A few years ago I wrote about practical life lessons learned from playing Dungeons & Dragons. Many roleplaying systems handle the advancement of character skills with a level system. Over time your character gains experience and when you reach a set threshold you gain a "level", which is a collection of abilities and skills. Your choice of character class defines the set of abilities you gain.
So far, so simple. Many years ago, I was playing in a game in which we were forced to enact a dangerous escape in a spaceship. My character was the most competent pilot in the group, which meant he had enough knowledge for the ship to not immediately drop out of the sky. A few very lucky dice rolls, and a suicidal ramming of another ship later and we limped out of the gravity well, escaping to hyperspace in what was left of the ship. Much fun was had, and I gained a level - which I used to improve my piloting skills. Immediately AFTER I needed them.
That scenario never came up again, of course.
In my experience, this is very common in roleplaying games - spend the time learning skills for a scenario that has already occurred. It's also something I see all too often in work. People learning about change management immediately after a change, for instance, or about HR processes immediately after struggling through a difficult piece of casework. In technical delivery, learning how to use a frontend framework properly after releasing an accessibility nightmare onto the public or how to monitor your service on $cloudProvider after implementing their new and shiny features and deploying using it.
I've done this myself many times. So why is it so hard to look forward and learn skills ahead of time? The broad-brush problems should be very predictable. Technical strategy should show which skills are going to be needed in the next six months and longer. Moving into a management role makes change management and some kind of HR process work pretty much guaranteed. For me, there are a couple of problems at play.
Firstly, management work can be far too reactive. More than that - being reactive is actually very seductive as it feels far more productive. It isn't; but the feeling of being needed because you're putting out fires is highly addictive, especially shortly after coming from a discipline with a strong way of defining productivity such as development. I spent most of my early days after moving into leadership trying to force myself onto the front foot so I could actually think ahead instead of running around fixing problems and if I'm honest I didn't really want to make this change.
Secondly, even when there is a chance to look forward we often don't actually have a chance to act on what we see. I know that dedicating hours to studying various aspects of management and reading supporting books will help me, but I certainly don't have the time to do it without making serious compromises in what I have to deliver or just consuming my non-working time. Neither of these solutions are acceptable. Part of this is about having any spare time during the working day, and to study there is a need for some quiet reflective time which is particularly difficult when everyone is trying to reach you for whatever Opinion is needed at that time. But also, I need to give myself permission to study and acknowledge that this is part of the job.
What should we expect from leadership? There are times of difficulties and change, but in general I think it's reasonable for people to expect some form of considered development from their place of work. In these enlightened times, we've moved past "bring them in and use them up" as a management style (insert correct cynicism here) and certainly in a knowledge-based job like development, constantly building skills is essential for an individual's future, as well as of benefit to the organisation. Not to mention retention and in-house skill development is far more cost effective than hiring and firing in this sector. This leads straight to an obvious point - we should be building organisations which value learning, and that means making time and expertise available. For those of us who talk about taking on apprentices and other "learning" roles (which done wrong can destroy someone's career as it starts) the point is that much stronger.
So what is the key thing to learn here? Well, it's important to look forward rather than backwards when deciding what to study. Beyond that, it's a well-rehearsed refrain at this point. Scanning the horizon is fundamental to a successful leadership role. Acting on what one sees there is essential. Both of these require time and carving out time is hard. However there is an extra thought here - giving oneself permission to find and spend time on learning is an important step, and being able to do so is part of the organisation's culture. This is important for anyone, but especially in a position of leadership where one can have a strong voice setting that culture and enabling others to grow.