MOVEMENT CHANGES THE CONVERSATION

Dialogue Miles™

Walking side by side changes the conditions of a conversation. Dialogue Miles gets you out of the conference room to build deeper, more authentic connections.

EXPLORE WAYS TO WALK

HOW IT WORKS

WHY WALK WITH DIALOGUE MILES?

Understanding someone changes how you work with them.

Most leadership relationships are built in agenda-driven settings. The focus is on the decision, the deadline, or the work that needs to move forward. Dialogue Miles creates space for something those settings rarely provide: a better understanding of how another person thinks and what is important to them.

That understanding can make difficult conversations easier. It can also reduce friction when people disagree because there is more trust beneath the work. The goal is to return to the table knowing the person beside you in a new way.

“We invest in courses to build our skills. We invest in exercise to build our health. Dialogue Miles is about investing in the conversations and relationships that build our careers.”

Joe Morgan, Founder, SIY

DIALOGUE MILES IN PRACTICE

One idea. Different kinds
of connection.

Dialogue Miles can be designed as an organizational experience, built into coaching, or practiced simply between two people who want to know each other better.

ORGANIZATIONS

For team building

Turn an event into something people participate in, not just attend. Dialogue Miles can be programmed into leadership offsites, conferences, retreats, and company gatherings to create meaningful connection beyond the agenda.

Great for: leadership offsites, conferences, retreats, team gatherings.

LEADERS

For 1:1 coaching

Some conversations move differently when you do. Taking coaching outside the traditional meeting environment can create more room for reflection, candor, and new ways of seeing a challenge.

Great for: executive coaching, founder coaching, leadership development.

EVERYONE

For the community

You don’t need an offsite or a coach. You just need someone to walk with. Invite a friend, family member, mentor, or colleague into a conversation worth having, then see where the mile takes you.

Great for: friendships, family, mentors, colleagues, reconnection.

Dialogue Miles | Leadership & Team Experience

Dialogue Miles for Teams is a facilitated experience within siY Advisory that helps teams build stronger working relationships outside the usual structure of meetings and roles. Joe works with leadership beforehand to understand the business context and what the team needs from the experience. siY then designs the walk around that context.

What the experience includes:

Advisory and experience design: The experience is tailored to the team and the moment.
Intentional pairing: Participants can be paired across functions or levels where stronger relationships would be valuable.
Guided Dialogue Miles: Pairs walk one-to-one with a small number of prompts to help open the conversation.
Reflection and leadership insight: siY can capture what surfaced, identify recurring themes, and reflect those insights back to leadership.

The walk is the setting. The value is what people bring back into the business.

BRING DIALOGUE MILES TO YOUR TEAM

One walk led
to another.

The miles accumulated, and so did the stories.

Dialogue Miles traces back to walks to the rocks at Moody Beach, Maine, and long porch conversations with Joe’s grandmother, early experiences that showed him the value of uninterrupted time with another person. As a CEO in the 1980s, he began walking with colleagues and saw how a change in setting could build trust and lead to better thinking. By the 1990s, he was inviting people out with no agenda beyond a single prompt.

The practice took on new meaning during the pandemic. In 2021, a walk through Central Park with Deb Cupp sparked 100 Miles of Dialogue, which became Dialogue Miles the following year. In 2024, the idea expanded through the Alumni Dialogue Challenge with College of the Holy Cross.

Today, Dialogue Miles is both a personal practice and part of siY’s work with leaders and organizations. What started as a way to make room for better conversations has grown into a way to strengthen relationships and surface perspectives that may not emerge in a meeting.