A Modern Leader’s Guide to Sales Success with Gui Costin

The Leadership Habit

In this episode of The Leadership Habit podcast, host Jenn DeWall talks to Gui Costin, CEO and founder of Dakota, sharing practical advice on building a winning sales strategy and creating a strong workplace culture. This episode is full of tips that any leader, sales professional, or sales rep can use to improve their approach and team culture.

Meet Gui Costin, CEO & Author

With over 35 years of experience in sales and leadership, Gui Costin has developed unique practices that have helped Dakota raise over $40 billion for its clients. But Gui’s story goes beyond just numbers – he’s an innovator who’s transforming what it means to build a thriving workplace culture in the world of finance.

As the author of Millennials Are Not Aliens and The Dakota Way, Gui brings new perspectives to sales, marketing & leadership in the investment world. His people-focused approach has led him to build two companies generating $20 million every year by prioritizing what he believes matters most: people.

His “no-policy policy” fosters autonomy and trust, while his talent for engaging millennial and Gen Z workers challenges traditional management styles. Gui’s journey from working in real estate to founding Dakota has given him many insights into building strong company cultures, modernizing sales processes, and adapting leadership styles that motivate and inspire teams across generations.

Putting People and Culture First

Gui Costin’s sales success is rooted in putting people first. “Culture’s about how you treat people…every time somebody comes to work every single day, what kind of experience do you want them to have?” he shared. Costin stressed the importance of a respectful and supportive environment, saying, “We won’t even tolerate bad clients…if they treat our teammates badly, we’ll fire them as fast as we can.” This commitment to protecting employees builds trust and boosts morale.

Costin’s approach shows that consistent actions and values are fundamental in leadership. Leaders who set high standards for how employees are treated create a workplace where team members feel valued and safe. This approach encourages loyalty and dedication — essential for long-term success. Costin’s philosophy proves that a people-first culture isn’t just good practice; it’s critical.

Creating Structure and a Clear Sales Process

Costin explained that success in sales starts with structure. He advised leaders to write down the sales process and explain the reasons behind each step. “The process at the end of the day is what’s most important,” Costin said. Clear roles, responsibilities, and processes help keep sales reps focused. This structure should be paired with supportive leadership. Managers should ask questions like, “Are you following the process? Talk to me—what’s going on?”

An effective sales process not only improves sales results but also helps team members grow. “It’s all about the connection…and building relationships with people,” Costin said. Leaders should guide their teams to see beyond transactions and focus on genuine connections.

Consistency in following a structured process builds confidence and resilience. When sales reps understand why each step matters, they stay motivated and committed. This clarity also helps them solve problems and adjust their strategies, making them more effective.

Effective Follow-Up and Outreach

Costin shared valuable tips on follow-up strategy. He highlighted the need to ask the right questions during meetings to avoid ghosting and miscommunication. “Ask the tough questions while the relationship is warm,” he advised. Clarifying if there’s an opportunity during the meeting saves time and keeps communication clear.

Costin also talked about the importance of authentic cold outreach. “You’re not going to make the sale over email. Just be a human being,” he said. Providing context quickly and clearly, along with a specific call to action, makes a big difference. He warned against vague emails, which can come across as lazy or rude.

Costin emphasized that follow-ups should be persistent but respectful. Sales professionals should focus on long-term relationship-building instead of pushing for quick results. This approach builds trust and leads to more future opportunities.

Adapting to Modern Sales Challenges

Sales today require adaptability. “Sales is an emotional game…constantly being rejected by somebody out in the ether who doesn’t know who you are,” Costin noted. Leaders need to help their teams handle rejection by encouraging discipline and consistency. “It’s about 12 to 18 months to fully develop the muscle…but if you stay disciplined, you’ll have more opportunities than you could ever imagine,” he said.

Leaders should also consider that today’s buyers are more informed and selective. Costin advised sales reps to adjust their techniques and use technology to create personalized, data-driven strategies that connect with their target audience. This adaptability ensures that sales professionals can effectively present their product or service in a way that resonates with potential clients.

Using Technology and Data Wisely

Costin spoke about how technology can help modern sales. Using tools that provide data and streamline processes allows leaders to target the right clients and improve outreach. Technology can automate parts of the sales process, freeing up time for more personal interactions. “Use data to inform your decisions, but never forget that the human touch is irreplaceable,” Costin said.

Tracking metrics and feedback through technology also helps sales teams refine their approach. While technology can make processes more efficient, Costin reminded leaders to keep genuine connections at the center. A mix of data-driven strategies and personal engagement can set a company apart and showcase its product or service in the best light.

Key Takeaways for Leaders

Costin’s main message was to stay thoughtful and empathetic. “Just always be introspective about how you’re treating people and making it all about them,” he said. For leaders wanting to improve their sales strategies, building a clear process, nurturing authentic connections, and focusing on team culture are crucial steps. The goal is to help others succeed while creating a supportive and positive work environment.

Leaders should remember that sales success is a journey. Building a strong team means supporting their growth, promoting respect, and focusing on lasting relationships. With these practices, sales professionals can inspire growth and achieve long-term success.

For those looking to sharpen their sales strategy, Costin’s insights serve as a guiding framework. Combining an effective sales process, compassionate leadership, and adaptability can set any team on the path to lasting success.

Where to Find More from Gui Costin

• Connect on LinkedIn: linkedin.com/in/guicostin/
• Visit his website: dakota.com
• Email him: [e-mail]

Thank you for listening to The Leadership Habit Podcast! If you want to learn more about Crestcom’s leadership development programs, contact us to schedule a free leadership skills workshop: crestcom.com/freeworkshop.

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