Real Careers: Jacqui Prospero

Join me for today’s Real Careers interview with Jacqui Prospero of Ontario, Canada.

Jacqui Prospero CAP, OM is an executive – and virtual – personal assistant doing business as Your Problem Solver. Here’s a look at her world.

Early morning must haves

I’m an early (5:30 a.m.) riser, with some must haves: exercise three times a week, coffee every morning and time with my spouse and dog, too.

My commute is about 50 steps, including a flight of stairs … I’m a virtual executive personal assistant. My home office is in the basement of my home, but it’s not dingy – it’s quite bright with natural light to keep me going.

At the office

Primary Responsibilities: In two words, I solve problems – any problems. I help executives and organizations run more effectively. This includes completing small tasks, big projects, and everything in between.

It’s not a job; it’s a career

Morning Routines: I check email, Teams, texts and voicemail messages for information and directions that came in overnight. I adjust the day’s priorities accordingly, and – if required – notify clients of changes to deadlines or deliverables. 

How long is your work day? I traditionally work a 10-hour day; being available to executives who are in a crunch is important. However, having a boundary around that is just as important; I try to establish how best clients can get me …

  • Call me if you need me right now
  • Text me for something in the next hour Teams – about the same time frame
  • Email me for something you need today
  • … but I will let you know if there is a deadline I can’t meet

Given health risks associated with views that sitting is the new smoking, have you adopted any steps to support good health? My workspace is in the basement and, although there is a bathroom down here and room for a kettle or Keurig machine, I go upstairs for it all. That forces me to get more steps and more stairs in each day. I even count going out for the mail each day as an opportunity to be away from my desk.

I also try to take my laptop away from the desk and go stand in the kitchen at my island for an hour each day – it provides a different view and stretches my legs, too.

What might be a typical lunch? Ninety percent of the time I get away from my desk. Although it’s just upstairs to the kitchen, it’s time with my spouse (if they are home) and the dog and, of course, perhaps a personal phone call or errand.

Are you involved in any employee groups/teams independent of your role? One of my clients has a robust employee support program, and I’ve joined several groups – including the Asian Network (I have some friends in Asia and always want to learn more), the administrative group for the EAs at a global organization, IAAP, LinkedIn and Facebook groups, etc.

Inside the career

What is the most challenging aspect of your day or career? For my day, I believe it’s managing other peoples’ expectations; I don’t sit at my desk just “waiting to reply to them”. I have other responsibilities and clients.

For my career, I believe it’s helping people understand the value of someone with years of experience at my level – you pay for that experience (expertise).

I can do what I do for anyone, anywhere in the world, in any industry

What do you most enjoy about your career? The sheer variety of work; being an admin, for me, means that I can do what I do for anyone, anywhere in the world, in any industry. I have one catch; they have to use English as their primary language. I’ve worked in hospitality, environmental services, government, healthcare, high tech software, etc. Variety is the spice of this type of career.

On Saying “No”

It’s not often a NO; however, I do use the “I can’t help with xxx at this time, but have time tomorrow (or next week) and could tackle it then – can you wait?” approach.

Not everything is urgent, and helping people to prioritize is key. C level executives and business people need to know that if they give you something to do, you will get it done – on time, on budget, etc., and if you have questions, you will ask. Set that standard.

Working during a pandemic

Tell us about your experience with remote working during the COVID-19 pandemic. I began full time remote work in the late summer of 2019, about six months before the world went into work from home (WFH) mode.

Having a dedicated work space that was mine, and leaving it at the end of the day, were my initial challenges. Now, making sure I get up from my workspace and get exercise regularly have become key.

The benefits include having more time with my spouse and dog, along with the economic benefit of spending less money spent on gas, clothes and so on.   

How would you rate your productivity when working remotely? Remote work ebbs and flows, just like in the office. However, it has a more immediate feel to it. When a colleague “pings” you on Teams, there is that feeling of urgency when, in reality, sometimes it’s not urgent. We have just graduated from calling people to instant messaging.

Making the time to be productive and focused has evolved in the last year, as the rest of the working world has had to develop coping mechanisms to get that type of time to drive innovation. Calendar blocking can help with this. For example, an appointment to “spend time doing xxx” is likely to be kept, versus the “I’ll get to it later” approach to planning.

What would be your ideal work scenario once we settle in to new norms? In my role as a permanent virtual EA, I hope to get back to a bit of travel. Clients like to see me in person and it helps to build the rapport and business relationships on an even deeper level.

Jacqui received Canada’s 2019 Administrative Professional of the Year award

What’s been your biggest career lesson/takeaway from the COVID-19 pandemic? There are so many opportunities, not challenges; sometimes you just have to look in the non-traditional places or with people on the fringe of your network to find them. What’s been your biggest life lesson/takeaway from the COVID-19 pandemic? Spending time with family is something I miss; I always “tried” to make time for it, but now I realize how much of a priority it truly is to me, especially as my immediate family is at least four hours away.

How has the pandemic impacted your approach to professional development? Have you been attending webinars, and/or what other approach have you taken to professional growth at this point in time?  I’ve always been a lifelong learner and continue to do so. When not busy with client work or training to support client work, I ensure that I’m reading the latest industry information and networking on LinkedIn and of course other social media feeds.

Online webinars and conferences have always been a “thing”, they are just more popular now that everyone has had to adapt. It’s a good thing, in my mind, as it provides more opportunity to gain knowledge and experience in a more economical form – you just have to be more disciplined to benefit from it.

I continue to offer my support and help to anyone looking for a job; that one share or encouraging word can make all the difference

I continue to offer my support and help to anyone looking for a job; that one share or encouraging word can make all the difference in a job search. As a virtual EA, I sometimes have to turn down a client as I don’t have the bandwidth to take on the extra hours.

However, I always offer to work with them to get a good understanding of what they need and then put up notices on VA groups that I’m a member of – the potential client is thrilled to have someone help, and I likely got to help another admin. Do I get paid? No. I do get the satisfaction of helping someone else, and building a relationship that might be beneficial in the future.

Environmental sustainability

Individuals and employers are increasingly aware of the importance of taking steps to reduce our carbon footprintsWhat steps are underway within your workplace to reduce carbon footprints? I recycle paper waste and printer/photocopier ink cartridges. When it’s time to acquire a new printer, computer, monitor, phone, tablet or other hardware, I recycle the e-waste. 

I reduce energy consumption by having sensors for the office lights. When there’s no movement in a room for seven minutes, the lights turn off. I pay attention to heat and air conditioning usage, and have reduced the volume and types of materials printed on paper. When it comes to records and information management (RIM), I follow data usage and storage practices, including attention to the size of email threads, information duplication/storage practices and sustainable/green web hosting services.

Set your boundaries as to when you can/can’t be reached; others may struggle to respect them at first, but give them time

Please highlight some steps you take to reduce your carbon footprint in your personal life. Many of the same business initiatives – including recycling, energy consumption and RIM – also apply to my personal life. We utilize timers and sensors for lights to ensure that we are saving electricity, and unplug devices that aren’t needed. In addition, we compost in our area and in a year we likely put out only one to three “bags” of garbage for pickup;  we recycle and compost the rest of it.

Jacqui’s world

Map of worldI was born in York, Ontario; it used to be a suburb of Toronto. I currently live in Bellville, about two hours east of Toronto. At heart, are you a city mouse or a country mouse? I’m kind of a mix; having grown up and spent many early career years in Toronto, there are huge advantages to the city. You can get anything you want, including car repairs, dry cleaning, Chinese food or even large print jobs at 3:00 a.m. Having been in Belleville for over 15 years now, I will admit that I do love my open spaces.

I guess I can appreciate what both have to offer. However, am leaning towards the country; I just wish our wi fi was better.

How long have you been in this career?  I started in administration of some kind or another 20+ years ago and never really left. What started out as a “for now” role captured my interest and continues to drive me. What was your first such role? As a teenager, I worked in a Toronto office for Deerhurst Resorts, which is in the Muskoka region. This was my first introduction to a formal admin role in a structured office environment.

I follow data usage and storage practices, including attention to the size of email threads

How did you learn about the opportunity that led to your current role? Since I have clients – there are several right now – my primary client came to me via networking. A former colleague saw on LinkedIn that I was “open to work”, and reached out to see if I would support someone in high tech again, in another time zone. I jumped at the opportunity.

Most of my clients are referred by other clients, which is great – since these clients have an understanding of what I can do, and my commitment to their success.

How do you like to spend your time away from the office? I’m trying to spend more with family but, honestly, some of my (motorsports-related) clients give me great adventure and fun away from my “office” when I work for them at racetracks. It’s an invigorating environment.

How do you decompress or reward yourself after a tough day or week? I create quiet time when needed. A five kilometer walk without the dog usually does it; a good pace and some sweat always help. Rewarding myself can take a variety of forms, from a good meal with my spouse to 10 minutes playing with the dog.

Your ideal holiday or travel adventure? Honestly, travel anywhere is good. I didn’t start to travel (outside of family visits) until about 10 years ago, and I can say that I have loved my time in Europe and hope to do more of it in the coming years.

Education and professional development 

My formal education (early on) was not related to the field I work in. At the time, however, a post-secondary (college or university) degree was a requirements for many jobs, regardless of specialty. Mine happens to be a BA in Geography & Physical Education from York University; I originally planned to be a teacher.   

I’ve earned credentials in Special Event Management with Honours from Humber College, an Associate Degree of Applied Science, Administration at Madison Area Technical College, a Diploma in Health Care Management, Health Care Management Studies from Ontario Hospital Association (OHA), and studied Conflict and Alternative Dispute Resolution at University of Waterloo.

Jacqui holds a BA and has earned additional credentials, including one in Special Event Management

Peer and Professional Associations: I’m a member of International Association of Administrative Professionals (IAAP), and hold its CAP, OM (Certified Administrative Professional, with a specialization in Organizational Management) credential.

I was President of IAAP’s Meyers Creek Chapter from May 2013 to May 2015. How did this leadership role positively impact you and your career? Our Chapter was the last chartered IAAP chapter before IAAP shifted its governance structure from one of chapter input to one member, one vote – a good change for the association. In going through the process of garnering interest in a local chapter, chartering, running meetings and providing education opportunities for administrative professionals in this more rural part of the province, it allowed me to flex my event management skills and be more cognizant of multiple stakeholders who want results each month. I needed to be thoughtful of each member’s desire for a variety of education and of fundraising, negotiating and governance skills, including awareness of Robert’s Rules of Order.

I’m a member of International Association of Administrative Professionals (IAAP), and hold its CAP, OM credential

What are the primary means of communication for network members? Originally, it was email. Since the shift in governance, IAAP has become more active on social media – Facebook, Twitter, Instagram, YouTube and LinkedIn, etc.

Networking, inspiration and achievements

Describe any positive benefits your networking has had on your career. Networking has garnered me more invitations to jobs and clients than anything else. Through my association and certification with IAAP, many I chat with about “work” realize that I’m serious about what I do. It’s not a job; it’s a career.

IAAP provided me with support that allowed me to work with my employer to get all of the admins in our office (at the time) involved in the local chapter. It supported the drive for education, training and development, including the recognition that there was a cost to these opportunities and a tradeoff that benefited the company and its staff.

Tell us about a career accomplishment or two of which you’re particularly proud. I’ve had the opportunity in my recent VA career to literally work myself out of a job. Many wouldn’t see that as an accomplishment, but I do. I helped a company realize they didn’t need a full time administrative professional; what they needed better automated systems to help them achieve goals.  

Inspirational reads? Harvard Business Review is my favourite business magazine, and then there’s the book Grit by Angela Duckworth.

Networking has garnered me more invitations to jobs and clients than anything else

Recruitment is often competency-based, with competencies reflecting both behavioural (“soft” skills) and technical (“hard” skills) competencies. Tell us about your behavioural and technical competencies that are relevant to success in your current position. I’m  customer service-oriented, regardless of who the customer is, and good and solving problems small and large. In terms of technical competencies, it’s my drive for challenge; if I don’t know a program/software, I learn it. I find efficiencies through the use of technology.  

Role models or mentors? I’ve had a few. Rhonda Scharf and Lucy Brazier were instrumental in helping me take the leap to recognizing that what I was doing for one corporation I could do for many – that the need for change, growth, development and challenge could be found in not changing jobs, but in changing what I was doing – expanding and doing it on my own.

Have you received or been nominated for any performance awards, through either your employer or a professional association? I received Canada’s 2019 Administrative Professional of the Year award and was recognised with the 2003 and 2004 PeopleSoft (Canada) Outstanding Contributor awards.

I solve problems … I help executives and organizations run more effectively

What steps do you take when you recognise that you need to move beyond your comfort zone? Recognize the end result – the end goal. I ask myself how I can help solve that problem and, if it means I’m uncomfortable, then I’m learning. It’s a good thing. So both the client and I win.

What skill(s) development or enhancement have you targeted for the next year? I’m focusing on expanded HCM (Human Capital Management) software knowledge; this is software a client uses. I’m also planning further development of emotional intelligence.

Do you have any career goals or accomplishments on your radar for the next five years? These include becoming a mentor to other admins, and helping clients recognize the need for a business partner not just an admin.

The Digital Age

What are your preferred forms of social media? LinkedIn for professional networking, and Facebook for social purposes and for more sports-related customers

What apps do you make use of in your professional life? I use any app or software that will help to improve my communication with a client or their customers. I learned to work with WhatApp when supporting a client whose primary contacts are in the Caribbean, as they don’t use LinkedIn as commonly.

I also use Zoom, FaceTime, Teams, Chrome River, CR Snapshot (for taking pictures of receipts that will go directly into an expense system), Signal, Instagram, Twitter and Telegram, etc.

How have digital assistants and artificial intelligence (AI) impacted your role? They have become great assets for me in keeping lists, but in reality I type fast enough to quickly add something to an open list on Trello, Asana and so on.

Most of my clients are referred by other clients

What positive impact(s) do you think AI, digital assistants and the internet of things (IOT) will have on the assistant of 2025?  I’m hopeful that the technology will be more integrated into company software, like MS Office products. However, I do recognize that in order for AI or IOT to work most effectively, it must have access to the most accurate information – which can be a challenge at times.

What forms of professional development would you recommend to assistants who want to ensure their roles remain relevant and rewarding in this digital age? Keep learning; take online or in person training when you can. If given the opportunity to learn a new piece of software or an app, take it. Growing and developing both professionally and personally will benefit your career.

Make time for what is important – your career and education. Treat finding the money to do these things like your vacation account; put a small amount aside each month to ensure you can afford that conference or training you are interested in.

Travel Planning

Travel or travel planning recommendations? Plan ahead; know your traveller. Does that person prefer window seats, a special meal, and so on. Always have a Plan B.

What apps or programs do you or your clients find useful for travelling and expense tracking? These are specific to the client. One utilizes Chrome River for expenses; some use TripIt; one uses a travel agency for convenience.

Lessons Learned

You’re talking to a counterpart embarking on a job search. Briefly outline the approach you’d recommend. Take your time; update your LinkedIn profile and get networking. Update your resume and be ready to spend time customizing your resume and cover letter for each opportunity. Volume applications will eventually pay off, but is it what you want?

Give us one or two of your best strategies for job interviews. Research the company first; do as much of it as you can ahead of time. Who is the executive that you will directly support? Who are the other execs you might interact with? Search for other contacts who work at or have worked at the organization. Ask for honest conversations. Check out Glassdoor – but with a grain of salt.

What bit of insight would have been most helpful to you in the early stages of your career? If you aren’t getting what you need where you are – whether that is financially, professional challenges or otherwise – move on, but be honest about why you need to move on and give the company you are thinking about leaving the opportunity to keep you. Ask them to help you find that new role, responsibility or raise you are seeking.

I like to encourage the “text me” in the evening hours approach if you need something for a deliverable before 10:00 a.m. the next day

What advice might you offer a new parent returning to the workplace? Set your boundaries as to when you can/can’t be reached; others may struggle to respect them at first, but give them time. We all know that the Monday to Friday, 9:00 to 5:00 workplace is not a reality anymore and everyone is different. Help others see that you are available, but on your terms.

Be kind to yourself. It takes time to get back at it for both home and work responsibilities.

What are a couple of suggestions you’d offer that new assistant on the block, in terms of how to build effective business relationships within the office? Be open to discussion – about anything, especially any advice. Better yet – ask for advice, even if it’s just asking who the best lunch supplier is for the area!

Your most effective time management strategy? Time block the calendar – especially for personal items. If you have a primary executive you support, ensure that there is a clear understanding of how to get in touch with you to drive priorities. For example, call me on the phone if you need me NOW; text if you need me in the next 30 minutes; use Teams if you need me in the next hour; email me if you need me in the next 24 hours. Set boundaries.

I like to encourage the “text me” in the evening hours approach if you need something for a deliverable before 10:00 a.m. the next day. This gives me the opportunity to determine if I want to do it at night or early in the morning. At least I’m aware of it.

Areas of upcoming professional development focus: HCM (human capital management) software and emotional intelligence

What are a couple of valuable early conversation topics you recommend an assistant initiate when beginning work with a new executive/principal? Find time for casual conversations about each other. It’s hard to ask an exec to share some of their personal life, but be interested in it; offer to add their children’s or spouse’s schedules to their calendar to ensure they get family time. Be proactive about making sure they can meet commitments.

Trust is key. Share something and ask for the same; the more you know about each other, the better you’ll work together.

Have some stretch goals that will help to drive your behaviour and your career

Your thoughts on goal setting? It’s hard to do for admins, but use the SMART method – specific, measurable, attainable, relevant and time-bound – works. Have some “stretch” goals that will help to drive your behaviour and your career.

Feel free to ask others to help you set your goals. How about a goal setting chat with fellow admins at your organization? Everyone can benefit from talking through how to get the right goals.

On professional development: Treat finding the money to do these things like your vacation account; put a small amount aside each month

For those interested in promotion: Plan for training/education. If you can, put training in your yearly review with your supervisor. Make sure you know that the company will cover this and, if they won’t, make your own plan. Set aside money and time (vacations) if needed; how important is your career?

Be curious. If there is an event or meeting you feel you might learn something from, ask to join in. With your boss’ support, ask if you can be involved in other departments’ projects to help support your need for learning.

 About Shelagh and her Real Careers interviews

At the age of 21, Shelagh was a direct report to a COO. Within the same corporation, she became an editor and then a corporate trainer before a relocation and an eventual return to what became an almost 30-year assistant career. Wrapping up that career in 2018 after a decade in governance, Shelagh’s been a direct report to four CEOs and accountable to four board chairs. Now, she delivers quality training internationally. She speaks at conferences, works with corporate clients, facilitates retreats, and delivers webinars to diverse audiences of assistants who want to perform at a high level.

Shelagh launched her Real Careers series in 2015. She interviews assistants around the globe in order to showcase individuals and the career itself. This series and the questions Shelagh poses continue to evolve. In addition to providing interesting reads and diverse perspectives, these interviews can constitute a form of professional development, as readers can explore different approaches assistants take to building and maintaining successful careers.

To date, assistants in 27 countries to date have generously shared the benefit of their experience with Shelagh. Shelagh has also assembled international Real Careers panels to explore perspectives on career dynamics, issues and opportunities. To explore any of these Real Careers interviews, follow drop-down menus on this page as follows: Real Careers/Interviews … and then dive into interviews by country.

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