Leap or Sleep

Sometimes, it seems that there’s an inverse relation between the number of people with leadership titles in a startup and how much initiative the startup actually has. Part of the responsibility of being a leader is to help your company take the lead (or maintain it). As you’re honing your 2024 roadmaps, let’s consider whether you’re doing what you ought to. Whereas good planning doesn’t promise success, no planning virtually guarantees you won’t accomplish anything worthwhile.

Going Through the Motions

I’ve been talking to many founders and executives recently, both clients and people in my community. A current theme, unsurprisingly, is their planning for 2024. A repeating motive I see is that plans are leadership “playing pretend.” Slides are created, Notion documents are written, all trying to exude authority and preparedness. However, when you scratch the surface and peer a bit deeper, you notice how hollow many of these really are.

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First, there are the sanguine roadmaps. These assume that the team just has to make sure the current efforts are maintained, and that’s it. This is very much “keeping the lights on” and assuming that the world is static. Whatever works now will also work a year from today at 3-10x the scale we hope to achieve. That’s rarely the case. There are pandemics, wars, economic crises, and technological advancements.

Then there are those whose strategy is just a shopping list of features. They’re not aiming to keep doing “more of the same” and intend to try several things, but those lack a clear unifying strategy and business-level objectives. Therefore, they quickly turn into Jira tasks that will be mindlessly worked through.

Another example would be the tech teams who want to “do something” and add on all sorts of technical changes. However, without any clear relation to business outcomes and realizing the company’s leverage points and strategy, these changes again become little more than shuffling tech around. These approaches might result in some improvements from time to time, but often at a meager effort-to-efficiency ratio.

Wake Up

As the title of this article suggests, if you’re not planning some leaps ahead, you’re sleeping. There’s no remaining static in tech—you’re either working to improve or slowly losing ground. You can only cruise downhill (I think that’s an Alan Weiss quote). Therefore, there are a few things you should consider as you iron out your plans for next year:

  • Form a clear strategy encompassing the company’s leverage points, vision, and winning plans. Don’t just “go with the flow,” don’t copy and paste last year’s plan with some updated numbers. Take the time to think about this and create a coherent plan. Then, convey this clearly to your team so it gains the needed strategic context.
  • Ensure your strategy contains a few bets that align with the overall goals. These should not be tasks you’re certain of because then they’re not bets. They should also be meaningful, meaning that winning some (or even one) would result in a genuine improvement for the company.
  • Throw away feature lists and create a plan that revolves around business objectives and goals that align with your strategy. This makes space for individuals to come up with their own ways of achieving goals and remain flexible as things change. You know the plans that are irrelevant two months into the year? When working with business goals, your plans become more robust.

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