After bootstrapping a company to profitability, being an early employee at a fast-scaling startup during the boom of 2020, working as a Chief of Staff and then COO to the executive coach that works with some of the most famous CEOs in the world, and branching off to form my own executive coaching practice (hi, thanks for being here!) — I'm often asked what my secret sauce is in being a hyper-competent, high-performing operator.
The secret is actually quite simple. Making constant investments in obsessing over small stuff separates world-class ones operators to just good ones.
Whether you're a Chief of Staff, operations generalist, executive assistant — if you're someone who aspires to be a COO one day, or you're someone who just wants to be a better operator, here are three stupidly easy things to do to separate yourself from the rest of the pack. I'm going to mostly be sharing examples from my Chief of Staff days, since I think they're the most fun to reminisce on and also illustrate my point the most on each of these three things.
Think deeply about end state.
Question you're asking yourself: “What needs to happen by the end of this project? What are some different ways to accomplish this project?”
Sometimes, operators are so caught up in their own workflows and checklists that they fail to think about the End State. This is a terrible mistake. If you don't think about the End State, you risk doing redundant work and therefore wasting precious time.
Instead of treating yourself like a dummy automation that must execute from beginning to end, think instead what the ideal End State is. What has to be true at the end of the project for you to be thoroughly satisfied?
Here's a ridiculously easy example, but something I see happen quite often.
Task: Cancel a meeting for your exec.
- End state/definition of done: the meeting is successfully canceled. Your exec has reclaimed their time. You haven't pissed off any key relationships.
- Your initial plan: You initially intend to send an email to the meeting stakeholder to apologetically cancel the meeting on behalf of your exec.
- In actuality: The stakeholder ends up emailing you before you email them, because it turns out they also want to cancel the session.
...aha! Hopefully, if you're following along, you now know there is no longer a need to send an email cancelling, or even sharing with the stakeholder your original intention was to also cancel. You are now able to pivot strategy and instead thank them for letting you know, and confirming the cancellation.
Don't be the operational monkey that still sends out an email anyway to cancel after someone else has already canceled! This happens too often. Think critically!
I know the example above was an easy one, but you can apply it to pretty much anything else. End State is one of the most important things every good operator thinks of. What does it look like in the end? This also ties into your exec's goals, which I've written about before here.
Back when I was chief of staff, Matt always had a million ideas of what he wanted to build or launch. If you're an operator and you work with a CEO, your CEO is probably like that, too. In the beginning, I felt a lot of pressure to bring all of Matt's ideas to life! But really quickly, I realized that this was just an example of shiny object syndrome: Matt liked having ideas, he liked saying them out loud, and just as quickly, he would forget he ever told me about the idea. So by the time I'd constructed a plan on how to bring Matt's idea to life and told him what my intention was to make it happen, he'd already moved onto the next idea.
How does this relate to End State? Well, if you are thinking about End State, you aren't thinking only about End State for each task or project; you're thinking about what the CEO actually wants in the very end when the company is hugely successful and business is booming.
Matt moving on quickly from his ideas taught me a very valuable lesson: it taught me to pause. I had to pause and think, "What would really make this company successful? Was this really in alignment with the goals he had for the company?"
Get the ball rolling to kickstart Fortius Ventures? Absolutely, this tied so clearly to his vision and goals! Opening a coworking space by his home so people could work nearby? Probably still fun, but less critical to what really mattered in the end (there was already plenty of space to invite people over to work, so purchasing a commercial building was certainly less urgent and much more expensive.)
Read emails - a lot.
Emails have a lot of context. Without context, you can never know what’s fully going on.
Additionally, emails are written communication. One of the quickest ways to learn how to think like another person is to see how they write and speak.
I was recently talking to another founder and was explaining to him that one of my biggest pet peeves was that though ChatGPT and other AI technologies have been amazingly useful, it still doesn't seem to be able to sound like me if I ask it to write an email pretending to be me. (This is also how you know I write each of these write-ups myself — as of 2024, ChatGPT still doesn't quite sound like me, so this is 100% me-written!) I lamented that though my assistant is quite good at drafting emails on my behalf (and certainly better than ChatGPT and Superhuman AI at it!), I still frequently have to go in and make corrections and edits before sending it out just to make sure it really sounds like Regina Gerbeaux, Executive Coach, actually wrote the email.
I then said to him, "I know it's sort of unreasonable, and I can't expect every operator to do this, but back when I was a Chief of Staff, I was obsessed with reading all of my exec's emails. Within the first week, I read as many of his emails as I could, to get up to speed on who was who, who was important in his life, who he had beef with, and which people he interacted with the most. I also used the emails to learn how he typed and what words he liked to use. It got to the point where if I wanted to draft an email in the sound of my exec, I knew I had to...
- Use the word "Therefore,..." at least once while explaining something
- Use double-spaces after each period
- Stay away from using semi-colons - he rarely used them, if ever
- Be less shy about using double exclamation marks after expressing gratitude (e.g.: "Thanks!!")
- Typed dates using dashes rather than slashes (e.g.: 11-21-24 instead of 11/21/24)
- Including spaces between ellipses (such as ... this example)
- Throw in something personal that would help the other person connect with him (e.g.: something about where he lived, a sports team they both liked, a place they liked to travel to, connections to any alma maters, relationships with mutual CEOs they both liked, something involving their family/kids/spouses, etc.)
I'm pretty sure if he were to read this list, he'd be only slightly freaked out that I identified his writing patterns this way. But this made me good at my job! By the end of my first month onboarding, I could triage 400 emails every morning and have three different drafts written for any requests he had received - a draft each if he wanted to say yes, another if he wanted to decline, and another if he needed more information.
When I explain this to founders, I usually get a blank stare, or a look of incredulousness. I have been called Regina AI several times. (I always take it as a compliment, for what it's worth.)
But the point is, you can't get to this level of operator ability if you're not reading emails and learning!
OK, here's a simple example:
In practice: Your exec has a bunch of meetings and you need to know what’s next.
- End state: You understand what the meeting was for, whom it was with, you’re aware of all communication that has happened leading up to and after the communication, and you assign action items for you and your client to do.
- Your plan: You go to your client’s inbox, search the person’s name, and read everything leading up to the call.
- You know you’re good when: You are able to say who the person is, what the purpose of the call is, how important the call is, and what your client hopes to give and gain out of the call. You know this so well, you’re able to essentially recap it to your client, without them ever having to tell you a single thing about the call. You essentially are a mindreader…through proxy of email. You could impersonate your client successfully.
Want to be a Top 1% operator? Get really, really good at building context through emails. Make yourself Operator AI.
Know your exec's calendar better than they do.
Calendars are the timekeepers for the most organized execs and operators. They just have so much crap to do, so it's the only thing that can wrangle them! You are an excellent operator if you can proactively anticipate what your exec needs.
I remember during my first week as a chief of staff, I was lost trying to figure out how exactly to onboard myself. (If you didn't know, I wrote the manual I wish I had here, so you can check that out.) On one hand, there was no manual, so I felt like a fish out of water. But on the other hand, I was completely, totally mortified at what I saw.
Logging into Matt's calendar, he had tons of double-booked — even triple-booked — coaching calls. I wanted to scream. How could this happen?!
So most of the emails I sent out my first month said something along the lines of...
Hi, my name is Regina and I'm Matt's new Chief of Staff. It's nice to meet you! (side note: yes, I had that saved as an Alfred snippet. I just typed ;intro and it would populate...because that's how often I was writing it!)
[insert apology about having to reschedule a double-booking happening in a couple of weeks; is there an EA or Chief of Staff I can work with to help move this to a time that works for both of you?]
Warmly,
Regina
The funniest part is, I don't think Matt ever knew that he had these double-books or triple-books. I just took care of it. It was clear to me that he hadn't quite yet figured out how to clone himself to be in multiple places at once, so we had no choice but to reschedule. And based on the emails I read, I knew which clients had tighter schedules (and also what timezone they were based in), and which ones would be easiest to move to make sure it worked for both parties.
My point is, if you want to be a great operator, look 1-4 weeks into the future to know what is on the docket for your exec. I did this perhaps a bit obsessively: each day, I would look at the upcoming week and notice any changes that had happened. I would look into the future weeks in case Matt decided to drop something in, like an HOA meeting or a haircut, that would inevitably interfere with his work schedule. And I would just take care of it.
I'd also use this as time to think about what else had to be updated. For example, until we hired an EA to support me and Matt on the administrative stuff, I was also generating all of Matt's meeting minute docs so we could all keep track of what he was teaching during any given coaching session. If I saw that a client got moved, I would immediately know I had to delete the erroneous document and generate a new one. I checked this literally every single day - because even though it only took five minutes of my time, it made sure the client experience was good and there would be no confusion on what doc anyone was using.
Here's your final example:
In practice: Your client is sick with COVID, and it is hitting them hard.
- End state: Your client is well-rested and focused 100% on healing. Everything on their plate has been successfully eliminated, delegated, or rescheduled. You are the captain of the ship, letting them know what has happened, who is taking over what, and giving them the peace of mind they need to recover quickly.
- EA’s plan:
- You find out your client is sick. You look at your client’s calendar. You proactively decide to reschedule as many of your client’s calls, knowing it will be impossible for them to take calls at 100% energy.
- You batch things into: reschedule, cancel, and take over.
- You know your client will want to reschedule anything work-related that results in income/revenue, like client calls. You email all these people and BCC your client, saying you must help them reschedule their call, and offer the soonest availability.
- For any social calls or calls that don’t have business-related ROI, you know it’s best to simply cancel the call to preserve your client’s energy. You cancel those calls by emailing them and apologizing for your client’s symptoms.
- For any emails, tasks, and to-do’s that you can take over, you take them onto your plate.
- Once all of these have been set in motion, you begin blocking off the calendar for your client to be OOO due to sickness, so they don’t have to worry mentally about any calendar events.
- You send a complete, thorough list to your client to inform them what you have done to clear their plate, with every call labeled as rescheduled, canceled, or delegated. You tell them to rest up/focus on their recovery.
- You know you’re good when: You know your client’s calendar better than they know their own calendar. You look ahead 1-2 weeks, even 4 weeks ahead, and resolve any booking issues. You think about whether they have all the documents or materials they need to take their calls (including links, researching who they’re meeting to send them information ahead of their call, understanding who every single person they talk to is.)
Summary
It's that simple:
- Think deeply about end state.
- Read a lot of emails to build context and also know how your exec writes, thinks, and makes decisions.
- Know their calendar better than they do.
These are the fundamental building blocks. Is there a lot more to master to be a great operator? Of course there is! But I think those are supplementary and built on top of this foundation. Why? Because if you don't nail these things, your exec will simply never trust you as much as they would if you were world-class at doing these things. These three things essentially turn you into an Operational Machine. Be an Operational Machine.
