Real Careers: James Sobczak

Exceptional EA showcases Real Careers, in which administrators from around the globe generously share the benefit of their experience. We’ve made virtual trips to 21 countries to date: Australia, Belgium, Brazil, Canada, England, Germany, Greece, Italy, Mauritius, the Netherlands, Nigeria, Northern Ireland, Norway, Republic of Ireland, Scotland, South Africa, Sweden, Turkey, Uganda, the USA and Wales.  Today, we make our first stop in Chicago, Illinois, to visit with James Sobczak.

James Sobczak is Executive Assistant to the Dean of Clinical Affairs and the Vice-President of Marketing & Communications at University of Chicago Medicine and the Biological Sciences. Here’s a look at his world.

Advance organisation

A typical work day starts the night before with an evening routine – I make my lunch, check the weather for the next day and lay out my outfit. I shower and shave the night before, thereby removing all the guesswork when I wake up the following morning. I tend to wake up at 6:30 a.m., put coffee on, and set up a “must-have” travel mug for the commute to work. All told, my commute is around 50 minutes: a seven- to 10-minute drive to the train station, and another 35-40 minutes by train to the University of Chicago campus.

What two or three musicians/composers are on your playlist for your commute? I tend to read on the train. If there is a rare day that I have to drive in, I’ll shuffle the playlist on my iPod, or I’ll listen to whatever CDs from my collection have grabbed my attention.

At the office 

Morning Routines: Another cup of coffee soon after I arrive is a given. I might spend a few minutes checking LinkedIn and sending birthday or anniversary greeting to people in my network, then I dig in to the day.

Primary Responsibilities: Calendar management is a huge slice of my responsibility list each day, as each of my executives has vastly different schedules and meeting loads. One of my executives has any number of contracts and professional agreements that come across his desk needing his signature. Keeping a running log of every document he needs to sign in order to track the documents and address questions/concerns about their status to various parties is part and parcel of my role. As another colleague and I work at the front of the office suite, she and I also share receptionist responsibilities throughout the day.

Each day is typical in that it’s a study in chaos theory, in that there are the exact same conditions in the office, yet subtle differences that make each day unique – there could be a Board of Trustees member or VIP alumni visiting; there could be faculty or staff recruitment going on; there could be a welcome or going-away party; there could be a day when many of the executives are off-site or at a retreat, and the assistants (myself included) hustle to get expense reports done and office supplies ordered and filing updated. Adapting to it and viewing it as “typical” is what we do.

How long is your work day? A typical work day is about eight hours for me.  I arrive at 8:00 a.m. and tend to leave at 5:30, after giving myself a half hour to wrap up stuff and lay out the following day.

IMG_9639What might be a typical lunch? While there are numerous options for food on campus, including a thriving food truck scene, it can get very pricey very quickly.  I’ll treat myself to lunch on a rare occasion, but I’m a chronic brown-bagger. More importantly, I ALWAYS get away from my desk. It’s not only just to eat in peace, as my desk is out in the open, but also for the disconnect from anything I was working on and approaching it fresh after a break.

Do you work from home in your “off” hours, or during your commute? I’m most fortunate that I don’t have to work during my off hours, either at home or on the train. I had a candid discussion with both my executives about this subject when I started working for them, as being in contact during off hours was standard for me at a prior organisation. While they themselves keep in contact, neither of them had such an expectation for me; in their mind, whatever was going on was not so earth-shattering that it couldn’t wait until the following day  If it was, they knew exactly how to find me. To date, that has been borne out. There have been some things that have caught me off guard when I arrive at the office, but nothing that couldn’t be handled.

Dealing with challenges

What is the most challenging aspect of your day or career? In fact, this is two questions, so I’ll answer the first one – answer two would be far too lengthy. The most challenging aspect of my day is my own time management. There are a number of instances when things I’m working on are all important and all need to be done soon. What needs to get done first is a best guess at times. In those instances I do have to split-screen my attention to encompass those tasks and, little by little, push them all forward throughout the day.

If all the world’s a stage, then this career is one of the greatest character roles – and one of the greatest sources of improv

What do you most enjoy about your career? I must confess I enjoy the inherent theatricality of my career and my profession.  If “all the world is a stage”, then my career is one of the greatest character roles I have ever had, and one of the greatest sources of improv in which I could participate.  Finding that theatre aspect in my work every day keeps me coming back to work, and keeps me happy when I’m there.

On saying “No”

I never just come out and say “no”.  For any executive assistant, such a thing is difficult to do, and it shows lack of diplomacy, which is a tool we have to utilise every day.  I remember hearing or reading somewhere that assistants have very specific customers – their executives. Those are the people to whom they say “yes”, but also from whom they get guidance on what they need to do every day and whether the asks from other people really fit in to the plan. A variation of “not right now”, along with a legitimate reason why, tends to work well, I have found.

There are a number of ways to think about career growth; consider each carefully

James’ world

Map of worldI was born and raised in the United States, in the Chicagoland area, and I have lived here all my life. At heart, are you a city guy or small community person (city mouse/country mouse)? While I love where I live, I think, deep down, I’m a small community person.

How do you like to spend your time outside the office? I like to go for walks, and I am a voracious reader. I have a wife and two children, so I’m focused there as well. I also attend some networking events when they come up.

How do you pamper or reward yourself after a tough day or week? I like to treat myself to a really spectacular cup of coffee as a reward, or occasionally a magazine I don’t get very often – American Bungalow, Fast Company, WIRED, Arts & Crafts Homes and the Revival or Dwell come immediately to mind.  I’ll also occasionally buy myself an MP3 of a song that I have heard on the radio or Pandora and really want to get.

What song or two are we likely to find you singing along to when driving, or if no one’s listening? As I make it a point to sing at least one song all the way through every day, it could be one of hundreds of songs that I know, though I tend to pull from The Great American Songbook more often than not.  If I’m in the car, and I hear a song that I know, I’ll work on singing harmony parts.

 A dream holiday or travel adventure? Two come to mind:

  • Going back to Ireland, finding a small hotel or B&B in a quiet town far away from Dublin, and living like a local for at least two weeks
  • Riding Prestige [First] Class service on The Canadian from Toronto to Vancouver, and then back
Education and professional development

How have education and/or professional development supported your career development? An interesting question. As I went to school for radio broadcasting, and I have professional “past lives” in radio, high-end retail, theatre, and the trade show/convention industry, I find I have this terrifically diverse background and, as a result, an equally diverse skill set that I can bring to bear every day in addition to the hard admin. skills.

Diplomacy: a tool we utilise every day

Peer and Professional Associations: I am a member of the International Association of Administrative Professionals (IAAP), the oldest such association of its kind in the world. I joined in 2008. The association has helped connect me with like-minded professionals and has given me a base of solidarity, networking opportunities, education, and camaraderie that I had been lacking in my career. I have served in a local chapter, as its Vice-President and Corresponding Secretary.



Preferred form(s) of social media? Facebook for personal use, LinkedIn for professional purposes, and a bit of Pinterest for things that intrigue me

Style and substance

What are your go-to pieces from your wardrobe to ensure confidence on an important day in the workplace? I have a custom-made charcoal gray vest – a gift from a past executive – that turns most two-piece suits into three-piece suits, and adds verve to certain sport coat and slacks combinations.  I’m fortunate to have it.

Preferred cologne: While I don’t wear cologne very often, as I work in a mostly scent-free workplace, when I do, I wear Inis, a subtle his-and-hers cologne that my wife and I found when we were on our honeymoon in Ireland.  As my sense of smell is slightly acute, and other fragrances can REALLY put me off, I wear this exclusively.

What might we find in your desk drawer? My frequently consulted files

Each day is typical in that it’s a study in chaos theory;  adapting to it and viewing it as typical is what we do

Travel or travel planning advice? A few bits of advice in no particular order:

  • When you plug appointments into your executive’s calendar, be sure to put in the cross streets for the address in question. Not every structure has numbers readily visible, and a description like “on the NW corner of 35th & Madison” or, “on the East side of the street between Roosevelt & Sinclair” can make all the difference, especially if your executive is in a new city or perhaps doesn’t have a good sense of direction.
  • Plug in your executive’s outbound and return flights, with the departure and arrival time as the start and stop time on the appointment, into their calendar, and be sure to concisely plug as much flight information as possible into the Notes section of the appointment. Enter confirmation numbers, the terminal name or number, if you can, as well as the travel itinerary, including departure and arrival times, especially if travelling between time zones. Also enter a scan-able boarding pass bar code, in a standardised manner, for your executive to have on hand.
  • Proactively and regularly ask your executive about any travel; don’t wait for them to tell you. You want to be able to build the travel planning into your work pipeline, add place-holders to your executive’s calendar, and start running recon on airfare and hotel.
  • Don’t always rely on the hotel’s on-line reservation system. Track down the in-house reservation staff if you can, as they sometimes have rooms set aside that don’t/won’t show up online.
  • If your company has preferred customer/vendor agreements with certain hotels in your city, the possibility exists that a sister property might honour that same agreement if you phone the hotel directly. You can reference the agreement in your city, and ask if they will honour that agreement for your executive travelling to their city. You could get a “yes”.

Remember to live your life in balance – your work life, home life, and the “you” life; the thing that is uniquely yours

Inspirational reads?

  • The Elements of Style, by William Strunk, Jr. and E.B. White
  • Eat That Frog! by Brian Tracy
  • The Sherlock Holmes stories by Sir Arthur Conan Doyle

Role models or mentors? My best role models and mentors have been my father, who is still around, and my late maternal grandfather. Professionalism seemed part of their genetic make-up, and their work and work ethic were always high-caliber. They knew that the results of their work came not just from them but from the people who worked under them, and they gave credit where it was due. They had a genuinely friendly word for everyone, from other executives and peers, to the folks who emptied the trash every day. No disparaging word was ever spoken about them; their reputation and credibility were utterly above reproach. If I do the above half as well as they did, I will be a VERY successful man.

I would like to do more dedicated mentorship work, especially with men who are considering or starting in the profession

Tell us about a career accomplishment of which you’re particularly proud. In a past organisation, I was brought in to on-board a new Associate Vice-President, serve as his assistant, and basically start up the office. This new AVP was heading up a newly created department and so everything we did was, in a way, uncharted territory, as no one had ever done his job or my job before, and it was just the two of us. There was a lot to cover, and mistakes were made, but I learned so much in the process, and it all got done. We ran a fast, tight, nimble ship as a result. I’m really proud of that.

Do you have any career goals or accomplishments on your radar for the next five years? I’m very happy doing the work that I’m doing, where and for whom I’m doing it. I have found in my career that new opportunities tend to come my way rather than my seeking them out. Speaking generally, I would like to do more dedicated mentorship work, especially with men who are considering or just starting in the profession.

Lessons learned

If you could offer a new executive advice on how to best capitalise on having an assistant, and working together, what would that be? Remember that you have a lot of big stuff to think about – that’s why you’re there – and your assistant is there to think about the smaller stuff on your behalf in order to give you the bandwidth to do what you need to do every day.

Also remember that your assistant is a field agent working on your behalf, one who has amassed a staggering knowledge base about things both inside and outside the work enterprise, and that gives your assistant some insight and perspective. Tap into that insight and perspective; let them in on what’s on your plate in order to best help you; look for their feedback when applicable.  You never know…

What are a couple of valuable early conversation topics you recommend an assistant initiate when beginning work with a new executive/principal? Talk about time parameters right away, spelling out how available your executive wants/needs you to be, while also advocating for a proper life balance for you. More often than not, there is always an equitable middle ground.

Go through existing meetings that a predecessor (if applicable) attended and chaired, and discuss which to keep, alter, or eliminate.

Discuss the small stuff: preferred airlines, hotels, livery when applicable, favourite office supplies, food allergies, favourite coffee, and how s/he likes coffee/tea made, should they ask you make it, etc.

Discuss the personal stuff – birthdays, anniversaries, school events (if applicable), and what kind of help your executive might need in that regard.

Your most effective time management strategy? Take any task you have, plug it in to your calendar and set a time duration to keep you focused and on track to complete it.  To play it safe, jot the pertinent details down on a note pad in case your computer crashes.

IAAP: helped connect me with like-minded professionals and given a base of solidarity, networking opportunities, education, and camaraderie

Advice for a new parent working to the workplace? Remember to live your life in balance – your work life, your home life, and the “you” life, the thing that is uniquely yours [knitting, reading, baking, volunteering, whatever it may be].  Those three things, when balanced, will make for a whole you.  It will be very difficult, as you might think you have to scramble to catch up or over-perform to prove you can still do the job, or over-focus on your new child to the exclusion of conversation with a spouse or other children (if applicable) or connecting with friends and family.  It will take some time, but finding that balance will be very worth it.

Advice for new executives on how to best work with an assistant: Think of your assistant more as a collaborator than a subordinate. The best working relationships are when your assistant works with you, not for you. Encourage your assistant to continue to develop him/herself professionally through training, or a conference, if it can be afforded.

This profession is both a means AND an end, and an immensely satisfying and gratifying one at that

For those interested in promotion: There are a number of ways to think about career growth, whether it’s gaining more knowledge, insight and wisdom in your position, or shifting to a new position in a different area of the enterprise, or taking on a project as part of a department-wide or company-wide initiative that you would otherwise not be able to do. There could be promotions to senior-level or C-Suite assistant positions, and there could be promotions to the management track if that is what you wish.  Consider each carefully.

You also need to really consider what a promotion means to you, what kind of promotion you want, and whether you will be happy and fulfilled in the long run, both personally and professionally.

Don’t make the mistake of thinking about any kind of assistant position just as a means to an end to get some “better” job. This profession is both a means AND an end, and an immensely satisfying and gratifying one at that.


… and now, a note from Shelagh. Readers not familiar with some of the people and resources James referenced may be interested in checking the following links.

To explore a range of resources recommended by readers, click here for Exceptional EA’s Resources Page or click here to see all professional associations and networks recommended by peers.

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