Jessica's Monthly Management Memo: August 2026


Hi Reader,

Let’s get to your Monthly Management Memo - as always with something bold, something new, something borrowed, and something to pursue.

πŸ”₯ Something Bold - Create a Feedback-is-Safe Culture
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I've been leading a lot of workshops this year on building a healthy feedback culture, the kind where people can actually say what's true to each other. And almost every time, nobody goes first until the manager does.

So if your team isn't there yet, go first. Just not the way most of us do it. Asking your team "How am I doing as a manager?" almost never gets you a real answer. There's something better to ask, and I made you a quick video about it.​

πŸ†• Something New - No Time to Think at Work?

​Society members can ask me a question anytime, in writing or by voice, and everyone in the membership gets to see all the Q&As (some folks stay anonymous, by request). This week someone asked, "I'm deeply overwhelmed at work right now with a couple of huge projects, and I feel like I don't even have time to think. I don't even know what I'm asking, but I'd love any tips!" I'm sharing it here in case it helps you, too:

Here's a thought experiment to see if you can free up a little space in a moment of overwhelm:
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If you knew you were going to be pretty out of commission with a migraine for four hours during your work hours sometime in the next week and a half, and you got to pick when that unfortunate situation would happen, where would you put it?
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Answer fast, you don't want to think about it too hard.
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Whatever you just picked is the thing you can probably skip.
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I like this one because we're all much better at "what would I miss" than at "what should I cut." Once something is on the calendar, it feels as important as everything else on there.
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Then you've got options. You can back out now β€” a plain "something came up, and I need to move this" is enough, and you don't owe anybody a dramatic reason. Or if it's one where it's trickier to back out in advance, hold the slot and send your regrets that morning, the way you would have if the migraine were real. Sometimes a little white lie is better than losing your mind, you know what I'm saying?

🀝🏼 Something Borrowed - When It's Time for Someone to Go
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This is a great toolkit for handling it when it's time for someone on your team to leave. I always advise managers: if you could press the "Easy Button" and one of your team members would tell you tomorrow that they just got their dream job and would be leaving in a few weeks, would you press it? If you would, then you probably need to move forward to help them find a different role, even though the Easy Button isn't actually a thing. It's a really hard thing to do, which is why this toolkit from Libby Fischer and Jess Skylar over at the Helia Collective is worth keeping.

πŸƒπŸΎβ€β™€οΈ Something to Pursue - Fall Fun​
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The new season can be an excuse to create a bit of joy with your team - whether it's a simple ice-breaker question about favorite fall activities; a treat left on desks with a fall theme of some sort (maybe a few of these or these?); apple cider served at a team meeting; or a team pumpkin carving afternoon scheduled for an upcoming date in October.

Last Month's Most-Clicked Management Memo Link: This article about how social change organizations are breaking the people who work in them.

Bring your team; I’ll bring my A-game. I love helping teams with workshops on productivity, team culture, and effectiveness at work. ​Find out more and book a free chat​ to see if I can be helpful to your organization.

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You can also find me on LinkedIn for daily tips.

Jessica Eastman Stewart, LLC is guided in our work by these values. We are a proud member of 1% for the Planet, committing at least 1% of all revenue annually to organizations working to protect our planet from the devastating impacts of climate change.

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Jessica Eastman Stewart, LLC, 2443 Fillmore St #380, Unit 4920 , San Francisco, CA 94115