Gui Costin shares how sales leaders can bring different generations together, build stronger teams, and create a workplace where people want to stay.

Outside Sales Talk with Steve Benson

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About This Episode

Today’s sales teams can span multiple generations, each bringing different experiences, expectations, communication styles, and approaches to work. For leaders, understanding those differences can be key to building a team that works well together.

In this episode of Outside Sales Talk, Steve Benson sits down with Dakota Founder and CEO Gui Costin to discuss how leaders can bridge generational gaps in the workplace. They explore building mutual respect, recognizing generational biases, adapting how you communicate, encouraging mentorship, and creating an environment where employees across generations can learn from each other.

What You’ll Learn

• How to build stronger collaboration across generations
• Why self-awareness matters when leading a diverse team
• How to recognize and challenge your own generational biases
• The role mentorship can play in sharing knowledge and experience
• How leaders can learn from younger, tech-savvy employees
• Ways to create a workplace where your best people want to stay

Watch the Full Episode

Listen instead: Spotify | Apple Podcasts | Pandora

About Gui Costin

Gui Costin is the Founder and CEO of Dakota, an investment services company that has helped clients raise more than $40 billion. As a leader in sales and marketing, Gui focuses on mentorship, career growth, and helping companies put processes in place that allow their businesses and teams to grow.

Connect with Gui: GuiCostin.com | Dakota.com

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Donald C. Kelly shares how field sales reps can use AI to save time, prepare smarter, and sell more without losing the human side of sales. 

Outside Sales Talk with Steve Benson

Watch on YouTube | Listen on Spotify | Apple Podcasts

About This Episode

AI is changing how salespeople research prospects, prepare for meetings, handle follow-up, and manage the work surrounding a sale. But where does AI actually help field sales reps, and where is the human side of selling still irreplaceable?

In this episode of Outside Sales Talk, Steve Benson sits down with sales expert and The Sales Evangelist host Donald C. Kelly to explore practical ways field sales reps can make AI part of their day. They discuss using AI for prospect research, meeting preparation, objection handling, and working on the go, while still keeping relationships and human interaction at the center of the sales process.

What You’ll Learn

• Where field sales reps can start using AI
• How AI can make prospect research faster and more valuable
• Ways to prepare for meetings and objections with AI
• How to use AI when you’re constantly on the go
• Where automation can hurt customer relationships
• Why the human side of field sales still matters

Listen to the Episode: Spotify | Apple Podcasts | Pandora

About Donald C. Kelly

Donald C. Kelly is a seasoned sales professional, speaker, and trainer on a mission to help sellers at all levels improve their skills and achieve bigger results. He has been recognized by Salesforce as a Top Sales Influencer for three consecutive years and as a LinkedIn Top Voice in Sales.

Donald is also the host of The Sales Evangelist, one of the longest-running sales podcasts in the world, with nearly 2,000 episodes and listeners in more than 155 countries.

Connect with Donald: LinkedIn | The Sales Evangelist

Never Miss an Episode

Get actionable advice from leading sales experts on Outside Sales Talk.

Subscribe on YouTube | Spotify | Apple Podcasts

Sell More. Drive Less.

Outside Sales Talk is brought to you by Badger Maps.

Badger Maps helps field sales teams spend less time planning, driving, and doing sales admin, so they can spend more time selling.

See How Badger Maps Works →

Get More Sales Tips in Your Inbox

Join 95,000+ subscribers getting actionable sales tips and insights from top sales experts with Badger Maps’ newsletters.

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