Is Rulebreaking Just Part of the Culture of Sales?

So the best sales reps are just so, so worth it.

They don’t just close 2x the average, sometimes they even close 5x-9x the average rep.  And they often do it more efficiently.  The best ones really do make your life easier.

But the best ones often break a few rules, too.

I‘ve recently asked a bunch of sales leaders about this and their teams, and at first they said everyone followed the rules.  But then I pushed a bit more, and they admitted many of their best broke some rules, Maverick-style, in pursuit of being #1.

A few examples:

• Hacking the CPQ system.  A “funny” one, a VP of Sales told me how one of his top reps got around the CPQ system via a software hack to provide slightly higher discounts.
• Churn-and-Burn Deals.  This one is a tougher one, maybe the biggest ones.  Founders often don’t want to close deals they can’t deliver on, and support and success never do.  But if a sales exec can make a quick, big commission — they’ll often close it.
• Side Deals.  These are tough — promises in email outside of the formal contract.
• Exploding Offers That Don’t Really Explode.  This may sound minor, but reps can take it too far.  See the next point.
• Threats.  While this may sound like something the best reps don’t do, in fact threats are part of many reps’ toolkit.  Sign today or we just won’t sell you the product.

These are just a few stories I collected over the past week.

My point is merely this: you want to micromanage sales.  You don’t want to be in the weeds.  But there are some inherent social conflicts between reps wanting to close the most … and following the rules.  And yes, that does include the very best reps.

So first, listen to calls and Zooms.  You got to.  Get emails logged into your CRM.  So you can see what’s happening, when need be.  And yes, a great VP of Sales will handle a lot of this for you.

Look if 95% of kids cheat, then at least a large percent of your reps, especially the best ones, are gonna break some rules.  It’s really the same temptation in many ways:

A related post with more action items here: