Perhaps the most common struggle for managers in general, and tech executives specifically, is trying to remain professionally “up to date”. Managers-of-managers rarely come across code in their day-to-day jobs, and that can quickly result in a feeling of disconnect, especially if you used to pride yourself on your technical skills.
There are of course a lot of benefits to maintaining your knowledge and staying relevant. It is always harder to lead an organization when your intuition can’t be used. Making strategical decisions has less risks when you can build on your years of experience. And, of course, I’ve seen many executives that eventually started a new venture and needed to be relatively more hands-on once more.
Yet, too often the attempted solutions here do more harm than good. It is too easy to appear to employees as micro-managing when you’re trying to be involved. And more times than not, executives that try to assign themselves some minor-looking tasks end up postponing them more and more, or completing them in a way that feels foreign to the team, with no one able to takeover maintenance.
Not all is lost of course, and there are a couple of ways to try and stay in touch that are less likely to blow up in your face.
The first one, which is unsexy yet quite good at keeping you connected with your employees’ day-to-day, and very appreciated by them, is making sure to take part in whatever on-call rotation you may have. You may not be able to take it for whole weeks, but even taking single days off of someone’s shift routinely will be helpful to all. When you’re part of the on-call you are likely to experience what is wasting your team’s time, what’s done great and where you’re lacking.
Another option is to do regular pair-programming with different people. Instead of you taking on whole tasks, routinely have 2-3 hour sessions with employees from all around the organization. That means you’re not being a bottleneck, you don’t have to only work on the tiniest of problems, and there’s no handoff necessary of whatever you do.
I suggest putting these on your calendar so that every week or two you have a session and make sure no one interrupts you while you work. As it may be intimidating for some people to work with a boss, I suggest making it something voluntary, or having their direct manager ask them if they’d like to do it.
I highly recommend having an open notebook nearby, as these sessions usually provoke many ideas and questions for later.
When doing this, it is crucial to make sure that you don’t “pull rank” and start telling your people how to do their work. Focus on being helpful, not leading the task, and observational.
Yes, these options mean that you’re not likely to know every nook and cranny of your tech stack, but I believe it fits right on the 80/20 sweet spot. You get to routinely stay connected, without a lot of overhead and minimize the potential harm to the team’s ongoing work.
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