It doesn’t have to be lonely at the top.

 

Being the senior leader means carrying complexity, pressure, and visibility that most others don’t see. You make decisions that shape people’s futures. You navigate tension between mission and margin. You face situations no one trained you for. And you often do it alone.

Leader Guidance gives you a guide, a confidant, and a structured space to grow in wisdom and effectiveness—right when you need it most.

 
 

What is Leader Guidance?

It’s a unique blend of:

  • Advising — to help you think clearly and act wisely in the challenges you’re facing now

  • Coaching — to grow your leadership capacity over time

  • Confidant support — because even the strongest leaders need a trusted sounding board

Each session is designed to address what matters most in this moment—without losing sight of where you’re growing long-term.

 
“This is the best money I spend every month.

I know I can show up every session with a clear sense of what to process — or no clarity yet at all.

We can use a session to get clearer on our company’s identity, redesign parts of our client journey, or even grow in the ways I’m leading my team members and preparing for future expansion.

I feel deeply known, and the very opposite of lonely at the top.”
— Caleb Borisuk, CEO of Second Home
 

What you’ll experience:

  • Two 90-minute sessions per month

  • Strategic frameworks and reflection tools tailored to your real-time needs

  • Ongoing access via email, voice memo, or video between sessions

  • A thought partner who helps you multiply progress and reduce isolation

  • The ability to access a wealth of guidance, troubleshooting, or design across a number of specialties, including:

    • corporate identity

    • leadership

    • planning

    • vital decision-making or problem-solving

    • professional relationship dynamics

    • personal effectiveness

    • mental or psychological hurdles

    • marketing & sales (which we call awareness & outreach)

    • messaging

    • team member journey design

    • client journey design

    • playbooking

    • expansion strategies

    • and more


Each session includes:

 

Ideal for high-impact leaders who are:

  • Navigating complexity or transition

  • Building something new—or rebuilding after a hard season

  • Holding significant responsibility and needing trusted perspective

  • Ready to grow beyond reactive leadership into strategic clarity and confident action

 
 

Your Guide: Dr. Will Gray

  • Founder of ALIGN

  • PhD, University of St Andrews

  • Recognized for an unusually rehumanizing approach to business

  • Advisor to 200+ organizations across many service sectors

  • Trained in: The Table Group, StoryBrand, Design Thinking, Co-active Coaching, Nonviolent Communication, and more



 
 

It starts with a Good Fit Conversation.

During part of an hour, I’ll:

  • Listen to your context

  • Reflect back what I’m hearing

  • Share how Leader Guidance could help—and explore out loud to see if we are a Good Fit for one another and for this work together

No hard sell. Just honest discernment.

If we turn out to be a Good Fit for each other, we’ll sign an agreement and schedule our first sessions. If we’re not a Good Fit, no worries — we’ll cheer you on as you move forward.