Jenna Caskie

I've been very lucky with the people that I've been able to work alongside. A big part of my success is a couple of the amazing leaders that I've had who have really built me up, supported me, believed in me, and gave me a really great example of what leadership can and really should look like. These were people that encouraged me, advocated for me, and were always willing to give me positive feedback and recognition, which is so important. There's a lot to be said about the people that you surround yourself with, and the people who are not going to hold back on building you up. Of course, that's extrinsic, and I think we also need to, as people, as women, focus on how we can empower ourselves. Coaching has been a great tool for that. Even through my own coaching program with my teammates, us all coaching each other has really helped me to see what I can bring to my role and to this leadership development space. I think coaching can be a very valuable tool for any woman looking to gain more confidence and clarity, and to learn ways to take ownership around building those qualities up within themselves.

Say yes to things that scare you. There have been several times when my current leader will ask if I want to take on a project, and sometimes these projects might initially make me nervous, or I might question whether I can be successful. But what I've learned is that if someone is offering you an opportunity to stretch your skills, it's probably because they believe in you and they believe that you can do it, so you should also believe in yourself. Saying yes to things that scare you helps to push you out of your comfort zone and ultimately helps you to learn and grow.

Remember your worth and remind yourself of that intentionally and regularly. Even if you have to make a list of those skills and those qualities, remember what has helped you to be successful in the past and what will help you as well in the future. And again, surround yourself with people who really make it their business to build you up. Imposter syndrome is one of the hardest things that I've had to grapple with, and I think it's something that a lot of people, and probably a lot of women, really struggle with. I've experienced that both in my career in leadership development and also in the ballroom dance world, just feeling like, do I deserve to be here? Have I earned this? Am I actually good at this? That sort of self-doubt has always been a bit of a struggle, and the thing that really pushes me through that is being able to remind myself of the skills and the qualities that I do possess, and that have helped me to be successful. Doing that self-reflection and focusing on the positives is an important step.

I believe one of the biggest challenges right now is the introduction of AI into the field of learning and development in general. I think it's a challenge, but I also think it's a space for opportunity. First of all, I think people are nervous that it's going to take over some of our jobs, and we just don't always know how best to utilize it. I think the challenge is really figuring out where to implement it and where to hold back and keep a more people-facing approach, as opposed to an AI approach. There are some things that AI coaching, for example, is going to be really good for, like learning skills and practicing those skills. But there's always going to be some things that you want to talk to a person about. If you're trying to process your thoughts and doubts, work through building confidence and gaining clarify within yourself, then these are factors where it's going to be more impactful to talk face-to-face with a human coach. So it's figuring out where the value in AI lies, where we should implement AI approaches, and where we should stick with other approaches, like those that are more human.

Empathy and transparency are the most important values in my work and personal life. Empathy is definitely a core value of mine, and it's something that I try to emulate, especially throughout my work with leaders and through coaching. I also think that doing one's best to lean into open communication and transparency is something that we should all strive for. Anyone in leadership, anyone working on a team, should strive to be as open, communicative, and transparent as they can, because that's how you build trust with the people around you and how you make it safe for others to do the same. Ultimately, by doing this, you're going to create psychological safety, build trust, and be able to work more effectively with others. If leaders are willing to be open about challenges and be open about mistakes with their teams, that openness and transparency is going to make others feel like they can be honest, admit mistakes, and ask for help. While this is hard to do because leaders often put pressure on themselves to have all the answers, the benefits of being open and transparent greatly outweigh the perceived risks.