Work With Charles Cain

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Something isn't working. Let's figure out what.

Maybe your team is capable but delivery keeps slipping. Maybe you've been promoted into complexity you weren't prepared for. Maybe you're good at your job but something about how you're leading isn't landing the way you intend. Maybe you're in transition and nothing you're doing is moving the needle.

This work is for people who are willing to look honestly at that and do something about it.

"I worked with Charles on my career transition. Nothing I was doing helped me move the needle forward. Charles and I worked together and as a result, I have landed my latest position. By far the best career coach I have worked with."

— L.C., Chicago

" I highly recommend Charles for his exceptional listening skills, expertise in project and people management, and his ability to serve as a true thought partner. Over a year of working together, he helped me resolve a chronic dilemma. I kept refining course materials right up to delivery, sacrificing punctuality for quality. A single insight from our sessions gave me a practical scheduling solution that eliminated that tension entirely.

From there, Charles helped me build sustainable project management habits, refine my continuous improvement process for teaching, and develop my management and communication style. He’s thoughtful, steady, and insightful. I highly recommend him."

- N.S., Billings

Who This Work Is For

Senior IT and Technology Leaders When delivery pressure keeps regenerating despite talented people, the problem is usually upstream. Charles works at the leadership layer where decisions stall, priorities blur, and friction gets pushed down instead of resolved. Engagements are contractual or fractional. Most clients begin to see stabilization within 90 days.

Retail Operations Leaders When the gap between what leadership expects and what the floor delivers keeps widening, it is a leadership problem before it is an execution problem. Charles works with retail leaders to close that gap at the source, not paper over it.

Executives and Leaders in Coaching Whether you are navigating a high-stakes transition, a stakeholder environment that has gotten complicated, or a moment where your current range is no longer sufficient, this work builds the clarity and relational capacity to lead through it. Grounded in LCP 360 assessment data and ICF-credentialed coaching discipline.

And you don't have to have a title to do this work. First-time managers, people in career transition, people trying to build something that actually fits their life, this is for you too.

What a Session Actually Looks Like

This isn't a pep talk or a worksheet exercise. You'll get honest feedback, real conversation, and practical thinking you can use before the week is out. Charles will push where pushing is useful and listen where that's what's needed.

Most people leave a first session with at least one thing they're going to do differently.

Pricing: Built So Cost Is Never the Reason You Don't Do This

Charles uses a sliding scale. Choose the tier that honestly reflects your situation. No proof required, no questions asked. If you're somewhere between tiers, pick what feels right.

Single Session

Directors and Executives (Director through CXO): $250

Rising Leaders and Managers: $160 (coupon: RISING)

Non-managerial professionals: $130 (coupon: PROFESSIONALS)

Creatives and freelancers: $130 (coupon: CREATIVES)

Underemployed (part-time or working below your skill level): $20 (coupon: UNDEREMPLOYED)

Unemployed: Free (coupon: UNEMPLOYED)

6-Session Package

Directors and Executives (Director through CXO): $1,500

Rising Leaders and Managers: $960 (coupon: RISING)

Non-managerial professionals: $780 (coupon: PROFESSIONALS)

Creatives and freelancers: $780 (coupon: CREATIVES)

Underemployed (part-time or working below your skill level): $120 (coupon: UNDEREMPLOYED)

Unemployed: Free (coupon: UNEMPLOYED)

The 6-session package runs across six Saturday 45-minute sessions. Expect real conversations, honest feedback, and practical tools you can use right away, and a path forward that actually fits your life and goals.

Corporate and employer-sponsored rates are available. Contact Charles here.

"Any organization would be fortunate to benefit from his wisdom, expertise, and unwavering support."

— Sunil N.

"He is an amazing coach who is passionate about bringing about positive change in the workplace and making the workplace more productive."

— Fahad C.

Ready? Pick a Time.

Choose the session type that fits where you are and select a time that works. You'll be on Charles's calendar in a few clicks.

A few things worth saying plainly before you do:

The sliding scale is real. It exists because this work should be accessible to anyone who wants to do it.

You don't need to have everything figured out before you book. That's what the session is for.

If you're not sure which session type fits, pick the one that sounds closest. You can sort the rest out in the first conversation.

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6 Session Coaching Package

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45 minutes

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Let's have a conversation

Not sure if coaching is right for you, or if this is the right fit? This is a no-obligation 30-minute conversation to find out.We will talk about wher... Read more

30 minutes

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45 Minute Coaching Session

Coaching is for everyone. I use a sliding scale so that career stage or financial circumstance is never a barrier.Please book at the tier that honestl... Read more

45 minutes

$250.00

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