Table of Contents

• Happy Mid-November!

• Upcoming Workshops & Cohorts

• The Illusion of Perfection (and Why Middle Manager …

  • The Data Is Clear—Middle Managers Feel the Least S …

  • What’s Driving the Silence?

    • 1. The Illusion of Perfection

    • 2. Structural Isolation

  • The Fix Isn’t Another Training. It’s a New Kind of …

  • For Organizations:

  • For Middle Managers:

  • One Last Thought

• 1% Solutions

• Things I’m Reading

Happy Mid-November!

I don’t know about you, but I feel like I am crawling to Thanksgiving. I knew that this was the trade-off for the mad sprint that I had planned these last 7 weeks but my body is starting to revolt (I am currently on the upswing after a brief and nasty cold).

And there have been some amazing things happening: (re)connecting with people, new clients, closing out a multi-week leadership cohort and hosting my first Maven course. But there’s been the downsides too— projects that weren’t the right fit, a rejection from a dream gig, and simply being tired (I am not 35 years old anymore!)

I’ve learned to think of work-life balance a bit more holistically (I personally prefer work life integration). There will not be balance every day or maybe every week. It may mean that you shut off early on a Thursday because you’ve been traveling Monday through Wednesday. It could also mean you’ve declared Sunday a complete potato day (which I have increasingly been doing). What are your stay sane tips when you’re in the madness?

Upcoming Workshops & Cohorts

Below are three opportunities for us to work together in the next few months, and one amazing opportunity led by a dear friend.

• You can’t write performance reviews on vibes or instinct- you need evidence to ground your review. This Thursday, 11/20 at 12pm EST, I’m hosting a free webinar on How to Audit Your Feedback (Before Reviews!) You’ll learn simple strategies to use now so you’re better prepared to deliver honest and unbiased reviews. Sign up is here.

• Performance reviews don’t have to be a scramble or a guessing game. In this two-day Sprint (Dec 9 & 11, with office hours the following week), I’ll walk you through how to organize your evidence, clarify your message, and write reviews that actually move people forward.I’ll share the tools, scripts, and AI prompts I use with my own clients—and you’ll have office hours to ask the questions you’re not asking anywhere else. If you want this review season to feel lighter, clearer, and way less lonely, join us. Email subscribers get a special discount using this link (but prices go up after 11/22)

• I’m leading my next Leading with Clarity cohort in February and then in April. If you are interested to get updates, sign up here.

And if you are a neurodivergent leader looking for support, I’d love to introduce you to my good friend and colleague in this work, Rita Ramakrishnan. She is a brilliant coach and fractional Chief People Officer who specializes in supporting neurodivergent leaders leverage their strengths, and she’s just launched a group program called the Neural Edge. It’s a leadership program designed specifically for Director+ neurodivergent executives who are ready to stop masking and start leading authentically.

6 months. 12 executives. 3 core components:
→ Personalized 1:1 coaching for your unique wiring
→ Industry-leading Hogan assessment with a full debrief ($2000 value)
→ Cohort learning with Director+ peers who think like you

If you are interested, email her at [email protected] 

The Illusion of Perfection (and Why Middle Managers Are Struggling in Silence)

I’ve loved cohorts since I attended Summer Principals Academy at Teachers College at Columbia— cohort 2, to be exact. (Still the best, in my humble opinion).

That program gave me my first real experience of what it means to grow in community—people united by values and frameworks, but wildly diverse in experience and perspective. We asked hard questions. We challenged each other. We normalized not having it all figured out.

That experience shaped how I see leadership today. Leadership isn’t about having all the answers. It’s about being in environments where you’re safe to figure things out. But that’s not the experience most managers are having today.

The Data Is Clear—Middle Managers Feel the Least Safe

A recent HBR article by Jan U. Hagen and Bin Zhao confirms something many of us have long suspected: Middle managers report lower psychological safety than both their bosses and their own teams.

That’s not an insignificant issue. Middle managers are the connective tissue of any organization. They translate vision into execution. They sense early problems and carry feedback both up and down the ladder.

So when they feel unsafe to speak up, ask for help, or admit mistakes—everyone loses.

What’s Driving the Silence?

Two major culprits stand out from the research—and I’ve seen both firsthand:

1. The Illusion of Perfection

The moment someone is promoted into middle management, the expectations shift. Suddenly, they're supposed to know, lead and deliver.

So when challenges come (and they always come), it feels like a personal failing.
They don’t ask for help—because they think they shouldn’t need it. They don’t name problems—because they think they should already have solutions. Slowly, performance replaces growth.

2. Structural Isolation

Frontline teams have their peers. Executives have their networks. But middle managers? Often, they’re navigating alone. They’re squeezed between the pressure from above and the urgency from below, with no safe place to reflect, troubleshoot, or even exhale. And for many that I’ve worked with, they are trying to care for their teams without having space for themselves.

This isolation isn’t just exhausting. It’s dangerous, because when learning disappears, stagnation follows.

The Fix Isn’t Another Training. It’s a New Kind of Space.

You don’t solve this with one off solutions. You solve it by creating environments where:

• Leaders can wrestle with hard questions out loud

• Mistakes are seen as part of the process, not a stain on your reputation

• Peer learning isn’t a perk—it’s the norm

Problems of practice, consultancy models and showcases are all examples of simple protocols you can use to create this space. It doesn’t have to be fancy or costly.

That’s also why I believe so deeply in cohort-based learning. Because it doesn’t just teach frameworks. It reminds leaders: You’re not broken. You’re growing.

For Organizations:

We must stop managers to lead in isolation. Create structures that normalize struggle and reward reflection. This can look like training senior leaders to run more effective 1:1s, and/or having regular manager trainings and facilitations.

For Middle Managers:

If it’s felt hard lately—you’re not the only one. This role is hard. That doesn’t mean you’re doing it wrong. It means you’re engaging fully in the work. Seek out peers both in and outside of your organization.

One Last Thought

If you’re serious about building stronger, safer, smarter leadership at the middle—start by making space where leaders don’t have to pretend. This sort of space can be the “scratch paper,” so to speak that allows them to execute more feffectively and authentically.

It’s not a luxury. It’s the system upgrade your organization needs.

👉 Hit reply and tell me—where have you seen the illusion of perfection show up in your work?

And if this landed, forward it to someone who needs to hear: You’re not alone.

1% Solutions

• Narrate decisions out loud- When you make a call, share your reasoning (“Here’s why we’re prioritizing X right now”). It builds transparency and teaches others how to think through tradeoffs.

• Recognize your team- 79% of employees who quit their jobs leave from a lack of recognition. And as we enter the holiday season in what has been a challenging year, recognition is even more important than normal. These don’t have to be long but should be specific. After all, what you praise will likely be repeated.

Things I’m Reading

• 14 Mistakes Leaders Make When Giving Feedback- This is a great article to review for yourself or to share with your midlevel leaders (if you have any). If you’ve been to any of my trainings or webinars, some won’t be a surprise. I personally loved the suggestion on identifying the Theory of Mind, and the questions shared to help guide you as a manager.

• Most Leaders Don’t Celebrate Their Wins- But They Should- As a leader, it can seem indulgent or selfish to celebrate one’s wins. But doing so anchors us, motivates us and helps us to stay resilient. This HBR article offers helpful advice on how to do so.