of the iceberg. Below the surface we waste a lot more in in unnecessary development, product bloat, and maintenance.

Dealing Honestly With Uncertainty

Business Strategy is where we face the highest levels of uncertainty. As we�re projecting years into the future, any concrete plan of action is very likely to fail

Even coming up with a clear set of choices (the more modern definition of strategy) is very hard

Here are some ways to do it.
The screenshot below is taken from a demo of Dotwork, a currently stealth startup whose CPO is John Cutler...

What I especially like here is the concept of Possibility Space, and how a set of strategic choices, in this case based on the writings of Roger Martin, creates one possible strategy. Comparing and scoring multiple possible strategies makes it hard for managers to fall in love with just one shiny object. Basing the scores on research forces the developers of the strategy to face reality

Ash Maurya, author of Running Lean and Scaling Lean (also highly recommended), gives similar advice to startups. He recommends creating a number of Lean Canvases (a derivative of Strategizer�s Business Model Canvas) to model various 0-to-1 strategies. Each canvas represents one possible combination of target market segment, problem, solution, value proposition, business model and other dimensions.

Once you�ve created a few plausible lean canvases, you identify the key assumptions in each and validate them, which will eliminate most ideas, but (hopefully) leave you with at least one valid option.

In the same vein, in this article I argue that some of the biggest strategic successes � the iPhone, the Netflix Streaming Service, and many of Google�s innovations � stem from a process of parallel strategic exploration which I call Multiple Strategic Tracks (MuST).

Back then it was a lot of launch-and-iterate and fail-fast (projects that didn�t work were killed, as it should be). Today we can probably be much more efficient using pre-launch product discovery.

Embracing Uncertainty In Goal-Setting

Earlier I said that optimizing for outcomes (what we want to achieve) is better when you face uncertainty because your goals are more likely to be right than your ideas. But even setting the right goals can be hard, perhaps because there are many potential goals to choose from, or because we�re not sure what�s possible. Good strategy should inform the goals, but many goals are tactical.

Objectives and Key Results (OKRs), with its top-down-bottom-up alignment process, can facilitate goal discovery.

The manager then gets back draft OKRs from the various teams that reflect what her org thinks the goals ought to be � things she specified as well as things she didn�t. That�s a good way to learn of other potential goals she may have missed.

Andy Grove, renowned CEO of Intel and inventor of OKR, argued that 60% of key results should be defined bottom-up.

It�s also good to think of goals as having a lifecycle. Instead of jumping directly into execution, it�s often better to start with research and discovery, which gives you some room to understand the goal better, refine it, or even (in rare cases) give up on it entirely.

Embracing Uncertainty in Roadmapping

The classic 12-month roadmap is the most obvious example of false predictability, which is why many orgs replaced it with shorter versions like Now, Next, Later roadmaps, or Shape Up cycles. These options still demand certainty about what we build in the next 6-12 weeks, and both offer at best a vague longer-term plan.

An alternative to consider is the Outcome Roadmap which uses goals as an underlying structure, and gradually fills-in ideas as we gain more certainty.

Embracing Uncertainty in Idea Prioritization

Growth guru Sean Ellis took classic impact/effort analysis and made it much more uncertainty-ready by adding a third element � Confidence � which indicates how sure we are that the idea will have the predicted impact and effort. Ellis codified the popular ICE scoring method. But how do you estimate confidence in an idea? The scientific method suggests you should base your confidence on evidence.

This is why I created the Confidence Meter that lists common types of evidence you may find and assigns them confidence weights.