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how to be a better assistant

a place to dump my unsolicited learnings and advice

Perhaps executive / personal assistants are better described as Chief Pattern Finders or Chief Energy Managers.

“you need an extension of yourself. i'll be your executive assistant.”

The above was about all it took to insert myself into one of the most difficult positions I'd ever taken on…

but really a lifestyle approach I decided to embrace. It launched me into a new life of learning what it's like to really “assist”, and with every learning came a new notch on the ladder of my expectations for anyone to follow suit [sorry 😬].

I'm not yet certain if the learnings have been a blessing or a curse.

In an attempt to work with founders I admired, I took on a role that was obviously needed and figured it would be a cake walk.

A cake walk it was not.

I kept messing up things like calendar appointments, tripping up on basic errors, questioning my entire academic background and intellectual being. Being someone’s assistant requires next level thoughtfulness and badassery. It’s also a thankless job, even for the most grateful of principals. You really have to view it as the chance to learn more than you could ever imagine, otherwise it's misery.

For me, it was a ton of painful fun. I quite enjoy fire-hose-to-the-face learnings and being a right-hand-woman felt cool to me. This was all exaggerated by how perplexingly interesting I found my principal to be, which made the role feel fun and exciting, even in its most hellish moments of stress, emotions, business turmoil. In this role, you really do have to genuinely enjoy your principal. If you don’t, run fast and far away. The down moments of the up-and-down journey won’t be worth it if you don’t actually like them.

I excitedly embarked on my own unhinged learning journey on how to level up. I asked a 4-session-long executive coach how she found her executive assistant to be, and how were they most helpful? I’ll never forget her response:

My EA knows what I need, before I even realize it. She even knows what I actually need, when I've communicated that I think I need something else.

Between this and reading Rosanne Badowski’s “Managing Up” book, I found this incredible. I quite enjoy being someone’s not-so-secret weapon, I'm a born collaborator and die-hard supporter. The book blew me away, too. While it was a bit out-dated – referencing things like using a highlighter pen to mark up faxes and some humor that is probably a little cringe – but despite all of that, the learnings were substantial.

In general, supporting smart + weird entrepreneurs is exciting as hell, and just as much so, terrifying. Stability feels laughable, and plans seem futile unless they’re shipped in the next 24 hours or so. I took my role seriously though, and it paid dividends.

Not only did it create an incredibly trusting + loyal friendships and what I imagine will be life-long camaraderie, we unlocked loads of possibilities with various business obstacles, created million dollar proof-of-concepts in months, destroyed substantial value with some spectacular f*ck-ups, and ultimately ended up hiring lots more employees from offshoots of ideas, entire departments, created companies, hired Presidents, fired executives, observed Boards, and loads more. And the best part is: none of this would have happened without the co-creation that resulted from defining these roles + responsibilities and the important of the role of a good EA.

the List:

I’ve kept this dumping-ground type list of anecdotes and learnings, and kept it from scenarios where I noticed and wanted to remind myself how I want to be, or from working with countless others.

Consider it a bit of tongue-in-cheek tips and tricks, with some cutting observations on what I personally think makes a good assistant, or rather, a better one.

• Everything is repeatable and everything must be retrievable. Just because you ordered something one time + on behalf of someone else, doesn’t mean you can discard that information. You need a rock-solid system to retrieve the minutia, for when your memory fails you. “Hey, what was the name of that one store where I bought that one thing?” “I’ve got it right here”.

• It doesn’t matter that you are dependable, it matters that you are dependable when it actually matters. Who cares if you are solid 9 through 5. If you aren’t dependable on the deadline of the eve of a big project, it doesn’t matter.

• “Is there anything else you need?” is actually the worst question. It places the entire burden on your principal to tell you what to do - basically, doing your job for you.

Preferred: here is what you need.

Or, if you’re learning, here is what I think you need, I hope I didn’t miss anything but please let me know feedback if I did

• If I’m training you, you either have to learn my system or prove yours is better

• You’ve already failed if you started with “I’m sorry but”. Find a way.

• If you see an event on the calendar that you aren’t sure about but don’t need to know about, don’t ask. Even though you are supposed to know everything, know where to be curious [and where not] and keep privacy matters separate. I often will ignore a new calendar put in by my principal unless I think it is in error, where I’ll then question.

• Exec assistant workings is just grabbing more and more of the end-to-end process from your principal after you’ve learned and have made right decisions. When I say end-to-end, I mean from:

idea —> research —> proposal —> execution —> payments —> calendaring —> other prep —> double checking —> documenting —> retrieving later.

A simple example is: “can you book me a haircut”:

Any regular person would just ask for the contact, call, and book.

Try this instead:

  • preempt when a hair cut is needed
  • propose a possible date for the cut
  • check the calendar for previous appointments so you don’t have to ask who did it last time
  • try to keep it around the same time of day or day of week, that probably works best
  • figure out how to pay ahead of time if possible
  • set up the next months haircut
  • put the drive time in the calendar, check it on google maps first
  • send a text to the stylist to ask for specific product or request a longer head massage if a stressful day

End-to-end process meaning the least amount of mental head-space from the principal, but delivering an even better experience

• Learning about your principal is most likely not a linear scale, especially if they are a high growth fluid person. You don’t reach Level 10 after reaching Level 9. The path is messy, and ebbs and flows with how in-tune you are. Stepping out-of-tune is not a bad thing, just shows a period of growth. Have grace around this and remain curious. I used to wear it like a badge of honor to know what my principal was going to say or think. It felt good, like winning a game… until I started losing / getting it wrong. Healthy second guessing can help, understanding that things can change is paramount, and checking in constantly is important as hell.

• Don’t interrupt me when I’m on the phone for your needs for my stuff I asked you about previously. Even if you, too, are on the phone.

• Let me give you a list, and then you thoughtfully take the time to think and then ask questions / take notes, batch all questions / blockers that come up (but first try to solve them on your own… in any way.

  • Missing payment? Pay yourself and request a Venmo from them
  • Need the telephone number or address? Check your phone or walk outside. Or find a piece of mail on the kitchen counter. And then organize the kitchen counter of sloppy mail while you’re there :)

• Don’t talk out loud when I’m working in front of you – remember that the goal is to set the experience. be mindful of noise pollution

• Be self-aware through your principal’s lens of energy leaks. The goal is not to be a suck on their energy, but rather, a creator of energy. If you’re not sure, ask. “Is it ok that I work on this over here? I know it’s making some noise - does that bother you?”

• Set up questions in a way that assumes the kindest / shyest of principals. Some principals aren’t comfortable being direct and asking for what they actually want.

• Preempt the possibility of building resentment, ask when in doubt but at a time that feels productive

• Don’t talk on speakerphone around me

• It’s important and helpful to know what’s within your scope as an assistant - comfort zones, preferences, skills. But it’s not ok to leave in a lurch. Not up for cleaning a bathtub? No problem! But please tell me how it’s going to get done / who / how much / when. Results are really all that matter here + other non-negotiables like privacy and care.

• As an assistant you are actually Chief Pattern Finder. You collect data. Inputs. Put them together in ways before your principal even notices. Document them for later.

• If you ask me for payments, give me the payment method. Don’t make me work harder to solve your ask, this is not a supportive dynamic.

• Care about the small details, they go a long way

• When a task is “research Conference X” - what does that mean to you? Let’s explore:

  • Google the actual event
  • Find out ticket prices
  • Find out satellite events + research important ones, organize them by location and recommendations
  • Find out flights
  • Find out lodging
  • Find out restaurants
  • Find out local experiences to the area
  • Put together an exciting example itinerary of everything coming together with photos and relevant info
  • Put together a summary that can be digested in 3 minutes or less, but has the ability to include more info if they want to read more
  • When you’re asked to figure out dinner plans:
    • Start researching, don’t ask what they like - research what’s the best in the area. Try to guess what time is the best. Book 5 reservations and cancel 4 when you have your answer. Think ahead. Be 10 steps ahead. Ask your friends for recommendations. Be resourceful. Don’t put the task back on the asker. Figure it out and figure it out better than they could

• Be prepared to fail and be prepared to figure it out the next time

• There is a huge chance your work isn’t going to be good enough. Make it a game to beat that expectation and understand where you missed the boat if you miss expectations.

• Don’t ask me a question that can be googled

• If I show you something, you have to document it well and store it for later / next time it comes up. its a fail to be shown twice

• if you aren’t getting asked to do stuff, it could be because your principal has lost confidence. try to address this head on and fire the confidence back up

• if your principal has to keep track of things themselves, your system isn’t good enough

• don’t pass on your stress

• before embarking on a task, make sure you already have all of the information you need. it will be frustrating for both parties to have to fire-drill in the moment

• your goal is to find the source of your principal’s stressors and anxiety, and line back for those where possible / meaningful.

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