#1: Assess the situation
This is the first thing you’re taught to do as a lifeguard, something I’ve consistently held with me through all my endeavors since I was 18 years old (arguably before then, but that’s for another blog post). I’ve learned some valuable lessons since my lifeguard days at Menlo Swim & Sport, where the only phrase that came out of my mouth at full volume was “WAAAAAALK!” to the poor young souls just trying to canon ball into the deep end at Mach 10 speed.
🏊🏻♀️Lesson 1: A drowning man cannot save another drowning man – if you yourself (the lifeguard) get pulled in so deep that you’re not effective, you’re all under water.
One of the first things I do is assess via observation, take meticulous notes, and translate that into a running Google Doc of all my questions. As I ask the executive these questions, they are (1) answered, (2) put into an action section, or (3) put into a research / deep dive section. Categories become king.
Clarity first. Movement second.
Because motion without clarity is just expensive chaos.
#2: What did they do well?
At least in the SF Bay Area public education system, this is the first thing you’re taught to assess as a teacher. Back in the “old days” teachers would mark up your work with the dreaded red pen, scarring your soul and precious life’s work you spent…3 hours on.
As a former teacher, I was trained to first ask or assess:
What did they do well? What went right?
On a deeper level this digs into the patterns and behaviors that you as the right-hand can amplify to accelerate an executive’s success. What are their natural instincts? Where do they create momentum without trying? What rooms do they walk into and immediately shift the temperature?
How can specific actions, behaviors, routines, quirks, and even “ticks” be applied across the board to succeed in other areas?
Because here’s the truth no one says out loud:
🦾You don’t build a great operator by obsessing over their weaknesses. You build a great operator by weaponizing their strengths.
This will also come into play when you will inevitably cover up, compensate for, and even engineer around your executive’s weaknesses.
My “peeps” in the admin and Chief of Staff field know this burden well.
👁️🗨️ We see the dropped balls before they hit the floor.
🔜 We catch the tone shift in a room before anyone else clocks it.
🆘 We rewrite the email that would’ve started a small war.
At times, it can feel like “damned if you do, damned if you don’t.” Invisible when it works. Hyper-visible when it doesn’t.
But in the moments when we act as the silent partner and witness our exec power through a challenge that only we can see and guide them through – it is one of the most rewarding and powerful things we will ever do.
To know someone to their core – to know someone beyond themselves – is an incredible privilege. And it is significantly understated and underestimated work.
We do the kind of work where our execs believe they’re walking through a garden, when in reality they’re walking through a minefield you’ve already cleared ten times over.
And we don’t need applause. We need alignment.
#3: The basics – can you articulate what you actually do?
You’d be shocked how many leaders can’t clearly answer this, so I start simple.
If it’s a startup:
What is the business?
What is the vision?
What is the mission?
What is the business model?
How do you actually make money?
Who is the customer?
Why do they care?
Then I ask them to pitch me:
Pitch me as if I’m a VC.
Pitch me as if I’m your ideal customer.
If you can’t articulate it cleanly, your team definitely can’t execute it cleanly.
Clarity scales. Confusion compounds.
If it’s a VC firm:
What’s the thesis?
What’s the stage?
What’s the sector or sectors?
What are your check sizes?
What makes you meaningfully different?
Then I ask them to pitch me:
Pitch me as if I’m an LP deciding whether to trust you with my capital.
And then I ask as if a founder:
Besides your name and a check – what is your actual value?
Support? Introductions? Operational depth? Pattern recognition? Brand lift?
If you cannot articulate your value-add, you do not have one. You have a story.
And stories without structure do not survive hard markets.
#4: Ownership – who owns what?
This is where things quietly break.
Who owns revenue?
Who owns hiring?
Who owns investor communication?
Who owns culture?
Who owns follow-up?
And more importantly – who thinks they own it?
Lack of ownership is the silent killer of momentum.
When everything is shared, nothing is owned.
When nothing is owned, everything is delayed.
Efforts are duplicated towards the same task. Or efforts are not made at all, and that’s when the ball drops.
Clear lanes create speed.
Speed creates confidence.
Confidence creates trust.
But with this, don’t hear what I’m not saying. This doesn’t mean silo your team and shove the phrase “stay in your lane” down their throat. This means: delegate and collaborate on ownership, and share progress. Nothing builds a team and culture stronger than sharing and encouraging wins.
#5: Execution – what is repeatable vs. what is random?
Is this organization operating on systems… or charisma?
What is recurring and documented?
What is one-off and dependent on one person’s memory…or mood?
Are board updates templated?
Is hiring structured?
Is fundraising a strategy or a panic response?
Startups and VC firms alike fall into the trap of celebrating adrenaline.
Adrenaline is great until you come down, and sinking back to reality without systems in place to catch you, sucks.
If something works once, that’s luck.
If it works repeatedly, that’s a system, and ultimately systems provide freedom.
The goal is not to make the executive less powerful or shove them in an operational box.
The goal is to make the organization less fragile.
Because a company that only works when one person is “on” is not a company.
It’s a personality. It’s hype and noise.
When I step in as a fractional Chief of Staff, I’m not there to be reactive. I’m there to create structure strong enough that we don’t have to be reactive.
1️⃣ Assess.
2️⃣ Leverage strengths.
3️⃣ Clarify value.
4️⃣ Define ownership.
5️⃣ Systematize execution.
Put behind you intensity. Put before you consistency.
Respect is earned on difficult ground. And this – this initiation is perhaps the most difficult ground. Speaking of…
Next week, I’ll share how Executive Assistants, Operators, and Chiefs of Staff can build trust quickly with their executives when first being onboarded to a new company.
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 👩🏻💻🦸🏻♀️