1-on-1 Coaching

Executive, Health, and Performance Coaching

I’ve worked with Amazon, Microsoft, PepsiCo, and more, and across every high-performing team, one truth holds: you can’t lead others well if you don’t lead yourself first. And leading yourself starts with how you think, how you recover, and how you take care of the one body and brain you get.

Inquire About Coaching

Jon Macaskill coaching a leader one on one

Why This Coaching Matters

Leadership today asks a lot. Executives face constant pressure to deliver results, navigate a changing world, and inspire their teams, often while running on bad sleep, skipped workouts, and stress they never actually process. Performance at work and health at home aren’t separate problems. They’re the same system. Coaching gives you the space, structure, and support to sharpen your focus, rebuild your energy, and perform at the level you’re capable of, in the boardroom and in your own life.

My Approach

I work 1-on-1 with leaders and high performers navigating growth, conflict, burnout, transition, or a body that isn’t keeping up with their ambition. My approach blends:

Performance Psychology

Practical tools for focus, decision-making, and mental clarity under pressure.

Mindfulness

Techniques to stay grounded, present, and resilient when the stakes are high.

Integrative Health Coaching

As a UHP (Unlock Human Potential) trained Integrative Health Coach, I take a whole-person approach to sleep, stress, movement, nutrition, and recovery. This isn’t a meal plan or a workout handed to you. It’s a partnership where you set the direction and I help you build behavior change that actually sticks.

Leadership Experience

Decades of lessons from leading elite military teams and advising executives in the corporate world.

The result: leaders who show up clear-headed, steady, and strong enough to sustain it.

What We Conquer Together

Navigating Growth & Transition

Moving into bigger roles with confidence and purpose.

Transforming Conflict & Communication

Building trust, defusing tension, and leading through challenges.

Burnout Recovery & Prevention

Resetting your energy and designing sustainable ways of working.

Sleep, Stress & Recovery

Fixing the foundations so your mind and body can actually perform.

Building Physical Capacity

Training, movement, and habits that support the demands of your life, whatever your starting point.

Mastering Habit Formation

Embedding daily practices that hold up under real-world pressure.

Coaching session in progress

How Coaching Works

Every coaching engagement is customized. It typically begins with an in-depth assessment of your goals, challenges, health baseline, and leadership context. From there, we design a coaching plan that may include:

  • Assessments and feedback tools to identify blind spots and strengths
  • Weekly or bi-weekly coaching sessions (virtual or in-person)
  • Practical exercises and action steps between sessions
  • Ongoing accountability and support to sustain change

The process is both structured and flexible. My coaching is anchored in your objectives and responsive to real-time challenges as they arise, whether that’s a board presentation next week or a stress pattern that’s been running your life for years.

Step Into Your Potential

If you’re ready to invest in yourself, your leadership, and your health, let’s start the conversation.

Book a Coaching Call

Explore Free Resources

Developing Self-Awareness workbook cover

This self-guided workbook helps you explore your mindset, values, and patterns. Discover the power of reflection to grow personally and lead with authenticity and intention.

Download

How to Overcome Challenges guide cover

A concise, action-focused guide that equips you with simple strategies to stay grounded, reframe adversity, and turn obstacles into moments of growth.

Download

Inspiration Journal cover

A beautifully structured journal with daily prompts to help you reflect, refocus, and find inspiration. Build clarity, gratitude, and emotional awareness, one entry at a time.

Download