The Perils of Having an EA Schedule All Your Meetings

Feeling overwhelmed with meetings and calls? If you’re using an executive assistant to schedule everything, that may be the source of the problem. Execs heavily dependent on EA’s for scheduling can easily become over-scheduled with low priority appointments. For two possible reasons as I see it…

First, exec wants to say “No” but can’t. Busy people often know, deep down, that they don’t have time to do a random meeting or phone call. But they can’t say no because saying no to somebody will disappoint them and cause that person, at a subtle level, to dislike you in that moment. Most of us strongly desire to be liked. So replying “Sure” and handing the interaction off to an EA allows you to win social approval in the moment, and the interaction disappears into a magical scheduling queue. And then you get back to work. No social disappointment, no studying your calendar in the moment, no immediate cost.

Alternatively, exec wants to say “Yes” but it’s a momentary emotion. The exec genuinely believes the meeting request is worth doing in that moment. “Hey great to hear from you, it’s been a long time, yeah let’s definitely hang out soon!” The EA is immediately CC’d. But. If exec had only spent 2-3 minutes encountering logistical friction when trying to schedule it herself, she would realize that, upon reflection, the benefits do not outweigh the costs. If your desire to do something cannot withstand even the slightest amount of friction, it’s probably not something you actually want to do. I analogize this to seeing books for sale on Amazon. When I encounter a book on Amazon that looks interesting, I often want to buy it right away. Instead I add the book to my wish list. When I visit the book’s listing a day or two later, I oftentimes find myself less interested in buying it. The enthusiasm turned out to be temporary. Adding a little bit of friction to the buying process causes me to be more honest about my true interest level. Adding scheduling friction to your meeting requests has a similar effect.

To be clear, there are opportunities to get scheduling leverage out of an EA. For one, EA’s are great at helping you schedule internal meetings — regular calls or meetings with colleagues. EA’s also are great to introduce at Round 2 of the logistics ping pong game. What I tend to do when I say yes to an external meeting request is to personally offer a few times that work for me and see if I can just schedule it myself in one email. This helps me internalize the “cost” of the meeting as I’m saying yes — I’m having to spend a few minutes looking at my calendar, hunting for convenient open spaces, and offering those times in a message. If none of my times works and the thread turns into a ping pong game of dates and times, and I’m still motivated to do the meeting, and the status dynamics make sense (i.e. I won’t offend a higher status person who’s scheduling with me directly), I’ll hand it off to an EA to finalize the scheduling process on my behalf.

Bottom Line: EA’s can give execs leverage, especially around scheduling. But if not managed thoughtfully, an EA-only scheduling process can cause you to become quickly over-scheduled with appointments you would not, with full perspective, actually prioritize.

Stop Asking Busy People to “Catch Up” With You

“Don’t be transactional. Build genuine relationships. Play the long game. Don’t keep score. Give first.”

All good advice when building your professional network. The Start-up of You is full of these sorts of lines. But good advice taken to the extreme becomes bad advice.

Here’s how. Say you want to maintain a relationship with someone busy in your network. Heck, maybe you even have a specific question or favor to ask of that person. But you don’t want to seem transactional. After all, “authentic” relationships in business involve mutuality and back-and-forth and personal rapport. You don’t want to come off as having a transactional agenda. Right? Right.

So you ping this busy person in your network and ask if they want to “catch up” with you sometime for coffee: “It’d be great to see you and catch up on life. Let me know if you are around next week?”

Unless the person is already a pretty good friend of yours, the answer you often get back is… Crickets.

What happened? The random coffee catch-up meeting request is the most common “external” meeting request in the world, largely because so many of us have been trained to not seem overly transactional when we stay in touch with our network. So when we reach out to busy people, we bury our agenda and hide behind “coffee catch up” as the vague purpose of the meeting.

The problem is, busy people are busy. In fact, they get hit up for coffee catch-ups multiple times a week. They can’t take coffee catch-up meetings all day. They actually have to get real work done. So they avoid your request for random coffee.

What will catch their attention instead? A specific transaction or topic.

“I’m considering taking this job opportunity and would love your perspective.”

“I saw you on stage at a conference and had some feedback for you on the virtual reality topic you spoke about.”

“I’m hosting a conference in a month and would love to brainstorm who we should invite as speakers.”

Best case, this transaction intersects with something they’re actually interested in and would fine useful. Medium case, it lends a finite crispness to the interaction — it feels “manageable” — and the person is likely to agree to a quick call or meeting if he knows it can be quickly resolved. Worst case, the topic isn’t of interest to the person at all — in which case, didn’t you both just save time by realizing that on the front end?

Oftentimes, when reaching out to someone busy, you’ll have a specific transaction in mind plus an interest in just general catch up and general relationship building. In these cases, consider leading with a “transactional bluff.” Lead with the transactional item you have in mind, but know that you may spend 90% of the meeting — once you’re actually in the meeting — talking about whatever general catchup topics you want to cover. Maybe you spend the first 10% of the meeting on the transaction and then you switch to “How can I help you?” and the other practices that fuel long term relationships.

Bottom Line: Busy people need a reason to prioritize scheduling your “catch up” meeting. If you don’t know someone well already — this means most people in your professional network — be candid about a specific transaction you have in mind when making the meeting request.

Low-Pressure Requests for Intro

A friend asked me via email if I’d be open to introducing him to another busy friend of mine. He then wrote:

If you are willing, and feel you could recommend a meeting with sincerity, then I’d be most grateful for an introduction. And if you have the slightest hesitation, please do nothing. In my mind, the latter choice is the default, so please know I have zero expectations.

I really liked the way he put this. It feels very low pressure. I’m going to start using the phrase “If you have the slightest hesitation, please do nothing….please know I have zero expectations.”

Asking Acquaintances About Mutual Friends

All business is people business ultimately, and so improving your ability to size someone up should be a relentless priority — it is for me, anyway. By “size a person up” I mean figuring out how much you trust a person, how you can best collaborate with him, whether you’d hire her, whether you should fire him.

One of the simple ways I size a person up is by understanding how they understand and judge other people. In this way, I start to be build a model of the person I’m getting to know. I get to know their likes and dislikes, their biases, their underlying motivations, and of course their meta ability to evaluate people — all by hearing them talk about friends I know well.

Practically speaking, when I meet someone new, I like to ask them about someone we know in common. “So how do you know Jane?” Sure, it’s a trite question. But it can lead to a substantive exchange. It doesn’t have to be gossip. How has this person partnered with Jane? What’s frustrated him about Jane? What have been the delights?

When you ask someone to talk about their relationship with someone else, they often inadvertently reveal a lot about who they are.

At a breakfast meeting, I once asked an acquaintance — who I was also evaluating as a prospective business partner — to describe how he knew a mutual friend. As I probed, I realized this acquaintance spoke in condescending, patriarchal terms about a person who I very much considered his peer. It was revealing. I may not have gotten a glimpse at this element of his oversized ego if we had not gone down this path.

In another case, by talking about mutual friends I realized the person I was speaking to grasped subtleties about a friend’s personality that I had missed, and it made me all the more excited about partnering with him because of his extraordinary ability to make sense of at least one complicated person — and likely many others.

Bottom Line: Get to know someone new by asking him or her about someone you already know well.