Leading Learning with Intention: Designing for Belonging and Impact

In anticipation of our summer Learning Forward Texas conference, we’re excited to continue highlighting the leaders who will help shape this year’s learning experience. Our Day 1 keynote speaker, Dr. Jill M. Siler, brings a deep commitment to thoughtful design, courageous leadership, and professional learning that truly moves people.

As Deputy Executive Director of the Texas Association of School Administrators (TASA) and a former superintendent for nearly a decade, Jill has spent years designing experiences for leaders across Texas, from massive statewide conferences to intimate leadership networks grounded in campus visits and collaborative design.

I recently had the opportunity to sit down with Jill to talk about what makes conference learning meaningful, how she thinks about designing professional learning at scale, and why “surprise and delight” isn’t just a hospitality concept, but a learning strategy.

Responses have been lightly edited for clarity and length.

Kathryn: You design and attend many conferences throughout the year. What makes a conference learning experience truly meaningful for you?

Jill: I am so excited to come out to the Learning Forward Texas conference. I do a lot of events, but this one feels like my people because it’s about learning, especially professional learning. After serving as a superintendent for nearly 10 years, when I had the opportunity to lead professional learning at TASA, I thought, I cannot give up this opportunity.

For me, meaningful conferences include cutting-edge thought leaders, both inside and outside of education. Will Guidara is a great example. He talked about the restaurant industry for an hour, and I walked out thinking entirely about what it meant for education and learning.

When designing keynote series, I look for a collection: someone in education, someone outside of education, someone who brings inspiration, someone who brings rich content. Together, they should reflect the diverse needs of leaders across the state.

And then there’s peer learning and in-person networking. Sometimes the conversations outside the room are just as powerful as the learning inside. Those connections are what you grow later, when you need collaboration, support, or even guidance through a crisis.

KL: You’ve spoken about designing not just for content, but for appreciation and belonging. How does that show up in the way you structure professional learning experiences?

JS: There’s a beauty to smaller events. TASA Midwinter serves 6,000–7,000 attendees. Our summer conference is 400–600. Both have a place, but in a smaller setting, you can design for belonging in a very intentional way.

One year, we completely deconstructed our summer conference and rebuilt it from the ground up. We asked, How can we create surprise and delight the moment people walk in?

We created an “Inspiring Leaders Wall.” We contacted each attendee’s team and asked them to share affirming words about that leader. We displayed their photo alongside those messages. It was a total love project, but it was incredibly impactful.

We also think intentionally about the rhythms of design: groupings, food, swag, movement through space. That smaller conference gives us room to experiment and play with design in ways we can’t always do at scale.

KL: When you think about high-quality professional learning, from classroom teachers to superintendents, what does that look like to you?

JS: I tend to lean into two bodies of research. For a long time at TASA, we were guided by Phil Schlechty’s transformation work and his attributes of design and really thinking deeply about what meaningful learning looks like.

More recently, we’ve been digging into Susie Wise’s work around designing for belonging. That has shifted how we think about the entire experience: how people enter, how they’re invited, how they engage, how they give feedback.

Beyond conferences, some of our most profound learning has happened in our networks. Our Future-Ready Superintendent Leadership Network includes about 200 leaders, and we use a design-team model. We host a design day each summer where we ground participants in the tenets of strong learning design and then guide them through building the experience themselves.

Every network is grounded in campus visits. We’re literally in schools watching teaching and learning, talking with staff and leaders. Those experiences have been game changers because they connect design to real practice.

KL: In your book Thrive Through the Five, you talk about navigating the hardest parts of leadership. What feels especially relevant for educators right now?

JS: There’s so much good work happening around teacher retention and recruitment, but I think the crux comes down to this: we have to go in eyes wide open to the real challenges people are facing.

I often reference Admiral Stockdale’s quote about never confusing faith that you’ll prevail in the end with the discipline to confront the most brutal facts of your current reality.

Part of my work as an inspirational speaker is to recognize those brutal facts. This work is hard. We have to acknowledge that. We have to value the people doing it. And then we have to talk about tangible strategies to move through it.

As leaders, we still have to hold high expectations—because that’s what our students deserve—but we also have to create environments where people want to be part of the work. That’s a difficult tightrope to walk.

KL: You’ve spoken about “surprise and delight” and the importance of touch points in learning experiences. Can you share an example of that in action?

JS: One of the biggest lessons I took from Will Guidara’s work is the remarkable power of giving people more than they expect. That idea of surprise and delight creates profound learning.

We hosted a Future-Ready event at a venue that happened to house the largest neon sign collection in the world. As participants were leaving, we had a table set up with custom neon signs featuring words we had explored throughout the event: vision, love, purpose. Each person chose one to take back to their district.

It was such a small moment, but it was powerful.

We’ve also been thinking about touch points, down to every single interaction someone has with your organization. From registration to greeting to seating, each moment is an opportunity to design intentionally. When we do that well, we elevate the entire learning experience.

KL: What can Learning Forward Texas attendees look forward to in your keynote session this summer?

JS: The keynote will align closely with Thrive Through the Five and acknowledging the realities of leadership while equipping people with strategies to move forward.

I would also love to dig deeper into intentional design in a breakout session and how we help others show up as their best selves for their work, while also making sure we are showing up as our best selves in our lives. That balance is hard, but it matters.

KL: What’s currently inspiring your learning?

JS: I’ve been speaking on executive presence lately and pairing that with Brené Brown’s concept of “grounded confidence.” I love the idea of pocket presence and what it looks like in the moment when you don’t have the full picture but still have to lead.

And honestly, watching my children grow into strong, capable leaders has been inspiring. As educators and leaders, we pour into others constantly. Seeing the impact of leadership and love in your own home is a powerful reminder that the work matters.

This conversation with Dr. Jill Siler left me both inspired and affirmed. Her commitment to intentional design, belonging, and courageous leadership reinforces why professional learning matters. After our interview, I discovered the newly unveiled Texas Promise visioning document, where Jill served as the TASA lead. This work reflects the needs, challenges, and aspirations of Texas public schools today, priorities that were woven throughout our conversation and clearly shape her approach to leading learning. I’m thrilled she will open our Learning Forward Texas conference this summer. If you’re attending, be ready to experience learning designed with purpose and grounded in a bold vision for what education can become.

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Dr. Jill Siler served as the Superintendent of Gunter ISD for nearly ten years and now serves as the Deputy Executive Director for Professional Learning for the Texas Association of School Administrators (TASA). Jill grew up in Rochester & Buffalo, NY and completed her undergraduate work at the University of Pittsburgh where she was a collegiate swimmer. She was a teacher and coach in Pflugerville ISD and began her administrative career in Marble Falls ISD. In 2004, Jill went to Lake Travis ISD where she served as a campus and district leader for 8 years. During that time, she completed her doctorate at the University of Texas.

In her first months as a superintendent, Jill faced a financial crisis along with many other challenges that leadership brings. In 2015, her school board was named a TASA Honor Board as one of the top 5 school boards in the state and one of her campuses was named a 2017 National Blue Ribbon School. Jill served as the Chair of the Future-Ready Superintendent Leadership Network (FRSLN) Design Team where innovative leaders across Texas gather to learn, share and grow together. 

Jill has a passion for helping others reach their goals and is the leader of Texas’ Aspiring Superintendent Academy and leads Texas’ First Time Superintendents Academy. Jill speaks at leadership and teacher conferences across the country. Her first book, Thrive Through the Five was published in 2020 and talks about how to thrive in the most challenging times. 

Connect with her @jillmsiler and jillmsiler.com 

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Kathryn Laster brings over 30 years of education expertise as a math teacher, instructional coach, and digital learning consultant. Now, as an independent consultant, Kathryn creates and facilitates transformative learning experiences through intentional, human-centered, tech-infused design.

Connect with Kathryn here and at Refined Learning Design.