Inspirational Leadership with Jess Jennings

I chatted with Jess Jennings who works as a Professional Development Specialist at University of Ottawa.

Jess told me a story about a time she accepted a role that was brand new. She told me it was exciting because she was going to be able to carve her own path in this new role that had never existed before, but that was also what made it a little bit scary. The mandate was fluid and though the role came with expectations and deliverables, how she got to those deliverables was undefined.

Luckily for Jess, she had an inspiring leader who trusted her ability to think critically, try things, and make decisions that she felt would be most beneficial for the organization – because at the end of the day that’s why she was hired!

She felt safe to experiment and think differently, and sometimes that didn’t work out, but sometimes it did and that was where magic was created.

The line that struck me the most while Jess was describing all this was, “He trusted me to do my job and he knew that there were many ways to answer the same question”

What I loved about that was, Jess found her leader to be inspiring NOT because he had the right answer, but because he DIDN’T.

He created a space of mutual trust. HE trusted Jess to do her job, and SHE trusted that he would be there to support her and encourage her to try-fail-learn.

This led to Jess feeling truly supported and inspired by her work. Jess attributes her ability to achieve some incredible things during her time in that role to this very inspiring leader.

Trust your team. As Jess says, that’s why they were hired!

Jess Jennings (she/her/elle) is a leader, collaborator, and lifelong learner, passionately helping youth grow their careers and develop new skills through meaningful experiential learning opportunities.

Currently, Jess holds the position of Professional Development Specialist in the Career Development and Experiential Learning Department at the University of Ottawa. Working directly with students in the CO-OP program, Jess provides career and professional development support services through one-on-one coaching and workshops to help students find meaningful work experience during their studies. Jess keeps Equity, Diversity, and Inclusion (EDI) at the center of everything she does. In her role at the University of Ottawa, Jess is co-lead of the EDI Committee in the Career Development and Experiential Learning Department, where she leads by example to drive awareness and provide education about EDI for the department’s employees and partners.

Previously, Jess held the role of National Program Lead for Early Talent Communities at RBC where she was responsible for strategically building and executing on a universal experience for over 2000 students annually from several different lines of business at RBC. Programs included opportunities for students to network with professionals and peers, participate in human-centric and technical skill building activities, and discover potential career paths at RBC. Jess played an integral role in the strategic creation and implementation of RBC Early Talent’s micro-credentialing pilot program where students earned official micro-credentials for the experiences and skills they developed while working at RBC. Jess also held a variety of other positions at RBC including Coordinator, Marketing and Corporate Citizenship where she supported community investment initiatives including the RBC Future Launch Program, RBC’s commitment to help young Canadians prepare for a drastically changing workforce.

Jess holds an Honours Bachelor of Arts degree with a Major in Communication and a Minor in Theatre from the University of Ottawa in the French Immersion Program. She also holds a Certificate in Social Media from Algonquin College. Originally from Peterborough, Ontario, Jess has lived in Ottawa since 2013. She enjoys exploring the National Capital Region, trying new restaurants and coffee shops, and spending time outdoors.

Sarah: Hello Jess, thank you so much for being here. I am so excited for this interview because I have been really, really fortunate to get to know Jess, actually work with Jess alongside her with some of the leadership development programs we’ve brought to organizations Jess has worked with. And I’ve seen her be the reason some people bring something outside of themselves, I didn’t even think they saw without you kind of seeing it in them first. I’m really excited to hear your definition of inspirational leadership, where you’ve seen that come to life. And so thank you so much for being here. And why don’t you start with, if you had to summarize what inspirational leadership is, how would you describe it?

Jess: I put a little bit of thought into this because I’ve worked for so many leaders with different styles before. Also recognizing that anybody can be a leader, whether you’re a people manager or not. But to me, inspiring leaders are humans first, but not just humans, but self-aware humans. It’s easy as a leader to fall into that boss stereotype where you’re managing the day-to-day rather than showing true leadership. So to me, inspiring leaders are authentic, they’re real. And they know that that’s the most powerful way to lead. But they also have trust in their teams to do their jobs. And I think that’s part of being self-aware. So even if the leader themselves is not an expert at the task at hand, a truly inspiring leader is not afraid to admit that they are learning and that they acknowledge their gaps and that they’re transparent about the things that matter to their team.
And that authenticity, that transparency builds trust ultimately with their employees. So that authentic bond that you create makes an employee feel supported, makes them feel connected to their work and ultimately helps them to achieve some really incredible things. Even if the employer, the boss, the team lead, whoever it is not 100% certain of what they need to do to achieve a task, if they are authentic, if they’re real, they acknowledge that and they hire the right people or they work with the right partners, that’s what makes inspiring is that they’re bringing in the right people, they acknowledge their gaps. So to me, it all comes down to being human and leading by example so that your team can feel like a human as well.

Sarah: I love that. Putting on a facade that you aren’t. To dig deeper into authentic. You did a really wonderful job of explaining that as understanding that you have more to learn or being open to learn I guess. What else is authentic, or maybe that is all that you see or that you would describe as authentic? Say a bit more about what authenticity would mean.

Jess: Yeah. So transparency is one thing. So talking about the information that you know and sharing what you can. The worst situation when you’re speaking with your leader is when you don’t feel like they’re telling you the full story or you feel like there’s something being held back because it’s hard to feel connected to what you’re doing when you don’t feel like you have enough information. So for a leader to be truly authentic and to be truly inspirational, they have to know when they can give as much information as possible and how that will help the work at the end of the day. So to me, authenticity is just always being open and being able to share and not feel like you need to hold back information to preserve, maybe it’s your own self-image or maybe it’s your own understanding of the work.
If you’re authentic, if you’re real, you know that there’s going to be gaps because we’re all humans. And I think that truly inspirational leaders know that they’re not always going to know the answer. And if you feel like you need to withhold that from someone to preserve your own self-image, then you’re not being authentic and you’re also not being a true leader because how is someone supposed to relate to you as a human and feel that inspiration from you if you’re not telling the full story?

Sarah: I love that. It’s almost like authenticity is showing all your cards, whether that is in the form of information you have or what you don’t have. That’s really, really well said, and I like that vision of authenticity. Now, because of your experience, I have no doubt you’ve seen what, whether it’s that definition or another because there’s so many definitions of inspirational leadership, whether it’s something tied back to that authenticity or something else. Where is a time where you’ve seen inspirational leadership in action? Walk us through that moment. What was happening? What were you thinking, and what was the result?

Jess: Yeah, for sure. So you’re right, I’ve worked with so many incredible people, it’s hard to pick one example. But I did some thinking about this, and I’ll pull in an example that you’re probably familiar with too. Before starting my current job at University of Ottawa, I had the really awesome opportunity to work in a position that was brand new. No one had ever done it before, the mandate was quite fluid, the role was fluid. There was certain expectations but at the same time how those expectations were achieved or how the work was carried out was up in the air. And it was up to me to make sense of it and to create something. There’s pros and cons to that. Structure is good but at the same time having space to be creative is a really great way to do things differently and think differently.
So in that role coming into it, I had a little bit of experience but not a whole lot of experience in that particular area. I was a little worried about my ability to execute on a role without having so much structure. But I was given the space to think creatively to try things, to sometimes fail but to learn a lesson and to carry on and try something else. And the reason why I had that space was because my leader created that space for me. He trusted my ability to think critically and to make decisions. At the end of the day, that’s why I was hired. So he trusted me to do that because he himself knew that it was okay to not know every thing, it was okay to try something new and to think differently.

And he was always transparent with me. So if there was, maybe I had a question, he didn’t have the answer, that was okay because we were going to figure it out together. We would discuss things. We would do some digging, some research, some investigation and figure out where are these gaps? How can we do better? How can we do things differently? And this really just came down to the fact that my leader was self-aware enough that he didn’t feel like he needed to have all the answers because he knew that not only he trusted me to do my job, but at the same time he knew that there are so many answers to every question you could possibly have, he didn’t have to have the right one all the time. And it was okay to not have the right answer as long as you’re willing to try and learn.
So that was really inspirational to me because I was able to see the potential in myself by seeing that leader lead by example and help me see that it’s okay to try and fail sometimes or to try something differently. And I think the cool thing about that is that that is the way that we’re working moving forward. We need to think differently, we need to be disruptive. We need to try things, try new things, try different things. And that’s just so important in business but also in how we build relationships and how we work with people. You have to think differently, you have to think critically. And I was given the space in that role that was brand new. There was expectations to an extent but not a whole lot of guidance on how I should carry about my day-to-day. So learning that it’s okay to try new things and be creative. The only way I was able to do that was because my leader led by example and showed me that it was okay to not have all the answers, but we’ll figure it out together.

Sarah: I think your note of leading by example is how inspirational leaders operate. What I hear from that too is that it provided you a sense of security or safety or maybe a predictability that allowed you to then be more creative and think a little bit more critically without fear of it failing.

Jess: Exactly. Yeah, there was a space where I could, if I had an idea, we could give it a go. And knowing that I had the ability to come up with a plan and to see what might happen and try it out. That was a lesson that I’ve taken to everything that I’ve done since. But it was the leader that showed me that it was okay to try things and be the first to do something. Often times we think we want to see what other people have done before we go ahead and do our own thing. But sometimes you need to be that front runner, you need to be that person that’s trying it for the first time. And sometimes that’s where the biggest successes come from. The leader that I had in that position really showed me that it was okay to try. And you know what, sometimes you’re going to fail, but you’re going to learn from it and you’re going to carry on.

Sarah: I love that. Was there an experience or something very tangible that you could walk us through of where you witnessed that leader go through something where they maybe did get it wrong or got it right and you were like, “I want to mirror that behavior”? And again, almost like an tangible format, what was the experience to the degree you can share of course?

Jess: Yeah, for sure. So one of the examples I can give is we created this, this is when I worked at RBC, we created a micro credentialing program. And this was something that we saw some other players in the industry doing but no one had really brought it to early talent, which was the space that we worked in, so working with students. There was this notion of doing things differently and trying to differentiate ourselves. And that was so evident in everything that we were doing. So we figured, okay, this is a great way to try this. It ended up being quite successful, we had a great pilot program, we really launched it. But it was something that my leader and my team we constantly had to keep advocating to say, “You know what, this is going to work, and it’s going to be different. And you’re not going to see other institutions doing it necessarily, but we’re going to try it.”

There were some hurdles over the course of the implementation but we got there eventually. Some parts were more successful than others, sometimes we had to try a little bit harder. And we did have to advocate a lot for ourselves. Having that space to think differently came into that project so clearly because we saw that if we want to differentiate ourselves, if we want to be different than our competition, we have to do something differently. We have to think outside the box, we have to think creatively. That was our outlet to think creatively.

And my leader really showed me that sometimes you’ll have to push forward, and it’s okay if you stumble, it’s okay if run into an obstacle, but keep going, keep learning from it. And I think it was that trial and error or like try, fail, learn process that helps not only that project but any project. And I think that that was the style of leadership that I found so inspirational was that we were implementing a huge project, and it was the first of its kind at the institution. And without that creative environment or that safe to fail environment, we wouldn’t have been so successful.

Sarah: I love that so much. Last question is really just if someone were to say, “Okay, I want to take Jess’s piece of advice, I want to become a more inspirational leader by leading by example.” And I love what you just said about I’m going to adopt the mindset, well, this might be your tactic, but I’m going to adopt the mindset of trial, fail, learn. Maybe that is the tactic, but what is the tactic? Someone said, “Okay, I’m going to take Jess’s advice. I’m going to lead by example, that’s how I’m going to show up,” what would you recommend? What is the tactic they can do that allows them to exercise that?

Jess: I think it starts with self-reflection because you have to be self-aware in order to know that it’s okay to fail. So you need to be aware of your own gaps, aware of your own areas of development or improvement. And that comes through self-reflection, but it also comes with humility and vulnerability. There are leaders who don’t know how to be vulnerable with their team. There are leaders who don’t know how to show that more humble side. And I think to truly practice inspirational leadership, do that self-reflection, think about what do you know, what do you not know? How can you improve yourself?
And that process is contagious. Your team’s going to do that, your employees are going to do that as well. And that is how you can take my advice here and practice the inspirational leadership is to just think about who are you, what do you have, what do you not have? Be vulnerable, ask questions. Know that you don’t always have to be right, you don’t always have to have the answer. And that’ll be clear to everyone. And you’ll show that example of it’s okay to not know everything. And that’s probably the best way

Sarah: I think that is so gold, be self-reflective, have humility and vulnerability. Tying back to what you said at the start, showing up authentically by showing all your cards and being transparent about what you know. And the fact that you said and that will be contagious, mic drop moment, I love that. Jess, this has been so wonderful. Thank you for sharing your brilliance with us and your really eloquent words on how we can exercise inspirational leadership. So really appreciate your time and can’t wait to share all your wisdom with everyone.

Jess: Thank you for having me, this is great.