Lesson Learned: Ruthlessly prioritize. Get use to saying “no” or “wait” to important things so that you can say “yes” to the most important things.

Alan Gilbert
2 min readJan 30, 2023

This blog post is part of a series of leadership lessons that I have learned from 40 years in tech.

Photo by Brett Jordan on Unsplash

I like the WIN framework, which directs you to ask “What’s Important Now?,” to decide where to focus your time and resources, and to defer everything else. At one company, where we focused strongly on leadership development, it was practically a religion. With each initiative we wanted to add to the plate, we would ask “is that WIN?”

One critical nuance of the WIN framework is that it does not mean that you should only think short term, and go only for immediate gratification. WIN should always include prioritizing things now that are required both for short-term and long-term success. But make sure you are doing only the things that have to be done now to win (see what I did there?), and make sure you properly define winning. The rest can wait or not be done at all. The question “what would happen if we waited until next month (or next year)?” is a great tool to sort out what is truly WIN vs. just a manageable pain point. Staying focused on WIN is especially important in product development, where there is a constant tension between managing technical debt and moving the product forward. WIN is a very effective framework in finding the right balance.

Another great prioritizing framework is the Pareto principle, or the 80/20 rule. In particular, look to 80/20 the company’s work where you can identify opportunities to focus effort and resources on the 20% that will provide 80% of the benefit. The math is simple: 20% of the cost to get 80% of the benefit is way better than 100% of the cost to get 100% of the benefit. In other words, don’t increase cost 5X to get 20% more benefit. Of course, this is easier said than done, and the numbers are illustrative, not exact. But great leaders and companies figure it out and apply the principal. One simple but effective approach is to simply ask “what would be good enough?,” and then consider doing just that. I’ve seen this framework applied effectively to decisions in business priorities, tech debt and scale-up, talent-management infrastructure, and manufacturing.