Intro

It's frustrating when you're trying to reach a key decision-maker, only to be stopped by their administrative assistant. It can feel like gatekeepers intentionally block your path to closing a deal. 

But what if their resistance isn't just about blocking, but about recognizing when your approach simply isn't up to par? In this episode, I speak with Natasha Bowles, a seasoned gatekeeper with over 25 years of experience, to uncover what truly gets her to engage with sellers. Tune in to get the inside scoop and learn how to improve your tactics to close more deals.

Meet the Gatekeeper: Natasha Bowles

• Natasha Bowles is the Founder of Natasha Bowles Professional Services, a staffing agency specializing in virtual and in-house administrative support.  
• As an executive-level administrator for over 25 years, Ms. Bowles has been a gatekeeper for high-profile individuals like medical professionals, property managers, venture capitalists, and notable public figures.
• She's not offended by the term "gatekeeper" at all, seeing it as her job to protect the time of the people she works with. Before letting just anyone chat with her clients, she needs to be sure they're prepped, will actually bring something valuable to the table, and have something that will genuinely benefit them.
• Natsha shares how execs tend to get about 250 to 1,000 a day! If you're not bringing anything worthwhile, it's her job to keep you from wasting their precious time.
• Gatekeepers are the first line of defense for decision-makers, and if you can't get past them, you won't be talking to the executive who calls the shots.

How To Get a Gatekeeper To Open Your Emails

• Gatekeepers see right through the holes in an executive's business, and they know when generic cold-calling emails are a total waste of their client's time.
• To get your emails noticed by gatekeepers, Natasha says you've gotta do your homework on the company and show that knowledge in your email.  
• Think of it like this: if you're trying to get an investor to fund your pizza place but emailing someone who only invests in tech, it screams you didn't bother to do your research.
• In your emails, include things like who the relevant department head is, some stats, a problem the company is facing, and why they need to know about your product. Show some initiative and prove you've looked into the company and why you genuinely believe your solution can help them.
• Also, don't be rude to the gatekeeper! They'll remember it, and it could come back to bite you. Natasha shares a personal story about dealing with a rude client and what happened. 

Is It Possible To Go Around the Gatekeeper?

• It's possible to bypass the gatekeeper. But honestly, it will be tough because executives usually don't pay much attention to their own emails. They rely on the gatekeeper to handle it because their time is just that valuable.
• Natasha points out that even if you do get lucky, you might still end up talking to the gatekeeper anyway.

Gatekeepers Can Move Deals Forward

• You don't always have to talk directly to the CEO to get a deal moving. Gatekeepers and executives often have a strong relationship, and sometimes the gatekeeper can even be given the green light to make decisions if the CEO trusts them enough.
• The gatekeeper might actually be the person you need to convince to close a deal. So, do your best to win them over when you reach out. Find that sweet spot where you show you know your stuff and how it can benefit the company.

"Protecting my client's time is my biggest task. I need to be certain that anyone wanting to speak with them is prepared, will add value to their day, and has something genuinely beneficial to offer. My job is to safeguard their time." - Natasha Bowles. 

 Resources

Connect with Natasha on LinkedIn

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

2.  This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails?Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

3.  This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and Produced by Brightseed and Hill.

Mentioned in this episode:

HubSpot and bluëmago | STUDIOS

HubSpot and bluëmago | STUDIOS hubpspot.com/marketers bluemangostudios.com