The Truth About Sales Success - Traits, Reality Checks, and What Actually Works

Over the last few years I've not only worked with a number of customers' sales teams, but I've also been directly involved as an individual contributor on our GTM team.

Through that work, and through a fair amount of self-study, I've been able to glean a few interesting insights.

With that in mind, I'm writing a series of posts on how someone who is earlier in their career can be successful in sales. In many ways, I'm writing for my younger self (and spelling out things I wish I'd have known and/or had the good sense to learn back then).

For my first post in the series, I want to talk about the top traits I (and many whom I respect) have observed among those who've done well in sales. Spoiler alert: it's not just about having a killer smile and a firm handshake…

The Top Five Traits of Successful Salespeople

1. Relentless

This one tops the list for me. Successful salespeople are relentless. They have enough grit to stay in the game no matter how dire things may seem.

2. Interested

The best salespeople take a genuine interest in figuring out how to solve a prospect's problem. They are deeply inquisitive - always digging deeper, asking questions, and uncovering the real needs of their prospects. They don't just sell products; they solve problems. And to do that, they need to be genuinely interested in their customer's world.

3. Adaptable

The ability to pivot, to change the approach on the fly, is crucial. Whether it's a new competitor in the market or a sudden shift in customer needs, the best salespeople can either immediately, or nearly immediately, adapt and overcome.

4. Confident

Let me be clear about something - confidence is not arrogance. Rather, confidence is something that is earned from training, preparation, and accomplishment. It's about knowing a product or service inside and out, understanding a market, and being able to articulate a value proposition with clarity and conviction. The best have this kind of confidence.

5. Disciplined

Sales isn't a sprint; it's a marathon. It requires a consistent, methodical approach. The top performers are the ones who stick to their routines, who follow up diligently, and who never let a lead slip through the cracks. They're the ones who show up day after day, ready to put in the work.

Most of What You've Heard About Sales is Pure Nonsense

The LinkedIn Fantasy vs. Reality

I'm guessing that on LinkedIn today alone you've already seen about a half a dozen "sales gurus" humble-bragging about their "massive wins," posting motivational quotes over sunset backgrounds, and telling you that "sales is all about mindset" while they try to sell you their $997 course.

Here's the reality: sales is a job. A real job. Not a lifestyle. Not a mindset. Not a chance to "crush it" every day while listening to podcasts and drinking energy drinks (full disclosure - I do both, but that's beside the point).

Real Sales Looks Like:

• Sitting at your desk trying to figure out why your prospect ghosted you after three great calls

• Updating your CRM because if you don't, your manager will have your ass

• Researching companies until your eyes blur

• Having prospects tell you "maybe next quarter" for the fifth quarter in a row

• Actually closing a deal and feeling like you just won the Super Bowl (until you realize you need to do it all over again next month)

The good news is that sales is a craft, that with the proper application of effort and time, you can hone nearly infinitely. If that's something you're committed to, then there is a TON of great content out there for you to learn from. If you're just getting started and aren't sure where to look, I suggest any (or all) of the following absolute experts: Chris Orlob, Sam Blonde, Jeb Blount, Jill Konrath, and Mark Cranney. You can't go wrong reading/listening to any of them (and as far as I can tell, none of them post motivational quotes over sunset backgrounds).

The Real Success Factors

Want to know what actually determines success in sales? Here are eight of the things that do:

1. Do the Work

Before you pick up the phone/log into a vid conf, you ABSOLUTELY need to know your: (i) product/service, (ii) market, (iii) prospect's industry, (iv) prospect's company, and (v) individual prospect.

2. Do the Work…Consistently

The top performers aren't the ones working 80-hour weeks and sending emails at 3 AM. They're the ones who show up every day, do the work, and don't get too high or too low.

3. Learning from Failure

You're going to fail. A lot. The question is: can you look at your failures without ego and figure out what went wrong?

4. Time Management

The ability to focus on what matters instead of getting caught up in busy work. This means saying "no" to things that waste your time and learning to prioritize like your paycheck depends on it (because it does).

5. Resilience

Not the fake "hustle harder" kind. Real resilience is being able to get rejected 20 times in a row and still make that 21st call with genuine enthusiasm.

6. Pattern Recognition

You need to recognize when a deal is going south before it crashes and burns. This comes from getting burned enough times that your spidey sense starts tingling when something feels off.

7. Emotional Regulation

The ability to not lose your shit when a prospect stands you up for the third time, that "sure thing" deal dies at the last minute, etc…

8. Business Translation

Taking technical jargon and turning it into something that actually matters to the person you're talking to. If you can't explain why your product/service really matters to your prospect, you're just feature dumping.

The Good News

If all this sounds daunting, good. It should. Sales is a real profession that requires real skills. But here's the good news:

• These skills can be learned

• The pay can be fantastic

• You don't have to be an extrovert

• You don't have to be naturally "good with people"

• You don't have to become one of those LinkedIn motivation merchants

What You Do Need:

• A willingness to learn

• The ability to handle rejection

• A decent work ethic

• Some basic organization skills

• A sense of humor (trust me, you'll need it)

The Skills Nobody Mentions (Or At Least Nobody Mentioned Them to Me)

You'll often hear about skills like "active listening", "finding the pain", etc. Those are great and you should figure them out. That said, here are a few skills that have really helped me along the way (and weren't particularly obvious):

1. Pattern Recognition

You need to recognize when a deal is going south before it crashes and burns. This comes from getting burned enough times that your spidey sense starts tingling when something feels off.

2. Emotional Regulation

The ability to not lose your cool when:

• A prospect stands you up for the third time

• That "sure thing" deal dies at the last minute

• You lose to the competition

3. Business Translation

Taking technical jargon and turning it into something that actually matters to the person you're talking to (remember - you know your product/service infinitely better than your prospect does). If you can't explain why your product/service matters in terms of dollars, time, or pain relief, you're just feature dumping.

The Truth About Quotas

Let's talk about the elephant in the room: quotas. They're not going anywhere, and yes, they'll sometimes feel impossible. But here's what nobody tells you:

• Most salespeople don't hit quota (seriously, look up the statistics)

• Your first year will probably suck

• Even great salespeople have bad months/quarters

• The key isn't to hit 100% every month - it's to not have too many bad months in a row

Your First Steps

Before we dive into the nitty-gritty in the following chapters, here's what you need to do right now:

1. Accept that you're going to suck at first (everyone does)

2. Commit to learning the craft, not just "hitting the phones"

3. Find one or two experienced people who'll give you honest feedback

4. Delete any sales guru bullshit from your social media feeds

5. Get ready to work smart (not just hard)

In the next post, we'll talk about the tools you'll actually use in your day-to-day job. But for now, take a deep breath. You've chosen a challenging career, but if you can handle the truth we just covered, you're already ahead of 90% of people who enter this profession.

Remember: Sales isn't about being a superhero. It's about being professional, consistent, and smart enough to learn from your mistakes. Now let's get into the real stuff.