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How to (Naturally!) Transition Into a Good-Natured Sales Pitch Over The Phone—Without Seeming Like a Total Greedy, Awkward, Weirdo Troll

In: Communication Skills

It’s the moment you’ve been dreading.

You’re there, on the phone.
It’s almost time to wrap up.
There’s THE awkward silence.

You know you’re suppose to try and sell them some kind of 3-month package—or some other salesy bullshit—but how do you transition the godforsaken conversation?! This is so not natural for you. The whole thing feels forced, contrived, totally fake. You’d rather lose the business than have to ever utter the words, “And now, for a limited time!” But guess what? Introductory sessions end. Those first few “complimentary” calls can’t be complimentary anymore. (And neither can your pricing.)

At some point, you’re going to have to have this conversation, and ask a client to commit to you. (SCARY AS MARRIAGE.)

This morning I was consulting with a client who needed a script to do just that. The nature of her work is very sensitive—think: therapy—and going from, “Soothe, soothe, you can trust me,” to “GIVE ME ALL YOUR MONEY, BITCH,” is really challenging. However, I reminded her that she can’t keep agreeing to do one-off sessions, because the health of her business requires more stability. She’d have to schedule some 40 sessions every month, with 40 different people, just to make her bare, bare, bare minimum income of $5K/month. In other words, not realistic, kill us all now.

Which means that, when you’re working with clients in any capacity, it’s useful to consider ways in which you can encourage your clients to commit to working with you over a period of time, rather than just chipping away at you one little request at a time. Not only does it help stabilize your revenue and add more predictability, it also helps your immediate cash flow, because in many cases you’ll be able to offer incentives for payment up front, for example—instead of paying little by little every week. (Which is a liability for you, FYI, because what if Jenny the Giant just decides to stop paying you? Quit her life? Disappear off the map? Clients love wishy washy! It also means that you’re deprived of money that you could be investing now—and we like now. We like now a lot.)

So how can you transition the conversation without feeling like a total greedy, awkward, weirdo, salesy troll?

Here’s the (soft, but effective) script I recommended she use, as the call was coming to a close:

Hey, {Client Name}—I'm going to push pause on our conversation for a moment, right there, because we have a couple of housekeeping items to go over, so I wanted to grab you for a couple of minutes to see what felt best for you.

First of all, I'd love to hear from you what YOU feel has been the most useful part of our conversation(s) thus far. {Let client tell you what they love about you.}

I'm so glad to be in a position to help you with {reflect back to her some of her insights}. I’m really confident that {say something positive, encouraging about her situation, and make a prediction for something inspiring in her future.}

So here's what I'm going to recommend we do next, {Client’s Name}: I believe it's worthwhile to continue the conversation, in particular around {insert something she struggles with}, so before I open up my calendar to any new clients next month, I wanted to extend you the same courtesy as I always do any existing client, and offer you priority availability on my calendar.

The way it works is this: I'm going to ask you to commit to a three-month block of time, which ensures that I'm able to commit to you, in return, and you'll get first pick over the dates and times that work best for your schedule. We'll schedule all twelve sessions in advance, and you'll be offered a discounted rate of $150/session instead of my normal $170. That said, if you're able to pay up front, in advance, for all twelve sessions, that rate comes down to $125/hour, which effectively locks in the same rate as you had during your introductory month, and comes to a total of $1500 from now until the end of the year, instead of $2,000.

Does that seem fair?


{She'll respond—hopefully positively to your $1500 offer. Then you tell her this:}

Great, so here's what I'll do next. Let's get off the phone now, and in the next fifteen minutes I'm going to email you my standard client services agreement, as well as a link to my calendar, for you to select your dates and times, and a place for you to submit payment. I'll ask you to process this today, if possible, but no later than Monday, October 2nd, so I can free up my calendar for other clients who are waiting.


{If, on the other hand, she responds that she'd like to continue but can't make the up front payment, then you can say:}

Completely understood. So here's what we'll do, then: I'll shoot you over my standard client services agreement that covers us for the next three months, and ask for your John Hancock. Next, I'll send over a link to the calendar, where you can select your dates and times, and then submit a retainer payment for the first three sessions only. At the discounted rate of $150/hour, that comes to a total of $450. Once those three sessions expire, you'll go ahead and purchase another block of three, and we’ll continue that way moving forward.


{If, on the other hand, she responds that she needs time to think about it, look over her finances, etc., then you can say:}

Completely understood. I’m happy to hold priority scheduling for you through Monday, October 2nd, and will follow up with you then to confirm. As you know, I'm unable to accommodate drop-in clients for one-offs—as much as I adore you!—so if there's anything I can do to make the three month block work for you, do let me know. I'm always open to proposals.


Because here’s a very important truth that often gets overlooked:

While you’re trying hard to not be pushy, your client is wishing that you’d take control and tell them what they should do. We ALL like to feel like we’re in capable, competent hands, and the best way to make your client feel that way is by having a defined process, a defined policy, and a defined way of moving the conversation forward. You aren’t being salesy—you’re doing nothing more but acting as a conduit, telling them their options. And guess what? THESE ARE OPTIONS THEY WANT TO HAVE. By not telling them—by cowering and saying something flimsy like, “I hope you’ll contact me again if you need me,” you’re depriving them of an opportunity they otherwise wouldn’t know existed.

Selling isn’t about pressure.

It’s about communication.

Update: The Unf*ckwithable Business Online Starter Kit, focused entirely on everything you need to know about legal, contracts & not totally f*cking it all up is now available!

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I'm a Bad Influence on Women

Hey, I’m Ash! Twenty years ago I was a small town girl growing up in a trailer park in rural Pennsylvania. Fifteen years ago, I lost my family and everything I knew right as I became the first to graduate college. Fourteen years ago, I found myself leaving everything behind for a new life in the city where I could be “normal.” Ten years ago I realized normal was the most disappointing thing that ever happened to me. Nine years ago I quit my job in advertising and pursued my dreams as a creative writer. Eight years ago, I built a 6-figure business doing what I love using nothing more than the Internet and my voice. And now, today, I’m the founder of The Middle Finger Project, an irreverent media co. that helps other women find their voice and teaches them to use it to build whatever the f*ck they want to. With a book coming out with Penguin Random House in February 2020 (YASSS, WE’RE A PRODUCT IN TARGET!) I’m proud to be a bad influence on women and guide them into doing something disobediently brave with their life and their career.

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