So often we hear “sales is really hard.”  But what does that really mean?

The truth is only the salespeople who are out there trying to hit their numbers really understand the ups and downs of this job. And we rarely get to hear them speak about their day to day.

That’s why we partnered with Keenan, the CEO of, to create The Real Deal of Sales, a show with real sales stories from real salespeople.

After nine episodes and many interviews with sales reps and leaders from across the U.S., it is time for a recap. Here’s what we learned about life in sales.

[New Data] The 2021 Sales Enablement Report

1) The hardest part is your key to success

When we asked salespeople what they believe is the hardest part of sales, their answers touched every aspect of the job — from staying consistent to dealing with rejection to handling objections.

And there are no exceptions. Everyone seems to be struggling with something. No matter how you break it down, something that is hard for somebody is easy for someone else.

Keenan Quote 1 The Hardest Part 2.png

“The hardest part of sales is where you need to be focused.” –Keenan (Click to Tweet)

Keenan’s advice: Figure out what’s the hardest part for you, lean in, and get better at it.

It’s essential to identify what challenges you because that’s where you need to focus your efforts. Ask yourself:

  1. Why do I find this difficult?
  2. Which skill(s) would make me better at this?
  3. Which experiences or activities would improve my abilities in this area?

If you’re committed, there’s nothing stopping you from improving and reaching the next level. Your efforts will be reflected in your results.

2) Awkward moments happen to everyone

You thought you were the only one who ever left a meeting feeling completely awkward? Well, let me tell you something, my friend: You’re not.

“Sales is the perfect storm for awkward moments.” –Keenan (Click to Tweet)

Is there a way for salespeople to feel less uncomfortable or have less embarassing moments?

Keenan’s advice: Be prepared.

Make sure you’re well-informed before you make a call or step into a meeting:

  1. Know your products and business
  2. Know your company
  3. Know your customer

If you come prepared, you’ll face fewer awkward moments. And in case you do find yourself in an awkward situation, like Keenan did early in his career, his advice is to just roll with the punches.

Want to know what’s Keenan’s most awkward sales experience? Subscribe and watch Keenan’s take at the end of The Most Awkward Moments in Sales episode.

3) If you’re not making mistakes, you’re not trying hard enough

These are just a few examples of the mistakes salespeople shared with Keenan:

  • Going after companies in the wrong industry.
  • Using social media wrong.
  • Giving up on a deal too quickly.

As it turns out, the longer people stay in this field, the more “mistakes” they add to their resume. And that’s not entirely a bad thing. Because mistakes can propel your career, if you approach them the right way.

Keenan Quote 3 Mistakes.png“Mistakes and failure mark the boundaries of your competence.” –Keenan (Click to Tweet)

Keenan’s advice: Make mistakes, but learn from them.

Experiment, get out of your comfort zone, and, when you make a big mistake, figure out what didn’t work before moving on. Do better next time.

4) Successful sales leaders care about their people

Sales leadership is hard. It takes a lot to balance managing performance metrics with inspiring your reps. What’s that secret ingredient most successful sales leaders share?

As Keenan was interviewing sales leaders, one thing stood out: They prioritize their people.

Keenan’s advice: You have to care about your salespeople.

Once you become a sales leader, you are no longer responsible for turning the screw. You have to motivate and support people to turn the screw for you. And for that you need to take the time to understand and support them. Great leaders put their team first.

“Great leaders get more out of people than people can get out of themselves.” –Keenan (Click to Tweet)

5) You can’t stop learning

We wanted to know the best piece of advice salespeople had for their peers. To our surprise, most of the answers pointed to “keep learning.”

Whether it’s choosing the right mentor, researching your clients, or reading books and blogs, stay on top of your game.

Keenan Quote 5 Lifelong Learner.png“Be a lifelong deliberate learner.” –Keenan (Click to Tweet)

Keenan’s advice: Commit to continually educating yourself and leveling up.

Here are some additional suggestions from Keenan:

  • Be coachable.
  • Do your research.
  • Know your customers.

And if you’re still not sure, go back to tip #1 and start with what you’re not yet good at.

6) Sales leaders aren’t accountable enough

We’ve all heard the story of the sales rep who got fired for not hitting quota. It happens all the time. But how often do sales leaders take responsibility for their team’s performance?

We thought we’d ask them. And guess what? They think most organizations put too much emphasis on the individual contributor and don’t hold leaders accountable enough.

Keenan’s advice: Sales leaders need to take more responsibility on the success and failure of their team. They can do that by:

  • Admitting their mistakes.
  • Setting the right expectations.
  • Being helpful and supporting their team.
  • Getting specialized leadership training.

“We need way more senior level accountability for the success and failure of the sales teams.” –Keenan (Click to Tweet)

7) Crazy things will happen

Last but not least, we learned that craziness comes with the territory.

Everyone who Keenan interviewed had his or her fair share of crazy stories to tell. Some of these stories were funny, some of them were downright insane. But every salesperson said the same thing: Working in sales is never boring.

Keenan Quote 7 Crazy.png“Anytime you’re working with people, you can expect crazy sh*t to happen.” –Keenan (Click to Tweet)

Keenan’s advice: Expect craziness and roll with it.

But having a little craziness in your life isn’t such a bad thing. In fact, it’s exactly why most salespeople simply love this job.

“Peace! I’m out!”

I couldn’t end this list without a final quote from our amazing host, Keenan, the creator of It’s been a great ride, and we learned a lot about what’s it like to be a real deal in sales.

You think we’ve missed anything? (I’m sure we did.) Tweet us at #TheRealDealOfSales and tell us what’s it like for you to be in sales. We’d love to hear from you.