Navigating your journey together.

Leadership is crucial to success but can leave you feeling unsure and isolated. In addition, you might lack the skills, mindset, tools, and strategies to be the leader your team needs to be successful.

We'll work together to navigate challenges through transformative dialogue, structured working sessions, leadership tools, and management frameworks.

It begins by determining if we’re a good fit.

 An image of two travellers walking on a path in a futuristic wilderness

Coaching Fit

It’s Important because it’s a partnership

Hiring the right coach can be a life-changing and deeply rewarding experience, while the wrong one can be disastrous. I’ve had both experiences. That’s why we invest time to make sure that we’ll be effective collaborators and create the value you’re looking for before committing to working together.

Book a coaching fit call
  • You’re looking for a collaborative thinking partner to work through challenges.
  • You want to talk through the challenges you’re facing with someone who can guide and support you.
  • You want an outside perspective who deeply understands you, your business, and your challenges.
  • You’re looking mindsets, approaches, and strategies to overcome your “people problems.”
  • You want to create greater clarity, focus, and leverage.

Programs

Our coaching programs are designed to scale. Based on your budget, team size, desired outcomes and level of support; we have a program that’s right-sized for you.

Working together

An image of two people working together in a windowed office with a view of the mountains in the background.

Your collaborative thinking partner

If there’s one thing I’ve learned, no one does it alone. Moving faster, making better decisions, reducing stress, and achieving tremendous success by surrounding yourself with trusting, candid, and supportive relationships will help you get to where you are going sooner and with greater joy and fulfillment.

After leading teams as a founder in small businesses, building teams in small B2B companies, working with early-stage startups, and managing teams at an enterprise level, I know firsthand how challenging, alone, and complex your role can be.

The good news is that you don’t have to do it alone. You don’t have to get stuck inside your head; you can reach out for the support you need to become your team's leader.

Who is Chris Caldwell

As a founder, he has used his strengths to unlock high leverage opportunities, and shows support and encouragement for my strengths... I feel completely comfortable disagreeing, reframing, or proposing differing perspectives on any facet of the business.

Brian Ragone

Chris actively helps others succeed and was instrumental for change in the senior team and strategy.

Lanny McNie

What really resonated yesterday was the identification of value creation and value delivery. I had a great chat with our CTO on it this morning.

Jay Maharaj