The “deep work” of assistance


It’s 7 pm on Valentine’s Day. I’m reading an email from Bossman and although he isn’t using the words “urgent” or “emergency,” I can feel his anxiety reaching straight through the phone and yanking on my shirt. Oh wait, that’s my four year old, trying to get me to stop looking at my phone.

My first instinct is to try to take care of this immediately since, knowing him as I do, I can tell he won’t be able to enjoy his evening until this is handled. But it’s bedtime for my kiddos and focusing on this is just not going to happen right now. I put the phone away, but as I’m bathing and brushing and PJing the munchkins, I’m sorting through the problem in my mind, and realizing I need more information in order to get it squared away.

Kids in bed, I pick up the phone again. It being Valentine’s Day, there’s a good chance Bossman is in the middle of a romantic dinner right now. But a stream of back-and-forth emails will A. take too long and B. likely result in miscommunication and mutual frustration.

Do I call? I ask myself.

I decide to trust my instincts. I call.

And within moments, the tension is broken and we are on track to get this handled quickly and to the satisfaction of all involved. The conversation takes all of five minutes, and we both get exactly what we need: I get control of the situation; he gets unburdened from it. I breathe a sigh of relief knowing I made the right call. As it were.

And as I sit down to take care of business, it occurs to me that I’ve just answered a question I was asking myself a few days back.

I was reading about deep work, which I will oversimplify here as work you could not train someone else to take over in less than two months.

Deep work is the creative, brain-intensive work that only you can do. And I started to wonder, as I read, what the “deep work” of an assistant really is.

So much of assistance is simply taking shallow work off of our exec’s plate, it’s easy to believe that we don’t have deep work of our own. But I realized that night how wrong-headed that is. Because although the task I ultimately took care of for Bossman (last-minute travel booking) was not particularly complicated, it would take far longer than two months to teach a new assistant how to:

  1. Recognize and properly interpret the subtle distress signals Bossman was sending.

  2. Know when to call, when to email, and when to just work with the info at hand.

  3. Compose a single question that will get all the needed info in five minutes or less.

  4. Send a clear and convincing “I got this” signal so Bossman can focus on other things.

  5. Take the wheel with confidence and steer with competence.

The deep work of assistance is relationship work.
  1. Learning an exec’s M.O. so you can fill in the gaps and patrol the blind spots.

  2. Getting inside the exec’s head, anticipating their needs, becoming so attuned to them that you come off as slightly psychic.

  3. Simultaneously staying outside of their head to help them prioritize objectively.

  4. Earning confidence in your expertise on the subject of this unique individual.

  5. Finding and pressing (and knowing when NOT to press) their motivational buttons.

  6. Building the kind of mutual trust that gives you access to, and the freedom to help with, your exec’s deep work.

  7. Mastering emotional transfer.

  8. Maintaining a sense of humor and positive attitude regardless of the circumstances.

All of this requires a lot of time and emotional investment. Unfortunately, it’s becoming more and more common for execs to go through multiple assistants rather than bonding with one over a long period of time. Which makes it very difficult for both parties to get to the point where they can do their best work together. And it makes it nearly impossible for either to experience the true benefit of the executive / assistant partnership.

And even when you do get the chance to work with someone long enough to really hit that partnership stride, the deep work of assistance often goes unnoticed and thus unappreciated. Being an assistant is a lot like being a parent. On the surface, much of what a parent does day-to-day is simple: a series of repetitive tasks such as cooking, cleaning, chauffeuring, etc. But that is only the shallow work. The deep work of parenting is learning and caring for each unique little soul, providing them with the specific set of tools they will need in order to succeed in life.

So it is with assistance. What we do on the surface is merely the tip of the iceberg. So although there are certain skills that are essential to success in this industry, I would argue that you will master those over time through sheer repetition, whether you want to or not. If you really want to make a meaningful impact as an executive assistant, focus on becoming an ideal partner for the unique exec with whom you find yourself paired, regardless of their level of awareness around that impact.

Live bravely, work deliberately, and eat good chocolate.

#challenge #portfolio #career #personaldevelopment #boundaries #relationship #boss #DirectCommunication

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