Strategy Feeds Execution

Strategy is among our most valuable work. In technology, it’s easy to get caught up in apps, features, and how it looks. We must consistently stop and consider if we are building the right thing. As I look back over years of building products and millions of times of code, my proudest moments involve software we avoided having to write. In contrast, the greatest disappointments involve a tremendous amount of time, energy, and effort spent on something that was ultimately wrong.

It comes back to strategy vs execution. Doing the work or deciding on the work to be done.

Great technologists are able to align technology with business objectives. This alignment shouldn’t only be at the beginning of the project. It must happen over and over as conditions evolve. This is typically the role of the technical cofounder on smaller teams and Chief Technology Officer within large or growing organizations. Building great software is important but far superior is knowing what is appropriate to build.

To illustrate the point, it’s worth exploring a few tradeoffs. Common tradeoffs include expectations, timeline, and quality.


What do they think they are getting? Assumptions are easy to make and hard to articulate. The phrase Minimum Viable Product, for instance, is riddled with assumptions. We all have different definitions of minimum and viable.

In the end, ‘expectation minus communication, equal frustration’.


When will it be done? The larger the project, the harder it is to predict. There is also an assumption that it has been clearly defined as to remove all uncertainty or confusion, which is rarely the case. Time is the most challenging constraint. It is always being spent. Whether we are planning or waiting, it is passing.

Rush through planning and the journey will contain more missteps. Take too long and the window of opportunity could close.


How good is good enough? As a child, there were times when cleaning my room took minutes and times when it took hours. The difference? Quality. Was I stuffing dirty clothes under the bed or cleaning, folding, and organizing them in their proper place?

Where a proper customer and market have not been identified, we’ve found quality to be less important. Without knowing who you’re optimizing for, it’s impossible to truly hit the mark. If building for existing customers, it’s worth the extra time and attention to get it right.

Continual Realignment

Historically, Strategy Sprints preceded each project. The tension emerges when constraints change while the work is underway. Is time spent adjusting based on new information or pushing forward on the given path?

You wouldn’t plan a road trip and jump in the car without a GPS or map. Strategy is a perpetual pursuit. Constant recalculating is crucial to long term success. For engineering projects, there seems to be a natural rhythm to proceeding two week at a time. Defined break-points forces pause, reflection, and reevaluation. Making informed adjustments will ensure you end up where you intend to go.

In the end, it does not matter what you’re driving, how much the trip cost, how long it took, or how you get there if you arrive at the wrong destination.