Will You Please Shut Up?

Early in my career, I had a boss, Phil, who was one of the nicest people you’d ever meet. Big heart. Big energy. And an even bigger love for conversation.

If you stopped by his office with a quick question, you’d better cancel your next meeting — because 30 minutes later, you’d be deep into stories about his weekend, his college days and a client he sold to in 1978. Those of us who have been in this business for any amount of time know that we can all suffer from this “affliction.” We’re great storytellers. In sales, however, a more critical skill is LISTENING.

But the real challenge wasn’t in the office. It was when that same storytelling showed up in front of clients. I loved “ride-along days” as a seller. It was a chance for me to show off and gain valuable insights into what I could improve. The challenge came when I had to coach the coach.

A quick sales call would turn into a rambling monologue. Momentum would stall. Attention would drift. And the prospect’s original reason for meeting would slowly disappear. I wondered how I could regain control without offending my boss.

Every salesperson has lived some version of this. (None of mine, hopefully, because I learned from Phil how not to do it.)

Here’s the tightrope: you don’t want to interrupt your boss. You don’t want to embarrass them. But you also don’t want to miss a great sales moment.

This is where the skill of managing up becomes essential.

Leadership author John Kotter in his book, Power and Influence, reminds us that influence doesn’t just flow down an org chart — it flows in every direction. The strongest professionals learn how to guide situations, not just follow titles.

When your leader is overly chatty in front of clients, the goal isn’t to shut them down. It’s about redirecting with respect—and protecting the sale. Clients already have a natural inclination to “talk to the boss.” During ride-alongs with my sellers, I would always redirect the client back to the seller. “That’s a great question, Bill, you might share…” After the third time I would do that, they forgot I was in the room. I recognized the meeting wasn’t about me; it was about the seller developing a relationship with the client and I didn’t want to get in the way.

Here are a few techniques high-performing sellers use seamlessly:

1. Bridge back to the business objective. When the story drifts, step in with: “That’s a great point — and it connects perfectly to what you were asking about earlier…” Then pivot straight to the client’s need.
2. Ask purposeful questions. Questions are the cleanest interruption tool there is. “Mary, can I check something with you on timelines?” It refocuses the conversation without cutting anyone off.
3. Use the agenda as your anchor. Start meetings with: “We’ve got three things we want to cover today, so we respect your time.” Now you’ve created a natural structure to return to when things wander.
4. Summarize and advance. “Let me recap what I’m hearing so we can talk next steps.” Summaries politely close the storytelling loop and move the meeting forward.
5. Debrief privately, not publicly. After the meeting, share impact—not criticism. “I noticed when we stayed tight on the agenda, the client leaned in and asked for next steps. That focus really helped.”

Here’s the bigger truth:
Clients don’t buy when conversations drift. They buy when conversations move toward clarity. (See the tip: Know When to Hold, Know When to Fold)

An overly chatty boss usually means well. They’re trying to build rapport, they are engaging and in my experience with Phil, his stories were always interesting and fun. But when I’m trying to engage with the client…

Your role is to pair rapport with results.

When you manage up well, you don’t undermine authority. You elevate the entire sales experience.

Bottom line:

• Respect the relationship.
• Protect the client’s time.
• And gently steer the conversation where value is created.

Because great salespeople don’t just close deals — they know how to navigate dynamics when it matters most.

Think Big, Make Big Things Happen!

Jeff Schmidt is the SVP of Professional Development. You can reach him at Jeff.Schmidt@RAB.com. You can also connect with him on X, YouTube, and LinkedIn.