A Meeting That Every Sales Leader Needs to Have with Their Team: "5 Things I Wish I Knew Way Earlier in My Career

When it comes to leading a sales team, one of the most valuable things you can offer is the wisdom you've accumulated over the years. Holding a meeting where you share “5 things I wish I knew way earlier in my career” is a chance to impart those hard-earned lessons to your team in a way that’s both engaging and enlightening.

Here’s one lesson it took me way to long to learn. It wasn’t until I reached my late 30s or early 40s that I truly understood the downsides of artificial harmony. Early in my leadership journey, I was quick to set up a culture centered around camaraderie and fun. We had happy hours, kickball leagues, and team lunches. It was all designed to build friendships and create a sense of unity. While these activities certainly fostered bonds among team members, they also led to unexpected turnover. Many people felt pressured to participate in these social events, even though some just wanted to focus on their work during the day and then head home to their families.

These days, my approach is different. I focus on creating a culture that’s fair and transparent, and I make a conscious effort to give people the space they need to thrive. As a result, my team members tend to stay around for 5 to 10 years—or even longer in some cases.

Finding your own “5 things I wish I knew” can start with asking yourself insightful questions. Reflect on how you've evolved as a leader over time. What are the key moments that reshaped your approach or perspective? Maybe consider the greatest pieces of advice you've received from other leaders. For me, two pieces of advice have been particularly transformative: “Never take a no from someone who can't give a yes” and “Never leave a meeting without a next step booked on the calendar.” Those two simple insights were GAME CHANGERS as a young professional.

Sharing these kinds of stories with your team is a way to give them the opportunity to learn from your experiences without having to navigate those same pitfalls themselves. It’s about creating a dialogue where your team can benefit from your insights and grow in their own careers with a bit more ease and confidence. - And while you are at it, bring in other leaders to do the same!

-Adam Morris