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sales call follow up strategy

Gatekeeper script: A proven way to turn gatekeepers into advocates when calling executives

Getting past the gatekeeper script by Greg Woodward

Raise your hand if you’ve ever called an exciting new prospect and couldn’t get past their assistant. 

This is a reality for any sales person making cold calls and it’s frustrating — you’re so close to getting in the door, yet so far.  This struggle between salespeople and gatekeepers has occurred for decades.

Entrepreneur and corporate strategist Greg Woodward, whose expertise in outbound is favored by many of the fastest growing companies and largest private equity firms, has a solution.

Our team at PhoneBurner recently worked with Greg through his 6-week Outbound Accelerator Program™ and I’m eager to share some of what we learned.

In this brief interview, Greg explains how to eliminates the struggle between sales reps and Executive Assistants (EAs), with a script that turns gatekeepers into fierce advocates.

Q: What is an issue you often see people run into when making cold calls to C-suite prospects or company owners?

A: When C-suite executives have EAs, too often reps will view them as an obstacle instead of a resource. The EAs job is to facilitate communication between the outside world and the prospect and that’s the mindset reps need to have about it.

If you make the EAs job easier, they will go out of their way to help you.

Q: What are people doing wrong when talking to EAs?

A: Well, at a high level, they tend to sound like everyone else. What you want to do is demonstrate what I call “drastic contrast.”

I’ve literally made this call more than a thousand times because when I was an M&A consultant, the C-suite was where our conversations needed to go. Like it is with any persona, if you talk to them enough, you learn what they find predictable. Gatekeepers are conditioned to spot predictable patterns inside of a few seconds and as a rep you need to break those patterns by demonstrating the polar opposite of what’s predictable.

Q: Tell me more about this drastic contrast concept.  How does it apply to this specific issue of reaching C-suite prospects?

A: Well to start, consider the fact that it’s actually easier to change a negative perception, then it is to create a positive one that has no prior context.

That’s why demonstrating drastic contrast where a negative perception exists, is so powerful. Think about what makes something or someone annoying to you… if you distill it down, it’s usually predictable repetition. Now ask yourself what an EA might find predictable about receiving cold calls? Maybe it’s being treated like an obstacle, maybe it’s that inevitable sparring match that they go through every time people call in trying to get the boss’s email address. We want to be aware of these things and craft our approach to demonstrate the polar opposite of what’s predictable.

Q: What techniques do you find successful in working with assistants and receptionists, instead of against them?

A: Well, there’s three principles that work well here. I call them “relevant clarity,” “drastic contrast” and “embedded subtle courtesy.”

For example, at the start of the call, you want to state your full name using a tonality that conveys to the assistant that their boss doesn’t know who you are. Doing this avoids triggering lingering questions in the assistants mind and it removes resistance long enough for you to get to the next part of the call. Then you want to give the assistant a mental picture of what you represent, why you’re calling and then you should ask them if they have a minute to speak with you. All of this happens in the first few seconds of the call which might sound something like this;

ASSISTANT: Jane Doe’s office, Donna speaking.

ME: Hi Donna, my name’s Greg Woodward from Woodward Strategies, I’m a consultant based in DC. I’m just calling with a question, do you have a minute?

ASSISTANT: Do you mean does Jane have a minute?

ME: No, no, you’re fine…do you have a minute?

ASSISTANT: Oh sure, I have a minute.

Now if you notice, I didn’t immediately go into a pitch or describe what I do. Instead I’m saying that I’m a consultant based in DC. Everyone can quickly form their own mental image of what a consultant in DC might look like. The mental image at this stage of the call is necessary to avoid triggering lingering questions. This is the relevant clarity principle (i.e. a mental image associated with something relevant or familiar).

Then, to provide necessary context and remove resistance, I explained that I was just calling with a question and then I asked if she has a minute. This is the embedded subtle courtesy with drastic contrast because most people calling will ask if their boss has a minute.

Later in the call I’ll use drastic contrast again to continue breaking the pattern of what’s predictable to a gatekeeper. It might sound something like this:

ME: Okay, well we have this letter that we need to put in front of Jane Doe about a development partnership that our firm’s establishing with a company in your space. In the letter there’s enough information for Jane to determine if this is something she’d be interested in chatting with me about.

Now at this point in the call, even though I did everything right in the beginning, the assistant is starting to recognize a predictable pattern with the next step being me asking for the bosses email address and that inevitable sparring match that follows when she tells me she can’t provide it. Back to the call:

ME: I’m wondering if that’s something I could send over to you?

ASSISTANT: Sure, you can send that to me my email is ________

ME: Got it… sounds good Donna and thank you for that. Would you mind if I called back in a few days to see if Jane’s had a chance to take a look?

ASSISTANT: Sure that’s fine.

Notice how I broke the predictable pattern with “I’m wondering if that’s something I can send over to you” and then immediately afterwards, I asked for permission to follow up. When you do this correctly, you’ll almost never get that “we’ll let you know if interested” response.  In my experience, with these principles applied to your script, gatekeepers tend to comply and even go out of their way to elevate your communication with the prospect.  


Reframing the way we, as salespeople, engage with EAs can quickly shift them from gatekeeper to champion. As a salesperson who was once also an EA, I can attest to the truth in Greg’s words.

When someone takes time to value and appreciate you, you put in extra effort to share their pitch with your executive. Oftentimes, EAs are called upon as character references as well, so a good word from them will go a long way. With a warm intro from the EA, you are much more likely to turn that cold lead into a happily converted customer.

This is a small snapshot of the techniques Greg has shared with our team. To learn more about Greg check out his bio. Or watch his recent talk at SES which expands upon the ideas shared in our interview.  

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