Questions, Questions

If I ask you a question, it is because I want to know the answer.


“Sally, do you know who the attendees are for that meeting?” is a simple enough question. I’ve gotten these varieties of responses:

  1. No
  2. That’s not my department
  3. I can find out for you if you’d like me to
  4. I think it is Jim and Jeff, let me find out
  5. The attendees are Jim, Jeff and Christie

Of the above options, only one is acceptable. The first two are obviously not acceptable. In a professional environment, this lack of ownership and interest is wrong. Number three is slightly better but wastes my time – of course I want you to find out. That’s why I am asking you! Number four is getting closer but is still not quite right – in the time it took you to tell me that you were going to go find out, both of us are wasting time.

But when you tell me directly what I wanted to know, that’s a winner!

Please, please – when I ask you a question, do what you need to do to answer me with accuracy. I promise I’ll do the same for you.

Power-Up your emails: Organize your Thoughts to Get Attention

Dreadful. You open an email, read through some information, notice a question, read some more detail, hear a story about so-and-so, read another question, then the sender drifts over to a completely different topic, comes back to the original topic, and ends with a suggestion.

Just yesterday I tried again to tackle an email just like this that was two weeks old – it had settled into the bottom of my inbox because it simply was too long and it wasn’t clear what information was pertinent to me. The truth was that I didn’t have time to cull this poorly worded email. That’s the sender’s job! In response to my query about how much time would be needed from my executive to keynote a conference, the organizer responded with details about the number of people at the event, what kind of gifts they would be receiving, her concerns about whether they should have a stand-up or sit-down dinner, and on and on. She never even answered my question! It was agony to decipher this email and in the end, I still didn’t get the simple information I was requesting: “What do you need from me?”

Ineffective emails take too much time to read, have unclear action items and slow down the flow of work in an office. Follow these tips to make sure that your email gets you the results you want:

  • Consider Composition: Start with a quick highlight of pertinent information then move on to ask for what you need.
  • Keep emails brief! Follow this wonderful rule about writing: if you can remove a word (or phrase, or paragraph) and still keep your message the same, then do it! Initially, this might take some practice as it requires you to re-read what you’ve written. I promise you, this will get easier and you will become a more effective communicator.
  • Discuss only one subject per email. Please don’t try to “save time” by including more than one topic in an email. When I complete the action item, I want to file or delete your email. If there is more then one topic, then it means I have to keep re-reading the email to determine my action items.
  • Use formatting tools to help the reader process your email quickly: Use short paragraphs rather than long streams of content and use bullet points to highlight information. One of my favorites is to use parentheses (to relay information that is useful but not critical).

Use a Napkin

The other day, I stopped to meet some VIP guests who were waiting to meet my executive. I shook hands with them, smiled, welcomed them to our offices and told them that I hoped they enjoyed our small town. They assured me that they were having a wonderful visit and were very impressed with our organization. They thought we had a great culture, loved our facilities and were looking forward to meeting our CEO. Smiling and nodding, I assured them that he would be arriving shortly and then I turned to notice our staff member who was hosting them at their casual breakfast. He turned to greet me and I noticed that he had sugar completely coating his lips. I was so shocked and for a minute, wondered if there was some way I could politely let him know. It was so out of place at this business meeting and made him look rather unprofessional, if not completely childish. I wanted to point to my own mouth as if to say, “You’ve got a crumb on your lip” but it was too far gone – there was sugar everywhere!

I was shocked and wondered how this group of visiting gentlemen who run a billion-dollar company must view this scenario. I didn’t think it looked good. Manners matter, all the time. When you are eating, be sure to use a napkin. If you are at a restaurant, place your napkin on your lap before you eat anything. And then use that napkin! When you take a bite of food, think about what your face looks like and clean yourself up!

Say What? Transcribe Those Voice Mails

In my office environment, voicemails arrive in my email inbox as an audio message. Since not all of them demand a quick turnaround, they can end up cluttering my email. In order to tame these, I now quickly transcribe them so I can read what they pertain to. This is a huge time saver if I don’t have to keep playing the audio file to remind myself what these were.

  • Jane Smith
  • 555-123-4567
  • Head’s up about book project

You can do this for voicemail messages that arrive on your mobile as well. Simply open an email and send yourself the same message in a format that you can easily read later.

Do a Shitty Job

I’ve gotten thrown in the deep end this year. My executive’s responsibilities have ballooned and as a result, he’s leaning on me more and more. A lot of the things I’m being asked to do, I have no idea HOW to do. But time is of the essence and I simply don’t have time to fret and stress about the perfect way to go about doing things.  Among some of the things I’ve done this year: contact the governor’s office to request help for a business associate, diplomatically guide a senior executive in a new direction, summarize our executive team’s thoughts from a strategy session I did not attend, and lead a project in an area I was unfamiliar with. And in every single case, there was moment in which I was frozen. I’ve simply not done any of those things before! I don’t have wealth of experience that would inform me of the proper protocol. Further, my preferred method of doing things is with excellence, right out of the gate.

In these scenarios, though, I didn’t have that option. I didn’t have time to come up with my 10-point plan for success. Even worse, I didn’t have anyone I could call on for help. This is intense on-the-job training. Trial by fire!

This has led me to championing what I like to call: Do a Shitty Job. I can’t take all the credit for this approach through. It goes to Anne Lamott (I love her books – if you are not familiar with them, check her out!). In her book, Bird by Bird, she encourages would-be writers to pen a “shitty first draft.” She contends that there is power in just getting your work out there. Don’t let yourself be paralyzed by fear, thinking that you must have the perfect words in your head before you commit them to paper. Instead, write them down and trust that the creative process will allow time for you to clean things up and to make your ideas clear. In a similar vein, I am approaching my work with that same permission jump right in.

Now, let’s be clear. I am not setting out to do a crappy job. In my mind, that would be producing work that is flawed and unprofessional. In contrast, a shitty job means that I am bringing all the things I am good at to the table. The difference between a crappy job and a shitty one is that you are just not resting on your laurels until you feel like you can do it perfectly. When you do a shitty job, you trust that it will all work out. If there is a mistake, you can fix it. If there is ambiguity, you can trust your gut to guide you through .

Need to plan a 200-person party and have 6 weeks and $50,000 to accomplish this task? Take a deep breath, know you can get it done and just dive in. Use the tools you already have (agendas/timelines/your friend who’s a creative whiz) and get started!

There is freedom in this approach that translates when you are away from the office too. Worried that you aren’t quite sure how to handle your kids, crabby neighbor, grieving friend, stressed-out spouse? Just commit to doing a shitty job and take a step forward. There is incredible freedom in allowing yourself to be imperfect.

Now, let’s go out there and give it a shot!

Work/Life Balance

Balance. For a dedicated executive assistant, this can seem like a near-impossible goal. Quite likely, our work is always on our minds. For many, our work follows us home with requests via text, phone calls and emails. The separation between work hours and personal time is not clear. This is not the kind of job where you can walk away at the end of an 8 hour day and leave your work behind.

In the early days of my career, I got a unique text at 7:00AM. It was a picture of a pile of doggie doo. A senior executive had arrived at the office early on a Monday morning, saw the offensive mess and promptly let me, the executive assistant to the President and CEO, know that this was happening in the office. So while I continued to put on my makeup and get ready for the day, I contacted facilities to execute a rapid clean up. I was annoyed that this leader couldn’t take care of it on his own but even more so was captivated at this notion: my role was vital. I quickly realized that my position was a hub for all sorts of communication.

And now, years later, I still am viewed as the keeper of information.

“I know you are taking the day off, but…. Could you answer just this one quick question for me?” Sometimes these requests are overwhelming, other times I like feeling like I have the finger on the pulse of what’s going on in our company. My boss sometimes texts me at 5:00AM because that just so happens to be the time that he’s thought of something and wants to get it on my radar. There are days that I can take a 90 minute lunch but more often than not, I am balancing my salad on my keyboard, trying in vain not to splatter my shirt with vinaigrette. There are times when I am pressed to do more and to do it more quickly. At other times I have space to process and catch up.

Throughout it all, one thing is constant: I am the only one who can monitor what feels fair and equitable. I am the only one who knows when work feels like too much of an invasion of my personal life. I suppose you could say that balance is not so much a set of rules and guidelines but is rather keen attention inward: “How do I feel about my job today?”. Ideally, I am in a state of loving my job and am happy to go there. But when I start to feel stressed, overloaded, maxed out, and used up, I am the only one who can do anything to fix it. For me, a people person, connecting with others is key. If I get overwhelmed by some of the BS (banal silliness) generated by the demands of my job, I spend 5-10 minutes doing what’s really important to me. I’ll find someone to connect with, encourage them, and validate them right where they are. Acting my values and purpose centers me and makes me happy. It gives me a big boost to keep pushing through the stress.

I’d love to hear from you – what helps to keep you sane enough to juggle the complex demands of being a kick-ass executive assistant?

Get Real: We All Make Mistakes

The world of the executive assistant revolves around details. Our aim is to get every single one 100% correct. And not only that but we should be anticipating where things might go south and have a contingency plan (or two) up our sleeves. It goes something like this:

PLAN A: Perfection

PLAB B: Smooth transition to back to perfection

But let’s face it: try as we might, we will drop the ball. We are human. That plan on which you’d just spent weeks or maybe even months could fail and you could find yourself holding the short end of the stick. For me, it happened at 2:00AM – a text letting me know that my boss’s travel was disrupted because he didn’t have a required visa to exit the foreign country he was visiting with his family. Oh shit. I quickly shot out of bed, tried to remember how to put on pants and drove immediately to my office. I was gutted that I had let this slip through the cracks. But it wasn’t so much that it slipped through the cracks. In reality, it had never even occurred to me that he would need a visa. It was an oversight, an oversight that ended up being a huge pain in the ass for my manager.

But I’ve learned a few things about mistakes in my tenure of working as an assistant:

  • The fear of making a mistake is no excuse to keep from being bold. A good assistant needs to act, often with little information. You can’t let the fear that you might make the wrong decision keep you from moving forward. Not sure how to word an email or what to say in an uncomfortable call? It’s OK, just move forward (a good time to let yourself do a shitty job).
  • Use the lesson you learn from making that mistake to help you shore up your procedures. You better believe that ‘visa requirements’ is now on my travel checklist. There is no opportunity for me to forget this again as I don’t plan a single trip without referring to my checklist.
  • That mistake you made? It is not you. It is something you did. There is nothing to be gained from feeling like a failure and ruminating on how awful you feel. It is a good time to remember that your boss has made a bunch of mistakes on their way to the position they hold. They learned from experience and you will too.

I’m taking a page out of my boss’s playbook on this one. He’s a self-professed ‘life-long learner’ – to me, that just means that he’s agreed to keep on moving forward regardless of any setbacks along the way. I plan to do the same.