The 1 character trait I search for in every sales rep I hire

The 1 character trait I search for in every sales rep I hire

I’ve shared hundreds of sales techniques since we started blogging here. Actionable advice from the frontlines of sales, such as how to deal with a prospect who just wants to get off the phone with you who tells you “please send me more information,” and the best way to structure your sales team.

But there’s a meta-skill that’s much more important to master. Unfortunately, unlike many of the things I teach on a tactical level, it’s not something that you can just read about and then apply immediately. Instead, it’s something that you must practice day in and day out.  

What is this mysterious skill that I’m talking about?

It’s the power to endure a difficult situation without giving way.

It’s being able to be unrelenting in the pursuit of your goals, even if you’ve been falling short for weeks or months. It’s a trait that I look for in sales reps. I look for this trait in colleagues. And it’s a trait that I intentionally strive to build in myself day after day, week after week, and year after year. Sam Sheridan once explained the value of endurance quite well:

“I discovered the key to building endurance: Push on when you feel you can’t, and next time that moment will come later.”

To further cement this idea, let’s go back in time a bit. Even if you’re not a boxing fan, it’s likely that you’ve heard of Muhammad Ali. One of the greatest athletes of all time, known for his ability to take and dodge hits and being one of the best to ever step into a ring. Early in his career, a reporter asked Ali how many sit-ups he did each day to maintain and stay in shape.

His response: “I don’t know because I don’t start counting until it hurts."

That’s the hardest thing. Taking note when it hurts and pushing on when you feel you like you can’t. The most successful sales people I know practice this every single day. A few years ago, when we had just finished up our time at YCombinator, I was raising funding and was met face to face with an opportunity to push through pain, or walk away.

You see… I had just gotten off the stage at Demo Day and the investor emails started coming through one by one. The rush and adrenaline were there and I felt like I was on top of the world! The intent was clear - these investors were really interested in what we were doing. So…

I took advantage of that. I replied to 30 or so inbound investor emails letting them know the terms that we wanted and an aggressive 3-week timeline. I wrapped it all up by saying if none of this works for you, it’s okay and we’ll potentially connect in the future when it’s a better fit.


You’re right… But GUTSY quickly turned to REGRET. Within 5-10 minutes, I was met with 5 emails saying that my timeline was too unrealistic or a flat-out ‘ok, not interested.’ Oof…

In 10 minutes I went from: I’m on top of the world, to I made a huge mistake...

And at that moment, I wanted to write every investor who didn’t write back yet and water that initial email down so that it wasn’t as strong. I was going to sprinkle "weak sauce" all over it by telling them that I do appreciate their time and they’re special, so if they need more time, we can make that work too… But eventually, a dose of better judgement came in.

I remembered the importance of sitting in discomfort. I remembered the importance of being okay with a little pain. And I remembered that 5 rejections aren’t representative of the entire group and there are more to come. So I waited…

I sat in my discomfort and, sure enough, the emails from those interested and accepting of those terms soon started to trickle in. It all worked out. But it could have quickly backfired had I attempted to press CTRL-Z on my original strategy without letting it sit.

This is a trait we all must practice and it’s a trait we look for in every hire we make.

Many times in life, the universe will test your resolve. It’s on you to ensure that your response to this test is one that aligns with your ability to achieve your goals.

If you’re in sales, this will happen every single day. Prospects tell you no. They reject your suggestions. They object your proposal. They will tell you all the reasons why they won’t do what you want them to do. Don’t waver.
How you handle rejection is the difference between the sales rep making $40k / year and the one earning millions. So ask yourself daily: What have I done to further push and improve my endurance? And if you haven’t done something to push your endurance a bit further—use thats moment to inspire you to take action and sit with however the world responds.

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