Episode 312 of The Business Development Podcast features a practical and candid conversation with Gordon Sheppard, CEO of Executive Wins, about what really holds teams and organizations back from growth. Drawing on more than 25 years of executive coaching experience, Gordon shares what happens behind the scenes when businesses stall, leaders feel overwhelmed, and execution breaks down. Instead of chasing strategy or quick fixes, he explains why structure, accountability, and difficult conversations are often the true levers that create lasting change.

Together, Kelly and Gordon dig into the habits of high-performing leaders, how to build teams that actually execute without constant supervision, and the simple but powerful questions every CEO should be asking themselves. This episode is a grounded, no-nonsense look at leadership in the real world, offering clear insights for founders and operators who want fewer fires, stronger teams, and consistent, scalable wins.

Check out Executive Wins: https://executivewins.com/

Check out The Executive Wins Podcast: https://open.spotify.com/show/1P1NEQVF744tV6xEjm5vRC

Key Takeaways:

1. Strategy rarely breaks businesses. Poor execution does. Most growth problems are alignment and accountability issues, not planning issues.
2. Leaders often hold onto too much. If everything funnels through you, your team isn’t built to scale without you.
3. Hard conversations are not optional. Avoiding them quietly compounds dysfunction inside teams.
4. Behavior change beats theory. Real leadership impact happens when people change what they do, not just what they know.
5. Status quo is usually the hidden decision. If nothing changes after the meeting, you’ve already chosen comfort over growth.
6. Great coaches and leaders ask better questions, not give better answers. The right question creates clarity faster than advice.
7. Psychological safety unlocks performance. Teams move faster when people feel safe enough to be honest.
8. Small, consistent improvements outperform big, dramatic initiatives. Daily execution beats occasional breakthroughs.
9. Structure creates freedom. Clear roles, responsibilities, and expectations remove friction and speed up decision-making.
10. Leaders must stay coachable. The moment you stop listening is the moment your growth plateaus.

This episode of The Business Development Podcast is proudly brought to you by our 2026 Title Sponsor Hypervac Technologies, North America’s leading vac truck manufacturer, and their new division Hyperfab, delivering custom industrial fabrication solutions built for performance and reliability.

If your operations depend on serious equipment and serious uptime, these are the people to know. Go check them out at www.hypervac.com.

Learn more about The Catalyst Club, Kelly Kennedy’s private community built for leaders, by leaders. It’s where founders, sales professionals, and business developers connect, sharpen their skills, and grow alongside people who are serious about moving the needle. Join us at www.kellykennedyofficial.com/thecatalystclub.

Mentioned in this episode:

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