How to Actually Build a Better Boss:

What mistakes or missteps are you seeing managers and organizations make over and over again right now — and what changes make you hopeful?

Melissa: Failing to train managers. I mean, perhaps we would say that. But holy shit does it keep happening. We promote people into management and we just hope that they figure it out. And then we stand, mouth agape, when things go sideways. And this isn’t just a problem for our new managers. We are 40 years into this strategy and now the overwhelming majority of the workforce came up through this same form of occupational hazing. Here’s a new job. It’s very high stakes. It’s totally different from what you’ve done to date. And the skill set isn’t intuitive at all. You’re smart. You’ll figure it out. And if not, you’re fired. Good luck. 

That’s the summary version of how most of North America’s leaders stepped into the seat. And that they are now propagating that out is a huge problem, especially for a modern workforce that anticipates and demands competent management. That’s part of where you see generational strife in the workforce. Where folks who have been at it for a long time say, “Well, this is how it’s always been. Why are you complaining?” But when you ask them, “Were there downsides to that approach? Can you point to ways that it failed, both people and organizations? Oh yes, absolutely.” 

OK then, let’s stop pretending we’ve got a working system for people stepping into leadership. Cause we don’t. And let’s get to work building something better. … 

Johnathan: … Most managers want to do a good job for their people.

This isn’t obvious to everyone, right? The popular writing about management is always a caricature: either a genius and perfect visionary, or a pointy-haired, micromanaging dictator. In our work, we have met very few of either. You can tell me that’s selection bias — that we only meet the leaders who work for companies that invest in management training — that’s fair. But we’ve worked with thousands of leaders now and we have seen a lot of bad management. We have seen “under-equipped”, we have seen “got some pithy-but-terrible advice”, and we have seen “hated a past manager and ran to the other side of the boat, making all the opposite mistakes.” I’m not giving those people a pass — that still sucks.

When you give those people some objectivity and some skill, though. When you pull them out of the worst of their Dunning-Kruger effect, they listen. They make connections, and ask vulnerable questions. The number of leaders we’ve had say, in one of our programs, “Shit. I’m realizing now how I screwed some things up.” That’s hopeful for me.

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