As a sales leader, are you coaching your team for the long haul, or are you scrambling in the final weeks of the quarter? In this episode of Two Tall Guys Talking Sales, Kevin Lawson and Sean O’Shaughnessey break down the difference between regular season and postseason play—whether in sports or sales. They explore why last-minute Hail Mary strategies can be damaging, how to manage time, and the importance of effective and consistent coaching. With March Madness and The Masters as the backdrop, this conversation is packed with insights to help you refine your sales approach and ensure your team is always in winning form.
Key Topics Discussed
- The Sales Tournament Mentality (00:02:00) – What sales teams can learn from March Madness and The Masters, and why only one team wins while the rest lose.
- Building a Winning Sales Team (00:03:30) – How business owners can prepare their sales teams to perform under pressure by ensuring the right people are in the right seats.
- The Role of Sales Coaching (00:05:00) – Why sales leaders must incorporate skills development into every sales meeting instead of just reviewing the pipeline.
- The Pitfalls of End-of-Quarter Desperation (00:07:50) – How last-minute discounting and rushed deals create long-term problems and train customers to buy at a discount.
- Mastering Time Management in Sales (00:10:00) – How prioritization and disciplined execution throughout the quarter prevent last-minute chaos and boost consistent performance.
Key Quotes
- Kevin Lawson (00:07:53): “If you’re behind in sales right now, don’t throw Hail Marys. Don’t discount. You’re teaching your prospects to wait until the end of the quarter for a better deal—and that’s a losing game.”
- Sean O’Shaughnessey (00:13:00): “You have one thing in sales you can never get back: time. If you wasted today, it’s gone forever. You can’t go back and fix it.”
- Kevin Lawson (00:09:00): “Salespeople with commission breath stink. If your only focus is closing the deal before Friday, your prospects will smell it a mile away—and that’s not how you build relationships.”
A Significant Actionable Item from this Podcast
Develop a Five-Week Sales Training Plan – Sales leaders should map out the next five sales meetings, dedicating at least five minutes to skills development in each session. Focus on topics such as pipeline progression, prospect qualification, and closing techniques. Training should not be an afterthought—it should be a fundamental part of your sales strategy.
Why You Should Listen to This Episode
Whether you’re a sales leader or a frontline salesperson, this episode is your playbook for maintaining momentum all year long. Avoid the common traps of end-of-quarter desperation, build a disciplined approach to sales training, and master the art of time management. Just like in sports, sales success isn’t about last-minute heroics—it’s about consistent execution.
Tune in now and take your sales game to the next level!
