How to Get Past the Gatekeeper — Unconventional Tips & Tricks

As somebody that cold calls for a living, gatekeepers can be one of the most frustrating and difficult parts of my job. But they can also be one of the best.

A well seasoned gatekeeper is often an inside salesperson’s worst nightmare. They’re deal destroyers. It’s literally part of their job description — to prevent you from reaching the one person you need to reach most (the decision maker).

I also have a sneaking suspicion that many gatekeepers take perverse delight in crushing the egos of young upstart salespeople like you and I.

For every objection you artfully weave around, they throw another twenty at your face. Your well-practiced jokes, instead of eliciting riotous laughter, lead to depressing moments of silence. And even if you somehow, against all odds, manage to exhaust their ability to fight back using clever sales witticisms and seasoned concern handles, they can always hang up without having so much as the decency to tell you “goodbye”.

So, yeah. Gatekeepers can be a problem.

But, believe it or not, they can also be huge assets if you play them right.

Gatekeeper — Friend or Foe?

“Asset?” you’re thinking. Yes, asset. Expert salespeople use gatekeepers to solidify their deals instead of destroy them.

Think about it — out of everyone at the office, who is closer to the DM than their secretary? Who else talks to them daily, handles all of their paperwork, and knows the intricacies of their comings and goings?

If there were one person who the DM trusted the most out of all of their staff, who might that be? And, considering the importance of trust in any sales interaction, what power might that person have in making your deal with the DM come to life?

The gatekeeper is thus your worst enemy and your best friend all at once.

How To Get Past The Gatekeeper

What follows is a few (unconventional) actionable tips I and many others have successfully used to turn cold, hard gatekeepers into warm fuzzy friends. Following these will not only make your cold calling more interesting — it’ll increase the likelihood of you talking to a decision maker.

Be transparent.

Make it very obvious that you’re cold calling. One thing that gatekeepers hate more than anything is when people try and sneak up on them.

An example of this is making excessive smalltalk before your pitch to “warm up” the lead. Instead of asking them how they’re feeling, or how the weather is, oftentimes you’re best served by frontloading with your pitch and building rapport after the fact.

I have found such great success with this principle that now I open many calls by explicitly stating “Hey [name], this is a cold call, do you want to hang up?” in an enthusiastic and friendly tone. A short example follows:

GK:“Hi, you’ve reached Fern & Co, Jessica speaking. How may I help you?

Me: “Hey Jessica, this is a cold call, do you want to hang up?”

GK: “Hahaha, what?! Uh, no, go ahead.”

They’re often thrown off-balance by your candor and openness, which helps when you’re making the ask later on. It also builds legitimacy and implies extreme confidence in whatever you’re selling.

Become part of their in-group.

Ever wonder why sports team rivalries are such a big deal?

Human social behavior is heavily based on the notion of in-groups and out-groups. Simply put, people naturally trust those in their in-group and naturally distrust people in their out-groups.

Examples of in-groups are your favorite sports teams, a camping group, your friends, and the classmates in your year at school. Each of the former are in-groups that members feel close to because of social context and time spent together.

Examples of out-groups might be a rival sports team, the camping group across the trail, your enemies, and the class one year higher or lower at school.

Thus, when speaking to a gatekeeper for the first time, you’re usually an outsider trying to penetrate their in-group, pitting you at a disadvantage. Remember — human beings love to take sides, even when they have to make them up!

One excellent way to use this to get the gatekeeper on your side is to leverage in-industry referrals and terminology. For example, instead of saying:

“I would like to book a meeting with John to show him how to get more sales for his used car lot”

Try something like:

“Terry over at TX Auto told me to give you a call to set up a time to talk to John. I can move these cars for you”.

Even if the gatekeeper doesn’t know who “Terry” is, the implied familiarity and the fact that you’re using industry-specific terms (moving cars) means they’re more likely to take you as one of them. Instead of being in the “cold call salesperson” group, you’ve now been mentally placed in the “automotive industry” group.

Parody Your Enthusiasm — Never Get Negative

Usually, I don’t make it past the gatekeeper on my first call. In fact, I usually don’t make it past them on my second or third calls either — it’s usually the fourth, fifth, and sixth calls that yield me the majority of my results.

Now, I know what you’re thinking. Six calls? How the hell do they not just hang up on you immediately? You sound annoying!

Not true. In fact, they’re usually happy when I call. I break up the monotony of their day by being sharp, enthusiastic, and fun. Most of them greet me with warmth in their voice.

The reason for this is because I make everything a big joke. When I call a gatekeeper for the second time a week after getting put down, I laugh about it and say “It’s me, your favorite person again! I know, I’m a sucker for punishment”. I most definitely do not say “Hello, it’s Nick. I know you said I couldn’t talk to John last week, but is he available this week?”

The reality is, the majority of a gatekeeper’s job is incredibly boring — they deal with prerecorded robocalls, boring administrators, and eye watering paperwork basically eight hours of their day. Sppeaking to somebody light and fun that they’ve built some familiarity with (even if it’s technically still a business call) is a pleasant break from the monotony, and I use that to build strong rapport.

Send Them Donuts, Chocolate, Or Pizza

If you’re competing in a market with a limited number of prospects, sometimes you have to get creative. Not every industry allows you to just “dial more” — some have so few people or businesses that you need to squeeze as much juice out of every lead as possible. One way of doing this is by literally sending them food.

First, look at your KPIs to make sure this is financially feasible prior to ordering. I say this because, from experience, it can be easy to get carried away. For example, if your average deal size is only $100, your DM close rate is 1/10, and your donut delivery service costs $10, you’re at best breaking even and at worst going broke.

But, if your average deal size is $100,000, all else being equal, you can’t afford not to press every advantage. And tasty food is a huge advantage. Plus, services like Foodora, Skip The Dishes, Doordash, and Uber Eats have made this possible and easy even if you’re not physically in the same city or province as your prospect.

Next time you’ve spoken to a gatekeeper more than five or six times to no avail, tell them “Look, I’m sending you and the whole team some delicious donuts, and I’m not taking no for an answer. They’ll be there in 45 minutes — what’s the address again?”. Then, if you’re in their city, show up with donuts in hand, or if you’re not, send them through a delivery service and call five or ten minutes after their estimated delivery time.

Best case scenario: you get to speak to a decision maker that has been thoroughly informed of your class, your hilarity, and your good taste in donuts. This edification goes a long way to securing the deal, and instantly puts you in their in-group.

Worst case scenario: the gatekeeper & surrounding staff love you, you’ve built a strong rapport-based relationship, and you can use that to segway into a meeting with the DM in several months when situations change.

I have done both many times, and it almost always opens a door in one way or another. Plus, can you think of a better story than landing a six-figure deal with donuts?

Remember: the gatekeeper can be your best friend and worst enemy. Respect their time, be transparent, make them laugh, and above all, follow up! Not only does does a happy gatekeeper help secure the open — they help close the deal, too.

Instead of being apprehensive next time you call a large corporate firm or office, get excited! Many people that were once faceless gatekeepers to me are now strong friends and excellent corporate connections. You can do the same with simple practice and consistent exploration of your boundaries and sales skills.