How Sales Reps Should Break the Rules

All’s fair in love and war—and sales.

At the end of the day, what really matters is whether the deal closed or if you were left holding the bag. 

Did you make quota this quarter? Did you crush your numbers? Or did you fall short?

If you missed quota, chances are you played it too safe. You followed the so-called ‘best practices’—the ones that average reps cling to.

Top performers don’t just follow the playbook. They know when to bend the rules, take calculated risks, and do what it takes to win.

https://www.youtube.com/watch?v=aDTi-bw6wtU

Be a Pattern Breaker

The greatest don’t stick to rules and expectations. They forge their own path in a sea of conformity.

They constantly reinvent themselves and their practices to push boundaries and find new ways to win.

What you won’t see is an elite sales rep following the same script day after day and struggling to escape mediocrity.

As venture capitalist Mike Maples Jr. put it on this week’s Sales Gravy Podcast, “People who are winning are the ones who change the rules and tell people how to think about it.”

Now’s the time to shake up your own sales routine and adopt the practices of Ultra High Performers.

Fanatically Prospect

You don’t have an option—prospect every day, or get left behind. The pipe is life. If you’re not feeding it, you’re starving.

Fanatical prospectors don’t just carve out time—they demand it. Every single day. You make calls, period. Distractions? They don’t exist. 

But too many sales reps think they need to follow traditional suggestions: Prioritize research over calls; call when you think your prospects will be available; warm leads up with social touches and emails.

These “rules” are screaming to be broken.

There’s no room in sales to avoid cold calling. The telephone is still the single most powerful weapon you have when it comes to selling.

Sure, the norm is to hate cold calling, avoid the phone, and send out dozens of emails because it’s easy. Rule breakers don’t do easy—they’re on the phone every day.

The best reps value prospecting and know that—even when they’re closing deals—they need to be watching out for tomorrow. Mediocre reps make fewer calls, qualify fewer prospects, and close fewer deals.

Don’t be mediocre. 

Ruthlessly Disqualify; Pursue Those Who Will Buy

Never waste your time on a prospect who simply won’t pull the trigger. There are lots of tire kickers out there who will intentionally or unintentionally waste your time.

Recognize early the deals that will never be done.

Most sales reps chase every lead because they’re told to ‘always be closing.’ The best reps break that rule by disqualifying early.

Be intentional in your discovery; ask all pertinent questions before spending precious time wooing a lead. 

You don’t have time to find out weeks down the road that your prospect wasn’t the decision maker or that there’s no budget for the deal.

You can even disqualify before you start prospecting.

When generating cold calling lists, zero in on a subset of your market that is most likely to buy—don’t squander energy parsing through every single business simply to tell your boss you called everyone. 

Jerome, a media rep in Texas, covered all of Austin. Instead of cold calling tens of thousands of businesses, he zeroed in on the ones most likely to be in the market for his services and who could afford them.

He weaned out businesses that weren’t strictly his target demographic and saved himself thousands of useless calls. 

Break the norm by cutting deadweight fast.

Play the Long Game 

Mediocre reps make useless calls and let the fear of annoying prospects sabotage their follow up game. 

Forget the outdated advice about not being ‘too persistent.’ Elite pros break that rule and keep showing up until they hear ‘yes’ or ‘no.’

They bend the rules of social niceties (i.e. don’t annoy your prospect) and keep calling, no matter how long it takes. Xant found that 50% of sales happen after the 5th follow-up, but most reps stop at 2. 

But it can take 20+ touches to engage a cold prospect. And great reps don’t stop there.

While most sales reps give up after a few attempts, rule breakers defy conventional wisdom by relentlessly pursuing prospects, knowing that success often comes after many touches.

I once picked up a call from a rep on the 73rd time he called. I admired the persistence. Had he stopped at 72, all he would have gotten was my voicemail and a missed opportunity for my business.

The lesson? Don’t let the rules of polite society stand in your way when prospecting or following up. Be the interrupter that you are and keep interrupting until you get in front of or back in front of your lead.

Don’t limit yourself to only calling either. 

Break out your social prospecting skills with LinkedIn connections, comments and notes. Send emails. Send snail mail. 

Find your way to a conversation—and potentially a deal.

Be Willing to Walk Away

Prospects can smell your misery. And they won’t respond when you’re overly eager, pushy or driving the deal too fast.

Top reps master the ‘takeaway,’ knowing when to make it seem like the deal might no longer be available. It’s about leveraging the fear of loss to make the prospect more eager to move forward.

If you approach a deal knowing you’re behind on your quota and lagging at the end of the quarter, you’re doomed because desperation stinks.

Sometimes ‘never take no for an answer’ and ‘always be closing’ just won’t work—rule breakers know when to execute the takeaway, forcing the prospect to make a decision and potentially flipping the deal in their favor.

Rule breakers won’t push endlessly for a deal with someone who can’t make a decision. They’ll walk away knowing it will force a choice that could land in their favor.

Strikeouts Don’t Matter

Rule breakers aren’t concerned with closing every deal. Sure, that’s the ideal. But the best reps know that strikeouts don’t matter.

You’re going to swing and miss the majority of the time in sales. That’s a fact. The best reps close just 15%-20% of the time.

It’s the grand slams that really count.

Most reps play it safe, always sticking to small deals and quota-chasing. But rule-breakers hit singles and doubles week in and week out—and go after whales.

Winners know not to let a big deal slip by just because it’s hard, going to take extra time, or might not pan out. 

Elite sales reps know when to go big at the bat. You should, too.

Keep swinging until you knock one out of the park.

Break the Rules. Win More Deals.

Sales isn’t about playing it safe—it’s about playing to win. The best reps break the rules that hold them back and push past the limits of “how it’s always been done.”.

They prospect fanatically, refuse to waste time on dead-end leads, and chase big deals without fear of striking out. They don’t let outdated processes or hesitation slow them down.

At the end of the day, the scoreboard doesn’t care how well you followed the rules—it only cares about results. So step up, take bold swings, and keep breaking the norms that don’t serve you.

There’s still time to work on your Q2 goals. Check out our Goal Planning Guide for tips on how to crush your numbers this quarter.