Professional Coaching

Make yourself a priority and make coaching a critical component of your overall success strategy. Begin your sales coaching journey today.

Awareness + Action = Growth


Coaching is about Improving your Performance

·  You’re intelligent

- You’re talented

- You’re innovative

- You’re high achieving

- You’re consistent…  

And yet you're falling short of your goals .


Coaching Focuses on the Future and the Present

·  Coaching is action-oriented 

·  Coaching focuses on what you want 

·  Coaching techniques accelerate your talent development.  

·  Coaching is grounded in the assumption that you are resourceful and whole and know best. 


Coaching is about crushing limiting, painful thoughts and revealing new possibilities

- Raise awareness and clear up distractions

-Find your best path forward

- Leverage existing strengths

- See yourself and others clearly

- Build more productive relationships

- Get clearer about your goals

-Achieve your dreams


Coaching is About Stretching

- Unlock your potential

- Maximize your performance. 

- Learn to trust your internal source of wisdom

- Move from awareness to action

Book Your Coaching Session

A one-hour Intro Coaching Session  ($125 Fee-Waived) can help us determine whether Cherilynn Castleman is the right coach for you.


Coaching Is Not...


Coaches don’t treat psychological problems, such as depression or anxiety.


Coaches don’t tell clients what to do. 

Coaching FAQs


What’s It like to work with a coach?

Coaches use tools designed to help you face change, dream big, and move forward with peace, grace, and authentically…

·  Coaches focus on the future

·  Coaches ask powerful questions   

·  Coaches provide support during career transitions

·  Coaches grow and develop leadership and sales skills

·  Coaches partner with you to discover your goals and develop strategies to achieve them 

How does coaching work?

During each session, together, you and your coach will work through a framework designed to help you unlock your potential and maximize your performance. By the end of the session, you'll learn to trust your internal source of wisdom and move from awareness to action. 

Who will benefit from 1:1 sales coaching?

- Women who have a fierce desire to learn

- Early career sellers struggling to make numbers 

- "Sidepreneurs" ready to grow a six-figure business 

- Executives and leaders at a crossroads in their career

- High performers looking to take their career to the next level

- AEs ready to call on contacts higher up in their target accounts 

- Sales professionals looking to increase deal sizes and shorten sales cycles

What's a coaching engagement?

A coaching engagement is a chance to increase performance, drive results, and change your life. But remember, if you don’t take action, there will be no positive outcome.  A coaching engagement is typically 4 to 8 one-hour sessions. 

How do I find the right coach?

With twenty-five years of experience as a general manager, educator, coach, and entrepreneur, Cherilynn Castleman’s in-depth knowledge of the sales and business world and its unique pressures will help make the most of your coaching time.

  A one-hour Intro Coaching Session  ($125 Fee-Waived) can help us determine whether Cherilynn is the right coach for you.  


Member Discounts

SIS members receive discounts on coaching and training.

 Learn more about Sistas in Sales (SIS), a community for women of color sales professionals to network, advance their careers and most importantly, find sisterhood.