In this episode of The Leadership Habit Podcast, Gui Costin, founder and CEO of Dakota, shares his insights on building successful sales teams, fostering a thriving workplace culture, and adapting to modern sales challenges. Host Jenn DeWall delves into Gui’s leadership philosophies, which prioritize respect, structure, and empathy as the cornerstones of a high-performing organization.
Gui emphasizes the importance of creating a positive workplace culture where employees feel valued and respected. At Dakota, toxic behaviors are not tolerated, even from high performers or clients, as maintaining a supportive and collaborative environment is a top priority. Gui explains that culture is built on clear core principles, and leaders must consistently align their actions with these values. By doing so, employees are empowered to thrive and grow, making work both fulfilling and enjoyable.
Sales, as Gui notes, is one of the most emotionally demanding professions due to constant rejection and the challenges of cold outreach. He stresses the need for a structured process to support salespeople, including daily check-ins, clear expectations, and time-blocking for outreach activities. By focusing on the salesperson’s growth and providing consistent coaching, leaders can help their teams develop resilience and confidence over time. Gui explains that mastering the "cold outreach muscle" is a transformative skill that can take 12–18 months to fully develop but delivers lasting career benefits.
One of Gui’s standout strategies involves addressing follow-ups during the initial meeting by asking tough questions, such as whether a prospect sees potential for a partnership. This approach avoids unnecessary follow-ups and ensures clarity while the relationship is still fresh. He also highlights the importance of clear calls to action in follow-up emails to respect the prospect’s time and facilitate meaningful engagement.
Gui discusses the evolution of sales in the post-pandemic era, emphasizing the need for authenticity and compassion in outreach efforts. He believes that sales success comes from building genuine connections rather than focusing solely on transactions. For leaders, Gui advocates for empathy, self-reflection, and prioritizing the success of their teams, sharing his own journey of personal growth as a leader.
This episode is packed with actionable advice for sales leaders and modern professionals looking to build effective teams, improve sales processes, and create workplace cultures that inspire growth and collaboration.