Tactical Advice

February 11, 2025

What’s Holding You Back?

What’s up, everyone! 👋🏻

Today’s topic is about overcoming adversity. Every salesperson faces challenges—it’s part of the game. But what separates the greats from the rest is how they deal with those obstacles.

If you’re feeling stuck or frustrated, you’re not alone. In fact, in a recent podcast appearance, I shared some of the most common challenges I see sales teams and leaders facing today—and more importantly, how to overcome them.

Here’s a breakdown of the biggest issues and a few actionable solutions to help level you up:

1. Can’t Capture Attention? (Join The Club)

It’s harder than ever to break through all the noise. Emails go unanswered, calls go to voicemail, and buyers seem harder to reach. Why? Because everyone’s competing for the same attention.

Solution:

  • Focus on value over volume. If your outreach feels generic, it’s going straight to the trash.
  • Personalize everything. Use specific details about your prospect to show them you’ve done your homework.
  • Switch up your channels. Calls and emails still matter, but try video, LinkedIn, old school mail, something completely new, whatever it is—change it up.

If you’re not experimenting with new ways to stand out, you’re falling behind.

2. Building Trust: It’s a Marathon

Trust isn’t built in a single email or call. If your approach is transactional, you’re going to hit walls. Buyers want to know you’re invested in their success, not just your quota.

Solution:

  • Lead with empathy. Ask great questions, actually listen, and show you care about their pain points.
  • Be honest. If your product isn’t the right fit, say so. Your honesty now can earn you their trust later.
  • Stay consistent. Keep showing up with insights and value, even when they’re not ready to buy yet.

Trust takes time, but once you’ve built it, you’re in for the long haul.

3. Struggling with Rejection? Learn to Let Go

Rejection is part of sales, but that doesn’t mean it’s easy. The key is learning to separate what you do from who you are. A “no” isn’t a reflection of you—it’s just business.

Solution:

  • Detach yourself from the outcome. Focus on controlling what you can: effort, preparation, and attitude.
  • Use every rejection as a lesson. What can you learn? What can you tweak for next time?
  • Celebrate the small wins. Every conversation, even a tough one, gets you closer to your goals.

Remember: no one bats 1.000 in sales. It’s about showing up, learning, and improving every day.

Sales is extremely tough—no doubt about it. Every challenge is an opportunity to get better. Whether it’s refining your outreach, building stronger connections, or bouncing back from rejection, the key is to stay in the fight.

If you’re struggling with these (or any other!) challenges, don’t sit in silence. Share what you’re up against, message me, send me a note—anything. We’ll figure it out together.

Check out the full podcast episode here for more tips.

Brick by brick 🏄🏼‍♂️

— SL

We partner with growth-minded early-stage companies looking to accelerate revenue.

Qualia, Salesloft, Lavender, Gong, Fundbox, Google, RigUp, and more.