Today’s dose of healthy common sense for tech leaders: You’re probably not planning things enough. The pendulum swing in the industry over the past couple of decades has made planning be seen almost as a complete waste. Yes, agile has taught us that detailing product requirements down to the pixel months in advance is a mistake, and managing huge backlogs is useless busywork. However, the utter lack of planning in many product-engineering organizations is the result of throwing the baby out with the bathwater. Continuing on the theme is pointing out the habits of 10x teams, healthy planning is there.

Bad Plans

Working with many leaders as part of the coaching and advisory I do, it seems like many operate in one of two extremes. On the one hand, we have those who are trying to nail everything down. This often happens with first-timers anxious about not making any mistakes. Frequently, this is coupled with weak delegation skills and micromanagement. It reminds me of myself 20 years ago, being very anxious about going to other cities without smartphones and internet. I’d print out pages of public transportation routes, addresses, and phone numbers, for any case. Clearly, this rarely holds past some short-term stage and the simplest of situations. However, the much more common issue is that leaders barely have any real plans.

Of course, they have something. Like quarterly roadmaps and maybe an (overly long) appointment called ‘sprint planning.’ But those are anything but long-term plans. Contrasted with Aviv of the early 2000s strolling streets with printouts of maps and directions, this is someone driving and randomly deciding which turn to take or opting to follow a car that “seems like it knows where it’s going” (if you got that Dirk Gently reference, we should hang out).

I don’t care if you’re doing Kanban or feel like your team’s roadmap is too volatile and will change. Planning is what’s needed to have a general direction and be able to take the lead. Otherwise, where exactly are you leading people? Without proper planning, you’re just a floating leader (one of my most shared articles ever).

Taking Control

Some of the best teams I’ve worked with and those publicly documenting their paths have proper planning put in place. For example, consider 37 Signals’ concept of ‘shaping’ features. It strikes the balance between overly detailing features and deciding without understanding what big features actually entail.

The easiest boost you get from even basic plans is that they tend to trigger discussions much faster. I’ve demonstrated that in my Straw-man Architecture article from many years ago. The gist is that to get teams moving I take a stab at a very trivial solution and immediately everyone is off debugging it and telling me why I’m stupid. It works much faster than asking people for generic feedback or thoughts.

Your plans shouldn’t just be limited to the work itself. For example, are you thinking from time to time about the direction your organization should be going? This can include topics like which teams are likely to be needed, maintaining a ‘leadership bench’ from which you can promote people, considering whether your next X employees will be colocated, remote, in a new site, etc. These are all plans that you’ll probably have to change, but the important part is not about having the right plans, but about using planning as a means to hone your leadership instincts. You are much more likely to make the correct decision if you’ve already given the topic some thought.

You should also have personal plans. First, personal as in for yourself. What do you intend to focus on as part of your growth? What do you want to change, learn, or explore? Push yourself out of your comfort zone regularly. Further, you and your management team should regularly set personal goals for employees as part of your internal coaching framework.

Where this planning might feel at first like a lot of overhead, especially if you’ve never done it before, it is what leadership should actually be about. Not about putting out fires or rushing from meeting to meeting. When one does not know what harbor one is making for, no wind is the right wind.