💡 Note: For the sake of today’s post in order to reduce wordiness, I will refer to Ops Leaders as “Chiefs of Staff” since the original person asking the question was a Chief of Staff. Even if you are NOT a Chief of Staff by title, you can sub out “Chief of Staff” for any other Ops Leader title. The Playbook reads the same.)

Prerequisite: Swear confidentiality. 💡 

Let me start by saying this: in general, your exec should NOT be a part of any of these calls between the Chief of Staff and EA! If your exec is present, both of you will likely withhold valuable and vulnerable information you should ideally share with each other.

In fact, in the very beginning, the Chief of Staff and Executive Assistant should swear absolute secrecy for all contents they discuss with each other. Stories of vulnerability and of the exec should remain strictly between the two of them, never to be heard by the Exec themself or anyone else on the team.

Neither party should go to the Exec and say, “Did you know that ____ said this about you?” If this behavior happens, the Exec should take appropriate actions to punish the disclosing party for violating confidentiality - not the person who voiced the story.

Ideally, your fellow Operator will become someone in the trenches with you whom you feel total trust confiding in. Operational roles can be lonely! Use this as your opportunity to build camaraderie with someone else who gets it, firsthand.

What if I think the other Operator has bad intentions?

The only time this rule can be overruled is if either the Chief of Staff or the EA believe the other person does not have the Exec’s best interest at heart, and is maliciously acting to sabotage the Exec and the company.

Even then, the person informing the Exec should NEVER disclose the contents of what was said to them - as that would still be a violation of confidentiality. Instead, the operator should surface that there may be alignment issues, and continue monitoring the situation. You could say something like this:

“I’ve noticed some potential misalignment issues with [offending party] and feel concerned that decisions aren’t being made in the company’s best interest.” Then, include examples that you can point to of malicious behavior or weaponized incompetence.)

By sharing it in this manner, you avoid this devolving into he-said she-said hearsay.

Step One: Build Mutual Respect 💡 

A prerequisite to working well together is that the Chief of Staff and Executive Assistant must absolutely respect each other. There can be no effective collaboration if either party thinks they are more important than the other.

Two common pitfalls I’ve seen in the Chief of Staff/Executive Assistant dynamic:

• Executive Assistants may become resentful of Chiefs of Staff that get hired for seemingly more complex projects.

  • The fear narrative usually playing through the EA’s mind sounds something like this: "I've been with my exec for years, and now this Chief of Staff comes in with more responsibilities and automatically inherits trust that I've worked towards for years! What does this person know? They don't know the exec nearly as well as I do."

  • When the EA thinks this, it translates into their actions. Here is what the Chief of Staff reactively thinks: "This Executive Assistant is defensive. They don't like me and they're afraid I'm going to take away their job. I cannot work with this person, because they have a massive ego and think they run things around here!"

• Chiefs of Staff may treat Executive Assistants with contempt or behave condescendingly if they’re not careful.

  • The narrative based on contempt usually sounds something like this: “I’m a Chief of Staff, so my exec trusts no one more than they trust me. This executive assistant can be helpful, but only with a limited scope and to a limited extent. Otherwise, why are they ‘just’ an EA? They must be an EA because they don’t have what it takes to be a Chief of Staff. I’d better do the operational heavy lifting.”

  • When the Chief of Staff thinks this, it too translates into their actions. Here is what the Executive Assistant reactively thinks: “This Chief of Staff is arrogant! They think I’m dumb and less capable of an operator than them. I cannot work with this person and their huge ego, because they think they’re better than me for [insert a multitude of reasons, including but not limited to: going to the right university, getting the right degree, being older/more senior/younger/more nimble, etc. - yes, reader…I’ve heard a combo of all of these!]”

Operator - please do NOT fall for any of these narratives. They are based in fear and contempt, which are governed by our amygdalae. You do not want this part of your brain to control your actions - and to combat it, you must actively fight these narratives.

(For further reading, please see my write-up on the recipe for contempt here.)

To build mutual respect:

• Get to know each other 1-1 beyond our roles and responsibilities at your current company.

• Here are some questions you can ask each other to build authentic connection:

  • How do you think your work experience thus far has informed the kind of operator you are? Don't tell me only the success stories, but tell me about the times where you felt like you were going to die, or where things were an absolute shit show.

  • Who are the most important people in your life? Why do they matter to you?

  • If I really knew you, what would I know about you? What is something you don't usually want people to know? (CoS should share first and share one of their deepest professional fears. This disarms the EA's potential fear narrative that the CoS has a huge ego and is a know-it-all. EAs should share after, and they should also share a vulnerable story about how they got to the role they're in today. This helps disarm the CoS's potential contempt narrative that the EA is dumb or lazy or unambitious.)

  • What is something you're passionate about outside of work? Why does that light you up?

• Make each other feel heard and thank each other each time after they share something vulnerable with you.

If you share vulnerably in this manner, you are having a courageous conversation. Courage takes vulnerability, and it's very difficult to hate or distain someone who discloses information that takes courage to share.

Once you've established this foundation of mutual respect and understanding, you can move on to discussing how to best divide and conquer your responsibilities.

Step Two: Understand your exec’s delineation of responsibilities between both of you. 💡 

Sometimes, people think there is work that falls under “CoS” work versus “EA” work. While there are themes, there is no one-size-fits-all, as your responsibilities will depend on:

1. What your company needs

2. What your exec’s strengths and weaknesses are

3. What each of your Zones of Genius are

4. How much support each operator has

Here are the two most common groupings I observe between a Chief of Staff’s responsibilities, versus those of an EA’s:

Your collective action:

Each of you should write a list ahead of time of your perceived responsibilities. Then, during your next meeting, compare the lists. Where is there significant overlap? Which roles do you enjoy doing, and which ones do you not enjoy doing or feel less competent at?

Step Three: Discuss your exec’s biggest strengths and weaknesses. 💡 

Now that you’ve laid out what each of you believe you’re responsible for, talk about what you each think your Exec’s Zones of Genius are… and what their Zones of Incompetence are.

This should be a really fun part of the conversation to have, as both of you likely have similar observations. This is a time to share laughs and exchange stories.

This is not meant to be treated as gossip: this is a time for you to exchange valuable information with another Operator, so you can better understand your exec (and each other.)

Remember the strict confidentiality you swore as a prerequisite? This is one of the many reasons why. The more candidly you can speak off the books, the more likely you will enjoy this part of the conversation (and the more you will connect with the other operator.)

With each zone:

• For Zones of Genius, brainstorm: how can we amplify this?

• For Zones of Excellence, brainstorm: how can we delegate this so it doesn’t suck away time from Exec’s Zones of Genius?

• For Zones of Competence and Incompetence, brainstorm: how can you and I divide and conquer so we minimize and/or handle this altogether for our Exec?

Compile a list of action items to do, and present it to your Exec. Share:

“____ and I came up with this list together on where we believe your time is best spent. Here is our plan on getting you to focus on spending majority of your time doing the things you love, and we’ll handle the rest. What do you think?”

Your Exec will think two things:

1. They trust the two of you more, because you have demonstrated teamwork and collaboration.

2. They feel relief, because you are allowing them to do the work that really matters in the long run.

Step Four: Tag-team on your respective Zones of Genius. 💡 

Okay, you’ve sworn secrecy, established mutual respect, figured out each person’s delineation of responsibilities, and exchanged stories of your Exec’s strengths and weaknesses.

To be a true Force Multiplier, it’s time to tag-team in your respective Zones of Genius. Let me explain:

Even though both of you wear the Operator title, one of you might be good at sweating the small stuff while the other is great at orchestrating.

One of you might know the Exec a little more personally, while the other knows the Exec more professionally.

Divvy up your work accordingly! Who is best at doing what? Who loves doing what? And for anything you both can collaborate on: understand each others’ working styles.

If you’re an EA, do you do best when there are clear orders of priority given by the Chief of Staff?

If you’re a Chief of Staff, do you need the EA to unblock the Exec’s calendar for him or her so that he or she can help align the Exec on mission-critical priorities?

Want more operational content?

Check out Coaching Founder for over a dozen free, downloadable Notion templates to use at your company, and tons of write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.