Cherilynn Castleman Discusses Using Empathy and Data to Connect with Clients

Managing Partner and Executive Coach at CGI, LLC, Cherilynn Castleman is an accomplished sales executive. She helps companies recruit and elevate underrepresented minorities and also trains women of color for sales success. She says, “I train Black and Brown women to be too good to be ignored.”

“The more that we know about our client, the more we can be a solution partner with them as opposed to a salesperson.”

Give Us Some Background on Your Experience and How CGI Came to Be. 

With over 30 years of global sales executive experience, Carolyn refers to her time in sales as having started before Girl Scouts Cookies were priced at $0.50 per box. Castleman equips women to take on C-suite, leadership, or entrepreneurial sales positions with a larger vision of seeing 1 million Black and Brown women sit at the “table of their dreams” by 2030. Castleman’s area of expertise is an answer to the challenges many women encounter including a lack of access or financial fluency to achieve their professional goals. 

How Can a Sales Person Find Connection Between Insight and Successful Client Relationships?

Castleman encourages sales professionals to make great connections with clients and build relationships. Know their pain points, their goals, vision, and what they’re struggling with. 

“The more that we know about our client, the more we can be a solution partner with them as opposed to a salesperson.”

What Are Examples of How Financial Fluency Can Help Salespeople When Selling to C-suite or to Enterprise Clients?

 “When you’re selling into the C-suite, you are closing a deal faster, and you’re shortening that sale cycle.” 

Castleman goes on to say, “What you have to understand is that in the C-suite they care about two things: making money and saving money because it drives shareholder value and so you have to understand and have financial fluency to have a C-level conversation.”

She lists the 10-K and Value Line as two essential documents for becoming financially fluent and aware of industry trends. The 10-K is an annual report that offers a detailed picture of a company’s business, the risks it faces, and the operating and financial results for the fiscal year.

Value Line details industry analysis and analysis of top-traded companies on a quarterly basis (you can find it at the public library). Once you’ve reviewed these documents, leverage your research in your next conversation with C-suite and enterprise clients. The knowledge you display will set you apart from the competition.  

How Can Sales Leaders Connect with Their Teams?

Castleman suggests asking your salespeople these questions to connect with them:

  • What are you getting right?
  • What is your superpower (what do you feel like you do really well)?
  • What do you wish you could do better?
  • Where do you see yourself six months from now?

You will know what’s going on in their world and you will know how you can help be a resource for them. Castleman also encourages leaders to give their team members credit for the hard work they do and talk about an area of growth.

“When you look at the bottom line, diversity does drive sales. It’s not just good business, but it’s good for business and that’s what’s so important.”

What are some advantages of having a diverse workplace? 

Castleman was a part of a recent study for LinkedIn where they commissioned a Forester report highlighting how diversity drives sales. The findings showed that diverse teams had greater customer satisfaction scores and their teams were happier. Castleman says, “When you look at the bottom line, diversity does drive sales. It’s not just good business, but it’s good for business, and that’s what’s so important.”

Teams have 12% higher sales, they have higher customer satisfaction, 28% higher conversion rates, and 3% higher sales just from having leading DE&I practices. Castleman advises businesses to look inward and determine what their strengths and weaknesses are to identify areas where they need to improve. 

Identifying Mentors


1. Someone that has mastered their craft 

  • If you’re an SDR, you can ask someone if they are willing to be a mentor. Start by asking for feedforward information. 

2. Someone who shares your intersecting identities such as gender identity, race, class

  • This person doesn’t have to be in your profession. 

3. Someone sitting at the table who will advocate and sponsor you

  • Update them about your successes and share your superpowers with them. 


  1. Being intentional about what you want to Accomplish.
  2. Taking responsibility for all Appointments.  
  3. Always having a meeting Agenda
  4. Following up on Action Items. 
  5. Having an Attitude of gratitude.

If you are a mentee, ask your mentors if there’s anything you can help them do as appreciation. It’s important to keep in mind that your relationship with each of them will always be different. 

What Are Trends You’re Noticing & Predictions for 2023

“In 2008, we were able to retain six accounts that were at risk. We were able to increase our sales by over 208% during that time. And we did that by connecting with our clients and being and getting really deep in our relationships with them.”

  1. Those people who take the time and build relationships with their clients are going to excel and fair well during the recession. 
  2. People who are optimistic, looking for opportunities, innovative and have repositioned their value story based on what’s going on during a recession will succeed professionally. 
  3. Knowing what your superpowers are and being able to expand those across your company will be an important factor. 

When companies begin a reduction in force, Castleman says her clients have been recession-proof and able to show that they can be a resource by displaying additional skills and the ability to lead from the middle. 

She predicts that sales professionals will find success by being optimistic, innovative, solution-oriented and focused on the future. 

If you are a woman of color looking to pave a path towards success in sales or your company wants to recruit, retain and elevate underrepresented minority sales professionals, connect with Cherilynn Castleman


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