Kelsey Cooling

I attribute my success to a blend of adaptability, creativity, and relationship-building.

My leadership style is very human-centered. I use a lot of humor, transparency, and honest communication to build trust because I’ve found people move through change more effectively when they feel connected, respected, and included in the process.

I’ve also been fortunate to have strong female leadership influences throughout my career. My sister Kate whose been has played a key role in helping me develop my mindset. My sister Jill, who has spent her career in senior roles with the tech space has normalized strong female leadership for me. Professionally, leaders like Karen Rohrkemper gave me my start in enterprise program management, and Leslie Peeler and Kelly O’Donnell have supported me in expanding and elevating my skill set in complex, cross-functional environments.

One of the best pieces of career advice I’ve received is ‘progress over perfection.’ Once I truly embraced that mindset, it completely changed the way I approached leadership and execution.

Earlier in my career, I put a lot of pressure on myself for everything to be perfect, but in fast-moving environments, perfection can actually slow momentum. Learning to focus on progress helped me move faster, make decisions more confidently, and help teams get across the finish line without feeling like every deliverable had to be a perfect work of art.

It also transformed my mindset personally. I became more adaptable, more resilient, and more comfortable navigating ambiguity, which is incredibly important when leading complex projects and large cross-functional teams.

My biggest advice to young women entering this industry is that your greatest asset is actually being who you are. Early in your career, it can feel like you need to fit a certain mold, especially in more corporate or technical environments, but I’ve found the opposite is true.

Most people are so focused on appearing polished or serious that they unintentionally remove any sense of personality from how they show up. But the people who stand out, and the people others genuinely want to work with, are the ones who bring authenticity, humor, and humanity into the room.

Being yourself, and staying grounded in who you are, will push you much further than trying to fit into what you think leadership is supposed to look like. It builds trust faster, creates stronger relationships, and ultimately opens more doors than perfection ever will.

One of the biggest challenges right now in project management is also the biggest opportunity: the rise of AI and how quickly it’s changing the way work gets done.

The challenge is that it requires leaders to rethink how we structure work, how we manage information flow, and how we ensure alignment across teams when the tools themselves are evolving so quickly.

At the same time, it’s an incredible opportunity. Project managers who lean into it, learn it, and get involved in AI-driven initiatives can fundamentally shape how organizations operate in the future. It’s not just about efficiency, it’s about rethinking how we deliver outcomes and lead change at scale

 The values that matter most to me are resilience, integrity, and joy. Integrity is about how you show up when no one's watching- doing the right thing consistently. Resilience is huge for me because failure is inevitable, and its rally how you learn from it and keep going.

And joy is something I think people underestimate. I don’t think we talk about it enough in professional spaces, but finding way to bring joy into your daily life actually make you better at everything you do.