As a sales manager or leader, one of the most crucial roles you play is helping your team navigate “The Dip”—that tough period where progress stalls, motivation wanes, and the path to success feels steep. Seth Godin’s The Dip highlights how essential it is to recognize these moments in ourselves and others, making the choice to either persevere or pivot. For your team members, the Dip can often feel isolating, leading them to question their abilities. This is where leadership can make all the difference.
Encourage individuals by acknowledging their struggles and reinforcing their potential. Sometimes, simply knowing they’re heard and supported can help them renew their willingness to push through. But it’s equally important to recognize when a challenge has become a “cul-de-sac”—a dead end that leads nowhere. In these cases, guide team members to re-evaluate their path. If their efforts aren’t yielding meaningful progress or if the market or strategy has shifted significantly, it might be time to redirect their focus.
The key is to distinguish temporary obstacles from enduring roadblocks. For challenges that promise growth and learning, encourage grit and perseverance. But for those that offer little return on investment, be willing to support a graceful exit. Ultimately, your role is to help them identify worthwhile pursuits and see them through, turning any Dip into an opportunity for growth rather than frustration. Leading with clarity and empathy creates a resilient, focused team ready to achieve lasting success.
Personally, I love this story from John Krasinski. It illustrates the impact of encouragement and how success, luck, and opportunities lie on the other side of the dip.
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