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Cold calling tips and tricks for dealing with the toughest gatekeepers

4 min readFebruary 20, 2019

There’s an ongoing debate about whether or not cold calling is dead. Regardless of what you’ve read or heard elsewhere, the truth is cold calling is alive and well. A recent study revealed that 71% of buyers want to hear from sellers when looking for new ideas to improve their business. In the same study, 70% of sellers connected with their buyers over the phone. The study concluded that both buyers and sellers agree that cold calling is still one of the most effective ways to generate initial sales conversations. This should silence any doubts you may have about the value of cold calling in sales today.

Say you’ve read our last blog about how to keep your motivation up to do the difficult task of cold calling. You start dialing down your lead or prospect list, and someone actually answers the phone! You ask for your prospect by their first name, and hear…

“I’ll see if she’s available, may I ask who is calling?”

You answer, but your heart drops, because you know the contact will come back and say one of the many common gatekeeper objections to vendor cold calls:

“She’s in a meeting right now.”

“She’s not available.”

“Can I get your name and number? She’ll reach out if she needs anything.”

Of course, you have value to offer, but your contact may not know it yet. Odds that you get a call back in this scenario seem low. In order to reach buyers, you can’t always leave your fate in the hands of a message left with the gatekeeper. You need tactics to get past those that seem to hold the “keys to the kingdom.”

Some of these executive assistants often seem more like guard dogs than allies. To help, we gathered some of the best tips and tricks to effectively deal with even the toughest gatekeepers.

Treat them right. Show respect, build rapport, learn their name and note it in your CRM, be polite and show some empathy. They field a ton of phone calls each day and, contrary to what you might think, they actually do want to help. Additionally, they are often very trusted by your target prospect to guard their busy schedules. Getting on their good side will only help your cause.

Establish trust by leveraging information from your pre-call research about their company. This separates you from all the other callers who’ve tried to reach the decision maker by showing you’ve done your homework. It lets them know you are prepared to provide value and that you are less likely to waste the boss’ time.

Warm up your lead by engaging them, via email or social, prior to phoning so they’re expecting your call. Try sending the prospect something of value, like a white paper and when they respond gain permission to contact them. Be sure to find out the best time to call while you’re at it so you know when you’ll be able to reach them. Other options include connecting with a prospect on social media or asking for a referral from a mutual connection to drop their name when calling. However you choose to do so, warming up your contact increases the chance they will accept your call.

Call during off hours by phoning outside the gatekeeper’s work hours or when they’re at lunch. This is when your contact is more likely to answer their own phone, increasing the odds of not being screened out before being able to speak with the decision maker.

Speak with confidence because coming across too tentative or unsure makes it more likely the gatekeeper will block you from the person you’re trying to reach. Speaking with certainty will give them less pause about transferring your call. It’s not only about what you say, it’s about how you say it. Enunciate and don’t mumble when talking to the executive assistant. At the same time, be sure not to come across as arrogant or cocky. So find the perfect balance to be perceived as self-assured and nothing more.

Don’t be scripted. It’s fine to rehearse with a script but, unless you’re an exceptional actor, don’t read one. It will impact your tone and make it more difficult to conduct a natural-sounding discussion.

Practice by role-playing all the different cold call scenarios so you’re ready for anything. You need to be ready to respond quickly and naturally to whatever the gatekeeper says or any objections they present.

The last resort is to ask to be transferred to voicemail and leave an excellent message for the decision maker you’re trying to reach. A great message, as part of a prospecting cadence, can make the difference between finally speaking with your lead and never connecting.

Give these tips and tricks a try. You’ll find that you’re able to more successfully deal with the toughest gatekeepers and schedule more meetings with decision makers.

What other tactics do you have that are effective when dealing with challenging gatekeepers? Share them in the comments below.