Reworkit with Jess Wass: Middle Manager Love and Podcasts
Published about 5 hours ago • 6 min read
Hi Reader,
TLDR:
Rewritten is officially live! The podcast I co-host with Teresa Sweeney just dropped its first two episodes. Links below.
My clients made it into Bloomberg. A few of them were interviewed as sources for a story on why companies are cutting middle managers in the AI era. I've got thoughts. Strong ones.
I recorded another podcast episode. This time on the other side of the mic as a guest, talking about what "having it all" actually means.
The Podcast is Live!
I met my friend Teresa Sweeney during a college visit weekend at Washington University in St. Louis.
You know the type. The person you immediately want in your group project because you know she's going to do her work, the slacker's work, and somehow make sure everyone gets an A. That was Teresa. Still is.
So when she came to me a few months ago and said she wanted to do a podcast together, I didn't really hesitate.
Not just because she's going to do most of the work (she will haha). But because she's someone I've admired for over 20 years, and she is genuinely one of a kind.
Positive energy, can-do attitude, the kind of cheerleader in your corner who makes you believe things are possible before you've figured out how. And it's infectious!
I've always been the friend with the sharp edges. The one who will say the thing out loud that everyone else is thinking but won't touch.
She appreciates that about me. I appreciate everything she brings. We are not the same person, and that's the whole point.
Because there are so many different kinds of working moms out there. So many different paths to honor your ambition and build a career that's actually yours.
Teresa stayed in corporate and figured out how to thrive on her own terms inside some of the most traditional industries, like finance. I left corporate and built Reworkit. We've made different choices at every major fork even though we started in the same place.
What better way to explore all of that than with someone you admire deeply and disagree with regularly?
Rewritten: Real Talk for Working Moms Who Want It Alljust launched this week. Honest conversations, specific stories, zero cheerleading content. (Well. Teresa brings the cheerleading. I bring the knife to cut through any BS. Between us, you're covered.)
If you're an ambitious working mom who's tired of being told to just hustle harder, this show is for you.
Two ways to be part of this community and conversation from the start:
1. Listen to the Podcast: We just dropped Episode 1 & 2. Check them out. Listen to them during your commute, your daily walk, or while doing the 15 million chores I know you're doing. Then reach out and tell us what you think!
2. Forward this to one person. The ambitious working mom in your life who would appreciate a real conversation over inspiration content. Word of mouth is how this grows, and we're counting on people like you to help spread it. We want to create a community of real talk with real ambitious women who are also real working mothers. Join us!
And if you listen, please reply back and let me know what you think. Your feedback will be instrumental to help us shape the future of this podcast and our content. We'd love to hear from you, truly!
My Clients Spoke to Bloomberg. Let's Talk About Middle Managers.
A reporter from Bloomberg reached out to me a few weeks ago working on a story about why companies are cutting middle management roles in the AI era. I connected him with a few of my clients as sources, and their voices and experiences ended up helping shape the piece. I can't say who, client confidentiality and all that, but I will say it's one of the things I'm quietly proud of: having the kind of relationships with reporters where they think of me when a story like this comes up. The piece is out now, you can read it here or read below for my recap and thoughts.
The short version of the story: companies are flattening. Average team sizes per manager have gone up significantly in the past couple years, and a lot of CEOs are betting AI can absorb the coordination work middle managers used to do, so why keep the layer at all.
Here's where I get genuinely fired up.
I know what it's like to be a middle manager. It's one of the hardest jobs in any company, because you're doing your own individual contributor work AND managing a team's worth of people. You're managing up to your boss, managing down to your reports, and getting squeezed from both directions at once. It's a lot. And it's exhausting in a way that's hard to explain to someone who hasn't done it.
So when I hear executives talk about cutting that layer because "AI can do it," I get a little offended on behalf of every overworked, underutilized middle manager out there. Because here's what I haven't seen any indication of: an AI bot that can do the actual human part of management.
AI can absolutely take the admin off a manager's plate. Scheduling, reporting, status updates, the stuff that eats hours and adds zero value. Great, take it. But AI can't:
Help a team member work through a problem by coaching them to the answer instead of just handing it over. Read the room when someone's struggling and needs support, not a deadline reminder. Advocate for someone internally when they're not in the room. Hand someone a stretch project because you see potential they haven't seen in themselves yet. Give feedback that actually helps a person grow. Sit with someone through a confusing org change and help them make sense of it. Make a human being feel seen, safe, and supported at work.
That's the job. That's actually the hard part of the job. And it's the part nobody seems to be accounting for when they talk about flattening the org chart.
And here's the part that really gets me: there's already a push to automate entry-level roles too. So I'll ask the question out loud that I don't think enough CEOs are asking themselves. If you remove entry-level roles AND middle management, how does anyone actually get from the bottom of your company to the top? You can't skip rungs on a ladder that doesn't exist anymore.
I stand with middle managers. Fully.
And if you're one of them reading this feeling a little anxious right now, here's my actual advice: don't wait for someone above you to decide what your role should look like in an AI-shaped company. Get ahead of it. Walk into that conversation with your own idea of how AI can take the lower-value work off your plate so you can spend more time on the parts of your job that are genuinely hard to replace. Be the one who proposes the shift. Don't let the decision get made about you instead of with you.
I Recorded Another Podcast Episode (This Time as the Guest)
A little fun, full-circle news. I just recorded an episode for Right There With You with Cass Cooper, the same Cass who originally recommended me to speak at WOTC West. It's always a good feeling when a relationship like that comes back around in a new way.
We talked about what "having it all" actually means, because I don't think it means what most people assume it means. We got into how to actually define what matters to you, instead of inheriting someone else's definition, and what tends to get in the way of people finding success in both their career and their personal life.
The episode isn't out yet, but I'll share it the second it drops. In the meantime, if you want to make sure you don't miss it, go ahead and follow the show now: