As I mentioned earlier, I’ve been in a management off-site this week. A lot of the work there has simply been about communicating where we are right now, with a fair amount of time also devoted to communicating plans for what we will do over the next eighteen to twenty-four months.
This is all necessary activity and if we weren’t at least trying to be serious about planning for the future we would be negligent as managers. The problem of course is that any manager with any experience at all knows planning is mostly futile. As many hacks have pointed out, it is a rare plan that survives the first shot on the battlefield. (And yes, we always revert to tired combat analogies in having these kinds of discussions, which is counterproductive at best. Business is not war, and selling free software is most certainly not war — more of a parlor trick, I sometimes think.)
I don’t need tired combat analogies to demonstrate the futility of planning — I can use my own career in software. Since I got into this dodge back in 1999, I’ve been involved in at least ten different software projects where the work we were doing was based on realizing some imagined future state that was more than a year out. Not a single one of those projects ever realized that planned state. That doesn’t mean they were failures, although many were — this is software after all. It simply means they didn’t go to plan.
So what is the point of even discussing “roadmap” (as we call it) in an industry where even our CEO says things like “Planning is dead?” I guess one alternative is just to be totally reactive — build a team that is super flexible so it can quickly jump on whatever opportunity arises. Nice idea, but hard to pull off in nature, partly because teams like this are expensive. Also, “totally reactive” doesn’t feel like a great way to be when people’s careers are depending on your leadership. We are compelled to try to imagine the future and try to position ourselves and the people who depend on us to take best advantage of it.
No, I think it’s best to continue planning, knowing all the while that the plans will be wrong. It’s just important not to depend on the outcome.