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8 / Want to hire great people? Learn to build a bench.

October 30, 2022

This Issue at a Glance

  • Preamble: A request for feedback via this survey here.
  • Big Idea: Bench Building: Investing in relationships way ahead of job openings.

Welcome to Issue #8!

Now that I’m eight issues in, I’d love to get some feedback, so it would mean a lot of you’d take a few minutes to fill out this survey here.

Why it Matters: I believe that management is about listening. Listening to yourself, your team, and your customers. You, wise reader, are my customer, and I’d like to listen to you.

If it’s helpful, here’s some context on what I’m trying to do with Hoo Boy. In April and May of this year, I came up with three goals:

  1. Pick a topic that could compete with Netflix for my attention and win fairly often to write about for a year’s worth of newsletters. Done. The topic? Exploring bad vs. great management for founders.
  2. Inspired by Morgan Housel, I’m going to write about what I think is interesting in hopes that others will find that interesting, too.
  3. Grow the newsletter to a substantial enough audience that I won’t need any other channel to occasionally market any services or products I come up with over the next five years. I promise I’ll keep this to a minimum.

If you’re interested in how I chose the topic for Hoo Boy, I wrote about that here.

Some Numbers: The Hoo Boy audience is small but growing. I sent the first issue at the end of July to 132 people. Today, that number is 323. Averaged across all issues, Hoo Boy has an open rate of 59% and a click rate of 14%, which tells me subscribers might dig the newsletter.

In another six months or so, I’ll share another update.

In the meantime, the survey is here, and thanks in advance for taking the time to fill it out!

Big Idea #8: Bench Building

Great managers build relationships with talented people way ahead of having an open role. I call this “bench building.”

Why it Matters: Bench building is one of those important but not urgent activities that fall into a black hole only to emerge transformed into “recruiting and hiring,” red hot and urgent because, damn, we need this role filled yesterday!

  • If you haven’t built a bench for any roles you might make down the line, or in the event someone quits or is let go, you’ll be starting from scratch instead of giving yourself a head start.
  • Most people, especially talented people, at any given point, are not looking for jobs. They’re employed, and without having established a relationship, convincing them to leave their company and join yours is rarely something that happens inside the compressed window of the month or so between, “Carl just quit, now we need to replace him, and I guess I’ll fire up LinkedIn and see if we can find anyone to replace him.”
  • Great managers focus on retaining great people, but sometimes people quit for reasons they can’t control, and great managers know that. Maybe Greg’s quitting because his wife got her dream job in London, and the job can’t be done remote—that kind of stuff. Great managers build a bench of people they can call if a role opens up.

To put it all together, if you’re a CPO, VP of Product, or other Head of Product type, then direct reports are likely made up of product managers and designers, so it makes a hell of a lot of sense to make sure you’re always meeting PMs and designers well before someone leaves or you get new headcount to fill. And beyond your direct reports, you probably work with a lot of software engineers, so it probably can’t hurt to be building relationships with those folks, too.

The Bottom Line: It is a core part of every manager’s job to plan, anticipate what might happen, and be ready for it. If someone on your team quits and you don’t have several people you can call who you have been “keeping warm” on the bench, then you’re dropping the ball as a manager. Similarly, if you thought at the beginning of 2022, you might need a sales leader and didn’t immediately begin building relationships with sales leaders, that’s probably why you still have an open headcount for a sales leader today. And that’s not a license for you to shame yourself for not doing the thing, but rather an opportunity to learn a real lesson and level up.

Reads & Resources


One of the most common tactical subjects I speak with coaching clients about is hiring executives and managers as they begin to build a management team. This piece by Elad Gil (and an excerpt from his book, The High Growth Handbook) is a terrific (and short) list of what to keep in mind when hiring execs. And what does he advocate doing? A form of bench building! He calls it, “Define the role & meet with people who do it well.”

From Twitter

Josh shared this video of an interview with Simon Sinek. It’s a short video, so I won’t spoil it here. My favorite part is the last 35 seconds about why companies pay experienced people more than folks with less experience, “I pay them more for a skillset I hope we never have to use.”


I listened to this back in October of 2020 and just revisited it. The interview spans a wide range of subjects, but Jennifer covers a sort of “map” for human development called the “Constructive Development Framework.” WTF? Read my notes on the subject in Notion here. That framework is a foundation for a conversation on how leaders grow, adapt, and integrate their worldviews with others’. A quote that’s stuck with me ever since: “A great leader makes you feel better about yourself—bigger—when you are in the room with them.”


While this book isn’t explicitly about hiring, I keep this book within arms reach of my desk, so I can hold its bright yellow cover up to my camera when a client asks me whether they think I should hire someone or not. The author, Derek Sivers, is a master at writing one or two-page essays on a theme, similar to Seth Godin or Steven Pressfield. And while the title isn’t exactly nuanced, the book is full of nuances. My favorite part? Derek says there are three things to consider when making a “life-size decision”: (1) “what makes you happy,” (2) “what’s smart—meaning long-term good for you,” and (3) “what’s useful to others.”

Dice Roll

Tom makes Japanese-style handmade woodcut prints of California landscapes. The stuff is beautiful. We recently ordered one of Tom’s prints, and I wish I had an infinite budget to order more.

That’s all for this week. I’m looking forward to what’s next!