Leading Through the Messy Middle
A reset for new leaders who’ve been winging it and are ready to lead with more clarity, calm, and confidence.
A lot of new leaders are just trying to keep up.
The scope has doubled, but the support has yet to exist.
They’re starting to manage people, budget, and business (on top of all that, some are still doing the IC work they were doing before making the jump)
And with that comes more pressure and uncertainty.
They were great at their work. Got results and had even better feedback!
That’s what got them here in the first place.
But now, the job is different.
And most days, they’re just trying to figure it all out on the fly.
If you’ve ever thought any of the following:
“Am I doing this right?”
“Why does this feel so frickin' hard?”
“Everybody must hate me now!”
Know that you’re not alone.
And this workshop is for you.
This 90-minute session is for functional leads in product, UX, engineering, etc. who’ve stepped into their first leadership role
and are finding themselves:
overthinking every word
wondering if they’re being too direct or too vague
and trying to strategically insert a bathroom break in between their back-to-back meetings.
I’ve been there too.
I created product strategies that didn’t get buy in. But compliments for the cool deck!
I tried a process that I learned from a PM conference. I got pushback at best, escalations at worst.
I once shared a feedback with my direct report but I got told that they were feeling coerced into agreeing. That ended in tears (mine).
But I managed to turn all that around and by the time I left my leadership role I've done the following:
Created a strategy for a domain that the entire company ended up using
Doubled the size of my organization to 100+ cross-functional experts based in multiple countries
And turned my feedback around that by the time I left somebody said that I was the best manager they've ever had
And now I’m coaching new leaders who are going through challenges, helping them to stop pulling their hair out of their heads.
So this isn’t theory.
It’s built from real experiences, real fumbles, and real shifts.
And the kind of support I wish I had back when I first got the “Lead” title on Workday.
We’ll slow down just enough to:
Name what’s actually making things hard right now
Get clear on the kind of leadership you want to have
Define the steps that move you from where you are now to where you want to be
This isn’t a course. There are no frameworks to memorize, and we’re not doing lectures on leadership archetypes.
It’s a reset. To help you surface the strengths and instincts you already have—but haven’t had time to access while juggling all the fires.
So you can stop reacting, and start leading from a place that actually feels like you.
You’ll also be in good company.
This session will bring together thoughtful leaders who are in the same messy middle.
There’s power in realizing you’re not the only one thinking, “what the hell did I get myself into?”
We’ll be doing guided reflecting — so bring a notebook, a pen, and a little curiosity.
And after this session, I would love for you to walk away with new clarity, your own words to lead by, and a next step that actually makes sense to you.