What does getting locked out of a house while cat-sitting have to do with sales? It's about drama. Getting locked out is a sudden, stressful, and expensive problem. A key safe solves that drama. And at its core, that’s what sales is: your job is to solve the drama for your client.
But in this episode, Benjamin explores a bigger challenge: the drama your client thinks they have is often not the real one. He shares a powerful case study of a company with flatlining sales. The manager was convinced the drama was a "lazy Gen Z" sales team. The real drama? An outdated sales approach that was demotivating the team and failing customers.
Too often, we jump to solve the surface-level problem without digging deeper. The most effective salespeople act like detectives, uncovering the root cause of the issue. By focusing on the real drama, the company in the story transformed its 47-second calls into 15-minute conversations and increased sales by 147%.
At Showing Up, we teach that your greatest value isn't just in providing a solution, but in having the clarity to identify the right problem in the first place.
In this episode, you’ll learn:
Exercise
Links & Resources
Learn more at showinguplearning.com
Subscribe to access our full library of sales training modules and get free access to The 12 Traits Clients Trust Most.
Every subscription funds a free scholarship for a young person through the Showing Up Foundation.
What can we learn from Starbucks? When the coffee giant lost focus and started adding cheese toasties to the menu, it diluted the very essence of the "third place" it promised to be. The brand struggled until it returned to its roots: coffee.
In this episode, Benjamin explores how this lesson is critical for sales professionals. A sales career doesn’t have to be a manic, 60-hour-a-week chase. The key to a calm, focused, and highly effective work life is knowing what you’re great at, who your ideal customer is, and—most importantly—which sales you should walk away from.
Too often, we pursue every lead, believing that more activity equals more success. This only wastes time on work you'll never win and dilutes your focus on the clients you are perfectly suited to help.
At Showing Up, we believe that knowing the sales you won’t win is just as important as knowing the ones you will. This clarity gives you more time, less stress, and better results.
In this episode, you’ll learn:
Exercise
Create a five-column checklist to define your ideal client.
Use this framework to decide which opportunities to pursue and which to walk away from.
Links & Resources
Learn more at showinguplearning.com
Subscribe to access our full library of sales training modules and get free access to The 12 Traits Clients Trust Most.
Every subscription funds a free scholarship for a young person through the Showing Up Foundation.
What’s the real cost of business FOMO? It’s more than just a fear of missing out; it’s a destructive habit that wastes time, damages your brand, and burns out your team by trying to be everything to everyone.
In this episode, Benjamin shares a candid story about a former workplace where a "say yes to everything" culture led to manic unsustainability. From there, we unpack why being selective isn't just good for well-being - it's the secret to a 92% proposal win rate.
Too often, we chase every opportunity, responding to every RFP in the belief that more activity equals more success. The truth is, this scatters your energy, dilutes your brand, and leads to countless wasted hours on work you were never going to win, damaging your reputation in the process.
At Showing Up, we believe that saying "no" is a superpower. We are meticulous about only taking on work where we know we can be the best partner for a client. That clarity and focus make all the difference.
In this episode, you’ll learn:
Exercise
Look back at the last ten proposals you submitted. How many was your company truly the best fit for? Now, calculate the hours spent on the proposals you were never going to win. What could you have done with that time instead?
Links & Resources
Learn more at showinguplearning.com
Subscribe to access our full library of sales training modules and get free access to The 12 Traits Clients Trust Most.
Every subscription funds a free scholarship for a young person through the Showing Up Foundation.
What can we learn from a fashion icon who was rejected by her industry? When Coco Chanel started, she was an outsider in a world dominated by men who dictated what women should wear. She refused to play by their rules, building an empire on a simple, powerful idea: "Beauty begins the moment you decide to be yourself."
In this episode, Benjamin explores how Chanel’s philosophy is a crucial lesson for sales. The biggest mistake salespeople make is playing a role - adopting a persona they think clients want to see. But people buy from people they trust, and trust only comes from authenticity.
Too often, we hide our true personalities behind a mask of professionalism, believing it’s what’s required to succeed. The truth is, your unique quirks, stories, and perspective are what make you valuable. The question is: are you brave enough to be yourself?
At Showing Up, we believe the most effective salesperson you can be is yourself. And that clarity makes all the difference.
In this episode, you’ll learn:
Exercise
What’s your version of authenticity? Get a blank page and draw three columns. In the first, list what makes you the "real you." In the second, write what your friends and colleagues value most in you. In the third, identify the work habits that feel inauthentic. Circle the authentic traits you can bring more of into your work.
Links & Resources
What does America’s first self-made female millionaire have to do with selling card-payment machines in London? More than you might think. Madam C.J. Walker, born to former slaves in 1867, built an empire by solving a problem everyone else ignored - the painful hair and scalp conditions affecting Black women. She didn't just sell a product; she sold a solution to an unspoken pain.
In this episode, Benjamin tells the story of Madam C.J. Walker and her army of sales agents. We explore how their success wasn't built on listing features, but on their ability to see, name, and solve a problem that was hidden in plain sight.
Too often in sales, we focus on what our product is instead of the problem it solves. We talk about features when we should be talking about feelings - the frustrations, losses, or missed opportunities our customers face. This episode is about making that shift.
In this episode, you’ll learn:
Exercise
Take a sheet of paper and draw two columns. In the first column, write down your product or service as it is: the features, the functions, the details. In the second column, write down the problem it solves. Not just what it does, but why that matters to the customer. Does it save time? Prevent loss? Make life easier? Create confidence?
Links & Resources
What can we learn from 99p? On the surface, it’s just one penny less than a pound. But in practice, it changed the way the world priced things. Not because it tricked anyone, but because it presented value in a way that felt lighter, more approachable, more human.
In this episode, Benjamin explores a brilliant moment from Mad Men, where Roger Sterling points to 99 cents as “true brilliance in advertising.” From there, we unpack why presentation matters just as much in sales as it does in advertising.
Too often, we bury what we do in jargon and clichés. The truth is, every sales conversation and every LinkedIn post is an advert for who you are and what you bring. The question is: how simply, clearly, and intriguingly can you say it?
At Showing Up, we don’t claim to be a “cutting-edge provider of human-centric performance enablement solutions.” We just help people be great at sales. And that clarity makes all the difference.
In this episode, you’ll learn:
Exercise
What’s your version of 99p? Write down as many simple, intriguing ways as you can to describe what you do. Aim for at least 50. Then test them with colleagues, clients, and friends. Notice which ones land. Keep those. That’s your 99p.
Links & Resources
If there’s one guarantee in sales and client work, it’s this: you will face objections. They might be about price. They might be about speed. They might be about your product not doing everything a client wants. But they will come.
So how do you handle them? By borrowing a page from Eminem’s playbook. In this episode, Benjamin breaks down Charlamagne tha God’s advice to “8 Mile them.” A strategy inspired by the legendary rap battle scene in 8 Mile where Eminem disarms his opponent by naming every possible criticism against himself first.
We’ll explore:
Whether you’re selling, consulting, or advising, this is a micro-lesson on honesty, confidence, and the surprising power of admitting where you’re not perfect.
🎧 Listen now and learn how to 8 Mile your objections.
In this episode, we explore how Smirnoff turned vodka - an unknown spirit in 1930s America - into a global phenomenon by rebranding it as “white whisky.” It’s a story of revolution, resilience, and clever positioning, with a powerful lesson for anyone in sales: don’t push people too far, too fast. Meet them where they are, then guide them half a step forward. You’ll walk away with a practical exercise - the Half-Step Test- that helps you sharpen your pitch and connect more effectively with clients.
