Manager School February 2021: Better Questions, Better Thinking

📄 Articles: On Schedule, Questions, and Feedback

🛠  Maker’s Schedule, Managers Schedule (Paul Graham)

This is one of the most important articles ever written about people management, especially for knowledge work. Investor, Paul Graham, helps us understand why meetings are the bain of existence for non-managers. This is a critical read for those working with anyone who spends most of the day creating.

“Each type of schedule works fine by itself. Problems arise when they meet. Since most powerful people operate on the manager’s schedule, they’re in a position to make everyone resonate at their frequency if they want to. But the smarter ones restrain themselves if they know that some of the people working for them need long chunks of time to work in.”

10 simple questions that CHANGED my life (twitter thread)

Questions you need to consider, especially as a manager.

Some of my favorite questions:

  • Can you really control that?
  • Did you start today with a victory?
  • What are you optimizing for?
  • Are you reacting or responding?
  • Are you seeking the truth or just validating your beliefs?
  • If you want to be more successful, start asking better questions.

(found via Nat Eliason)

💬  Giving Critical Feedback Is Even Harder Remotely (HBR)

Critical feedback is hard in the best of circumstances. Remotely is becomes even trickier. You can’t influence the environment as well and it’s harder to read body language over video.

This suggestion was especially on point to ensure alignment walking out of a feedback conversation:

Save time at the end of the conversation to ask, “What are your top three takeaways?” It may feel redundant, but you’ll learn if they’re taking a negative nosedive, and if so, you can reframe the message.

🛠 Tools: On Better Thinking 

Mental Models are invaluable tools for managers. Untools is a new place to learn about thinking tools and frameworks that can help you in your work.

If you’re a fan of mental models, Farnam Street is another resource I highly recommend (especially their mental models roundup post).

⚡️ Tips: On Value Beyond Money 

2 Tips this month, both about how to think about value beyond the bottom line.

💸  Non-economic value is worth more than you think

At the end of your life, you won’t be thinking in economic terms. At work, it’s easy and natural to think and talk about the value of salary, benefits, costs, price, etc.

“Rarely today can people verbalize their values in any other terms than the economic.” (A Lesson from Medieval City Centers about How to Gain Career Fulfillment)

Not everything that matters is easy to measure. Knowing what you value and how that matches up with the culture of a new potential company/job is critical to fulfillment at work.

When it comes to motivating yourself and other people, take a few minutes on a regular basis to consider these questions:

1. What matters most in my career?
2. How could I remind myself/my team about why we do what we do more often? Do I have a daily, visual reminder of what I’m doing and why I’m doing it?
3. Am I celebrating the wins along the way? How could I share and celebrate more openly with others?

Also related is this story I shared on LinkedIn.

😁  The impact of attitude. This story was shared with me by Kim Chaplin (Talent Leader @ Cisco):

13 years ago I was promoted into a management role primarily because of the way I handled an organizational change that impacted me personally.

The software company I was working for announced that they were moving their corporate HQ from San Jose, CA to Austin, TX. My role was identified as not moving to Austin and I was given notice that my job would be transitioned out. But the transition was really long – 6 months—so I wasn’t upset, I knew I had plenty of time to find another job.

The day that my manager told me, I happened to run into her manager, the SVP of HR, in the hallway. I acted like it was any other day and greeted him cheerfully. He went immediately to her office and questioned her – disbelieving that I was handling it so well!

A month later, they asked me to move to Austin, and 3 months after that, promoted me to manager.

I’ve told that story a hundred times to demonstrate what you said—“our attitude and approach has incredible influence over how work happens.”

That’s it for this month’s roundup!

In my work building Groove, I speak with a lot of people about how work happens. And there’s a consistent drumbeat of feedback:

  • being a manager is hard
  • management is often done poorly
  • companies don’t do enough to support new managers.

I started this roundup to equip and enable managers.

If you found this valuable and want to support the cause, please share the newsletter with fellow managers on Twitter, LinkedInFacebook, email, or on your company slack (

Also, join the Facebook community to learn with other managers.

Upward and Onward 

—Ryan Seamons


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