Strictly Sales Episode 10: How to Make Assistants Your Allies

In this episode of the Strictly Sales podcast, sales executive and educator Jeff Hoffman shares his tips for turning one of your biggest roadblocks into one of your greatest assets. Learn how cold calling gatekeepers can get you better results.

As a sales person, by now you’re used to rejection. And one of the most common ones you’ve likely received comes in the form of a deflection from a gatekeeper. “They’re unavailable right now. Why don’t you give me your contact information, and I’d be happy to pass it along.” Sound familiar?
So how do you get past that initial roadblock? In this episode of Strictly Sales, Jeff Hoffman explains his best tricks for turning an otherwise waste of a phone call into a meaningful conversation that gets you what you want and leaves a lasting impression. After all, gatekeepers don’t need to be your enemy. In fact, if you approach them correctly they can even be one of your greatest assets.
This week, learn how to stop assistants from giving you the brush off and start getting you through to the decision makers.

Listen Here

Or Listen and Subscribe to the Podcast on iTunes

Key Takeaways

  • Speaking to an assistant can be very powerful (if you know what you’re doing). Most of the time, you’ll get a better response rate from leaving a voicemail to the decision-maker directly than you will with a message with an assistant. But not always.
  • Make sure the conversation is memorable. Ask the assistant how long they’ve been with the company, make them feel valuable to you.
  • Ask the EA what message you should leave to inspire a response. No need to try figuring this out yourself, brainstorm a message with the person who works closest to your prospect.
  • Ask for their name at the end of the phone call. It comes off as more polite and personal.


Announcer: This is Strictly Sales with Jeff Hoffman and CeCe Bazar. For more information, go to OpenView Labs or
Cece: Thanks for tuning back in to the Strictly Sales library with Jeff Hoffman. Jeff is here to talk to us today about how you can get over some of the common objections you hear on the phone. The next one that we’re going to be talking about is gatekeepers.
Jeff, when I hear people calling into gatekeepers, where they’re often getting stuck is, “Oh, person X is unavailable right now. Why don’t you give me your contact information, and I’d be happy to pass it along.”
Jeff: Sure.
Cece:  Any Tips here?
Jeff: Yeah, I mean, there’s dozens of objections that we are well accustomed to, from what we call gatekeepers or people that are blocking us, either formally or informally, from access to the people we want to reach. We know, certainly, back in the Strictly Sales podcast library, we had a long one talking about gatekeepers. But for that specific objection, I think there is some stuff you can do. There, unlike other objections early, it doesn’t necessarily mean they don’t want to talk to you. I mean, they’re taking the message, but realize that taking your message or taking your name and number or getting information and passing it on, that passing it on actually decreases the response rate.
You have a better hit rate or response rate from a voicemail to power than you do from a written message from an assistant. That being said, speaking to an assistant is very powerful if you understand what you should be closing for.
So why don’t we do it in a role-play, and we’ll talk about it, and I’ll time us out a few times. Cece, I guess you’ll be the assistant here for, let’s say, Jerome . . .
CeCe: Okay.
Jeff: . . . and I’ve just asked, I’ve told you something about a company. We’ve spoken briefly. I asked for Jerome, and you’re going to say “He’s not available,” take a message kind of thing.
CeCe: Excellent.
Jeff: So we can pick it up kind of there.
CeCe: Well, Jeff, Jerome is actually unavailable right now, but if you’d like to give me your name and the best phone number for him to reach you back on, I’d be happy to pass it along.
Jeff: I’d be happy to do that. But let me ask you this. I actually don’t know Jerome personally, so I’m not even sure if I need to speak to Jerome on this. What’s your role?
CeCe: Well, I’m Jerome’s Personal Assistant, his Executive Assistant.
Jeff: And have you been with the company a long time?
CeCe: Oh, yeah. I’ve been here for about ten years now.
Jeff: See, I bet you can help me. Do you have like two minutes right now, and then we don’t have to bother Jerome?
CeCe: Yeah, I have two minutes.
Jeff: Time out. So that’s one thing I might do, is, look, we might still go to Jerome. I mean, I’m not saying I don’t want Jerome. I said, maybe, but I’ve got a live person on the phone, who is Jerome’s Executive Assistant, who’s been there for a decade. I’m pretty sure that she’ll either give me the right name, confirm it’s Jerome, but either way, give me a lot more detail. If she takes 25 messages for Jerome, I want to be the one where there was a conversation she somewhat remembers.
CeCe: Totally.
Jeff: So I’m going to use that way. The first thing I ask, in this stage, I did not ask what was your title or what your relationship was with Jerome. All I asked was what was your role.
CeCe: Right.
Jeff: Once you told me what it was, I said, “How long have you been with the company?” That’s going to confirm the answer. Unless she says, “Today’s my first day”, if she said three days, I would say, “Well, you know what? I bet you can help me.” It doesn’t matter if it’s 300 days or 300 years.
CeCe: Right.
Jeff: You’re going to be able to help me.
CeCe: Absolutely.
Jeff: Also notice that I didn’t say great, fantastic, super on everything you told me. I just listened and answer. That would be one. There’s another thing you could do. We’ll try again this time. Do the same thing and kind of say Jerome’s not available.
CeCe: Okay. Jeff, Jerome’s actually out of the office right now, but if you want to give me your name and your information, I can pass it along to him.
Jeff: Okay. Does he often call back unsolicited sales reps, like me?
CeCe: Oh, I don’t know.
Jeff: Well, if he were going to, what would my message be so he would be inspired to call me?
CeCe: You know Jeff, that’s the first time anyone’s ever asked me that question.
Jeff: All right. Timeout. That’s probably true. That probably is the first time anyone ever asked the EA that question. You know, I don’t understand sales reps that spend their time writing proposals by themselves or writing emails to important executives, with success criteria, by themselves.
If you want to inspire someone to respond, why don’t you ask what they want to see? You know, I didn’t say, “Will he call me?” I said, “Does he often call back reps like this?” There was a pause, and it was awkward. She’s like, “I don’t know,” and we know full well she does. The answer is that he doesn’t.
CeCe: The answer would be no.
Jeff: I gave her the out. Hey, if he’s going to call me back, what should my email say? What kind of message do you want to take?
CeCe: That’s fantastic.
Jeff: What should you and I come up with, CeCe, where Jerome’s going to like what we do? You know Jerome. What should I say? People always engage on this, because they’ve never heard that before, and it’s a sensible thing to say, that’s kind of disarming.
CeCe: Totally disarming. That’s what I love about it. That’s completely disarming, and now I like you, and I kind of want to help you.
Jeff: Yeah, you might. We’ll laugh. I guarantee you and I are going to laugh on this exchange. It’s like you’ll say something, and I’ll laugh. I’ll say, “Well, I was going to say something totally opposite of that, so I’m really glad you told me that.” Then she’ll laugh and I’ll laugh, because it’s funny. Then when we’re done, usually you’ll get that kind of like, “I’ll make sure he’ll at least hears the message and calls you.”
CeCe: Fantastic. You know, Jeff, the thing I like about this the most is that you’re not exchanging any of that corny like, “How are you doing today? What’s new?” You’re actually getting valuable information, while still having a conversation.
Jeff: Yeah. Notice too, in these exchanges, I’ve never asked your name. Did you notice that?
CeCe: Interesting.
Jeff: I never asked your name, because I think it’s rude. I think it’s rude to ask someone’s name when you call them. Like, “Hi, can you help me?” “I’ll try.” “Great. Who am I speaking with?”
CeCe: Yeah.
Jeff: It’s like, “Screw you. You called me. Why should I have to tell you who I am? You should know who I am, you called me.” So I always ask for the name after I got my close. So if we get through this, and then you say, “Yeah, I’ll tell him you called. I’ll make sure he calls you, Jeff,” then I’ll say, “I appreciate that. What’s your name by the way?” Then you get it, and you get it in a much friendlier way, because then all I get to say is, when you say, “Oh, it’s CeCe,” I say, “CeCe, thanks.” Done.
CeCe: I mean done. Exactly.
Jeff: How powerful is that?
CeCe: So powerful. That’s great. So for all of you out there who are saying gatekeepers are where I’m getting stuck, now you have your answer and your solution. Thanks, Jeff.
Newsletter signup bottom

Photo by: Alan Clark

You might also like ...
4 Steps to Becoming a Product-Led Sales Organization
A dramatic shift is underway. Product-led go-to-market practices across the SaaS spectrum, and the need to deliver stellar customer experiences,...
by Despina Exadaktylou
Establishing Data-Driven 1:1s as a Sales Manager

Being a data-driven sales manager means, at a high level, understanding how metrics impact one another, how to approach setting goals against key performance indicators (KPIs), and how to coach to the achievement of those goals. But, how can a manager incorporate data into her ongoing managerial cadences? 1:1 meetings.

by Karen Rhorer
Summer Slump Series: Resources to Thrive in Sales

Our Summer Slump Series continues with top sales content from our blog to help your team not only meet, but exceed goals during a slow time of the year.

by Bayley Dietz

“I don’t understand sales reps who spend their time writing proposals by themselves. If you want to inspire someone to respond, why don’t you ask what they want to see?”

— Jeff Hoffman, M. J. Hoffman and Associates