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Winning over a gatekeeper can often be the major differentiator when you’re in fiercely competitive situations.


Gatekeepers. Ahhhh, my favorite. No really; they are. In high school, I used to love the challenge of winning over the ultimate gatekeepers: my dates’ mothers.

I think that’s honestly where it started, but I still love the challenge of winning someone over who has been strategically placed in my path to thwart me.

During our trainings and workshops, we’re frequently asked how to deal with dreaded gatekeepers. My favorite part of being asked this question is that it’s often done so within a context of terror, as if the person is picturing Gandalf slamming his staff into the stone and yelling, “YOU SHALL NOT PASS!”

The first thing you need to remember is that behind the scary mask, there is a human.

They have feelings, respond to human influence networks, and like to feel important just like the rest of us.

The only difference is that they’re put in place to filter (and sometimes flat out stop) people like you from accessing the “boss.” Some are good at this without being mean, callous, or crotchety, but many others are harsh and seemingly unlikeable.

The second thing you need to remember: You just need to accept the fact that they’re there.

I’ve found that trying tricks or tactics to “bypass the gatekeeper” may get you some surprise face time, but it’s often at the expense of the deal.

Getting “past the gatekeeper” needs to be done by embracing them and leveraging their influence over your target’s calendar. Remember, you’re talking to the person with the MOST influence over who your target talks to, meets with, and ultimately does business with.

Do you really think that a trick to bypass them will result in a meaningful relationship? No. Probably not.

The third thing you need to understand is that many executive assistants (EAs) and gatekeepers (GKs) are very influential. If they are your ally, they can help you during the sale, negotiation, and other parts of your buyer’s journey.

Winning over a gatekeeper can often be the major differentiator when you’re in fiercely competitive situations.

So, with those three things in mind, here’s what I do with gatekeepers…

Me:

“Good morning, Sally. Is Buck Rogers available?”

Sally:

“Is Mr. Rogers expecting your call?”

Me:

“Thank you for asking. No, he is not expecting my call. That said, are you who I need to work with to try and get on his calendar?”

Sally:

(coldly) “He doesn’t take unsolicited calls or meetings.”

Me:

(positive tone) “I don’t blame him for that at all. I’d love to have someone that helps me spend my time where I should be spending it. Ok, so Sally, I most certainly don’t want to be a pest, and I absolutely respect that you are in charge of who he meets with. That said, would it be possible to get 15 minutes with you on your calendar to learn more about your company to see if we would even be a good fit? I know that you’re very busy, so would Thursday at 2pm work for a short call?”

Sally:

“I don’t usually do that, and I don’t think we’re interested.”

Me:

“Sally, that’s exactly why I called. Not everyone is worth setting time aside. But, most of the clients I have today that have done business with us for years started with me working directly with the executive assistants like yourself. I assure you that I won’t bother you if we aren’t a good fit, so could you meet with me anyway? Say, Thursday at 2pm or Friday at 8am?”

Now, I clearly just made up a dialogue, and as the writer, I can make myself look as good as I would like, but this exchange has some elements that (if used properly) will help you establish fluency and success with gatekeepers.

In his mega-bestseller Sales EQ, Jeb Blount discussed the Five Most Important Questions in Sales.  Let’s look at this dialogue in the context of how people subconsciously ask and answer these questions when you interface with them.

  1. Do I like you?

    Most prospectors that call can’t rush off the phone fast enough or don’t take the time to acknowledge the gatekeeper’s role and responsibility. Acknowledging them as important increases the chances of them liking you. Also, be likable. Be positive. Be empathetic to the fact that they have to pretend to be an asshole all day to people who randomly call.

  2. Do you listen to me?

    People like to be heard, and by acknowledging them and the importance of their role, they’ll feel heard. Make sure you (truly) listen and engage them with questions based on their information. We often confuse listening for waiting for our turn to talk, so it’s paramount to make them feel heard.

  3. Do you make me feel important?

    Acknowledging the importance of their role is critical. GK’s sometimes feel like the ugly sister who always has to entertain her beautiful sister’s suitors while she’s still getting ready. Make them feel important. Sincerity. You can’t be fake. If you think about it, some of these people that are the EAs or GKs for important CEOs are really the ones in charge of the world. Keep that in mind.

  4. Do you understand me and my problems?

    Empathy is important and acknowledging that they’re busy and need to schedule appointments is a form of understanding them and their problems. Asking them for time to share problems from their point of view shows that you’re trying to sincerely understand them along with the people and the organization that they support.

  5. Do I trust and believe you?

    Can they trust that you’re sincerely wanting their time to meet and that it’s not just a tactic you’re using to “get to the boss”? Can they believe that you’re really trying to gauge whether or not they’re a good fit for you? Delivery of your message matters as much as the message itself, and some of these GKs can be shrewd; they can smell fear, weakness, and insincerity like a shark smells blood in the water.

So folks, in closing: Calm down, take a deep breath, and try to enjoy a conversation with someone that has a crappy responsibility. Remember that, just like you, they’re a person who has a job to do.

Remember that they, like everyone else, like to be valued and heard. Be a human and earn their trust and devotion.

And think of this: If you get them on your side, they’ll start gatekeeping for you and start sending your competitors packing. Allied gatekeepers can be amazing influencers when you need them, so embrace and cherish them.

PRO TIP:

When you do land time with a gatekeeper, make sure you follow it up with a handwritten note thanking them for their time. It’s a lost art and a massive differentiator.

About the author

Jason Eatmon

Jason Eatmon

Jason is a Nebraska native which is where his work ethic and sense of…

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