“Today is your last day at Boost.”
June 24th, 2025.
At the time, it hurt. A lot.
In hindsight, it became one of the most clarifying and freeing moments of my career – one I’m deeply grateful for. I still champion that team to my network today. (LFG!)
That experience revealed a pattern I hadn’t yet named: I tend to grow quickly in the rooms I’m in.
Many organizations hire for the “above and beyond” candidate – the operator who brings structure, momentum, and sharper thinking. And when that person begins to expand the scope of what’s possible, one of two things happens:
✅ There’s alignment.
❌ There’s friction.
Not because anyone is wrong. It’s because growth requires shared appetite.
I’ve learned that sometimes what looks like a “glass ceiling” is actually a misalignment of ambition, pace, or long-term vision. Some companies are built to scale aggressively. Others are intentionally built to stay lean, steady, and founder-led.
There is nothing wrong with either.
Where tension creeps in is when expectations around growth, autonomy, and scope aren’t clearly defined at the outset.
Founders and GPs/MDs: if your company is designed to stay small, highly founder-controlled, or relationship-driven, great. Own that. That clarity is powerful. If upward mobility is limited or undefined, say so. If priorities will shift frequently, say that too.
Operating in ambiguity isn’t the issue.
Operating blindly (unspoken expectations) is.
So how do you avoid this misalignment?
Know what you want. Even if it’s evolving, communicate it early and often.
An EA or Chief of Staff can bring structure, prioritization, and operational lift, but they cannot sustainably execute against a vision that hasn’t been articulated.
Execution amplifies clarity. It can’t replace it.
Many EAs and CoS operate in environments where they are expected to “figure it out.” Sometimes that works beautifully. Other times it leads to frustration on both sides when outcomes don’t match unstated expectations.
The most effective founder–operator relationships I’ve seen share a few traits:
🔁 Direct feedback loops
🫵 Explicit delegation
🙋🏻♀️ Clear decision rights
🫂 Psychological safety around hard conversations
Trust builds gradually. It’s not blind. It’s built through consistent delegation, honest dialogue, and follow-through.
And yes, it is hard to trust someone new with your dream. Especially if you’ve been burned before.
This year, I’ve been practicing something simple and uncomfortable: naming the tension out loud.
It sounds like this:
“I want to share feedback I’ve heard about your pitch from multiple VCs. Is there a structure or format that works best for you when receiving input? My goal is to amplify your strengths and support the outcome you’re aiming for. I want to set you up for success.”
Or:
“This might be a hard conversation. Before we dive in, can we align on what productive disagreement looks like for you? I want to make sure we’re solving for the same thing.”
Or:
“I’m missing some context that would help me execute at a higher level, and I don’t want to let you down. Can we align on priorities so I can focus my energy where it matters most?”
To my EAs, CoS, and Ops leaders: communicating this directly can change the trajectory of your career.
It can deepen trust.
It can clarify fit.
And yes, sometimes it reveals misalignment.
Before I walk into those conversations, I ask myself: if the outcome isn’t what I hope for, will I still respect myself for speaking up? Am I ok with a worst-case scenario?
Earlier in my career, I made assumptions. I projected my own ambition and pace onto leaders and organizations without fully validating whether that growth path was shared. I moved fast. I built aggressively. I filled gaps before confirming they needed to be filled.
Sometimes that created incredible momentum.
Sometimes it created tension.
Both were valuable teachers.
If you’re a founder still shaping what you want, that’s not a weakness. Early-stage vision is often pixelated before it becomes precise. The right operator doesn’t override that vision; they help sharpen it.
A strong EA or Chief of Staff can:
📈 Translate ideas into execution plans
📆 Create operating cadence
🔮 Clarify decision-making lanes
👩🏻💻 Reduce cognitive load so you can stay focused on high-leverage work
The goal isn’t control. It’s coherence. Speaking of…
Next week, I’ll share how I approach my first 30 days inside an organization: what I assess, what I prioritize, and where I intentionally wait before acting.
If you’re scaling faster than your systems, I offer fractional Chief of Staff support to help founders and GPs/MDs regain execution momentum. Drop me a line 👩🏻💻🦸🏻♀️