What Have You Outgrown?

Keynotes and workshops that help leaders recognize what’s in the way — and lead from who they’ve become.

The Shift.

Most leadership challenges aren’t caused by a lack of skill, effort, or commitment.

They show up when the habits, expectations, and ways of leading that once drove success no longer fit the reality leaders are in now.

The very behaviors that once drove success can become constraints on clarity, capacity, and impact.

Growth doesn’t come from pushing harder.

It comes from recognizing what’s outdated, misaligned, or simply no longer necessary.

This is where the work begins.

This Isn’t A Motivational Talk.

My work is designed to create space.

For reflection, honest conversation, and clearer leadership decisions.

Leaders don’t leave with a list of things to do differently.
They leave with a clearer understanding of:

  • What they’ve outgrown

  • What’s quietly getting in the way

  • What actually needs to be let go of to grow

I don’t believe that real change comes from simply being inspired.

Real change that leads to growth comes from seeing differently.


Ways We Can Work Together.

These experiences are designed to meet leaders where they are — and create space for what’s next.

Empowering Workshops

A session intentionally creating space for leaders to slow down, reflect, and apply insights directly to their day-to-day leadership.

Customized workshops move beyond awareness into conversation and practice — helping leaders identify what’s getting in the way and what needs to shift now.

Best for -

  • Leadership teams

  • Department or functional groups

  • Offsites and professional development days

Facilitated Leadership Labs

Leadership Development Labs are deeper, custom-designed experiences for teams navigating complexity, growth, or transition.

Labs provide ongoing space for reflection, dialogue, and integration — supporting leaders as they let go of what no longer fits and build new ways of leading together.

Best for -

  • Senior leadership teams

  • High-potential /emerging leader cohorts

  • Organizations and teams in the midst of change or scale

The Interactive Keynote

A high-impact session customized for your organization, designed to shift how leaders think — not just how they feel.

Here I introduce the outgrown lens, invite reflection, and create a shared language leaders can carry forward. It is engaging and participatory, while still honoring time and scale.

Best for -

  • Conferences and large leadership events

  • Company-wide meetings or summits

  • Audiences that need alignment and perspective, quickly

Every engagement is customized. The goal isn’t motivation — it’s clarity leaders can act on.

Start the Conversation

If you’re exploring an interactive keynote, workshop, or leadership lab, share a few details below and I’ll follow up personally.

Jen Engages & Empowers the Crowd From Start to Finish

Jen Cáceres is a seasoned speaker and certified executive coach with over 15 years of experience working with and inspiring leaders from all levels, backgrounds and industries to get out of their own way and grow.

Whether you’re hosting a leadership summit, a wellness retreat, strategic planning meeting or motivating students in leadership - Jen will inspire your audience with real stories, candid humor and leave them with actionable takeaways from the moment they take their seats.

One of Jen’s original keynotes delivered to the National Association of Women in Construction, NAWIC Chapter #325 in the Chicago suburbs