How Cherilynn Castleman Sells: Focus on Insights, Relationships, And Your Superpowers

Cherilynn Castleman’s sales career started when Girl Scout cookies were still 50 cents a box. 

Even though she was only five when she joined the Scouts and probably dreamed of becoming a doctor, she loved sales from the get-go. The thrill of making a sale. The joy of fulfilling a need and making people happy. The fantastic connections she was making. 

Fast forward a few decades later, Cherilynn built a high-flying career: from financial services to medical education and SaaS sales. She was consistently recognized as a top seller and led sales teams responsible for $160+ million in revenue.

She was successful but lonely at the top. Cherilynn was among the few Black women in Corporate America who broke ‘The Black Ceiling.’ For years she was the only woman generating millions of dollars in revenue, sipping cocktails in business class, and parking her luxury car next to the men in suits. And they would still call her by the names of their assistants! Other saleswomen told stories about how their male colleagues said they were ‘being paid enough for women.’ Cherilynn decided that was enough. This narrative and practice needed to change. 

She left the corporate world to become an entrepreneur and coach at CGI Executive Coaching, which helps Black and Brown women get the confidence, resources, and tools to become ‘too good to be ignored.’

Cherilynn’s got a bold mission: to help one million Black and Brown women get recognized by 2030 and ‘sit at the table of their dreams.’ An admirable vision that she’ll also need to sell. 

So, let’s find out how Cherilynn does it.

1. What do you love most about selling?

Helping people realize their visions and dreams. That’s what gets me up in the morning: when I learn about their challenges and solve their problems. 

To provide clients with something they need, equip them with new solutions and tools, and then see them succeed is my ultimate driver, and I think that’s why I love sales so much.

2. What’s your sales philosophy, in three sentences or less?

 I learned the essence of client management, relationship building, and selling from my father. While I was still a child, I watched him run his Castleman Construction business and build strong relationships with his clients. He would invest much time to learn about their goals, then move mountains to bring their visions to life, and it always blew people away.

So, instead of three sentences, let me give you what I see to be the three critical skills for successful sales: 

  • Immersing yourself into the customer’s world and getting insight.
  • Building deep relationships based on empathetic listening.
  • Discover your superpowers and leverage your story to uncover your ‘why’. 

3. Is there anything that makes your sales process unique?

A good salesperson knows how to make everything about the customer. My way of doing it includes recognizing people’s unique characteristics, traits, and skills and then helping them leverage that to achieve their dream. 

I believe one of my superpowers is to help people think bigger, create a vision, figure out what they’re good at, and how to use that to get to that point. That’s also the one thing that sales and my current coaching business have in common.

For example, if you’re super analytical and great at reading financial statements, leverage that with your clients. If you are solution-orientated, ask more powerful questions.

Everyone is better at something than 90% of the population. I help my customers find out what that is for them, focus on their unique story, and use it to reach their goals.

4. How do you make your prospecting stand out?

 By immersing myself entirely in my clients’ world.

That works so well because of the process that comes with it – turning data about your clients into insight that can help you understand them on a deeper level.

Let me give you an example. I’m a kayaker, and I moved from Maryland to Florida. You need a more stable kayak in Florida than in Maryland because you are kayaking around alligators. 

Data is knowing that I’m a kayaker and I moved from Maryland to Florida and asking me if I want to buy a new kayak. 

But why would I buy a new kayak when I already have one?

That’s where insight comes in. Insight is telling me that the alligators require a more stable kayak in Florida. Now, you have my attention because you are giving me something valuable.

How do I gain those insights?

I go on LinkedIn. I read a 10k (the most critical document salespeople never read), and I use Value Line. I immerse myself in my client’s world. From that, I hope to understand their industry and company and lead with that insight.

5. What’s your favorite discovery question?

I have four ‘Fs’ that I typically ask in a customer conversation:

  • First. Everyone has a first experience.

What’s your first day in your new position like? For example, what was it like the first day you discovered cloud computing? Ask about anything related to your product first because it’s an easy topic for your client to discuss.

  • Finest. Everyone is getting something right.

Ask your client – what you are getting right about your search. What are you doing well right now?

  • Failure. Everyone has some room for improvement.

What would you like to do better? Where can you improve?

  • Future. Everyone likes to envision a bright future.

If I were to give you a magic wand, what would this situation look like a year from now? What would ‘perfect’ look like for you? 

Once someone tells you their experience, what they’re doing well, what they could improve, and where they’d like to go, you’re ready to find a solution with them. That’s what I do. 

6. Is there a habit you have outside work that helps you sell better?

Box breathing

There are many breathing techniques, but one of the simplest is box breathing, and I teach it to all my coaching clients. It’s four steps – you breathe in for four seconds, hold your breath at the top for four seconds, breathe out for four seconds, and then hold your breath at the bottom for four seconds. 

Box breathing will quiet your brain, slow your heart rate, and lower your blood pressure. If you do that, you automatically listen better and connect with people better because all your internal chatter goes quiet.

Before I meet with a client or jump on a call, I do a box breath. It helps me focus.

7. How do you use LinkedIn when selling?

I use LinkedIn for insights.

For example, I can look at someone’s LinkedIn profile and determine their Social Style – are they a driver, expressive, amiable, or analytical? That helps me better understand them and ultimately build a relationship with them.

I also use LinkedIn to establish myself as a thought leader and post content for all four Social Styles. That helps me build my brand and my company’s brand.

And lastly, I use Sales Navigator to stay on top of my clients. For example, I have the top 100 DEI leaders saved in an account list because those are my clients. With that, I gain insights into them and understand their changing jobs, what they’re focused on, whom they know, and on and on. It’s an excellent tool for getting that deep insight into your buyers. 

8. What has been your biggest failure in sales, and how did that experience transform you?

Remember the first of the three pieces of advice I gave at the beginning – immersing yourself in your customer’s world? Well, that’s precisely what I did wrong when I worked for a hospital, selling medical education conferences to physicians. 

At the time, I was living in Colorado and had no problem selling out ski conferences in Colorado – doctors love to ski.

But what about all the physicians who don’t ski, I wondered? I just assumed they would love to come to Colorado in the summer instead. There’s a big summer jazz festival in Colorado, and so I planned this huge medical conference around that event. I even sent out branded recorders to hundreds of physicians to promote it. 

The result: one person registered for that conference. One single person! Usually, I would get hundreds. So it was a massive failure, and the hospital lost a lot of money.

All because I never asked physicians what they like to do in the summer (I learned later that they want to go to a golf resort, Disney World, or Hawaii, but definitely not to Colorado).

There’s an old saying that prescription without diagnosis is malpractice. In this case, I committed malpractice because I prescribed something without talking to my audience first. I realized that you must do your discovery questions before putting your solution on the table. 

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