Michael Miles

Leader | Mentor | Runner | Coffee & Happy Hour Enthusiast

  • Former GM, Cloud Infrastructure @ Microsoft (retired)

  • Board Chair @ Watson Institute

  • Fractional Executive @ Series A Startups

  • Executive Coach

  • Adjunct Lecturer & Mentor-in-Residence @ University of Arizona

Portrait of Milestone Leadership founder, Mike Miles, wearing a dark jacket over a light-colored shirt, standing indoors with one hand in his pocket and smiling.

I’ve spent two decades leading global teams, launching innovative products, and scaling businesses at Microsoft and beyond. Now (mostly) retired from corporate life, I focus on empowering entrepreneurs, mentoring leaders, and supporting organizations that are driving real social and economic impact.

Whether it's working with mission-driven startups, coaching executives, or helping impact-focused organizations scale, I’m committed to building leadership that not only drives results but also creates lasting, positive change.

I spend my time coaching and mentoring senior and impact-driven leaders, working with people I’d genuinely enjoy grabbing a coffee or sharing a happy hour with. I believe the best leadership isn’t just about success—it’s about building something that matters.

I’m committed to continual improvement, both personally and professionally. When I’m not advising startups, teaching at the University of Arizona, working with amazing leaders or chairing the board at Watson Institute, you’ll probably find me on a long run, planning my next travel adventure, or enjoying time with family and friends.

I try not to take myself too seriously—but I’m very serious about leadership, innovation, and making a real impact where it counts.

Mike Miles running outdoors on a trail with mountains in the background, holding trekking poles, wearing a yellow jacket, black shorts, sunglasses, and a race bib with the name Mike and number 186.

My Mission

Milestone helps senior and impact-driven leaders lead with clarity, resilience, and purpose, whether scaling a company, driving innovation, or navigating complexity. We build the mindset, systems, and habits that sustain impact and well-being over the long term.

The best leaders aren’t the ones who lead through exhaustion; they’re the ones who develop the systems, habits, and mindset to navigate the complexity of their organization. They lead with vision and confidence and create environments where people and businesses thrive.

Great leaders take on immense responsibility. They drive results, navigate uncertainty, and show up for their organization day in and day out.

Too often, leadership comes at the expense of well-being and when that slips, so does impact. Many of us push through, solve problems for everyone else, and put ourselves last until we’re running on empty.

I work with senior and impact-focused leaders to manage complexity, build momentum, and integrate wellness into how they lead.

The most effective leaders aren’t the ones who endure, they’re the ones who cultivate the resilience, clarity, and energy to sustain meaningful impact.

My Approach

My approach is real, direct, and rooted in lived leadership experience. I help leaders focus on the essentials, stay balanced under pressure, and lead with clarity, even in the middle of constant demands.

Are you ready to:

  • A white lightbulb icon inside a speech bubble on a gold circular background, symbolizing ideas or innovation.

    Gain Clarity

    Focus on what truly matters for yourself and your organization and align personal mission and organizational strategy with values.

  • A person standing triumphantly on top of a staircase made of ascending blocks, with arms raised in celebration, on a gold circular background.

    Build Resilience

    Establish the habits and systems that support clear decisions, sustained energy, and long-term effectiveness.

  • A white outline of a target with an arrow hitting the bullseye, on a gold circular background.

    Increase Impact

    Lead effectively and create a workplace where people feel energized, supported, and capable of great work.

Silhouettes of five hikers climbing a grassy hill at dusk or dawn.

My Values

Values are the compass of great leadership; these are the principles that guide what I do.

  • Resilience – Push beyond limits. Develop the mental, emotional, and physical endurance to navigate leadership and life’s toughest challenges.

  • Self-Awareness – Tune in. Gain clarity on strengths, blind spots, and stress triggers to lead with greater intention and impact.

  • Growth & Continuous Improvement – Elevate every day. Commit to learning, adapting, and pushing past old boundaries, physically, mentally, and professionally.

  • Authentic Connection – Lead with presence. Build meaningful, trust-based relationships that foster deeper collaboration and shared growth.

  • Purpose-Driven Leadership – Align with what matters. Strengthen the connection between values, actions, and impact to lead with clarity and conviction.

Are you ready to elevate your leadership?

Leadership should be sustainable, fulfilling, and impactful.

Is yours?