HFUIYM?

I read my fair share of business books, usually knocking out one every month or two. For the most part, I would describe the genre as helpful. Some books remind you of things you’ve learned; others spark a new idea or approach to something you’re stuck on. But every now and then, one of these books reframes your assumptions about what it means to lead and manage others. How F*cked Up is Your Management? is one of these books.

Written by the husband and wife team of Johnathan Nightingale and Melissa Nightingale, the book is a collection of essays from the couple’s co-pour blog. In that way, it’s not a linear treatise on how to do any particular thing, but more a pastiche of experiences, trials, and insights gleaned from years of managing in the trenches of tech.

The stories Johnathan and Melissa share are fresh, raw, experiential, and practical. It’s not necessarily easy reading — the subtitle is “An Uncomfortable Conversation About Modern Leadership” — but facing some of these conversations head on is the job of management. There’s so much in this book that’s worth reading, but for now, here are two of my favorite takeaways, one from Melissa, and one from Johnathan.

Melissa: “Obvious to you is not the same as obvious.”

“Lucky us,” Melissa writes. “We employ you. We benefit from you thinking about one area of our business in depth, be it product, marketing, design, recruiting, or something else entirely. We reap the reward of you having all the context that comes with sitting in your seat. But we don’t get any of the value of you having that full-time vantage point unless you share what you see.”

Isn’t this so obviously true?! And yet, this has confounded me time and time again as I’ve tried to communicate with my team. Our natural bias as humans is to assume others view the world in the way we do, that we can say it once, and move on. “I no longer find it surprising that faced with the same access to the same information, that several reasonably clever people draw radically different conclusions,” Melissa writes.

As a manager, it’s helpful to understand the layers of context you bring to your role. There’s the context of your tenure at the organization: the longer you’ve been at a company, the more your knowledge of the place and how it works settles into your subconscious and how you shape decisions. Then there’s the context you have through your access to others, from the meetings you attend to the relationships you have with leaders, fellow managers, members of other departments, and customers. There’s also the context of your life and career. After all, only you have lived through your past experiences and know what they have taught you.

This context shapes how you act. How you make decisions. How you know what levers to push and pull. How you get things done. But management is the act of doing through others. For your reports to have the same decision-making capability and autonomy, they need your context. As do your fellow managers. And your boss. A manager must share this context, again and again and again.

Johnathan: “A manager’s job is to maximize the investment the organization makes in her team.”

Johnathan begins “How to be a Better Leader in 4 Badly Drawn Charts” by parsing the difference between two models for success often held by new managers. The first model views relationships as the path to success; the second model focuses on results. Both models, Johnathan explains, are incomplete, which he highlights by reframing what it means to be a manager:

A manager’s job is to maximize the investment the organization makes in her team. A company hires people to do a thing. That’s an investment of time, money, and risk. The reason you’re allowed to exist is because we believe you’re going to help that investment pay off. That means we believe at least some of the following:

  • your team will do more work with you holding them accountable 📈
  • they’ll align their work better with other teams through stronger communication and coordination ❤
  • they’ll do higher quality work with you managing and mentoring them ❤📈
  • they’ll do more of the right work and less of the distracting work with you focusing their efforts 📈
  • they’ll elevate the kind of work they do with you helping them grow and develop ❤

As this list shows, great management requires a focus on both relationships (the ❤s) and results (the 📈s). But as managers, how do we cultivate both, especially if we are comfortable with one mode over the other? For instance, I’m cut from the relationships-oriented management model, and switching to an equally results-oriented mindset doesn’t match my style. Johnathan addresses this with the essay’s fourth and final chart:

In short, harness your style, but don’t go all in. Here’s Johnathan’s take: “If empathy is your strong suit, my advice is to pull yourself towards center, but not too far. Set high standards and be clear about them. Your natural ability to earn trust and respect gives you more permission than you think to be direct. … If you’re driven by results, my advice is to pull yourself towards center, but not too far. Check in with your team individually. Give them room to talk about something other than status updates. Once they realize they have room to do more than just run their list, they’ll give you insights you missed.”


These are only two of the lessons housed within How F*cked Up is Your Management? There are thirty-eight more. Consider picking up a copy, and happy managing.

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Originally published at Manager Companion.