December 8, 2020
Cherilynn Castleman is the Managing Director of CGI Consulting, a Global Sales Keynote Speaker, and the Chief Learning Officer of Sistas in Sales. From this vantage point, she has a unique perspective on where the sales sector is headed. We asked her 22 questions. Here are her 22 answers.
1. What did you have for breakfast this morning?
As a native of Minnesota, when the weather gets cold, I turn to oatmeal — steel cut, with grated apples, pears, dried cherries, and almond slivers with a splash of coconut water.
2. What’s the last great thing you binge-watched?
I watched “The Great British Baking Show.” As someone who doesn’t cook, the best thing I make is reservations. Watching passionate bakers fascinates me!
3. How has COVID-19 affected how you/your sales org operates and in your adoption of virtual selling practices?
Before the pandemic, as a global sales keynote speaker, executive coach, and sales trainer, my work was primarily conducted in person, leading workshops and delivering keynotes. Today, I’ve taken my coaching, training, and speaking work online, where I continue to focus on empowering women of color across the sales sector and sharing knowledge and resources to build community, sisterhood, and empowerment through mastering the sales craft.
4. Which among these changes from COVID-19 will continue in the years after the pandemic subsides?
As the economy continues to recover from the pandemic, modern consumers expect more and will continue to expect more out of their salespeople. The key to success in this new sales environment is sales teams’ ability to empathetically connect with their customers and to use the insights gained from these connections to collaborate with clients and tailor solutions to fit their specific needs.
5. Tell us about Sistas in Sales. What’s your involvement and what are your goals for the organization?
Since 2017, Sistas In Sales (SIS) has empowered women of color through distinct networking, training, and career opportunities across the sales sector. SIS is the first national organization to serve women of color in professional sales careers with more than 2,500 members across the United States. SIS’s membership represents a broad range of diverse women in media, software, finance, IT, education, and tech sales, focusing on sharing knowledge and resources. SIS strives to level the playing field with transparency by pulling back the curtain on what it takes to succeed in sales.
6. What does the term “buyer first” mean to you, and is a buyer first approach operationalized in your sales org?
The Buyer First concept is perfectly aligned to the needs of this moment. Now more than ever, the key to selling mastery is being able to connect empathetically with your clients by speaking their language and helping them understand how your solutions address their needs.
7. If you were building a sales tech stack from scratch, what would it contain?
- CRM to track sales professionals’ efforts across email, calendar, and phone.
- Artificial Intelligence (Both Conversation Intelligence – to leverage current remote sales environment, and Sales Intelligence – for social styles and personality insights.)
- LinkedIn Sales Navigator
- E-contract and e-signature tools
- Virtual meetings with screenshare
- Phone/email outreach/systems/solutions/dialer
- Data analytics, forecasting, and dashboards
- Team communication IM
- Live chat for customer support
- Team revenue — sales/marketing alignment
- Email verification/validation
- Sales automation and acceleration – automated workflows
- Prospecting and Leadgen List Creation
- Smart calendar Scheduling
- Document Sharing
8. How do you go about building trust with prospects?
In sales, empathetic listening is more challenging than basic listening, because, during this global pandemic, clients may feel worn down as they navigate anxiety, isolation, and uncertainty. Empathetic listening and asking powerful questions are always the keys to engaging and building trust with clients, but they are especially vital now.
Empathetic listening is when you refine your ear and become more closely attuned to your clients’ priorities and pain points. To build trust, sellers must fully comprehend what their clients are saying — try to put yourself in their position and internalize their reality. What are the stressors they experience on a daily basis? How has COVID-19 impacted their previous professional superpower? Does success seem possible? If so, how would it feel?
To build trust, sellers have to harness authentic empathy and leverage powerful questions to understand your clients’ needs better. I challenge my audience and clients to develop a more attuned ear and hear what is not being said.
9. What sales tech and other tools do you use (and how do you use them) to research prospects before reaching out?
For enterprise and selling into the C-suite, I teach my clients financial fluency, to see what they can discover when they immerse themselves in a client’s world and to look beyond a company’s business information, objectives, and risk factors. Research helps salespeople gain insights to influence a customer’s operational, financial, and long- and short-term goals. They learn to leverage research to validate their assumptions and look for insights about trends and challenges.
I advise my clients to review the words and the numbers.
Words: Examine documents for themes, patterns, or movements (analyst reports, leadership presentations, CEO letters, annual reports, proxy statements, and quarterly earnings calls). See if you can discover enterprise goals, “big bets” (new strategic initiatives), key objectives by business unit and line of business, departmental initiatives, external environmental factors, and KPIs.
The Numbers: If you’re like most salespeople, your eyes glaze over at the sight of your client’s 100+ page Form 10-K. Big mistake. As the pandemic continues to unfold, a client’s 10-K and 10-Q may be the most important documents that a salesperson has never read. Public companies will provide insight into how they’re adapting business strategies and navigating through the ongoing coronavirus pandemic.
Data can be described, counted, and manipulated (cash-flow financial statement, income statement, and balance sheet). The financial metrics salespeople uncover during research can be used to identify business opportunities and pinpoint trends.
If salespeople can leverage client research and insights, they can make their sales story/value statement compelling, thought-provoking, and remarkable.
10. What jobs did you have in high school and what lessons did you learn from them that you still put into practice today?
I grew up in a tight-knit family with my three siblings and parents. My father and mother were my first and best teachers and believed in leading by example, something I subscribe to as well. My father was a business owner who thought that you could achieve great things with hard work, trust, and ingenuity. I started working at his general contracting business when I was in high school.
My dad’s customers, Dave and Delores, had hired my dad to convert their attic to a master bedroom suite. While my dad showed Dave how the double-headed shower worked and ran water in the oversize Jacuzzi to demonstrate how the jets worked, Delores and I were in the kitchen on the main floor when I heard a popping sound. I looked up to see the ceiling plaster above our head begin to crack. My dad and I spent the next two weeks and all of the profit we’d earned reconfiguring the bathroom, moving the tub over a weight-bearing wall, and repairing the plaster—and that’s how I learned my “good enough isn’t” work ethic. I challenge myself to achieve mastery, continuously improve, and not settle. By watching my father, I also learned how to manage others and build client relationships.
Working alongside my dad reinforced the sales and client relationship skills I learned because the abstract was made concrete and personal. Similar to my hands-on learning experience, I developed sales expertise and mastery by applying these sales skills and improved my sales competence to a higher level with continued sales experience.
11. Since you started in sales, what’s the biggest change you’ve witnessed?
When you think about sales, the most important thing is speaking our clients’ language and connecting with them over their pain points and how our solutions address their needs. Historically, we as professional sellers spent 20% of our time building relationships and 80% of our time selling. Today this has flipped; successful sales professionals spend 80% of their time getting closer to the customer and their problems and 20% of their time on the solution.
12. What are the key metrics for measuring the success of individual salespeople and the entire sales org and how have these changed over the years, if at all?
In my work with clients, we use a 360o sales feedback assessment tool to measure progress against key success metrics in three key areas: sales competencies, interpersonal skills, and intrapersonal skills. With the shift in how successful sales professionals spend their time – now spending 80% of their time building client relationships and 20% of their time selling – we’ve adjusted our 360o assessments accordingly. The key success metrics we focus on now, both for individual sellers and companies, center the client relationship and the skills needed to further strengthen and develop it. These metrics include cultivating a consultative sales orientation and service focus, social style versatility, enabling trust, demonstrating respect, listening, and remaining resilient in the face of challenges.
13. How do you use LinkedIn for your job?
You know that horrible dream where someone with a knife is chasing you, and you try to scream, but nothing comes out? Many of my clients feel like posting on LinkedIn is just like that.
Not the knife part, but the silent scream. Yet, they are amazing, intelligent, professional women, business leaders in their field, or company in real life. They know that their peers and colleagues at work admire them. Yet, they avoid connecting on LinkedIn out of fear. Fear of being judged, fear of looking uninformed, or fear of being humiliated in front of everyone.
With today’s rapidly shifting technologies, I teach my clients that their next career opportunities, next big sales, next pivotal relationship, and the ones after that will be redefined by the power of social selling and social media.
I help my clients discover LinkedIn’s solutions:
- Have a social media vision.
- Invite people to connect.
- Build relationships, awareness, and visibility.
- Implement a social selling strategy.
- Leverage keywords in their profile, posts, articles, and advanced searches.
Ultimately, they learn that a LinkedIn presence is necessary, and staying in their comfort zone will lead to extinction. I remind my clients that you are the only person who manages your career. If they don’t take the initiative, no one else will. I help them take the first step.
14. What’s the best sale you’ve ever made?
After school, I started my career in social work, where I researched and wrote a proposal and secured United Way funding for an inner-city community-based corrections program for incarcerated mothers with young children. (Note: However, after a few years, I ran into trouble securing additional funding for the program and determined that I needed to develop my sales skills. I landed a job selling life insurance door-to-door and was quite successful. I had always wanted to live and work in Europe, so I joined an insurance company’s German office. I led the district in sales within a year, and the rest is history!).
15. Are great salespeople made or born?
Both. With the right coaching, training and leveraging strength-based techniques combined with the power of a growth mindset, a leader can cultivate the confidence and skills needed to amplify a salesperson’s skills to succeed professionally and personally
16. What do top-performing salespeople do differently than their colleagues?
Top salespeople find repeatable, scalable, and proven sales methodologies and leverage AI along with modern selling tools to drive successful outcomes.
17. What song is on repeat for you right now?
During election week and beyond, I have Better Man by Blues singer and guitarist Keb’ Mo’ on repeat: “I’m gonna make my world a better place, I’m gonna keep that smile on my face, I’m gonna teach myself how to understand, I’m gonna make myself a better man… I’ll just hold on the best I can, And if I fall down, I’ll just get back up, It’ll be alright, It’ll be ok…”
18. What are the key talents you look for when hiring salespeople?
I look for a S.A.G.E. sales professionals who have achieved mastery. Sages are known for wisdom and intelligence.
S – Self-aware: A seller who has a clear perception of his or her personality and can flex to “mirror and match” others’ communication style and personalities with ease; a seller who has interpersonal fortitude; self-awareness that allows them to understand customers.
A – Assertive: Sellers who have the confidence to challenge clients with insight and value. A salesperson who can tailor a value story to a customer’s specific needs and objectives.
G – Great communicator: A seller who can connect with clients and prospects. Do his or her emails generate responses? Is he or she articulate and a great listener? Can he or she tell engaging stories and make empowering presentations?
E – Empathetic: A salesperson makes clients feel like they are the only one in the room. A salesperson who can connect emotionally with a client and their pain before proposing solutions.
19. How do you work with marketing and how would you like to see that relationship changed?
In this new sales environment, it’s imperative for marketing and sales to align and create united strategies to connect with prospective customers to build relationships that lead to sales. I would like to see “Team Revenue” (Sales and Marketing) alignment around goals, strategy, and compensation.
20. What’s a great book you read recently? And what’s a great book that salespeople should read?
I read Brene Brown’s Daring Greatly: How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead. It is based on the below quote by Theodore Roosevelt:
“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”
A great book that sales professionals should read – I have had every sales team I have ever led read it as a team. “You Can’t Win a Fight with Your Client: & 49 Other Rules for Providing Great Service, by Tom Market. It a short, easy-to-read book that provides smart, timeless advice on how to delight your clients.
