When Does Sales Persistence Turn Into Harassment?

Pete Caputa
Pete Caputa



Cold calls put hair on your chest. If you don't get an unexpected dial-tone in your ear a few times per day, you're not doing it right. You're not sending enough prospecting emails if you don't get a few one-line "unsubscribe" replies.  What, no framed cease and desist letter in your cubicle from a prospect's lawyer? That means you haven't made it yet.

Okay, just kidding. We all know persistence is an important part of sales. But where’s the line? How many attempts is too many? How many are too few?

Most salespeople are certainly not persistent enough. Forty-four percent of salespeople give up after one follow-up and the average salesperson only makes two attempts to reach a prospect.

What many struggle with is figuring out how to be persistent enough without being annoying or sounding desperate. Some reps hold back, while others take it too far and step over the line between persistence and harassment. Figuring out how persistent to be and how to find time to do it all is a real struggle for almost all salespeople.

Most self-respecting salespeople have had the “too persistent vs. not persistent enough” debate with themselves, a manager, and probably a prospect or two. But it's rare to witness this debate between two heavyweight sales and marketing pros. That's exactly what happened when sales mogul Grant Cardone invited marketing vlogger Gary Vaynerchuk into his office for a visit (video camera rolling, of course). If there were ever two multi-millionaire hustlers to test the limits of acceptable persistence, it is these two gentlemen.

Without further ado, here's the video compiled, edited, and narrated by Will Barron: (Warning: Contains some NSFW language. Headphones are advised.)

Here's a transcript for those that don't want to or can't watch it right now (note: I've lightly edited for grammar and readability).  

Grant Cardone: This guy just got a cease and desist [letter] from a car dealer [because we call him too much]. (Sales Guy's co-workers erupt in laughter.)

Sales Guy: I want to call him again.

Gary Vaynerchuk: (Smiling, but not laughing.) But, you know what -- here is the truth. We as hustlers love that. Ten years ago, the three of us in the office trying to sell something, that gets a high five. That means we're grinding.

GC: Yeah.

GV: But the truth is, in a world of Twitter, in a world of social media, and a world with big data -- I don't believe that's a high five today.

GC: It's a car dealer, dude.

GV: But you know what I would say to this: I'd say that that car dealership or the individuals that work there like the CEO or the decision maker, probably has a LinkedIn account at bare minimum and at maximum has [a few] other [social media] accounts. And, I think -- let me rephrase -- I know that if he spent time and realized that the guy was a Cardinals fan or into fishing or things of that nature, [it'd be different].

GC: Exactly.

GV: I think we all hustle, but I do think that we need to spend more time on context. You'll always get it done [with hustle] but you'll run through that glass wall when there was a door right there.

GC: Yeah. Yeah.

GV: We live in an incredible world of sales where if we take a step back and do a little bit more context building, we can do so much more damage. Here's the punchline: Picking two people. One's just like cease and desist and crushing and f***ing working 18 hours a day and somebody else is plodding just tortoise and hare. I think if we [ask] "How did the month go?" and Sally in the corner who is super quiet and searches Twitter all day and understands everything about every person before she calls says, "I sold 49." Meanwhile Rick who is f***ing punching everybody in the mouth [with incessant cold calls] says, "I sold 17." Sally won.

GC: We want to congratulate them both.

GV: I'd like to think "Mr. 10x" Man that you're going to to celebrate Sally more because she sold 49 and Rick [only] sold 17.

A few of Sales Guy’s co-workers: Yeah!

GV: I'd like to think you'd celebrate the one that's winning.

So, which salesperson wins in your organization? Sally or Rick? The quantity-over-quality prospectors who blindly hustle, call, and pitch everyone, like Gary's fictional Rick? Or the salespeople like Sally who go a bit slower, but always do their research and engage using the context they find? My opinion: If we're being "honest" and telling the "truth," neither really is the 100% clear-cut winner. The truth probably lies somewhere in between.

The problem is that even if you hustle as many hours as Gary Vee does, quality reduces quantity. How? Every minute spent doing research is a minute not spent on the phone. On the flip side, when a salesperson can start a conversation using research, the prospect is more likely to engage because they're not feeling like they’re being “sold” to. Instead, they feel like they’re talking with a peer, a friend, or an informed expert.

So, how do you build the right amount of persistence into your sales plan? Try the guidelines below.

How to Be Pleasantly and Patiently Persistent Without Being Annoying

1) Get your head right.

Getting your head right about sales requires balance. You must be willing to risk rejection. But you also need to be smart about how and how often you approach prospects.

In other words, if you’ve received a cease-and-desist letter, you’ve probably gone too far. However, if you’re living on Twitter all day waiting for that perfect conversation-starter to pop up in your feed, you’re probably letting your fear of rejection prevent you from doing what you need to do.

Don’t let the pursuit of your personal goals lead you to conclude that aggressiveness is necessary -- especially to the point where it costs you the trust of your prospects. Your goals and your commitment to helping should never be in opposition. Start every relationship right by being as helpful as possible out of the gate. Build a prospecting process like the one I describe below in order to start “giving” right away and set the table for a prosperous relationship.

Bottom line: Don’t be a jerk. But don’t let sales weaknesses prevent you from putting yourself out there either.

2) Do research quickly.

Gary Vaynerchuk makes some great points. But I don't think his rant was a very fair argument, either. Gary's story paints a conclusion that isn't always true. Salespeople can't mine Twitter all day and expect to hit quota -- let alone book four times the revenue of the salesperson to the left of them who is picking up the phone all day. So, while these gentleman painted the problem well, I'm not so sure they do the answer justice.

The key to doing research effectively is to have a repeatable system that leverages multiple sources of lead intelligence. Each piece of intelligence should ideally be relevant to what the salesperson sells.  

A repeatable step-by-step system enables salespeople to complete research quickly. For example, a salesperson might first go to a company’s website to see what they sell, then their blog to learn who they target, next, their LinkedIn account to get a sense of how they describe their role, and finally their Twitter profile to discover what they find interesting -- and throw in a Google keyword search to find a few competitors. Salespeople who get good at ritualizing a process like this can probably get it down to a few minutes. Depending on what the salesperson sells and how warm their leads are, they may even be able to do research while they’re waiting for the prospect to pick up the phone. Of course, the best salespeople have a handful of pre-written sales email templates which they can quickly customize with what they discover from their research process.

Admittedly, it's easier for some salespeople to do research than it is for others. It's easier to sell to front-office salespeople at smaller firms than back-office executives at larger ones. For example, salespeople who sell to marketers, salespeople, recruiters, or service professionals at SMBs have a relatively easy time finding out information about their buyers as those people publish information online about themselves and their companies frequently; plus, at least part of their job is to be "available" to interact with others outside of the company. Salespeople who sell to back-office professionals like finance, IT, and engineering folks may have to dig a bit more when researching companies and contacts.

If this is a weak area for you, consider using software and third-party data sources to speed up the process for yourself. Use social media listening software that tracks the contacts you've already decided to pursue. Use third-party data services like HubSpot CRM’s company database, Datanyze, Zoominfo, DiscoverOrg, and Linkedin Premium.

Not sure what to look for when researching? Here are 30 sales trigger events that should get your creative juices flowing. 

3) Vary your message.

Once a salesperson completes their research, they should use it to customize their approach. To plan for a few attempts, they should jot down a handful of things they find interesting about a person or a company as they're doing research.

I recently received an email from a salesperson selling staffing services. Like many prospecting emails I receive, it could have been sent verbatim to thousands of other Sales VPs like me and not one of us would have noticed. In other words, there was no mention of me, anything I've done or said, or anything about my company. Other than addressing the note "Hi Pete," there was no attempt to personalize the message.

While that's bad, what's worse is that the rep forwarded the email to me not once, but twice with notes like, "It's me again ... Curious if you're getting this email or if it's not sending for some reason," and "I know you're busy. Moving this back to the top of your inbox and hope it makes its way to you."

Don't. Do. This. I'm pretty high on the list of people easy to do research on. I publish on Twitter, Facebook, and LinkedIn every day -- usually multiple times per day. I've also published literally tens of thousands of words online in articles and blog posts. Plus, you could talk to any one of hundreds of people inside or outside HubSpot to get an introduction to me. There’s no reason why attempt #1 couldn’t have cited a blog article I wrote, attempt #2 a tweet I posted, and #3 a common connection.

4) Tone down your call-to-action.

Salespeople and especially sales development reps are way too eager to book a phone call. Instead, end emails with a question. 

If the salesperson knows that the lead is in market for their service and the prospect likely already regards the salesperson as an expert, by all means, they should offer to join a call. But, the key word is "offer." Write, "If it makes sense or is easier for you, I'm available to jump on a call." Anything else risks sounding too aggressive or too desperate -- not like an expert problem solver with more demand than time. Which do you want to be perceived as?

5) Focus on getting a response, not a sale.

You are not a value prop. They are not a purchase order.  You're a person. Your prospect is a person. So, start acting like one by treating them like one.

Contrary to popular belief, salespeople should not put their value proposition in their first email. Instead, reps should keep their value proposition in their back pocket and only pull it out when prompted by the prospect sharing their needs.

Make your first email or initial conversation about them as a person. They might want to get down to business quicker than that, but you need to slow your roll in case they don’t. It never hurts to start with common connections and interests, (genuine) flattery, and a few open-ended questions. You can always send your value prop later if you’re afraid you’ll miss your opportunity to tell them.

When in doubt, remember: Relationships first. Business second.

6) Work backwards from your goals to determine quantity.

So now that you're efficiently doing research, connecting the right way, and building relationships, how do you make sure you do enough business to achieve your personal goals and your company-given quota?

Let's do the math. Let's say Sally (or Rick) needs to close five deals per month each worth $12k annual contract value (ACV). To do that, they each need to complete 20 exploratory calls. That's one per business day. To book 20 exploratory calls (assuming a connect rate of 10%), they need to reach out to 200 people. Since there are 20 working days, they need to reach out to 10 new people per day. And taking into consideration the fact that they’ll most likely need to reach out to each prospect several times (with varying messages, of course), let's say they also need to do 30 additional follow-up emails and voicemails. (Naturally, Sally is tracking which of her leads open and click links in her emails and which of her prospects are visiting her website. This will help her figure out who to keep attempting to connect with or when to cut bait instead.)

While your numbers will be different, and you might have a few additional steps built into your sales process, roughly the same logic applies. Improve the quality of your sales approach and your conversion rates will get better, making quantity less necessary.

Don't believe me? No problem. Keep doing the volume approach. Just start augmenting it with the more thoughtful, but still efficient approach I’ve described above. And before you completely dismiss it, read below to see how this latter strategy scales.  

7) Build relationships to build scale.

The great thing about approaching prospects like the three dimensional human beings they are -- not just as "targets" -- is that they may actually want to keep in touch with you with the intention of booking a call with you eventually. And even if they don't buy from you, they might just refer you to someone who will. If you are smart and savvy enough to publish content online like Gary Vaynerchuk and Grant Cardone, your improved approach might compel prospects to follow you and share your content with others, helping you attract other buyers to you too. In this way, the benefits of building relationships are long-lasting.

If you do your prospecting correctly, this relationship-centric approach should start paying off for you quickly. You might get lucky and find some in-market customers that close in short order because you prioritized getting to know them first, before trying to sell them. But even if that doesn’t happen, you’ll certainly build relationships with prospects who aren’t even in market yet, but who close down the line after they realize they need what you have.

If you’re a new salesperson or a sales development rep, it might be hard or feel risky to spend more time per prospect. But, with a few decades of experience behind us, Grant, Gary, myself, and other seasoned salespeople know that relationships are what build careers -- and persistence, not pushiness, is what makes relationships grow.

Neither Grant nor Gary ever make excuses and they always hustle. But, given their success, I'd wager that they work even smarter than they do hard.

So, stop procrastinating, set unreasonable goals, and get thoughtfully hustling now.

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