Learn How 2022 OfficeNinjas All-Star Leanne Bailey Got a Seat at the Table

Editor’s Note: OfficeNinjas All-Star Awards is part of Admin+ Month (April 4–29, 2022), a fully virtual celebration of captivating learning, global recognition, and joyful connection.

2022 OfficeNinjas All-Star Leanne Bailey has achieved something many Admin+ professionals aspire to in their careers: true partnership with her executive and the palpable confidence that comes with knowing her voice is welcomed, heard, and respected.

Leanne didn’t set out to be an Executive Assistant. In fact, she stumbled into the role when she returned to the workforce after raising her three children. While hers begins as the story of being in the right place at the right time, that can only get you so far. Leanne’s willingness to take risks — as well as the initiative to capitalize on every opportunity that came her way — led to her meeting the executive who would help her transform her career into one where she feels truly seen, valued, and empowered.

But Leanne isn’t content with knowing that she’s gained the respect of her teammates, colleagues, and company leadership. She also wants other Admin+ professionals to know that it’s possible for them, too — with the right strategies in place. One reason Leanne was especially thrilled to receive an OfficeNinjas All-Star Award? She believes this accolade is living proof that there IS recognition out there for Admins who may find themselves feeling unseen or undervalued. Leanne’s words of advice? “If this is what you want, you CAN attain it.”

Get ready to go up-close-and-personal with the determined and indefatigable Leanne Bailey. We’re delighted to honor her with a 2022 OfficeNinjas All-Star Award, and we can’t wait to share her inspiring story with you.

How long have you worked as an Admin+ professional? What path led you to this career, and what makes it a good fit for you?

I have been an Admin+ professional for more than 18 years now. My path was an interesting one. I started my career in a small, two-partner accounting firm here in Toronto before moving into the area of non-bank lending. I ran the Accounts Payable department while working towards my accounting designation.

Skip forward a few years and three kids later… and I found myself sitting on a board as a treasurer. In that capacity, I met a telecom CHRO who thought EA work would be right up my alley. That began my EA journey in telecom, of all places. From there, I moved to Lowe’s Canada, where I supported the President of the company.

That job was where I met my current CEO, who was a consultant at Lowe’s at the time. When he decided to leave for an SVP role at Canadian Tire, I went with him. After tons of hard work and dedication, he was named CEO of Canadian Tire in March of 2020.

Where does your drive come from? What keeps you motivated?

I work for an outstanding leader who respects the role EAs play and the amazing work dynamic we share. Our partnership is built on trust and respect. It is easy to stay motivated and have drive when you are respected and supported.

Our CHRO is also an excellent example of someone who keeps us driven and motivated. He encourages all Admins to feel like equals in the meeting room. He asks questions and listens to our answers, which allows us to add value to the conversation.

But it’s not only in the meeting room. You can also just pop into his office, tell him something that’s on your mind, and know that he’ll listen without judgment. That kind of understanding is rare and remarkable.

Another way I stay motivated is by listening to podcasts — specifically Brené Brown. Her work, along with her positive energy and truth, is very inspiring. Her book, Dare to Lead, really speaks to me.

The other motivational I’m currently listening to include Unf*ck Your Brain with Kara Loewentheil; Yoga Girl: Conversations from the Heart with Rachel Brathen; Unlocking Us with Brené Brown; and Super Soul with Oprah.

What are you most proud of outside of work?

My three outstanding children are what I’m most proud of! They have become thoughtful, caring, and kind humans who are happy.

I am a ballet dancer and teacher, which I love and am proud to have continued to nurture. I have danced since I was a little girl, and the stage is a freeing place for me. I love everything about ballet: going, dancing, and creating. There is a saying that I love: “If ballet was easy, they would have called it football!” Pink tutus and glitter are my jam!

I’ve also become a YogaFit instructor, which complements my love of dance and teaching. It also keeps me moving.

What’s a unique system you’ve followed that has accelerated your career goals?

One of the things we do is “map back” on the calendar when we look at our upcoming board meetings. Canadian Tire is a large organization with many entities and boards for each. When they meet, it is often for long periods of time — usually days in a row. As CEO, my exec sits on several boards, and he is tremendously busy.

So his chief of staff and I started putting all of his board meetings on the calendar and then assessing how much time he’d need to prepare and what documentation he’d need for each. Then, we’d identify where to carve out that time — whether it be 5 hours or 2 days. This process is incredibly time-consuming upfront, but it saves a lot of wasted time in the long run.

It also prevents you from disappointing people. For me, that’s one of the primary drivers of implementing this process. Our CEO has a lot of 1:1 meetings, and people really value these touchpoints with him. The last thing you want to do is cancel and move these meetings at the last minute, but that’s often what was happening. Our mapping back process alleviated a lot of that. In allowing us to help him honor his commitments, it also means we’re holding his personal brand to its highest measure.

This doesn’t mean I never have to move or cancel a meeting. Sometimes I’ll underestimate the time. Just this morning I realized that I had to juggle his calendar, but I always make sure to call people before I do it. I’ll say something like, “Listen, I’ve got to move this meeting. But it’s still going to happen.” This shows that we recognize that their time is just as valuable as his, and also I make sure they know that the meeting isn’t being moved because it’s not important, but because I’ve got to carve that time out somewhere.

Being accountable for the movement of meetings is critical. When you are accountable, people trust you. They know you’re not going to say you’ll reschedule, and then not do it.

“When COVID started, Leanne understood the severity of the situation and how critical her role was to help the new CEO steer this almost-100,000 employee organization through the crisis, all while working from home.

Leanne took charge, learning with no help from a successor how to navigate the office of the CEO and how to connect the dots between that office and the various stakeholders the corporation was dependent on, from board members to employees, dealers, and Investors. She put processes and procedures in place to help the CEO stay on top of all issues — including coordinating multiple daily senior executive touchpoints, the setup of technology in key stakeholders’ homes, becoming the first point of contact for board members and dealers, and coordinating daily disaster recovery efforts.

She galvanized a team of over 100 Admins around the organization to keep them connected and engaged in order to effectively support their leaders for the benefit of the overall corporation.” — Rachael Awe, Chief of Staff, Canadian Tire

One nominator shares that despite the many challenges you faced in your new role as EA to a new CEO at the start of the pandemic, your “confidence never wavered.” To what do you attribute your ability to maintain your confidence, while also serving as a “pillar of strength” for others?

“Fake it till you make it” comes to mind!

I always strive to give 100%, and I knew this was the most unique opportunity I would ever get to ensure that people felt supported and heard. It was such a unique time with so many uncertain moments, and I watched people really suffer over what to do. I wanted the team and my executive to know that no matter what, they could count on me.

I work best under pressure and I excel when things are most complicated. There were many moving parts, and I knew I could manage them — for myself and for everyone else, too.

You’re described in one nomination as a true “partner” to the CEO you support. What advice would you share with other Admin+ pros who aspire to be seen as partners?

The advice I share is this: stay curious, request a seat at the table, attend team meetings, sit in decision-making meetings, ask questions, and make a point to understand all the moving parts that go into a decision.

One way I do this is by reading the same business books as my executive does. The latest one is Going Horizontal by Samantha Slade. And I ask questions and work hard on understanding how everything ties back to strategy and leadership.

I also know that relationships are held up by trust and respect. I believe that is my true key to success. A primary focus of our strategy right now is moving toward a more horizontal base of working — a place where everybody is equally supported. Along with another one of our senior EAs, we’re working to create a path by which all Admins can feel heard.

I think this is one of the things that makes my partnership with my CEO so unique. There is never judgment. We listen and always try to understand. Like many things in life, even if you don’t fully understand something, try to accept it. My boss and I can respectfully disagree, and that’s okay. One example of this might be if I think he might not be seeing someone for who they are. We may argue and go back and forth on it, and even if what I say doesn’t change his decision, I know he’s hearing me, and that allows me to be my full self.

“From day one of our CEO’s tenure, Leanne has been his partner in managing the many challenges and opportunities that come along with running a large company through a pandemic. Over the past two years she has persevered in creating strong and trusted relationships with key stakeholders inside and outside the business – including all the business leaders across CTC, the Board of Directors and the Board’s Chair, vendors, and the analyst community.

Leanne has been a key team member in driving forward critical new initiatives for the organization, including an all-employee share out of the new enterprise strategy, a highly successful Investor Day, and multiple board meetings and engagements.

These initiatives have been a great success and Leanne has played an important role in each of them. Leanne’s dedication, passion, determination and perseverance are unmatched. She consistently ensures [our CEO] and his team are supported to deliver business results.” — Erin McFeetors, Executive Business Partner, Canadian Tire

Tell us about the craziest day you’ve ever experienced in your role.

The day my boss was appointed to the CEO position, I was filled with so much pride for his accomplishments. However, it was also the day after the World Health Organization (WHO) declared COVID a global pandemic.

We often joke that on that day we assumed we would stay home for just three weeks and then be back in the office. How could anyone have known then that it would be two years and things would STILL be so up in the air?

I remember sharing a celebratory toast with the Senior EAs in our little kitchen on the executive floor and wondering whether we should really be standing that close together. What made it crazy is that there was so much joy regarding his appointment on our team, but also so much uncertainty in the world. It was a year and a half until he had his full team in the same room together.

How do your employer and team members help you succeed?

Canadian Tire helps us succeed by providing us with the tools and the opportunity to be the best we can be. Our core values speak to us all and drive us to be there for our fellow Canadians. Even though we are an international retailer, our heart is truly Canadian.

We have an internal program called Triangle Learning Academy (TLA) which is designed to help employees learn about the business, because it is a unique business with a unique culture. Additionally, because it’s a big company, there’s always someone there who can help you succeed. A few years ago my boss was the primary speaker at a convention, and he was really into Prezi at the time. I wasn’t familiar with it, and it was really hard for me. But the great thing about Canadian Tire is everything I needed to learn was readily available. There were in-house resources and people to help me learn the skill I needed. Any idea my boss might come up with (and he comes up with ideas all the time), I know I’ll have the support to execute on it. And, again, that’s the great thing about Canadian Tire. We’re a giant ship.

The amazing group of EAs and Admins I work with helps me succeed by operating under a shared work ethic. Their support and trust in new learning initiatives is the best type of success.

“Leanne has the right combination of fearless determination to support her CEO while also ensuring that she is supporting the other EAs that work around her. She is constantly seeking to do better in her role, as well as support the team of EAs she works with.” — Jane Nakamachi, Executive Business Partner, Canadian Tire

How do you help your employer and team members succeed?

Like all of my colleagues, I live by our company’s core values. I’m committed to leading by example to do my part to ensure that Canadian Tire succeeds.

I help the Admin team succeed by putting learning & development programs in place to help them be the best they can be. For example, I started a spotlight series within our dedicated Admin Alliance group that features different Admins from across the organization so we can learn more about each other.

Along with another senior EA, we also hold quarterly town halls. These are fun, inspirational, and empowering. We’ve incorporated an array of topics into the meeting — everything from talks about mental health during COVID to presentations about how a quarter-end or board meeting comes together. Because even though we might all touch these things, many of the junior admins don’t have the full exposure. So if they’re thinking of moving up, it’s helpful for them to be aware of the fact that there are certain times you can’t take a vacation — like during a big board meeting or other commitment.

I also started a new learning & development program launching later this year which will leverage what TLA does by supporting team members in acquiring and growing their skill sets in systems, business acumen, executive function, and writing skills. The goal is to build a strong bench of amazing Admins who are confident in their career path and its growth potential.

We’ve already gotten started with a speaker’s series and “lunch & learns,” during which all 100-plus team members come together to work on new systems for travel and expenses. The team is also working on detailed onboarding and offboarding documentation, which will ease the process and make it much more digestible for those who don’t do it often.

Although the concept for the learning & development program is mine, nothing is born in a bubble. I am so lucky to have an amazing team that works to help me bring these things to life.

Being honored with this All-Star Award will also help my team strive to do different things, knowing that there IS true recognition out there — and a whole world of Admins standing beside them. To know they can be recognized for the work they do is a powerful thing. If this is what they want, they can attain it!

“Leanne is passionate about helping others develop and grow in their careers. She is developing and leading a brand new learning & development program for the 100+ Administrators across the organization. She has great passion for the profession and identified a need for development opportunities for Administrators, so she has constructed a program and is working cross-functionally to develop the details and launch the program across CTC. The program incorporates skill development, mentorship opportunities, guest speakers, and recognition elements. Not only is she passionate about her own development, but she is a great advocate for the development of others.” — Erin McFeetors, Executive Business Partner, Canadian Tire

What’s your greatest professional achievement?

My greatest professional achievement to date is supporting our CEO. His drive to be the best leader he can be while staying grounded, humble, and sincere is something I watch and learn from. I am lucky to have worked with many great leaders throughout my career, but our CEO is truly the very best I’ve had the honor to work with.

Canadian Tire’s Women’s Leadership Network has an initiative called the SHERO Spotlight, which highlights females across the organization. I was selected to be the first SHERO Spotlight of 2021, and my CEO was asked to introduce me. He gave the impression that he wasn’t preparing for it, but I was wrong.

When the big day came and it was my CEOs turn to talk, he got up there and started telling some of our old stories, including one about how when we first met and he was still a consultant, he sat behind me in this tiny dark cubicle. He spoke to the fact that we’re absolutely a team, we supported each other professionally as well as through personal challenges we’ve been through over the years with our families, and how we’ve always both gone the extra mile through all of it. While I’d always known it on some level, during that speech I became much more aware that we don’t just work together; we’re friends. Hearing him say all of that meant so much to me. I was speechless.

You’ve dedicated yourself to being “the best in [your] field” with an ongoing commitment to professional development. What steps have you taken to prioritize your professional development while also balancing your immediate career and family commitments?

I work best when I am busiest, so making and carving out time is something I feel I do extremely well. My husband encourages me to run at full speed in my career, and he has always been there to manage the other moving parts of our lives. I am truly lucky and blessed to have him.

I think my professional development drive comes from wanting to be a true contributor in conversations and to add value wherever I can. My tip is always this: find what moves you, ask questions, and listen. Always listen. Then, take something new away from listening and learn about it.

When my CEO first assumed the role, I knew I needed to build up my business acumen, so I committed myself to asking a lot of questions around learning the cadence of the business — things like:

• What makes our company different?
• Why is our board so big?
• What makes a good director?
• How are we choosing directors?

Answering these questions helped me entrench myself and understand the upper level of the business. But also, it’s not for everyone.

We had one EA who’d been promoted to support one of our Senior VPs, but she wasn’t really loving it. She wanted to be doing more of the detailed work she’d been doing before. So I encouraged her to talk to her boss, and she ended up going back down to support at the VP level — because that was what moved her, and it’s where she really felt she was making a difference. It might have seemed like a step backward, but all of us actually applauded her for putting her hand up and saying, “You know what? This isn’t working for me.”

What’s one thing you’ve done that’s been the most impactful in advancing your career? Did you know at the time the significance of that move? Were there any risks involved?

When I was considering moving from Lowe’s to Canadian Tire to work with my current boss, I knew it would be very interesting and exciting. But there were risks, too: new place, new dynamic, a huge new pool of Admins, and being the new kid on the block. Canadian Tire has an amazing 100-year history, and while it’s an international company, our roots are very much Canadian. It is a very unique retail experience, and anything but a traditional one because we own so many other businesses.

Later when I moved jobs within the company when my boss was promoted to CEO, I experienced yet another form of culture shock. Even though I was moving within the company and technically doing the same role, it was like doing an entirely different job. It was absolutely the right thing to do and I wouldn’t trade it for anything. I might have said something different last week, though, because it’s also very challenging.

What’s the one thing that’s ALWAYS on your desk and why?

The one thing I have on my home desk and my office desk is a rose quartz, which has healing properties that:

• Encourage self-love and acceptance
• Heal emotional body
• Open the heart for giving and receiving love
• Relieve loneliness
• Release repressed emotional pain
• Offer inner peace
• Brighten one’s mood

Being an EA can be lonely at times. You need to stay confident and work through things — often on your own. The rose quartz helps me keep my feelings in balance.

“Leanne is the epitome of ‘All-Star.’ As mentioned above, her ability to remain calm and professional in any given situation is remarkable. She is strong yet empathetic, and she doesn’t shy away from tough conversations but would be the first one to offer kindness or a shoulder to cry on if one of her teammates needed it. Leanne is tough when the situation calls for it but plays just as hard as she works and can make us all laugh when we need it the most. She embodies everything that makes a great Executive Assistant even better and I am so proud to be a part of her team.” — Lori Guillot, Executive Assistant, Canadian Tire

What does the “Admin+” unifier represent to you?

The Admin+ unifier is so powerful and something that means so much to me. It is imperative that we all row this ship in the same direction for the good of the company and our sanity. I believe that kindness is contagious, and the Admin+ unifier captures the kindness within our community.

It is so important to me that our entire team knows that even though we all work in different parts of the business and have different reporting lines, we are unified in our common experiences, struggles, and goals. The Admin+ unifier encompasses the good, the bad, and all of the opportunities available to all of us. It doesn’t judge us or separate us; it brings us together as people who listen, try to understand, and want to help.

Share something that you used to believe about the Admin+ profession but you no longer believe.

When I first became an Admin, I believed that my opinion was not the right opinion, and that I would be judged for voicing my thoughts. The fear of rejection is real. But with experience and the right leadership, I have learned you can leverage this profession to launch any career you want. You have the unique opportunity to get to know many people from inside and outside the organization.

I have learned that whether I chose this career or it chose me, I always have a choice…and that is a pretty empowering feeling.

What’s the best (actionable) career advice you’ve ever received? Who shared it with you, and how have you used it in your career?

There are two things. One is, “The truth will set you free.” The other is, “They don’t hire pilots to land a plane in sunny weather. They hire pilots to land the plane in stormy weather and that’s what good pilots do. Be a pilot!” Staying calm and determined in times of stress or crisis makes you the best possible pilot, and getting information and help when you need it will set you free.

Leanne Bailey is an excellent example of grace under fire and perseverance through the most challenging of situations. We’re delighted to honor her commitment, steadfastness, and achievements with a 2022 OfficeNinjas All-Star Award!

We want to hear from YOU!

Take a few minutes to congratulate 2022 All-Star, Leanne Bailey, and share what her stories and insights mean to you. And if you have a question for Leanne, please include it with your comment.