Embracing Those Valuable ‘Windshield Moments’
Spending time with reps on the road, online, or away from formal sales calls is one of the most valuable things a sales leader can do. These “offline” moments provide the perfect opportunity to strengthen relationships, discuss strategies, and build trust. Whether it’s a casual chat on a plane, a late-night debrief over a pint, or a quick conversation in the hallway between meetings, these moments create an open, high-trust culture that fosters better communication and accountability within the sales team.
Spotting Strengths and Areas for Improvement
A key part of sales leadership is identifying our reps’ strengths and coaching them on areas for improvement. The best way to do this? Observe them in real-world sales situations—during prospecting, discovery, and closing meetings. High-stakes interactions reveal true selling abilities, and by being present, we can offer constructive feedback that helps reps win more business and advance their careers. Sales coaching isn’t about adding pressure; it’s about providing the right support to help them succeed.
Lending a Hand During Sales Calls
Joining reps on sales calls allows us to provide guidance while ensuring they remain in control of the conversation. Before stepping in, leaders should collaborate with reps to define their role in the meeting—whether it’s taking notes, handling objections, or supporting specific talking points. For new hires or struggling reps, this is a great opportunity to model a strong sales conversation, but in most cases, leaders should act as a support system rather than take the lead.
Getting a Real Feel for Client Interactions
Sales leaders who observe reps in action gain valuable insights into how they present themselves, interact with clients, and represent the brand. Seeing firsthand how reps handle different situations allows for meaningful coaching and guidance, ensuring they are effectively engaging with clients in a way that drives results.
Staying in the Loop and Building Trust
The more time leaders spend in the field, the stronger their credibility becomes. Sales reps respect leaders who actively participate rather than just monitor CRM reports from behind a desk. These interactions also keep leaders informed about market trends, customer concerns, and industry shifts. Often, reps encounter changes in the marketplace before senior leadership does, but they may not recognize their significance. Leaders who are in the trenches can spot these cues and relay valuable insights to senior management.
The Three Sales Management Tools
To see strong results in 2025, sales leaders should prioritize three key management tools:
- Spending time in the field with reps
- Proactively coaching their team
- Implementing proper 1:1 accountability meetings
If you commit to these three things, I guarantee you’ll see great results in 2025!
Cheers,
Kyle Jager
