The fail-safe, sleaze-free guide to selling freelance gigs over the phone

In my last post I got into the basics of selling the heck out of your design services. That post left off with how to shift the conversation from email to phone. Why? Because on the phone, you’re going to sell more high-ticket items with much greater ease. And low-ticket items are a piece of cake.

(All that and more is explained in the last post, here.)

Today, I’m going to talk about how to handle your phone calls with prospects so that 8-9 out of 10 will actually turn into clients.

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Then let’s do it!

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A note from Preston: this post is written by David Tendrich, a super-talented writer and entrepreneur who runs a number of businesses including Reliable – a top-notch PSD to HTML shop. Members of Stoked get 30% OFF PSD to HTML services from Reliable. Join me in welcoming David to the Millo writing team by leaving a comment on this post.

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Ok, back to David who can tell you more about his freelancing journey.

• • •

But wait just one second…

See, after I wrote my last post, it occurred to me that… well… you have no idea who I am! Why should you take advice from me – especially business advice?

So I wanted to take a second to tell you a bit about who I am, and why I could be a pretty good guy to listen to. Sounds good? (I promise to make it fast…but if you’re REALLY in a hurry, jump past the story here.)

Here’s the scoop:

5 years ago, right around this time of year actually, I co-founded the creative agency Unexpected Ways. My main strength was copywriting, and my then girlfriend (now wife) was an amazingly talented designer.

So with our powers combined, we formed Unexpected Ways (much cooler than Captain Planet, trust me).

At first we had a ROUGH go of it. In fact, it’s a miracle we paid the rent and fed ourselves for like the first 2 years of business.

There were too many months where a “miracle client” came out of nowhere the week rent was due. Once, when we had run COMPLETELY out of money, a guy hired us at 9pm on a Sunday night, drove to us that night to meet in person, and gave us a cash deposit.

That deposit fed us for the next few weeks.

I don’t want to turn this post into a novel, so I’ll cut to the next part: we finally got our stuff together. We started getting more clients than we could handle, charging prices we were worth, and really started getting a glimpse of this whole “success” thing.

Fast forward to today, and I’m writing this post to you from Annecy le Vieux, France, a small French mountain town right on the Swiss border. 

About 3 weeks ago we dropped the lease on our Brooklyn apartment and decided to go explore the world. We bought 1-way tickets to France. I have no idea where we’re headed next 😉

Here’s the cool part…

Our businesses are growing through all of this!

Things just keep getting better and better while we travel and really live life. In fact, less than a year ago we even started another business as well, – a PSD to Code service born out of hatred for PSD to Code services (lol).

Now please don’t take this the wrong way! I really hope this does NOT come off as bragging. 

I really don’t mean it that way. And I don’t think there’s anything to brag about, because I truly believe you can achieve this too (if you haven’t already – and if you even want to achieve it at all).

My businesses have been an amazing tool for me to live the life I’m inspired to. In these past 5 years I’ve learned a LOT and grown a lot to get to where I am today. I’d just like to share some of that knowledge so you can do the same.

Or maybe you already are living an amazing life and business is rockin’ and rollin’!

If that’s the case, maybe I can help you make it just a tad cooler.

Fair enough?

Then let’s get back to this whole selling thing. Because it’s one of the most powerful tools I’ve developed to grow my business — and my life — to where it is today.

Okay, so if you followed the advice of my last post, you now have phone calls set up with your prospects (good on you!).

Here’s the flow of my prospect conversations that usually results in a sale:

Phase 1: The Greeting.

This seems obvious, but there’s some ninja psychology at work here. First, you have to imagine the mindset most people have when they call a business. Most people are expecting a disgruntled, unhelpful drone to pick up and make their lives more difficult.

So do the exact OPPOSITE. When you start your call, make it a point to ask how Mrs. Jones is doing in a really warm, genuine way. If she says something like,

“Ah, long day! You wouldn’t believe it!” 

Tell her, “Oh no! What happened?”

Be super cool, nice, and awesome. Be so awesome you catch your prospect off guard, forcing them to open up and let their guard down.

The “greeting” phase is where you let your prospect know, “Hey, I know this is a business call, but we’re just weird, awkward, just-want-to-be-happy-in-lfe people first, right?”

The key is you have to just really be genuine and genuinely care.

Phase 2: Getting down to business.

The small talk / greeting phase will naturally wind down within a minute or two. At this point, I usually say…

“Okay, so what can I help you with today?”

Even though we’ve gone back and forth with email to get to this call… I still ask this because it’s just a good way to break the ice and switch the subject to business.

And this is what I do next: nothing! 

I just sit and listen. Usually the prospect has a lot to say. They’ve been thinking about this project for maybe months and have a lot of built up thoughts / ideas.

I just “Hmm” and “Ahh” and “I see” my way through it until they let it all out.

When appropriate and natural I ask questions and ask for more detail. Sometimes this can last for 45-60 minutes by itself (sometimes longer!). But this is important. Take notes! Get everything they need down on paper. Because you’ll need it in phase 3…

Phase 3: Mirror & Build.

Before I start yapping to Mrs. Jones about how great we are and such, I ask a very important question:

“Great! Is that all, or is there anything else?” 

If there’s more, I listen, and take notes. And then, I ask that question again. As many times as I have to.

Why? Because I want my prospect totally clear and focused when I start talking. And if they’re thinking of an idea they forgot to say, etc., they won’t be focused on me. On the other hand, with all of their ideas out of their head, they’re now a proverbial “empty cup”.

Once they’re in that state of mind, I start talking.

At first I “mirror” back to them what they told me they need, only I put it into my own words. And I elaborate using my advanced design / marketing / coding knowledge which they don’t have (I “build” on what they said).

I’ll say something like…

“Great, well before we go any further, I just want to make sure I understand you perfectly. You’re looking for [insert “mirroring and building” here]…”

After that, I ask,

“Did I miss anything or does that about cover it?”

Usually they’re super impressed that I listened to them and got it all on the first try. Listening is a rare trait in this world, and showing your prospects that you actually took in what they said is the biggest thing you can do to make a sale in my opinion.

People want to feel heard and acknowledged more than just about anything.

Phase 4: Talk about yourself

After I’ve established that I really understand their needs, I say something like this:

“Great, well first off I just want to tell you that we’re 100% capable of getting this done. In fact, just recently we had a similar project where [insert similar project story that shows you’re capable]. 

“But before we get into specifics, I’d like to talk to you real quick about how we work, because there’s a good chance our methods are very different from most companies you’ve encountered…”

At this point I talk about us. How we work, what we do differently, why we do what we do. I educate them on our strengths.

It’s amazing how good of listeners people become after you’ve first really listened to them first. They love hearing about you after you’ve first shown them that you actually care about them.

Phase 5: Back to… email?

LOL yes, in step 5 we’re taking things BACK to email!

First, I ask my prospect if they have any further questions about who we are or how we work. I ask them if there are any lingering needs or specs they forgot to mention. I make sure we’re 100% donezo.

THEN… I tell them,

“Great, well I’m going to review all of this with my partner and we’re going to put together a solid proposal for you. I should have it ready for you by tomorrow afternoon at the latest. If everything looks good in the proposal, then we’re ready to get started ASAP!”

If they ask about price, I inform them that I’m unable to give a price without consulting my team and discussing the best possible methods of achieving their goals. This is true of course, but it also serves another purpose:

The proposal outlines EVERYTHING. And it’s usually quite a lot. It opens people’s eyes to how much work and time are involved in the design / marketing process – something most people don’t realize.

I want them to know this before they see a price. So I want them to read the proposal.

At this point in the call we say our goodbyes, and we get to work on the proposal.

So now, all you have to do is knock their socks off with a thorough, well-designed proposal.

After going through this entire process, the proposal should really just be the icing on the cake. They’re really sold in the phone call when they see how attentive, competent, and awesome you are.

But hang on there, tiger! We’re not done yet!

Because after the proposal is often the most crucial point in the sales process (next to the phone call).

Because sometimes your prospect sees the price… and doesn’t like it!

If this has ever happened to you, or happens to you regularly, stay tuned 😉 Meanwhile…

Have a question or comment? Ask / write away!

I’d love to hear your thoughts. In fact, it’d make my day 🙂

Comments here.

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  1. Hi folks!

    How I make sure the client is worth my time? I have a lot of potential clients that have an unrealistic idea about prices and such a small budget that in the end they decide for a website builder instead. You never check that first?

    1. Hey John,

      I think there are a couple of ways to do this:

      1. Have a website that conveys your price. A high-end design conveys a high-end price, and vise versa for a low-end one.

      2. In your contact form, have a dropdown menu where the client chooses their budget. Have increments starting with your minimum prices and building up (like you could have options for $500-$1500 / $1500 – $3000 / $3000 – $5000 / etc. – whatever your prices are)

      If someone sees a minimum of $1500, and they want to spend $50, they’re not gonna even bother to reach out 😉

      Does that answer your question?

  2. First of all we had a good laugh here David 🙂 Those magical clients that appeared right before the rent is due :)) I don’t even remember how many times that happened to us 🙂 but it was a lot! Same story David :). Its so funny and interesting to hear someone has gone trough the same thing. I (designer) founded InfinPixels with my husband (developer) in our first year here in London. Our English was terrible. So I think its from that time, I still have a fear inside me when I talk to someone on the phone particularly if they are native speakers. I feel I am in my English class back in high school :)) The others, especially if they speak terrible English, oh I would like to invite them for dinner 🙂 I feel so conformable talking to them. Till today we closed all our deals with emails and face to face meetings. But after I read this I will definitely start talking to people on the phone. That would just save a lot of time! But there is one thing I am not doing anymore is to prepare proposals. You say it takes 1 hour or so but man it takes a whole day for me. And I guess when they read it, it confuses them. So many things they had no idea in one place. So that’s why I send them the price, whats included and our process. Simple and I get the job. One question; Do you send the contract with the proposal? or is it to early. We send the contract and the invoice once we accept the quote. I don’t know if they need to read all that boring and scary looking stuff (terms, contracts) before we get the deal.

    Big hugs to you and your wife from us! 🙂
    Thank you

    1. Hey Ezgi!

      That’s so funny. Always great to meet kindred spirits 🙂

      When you say..

      “So that’s why I send them the price, whats included, and our process.”

      .. that to me sounds like a good proposal! That’s exactly what ours spells out actually.

      It takes us about an hour to customize because the bulk of it is already written – we just go in and adjust things for each person who comes our way.

      To answer your question, I think your hunch is right: we don’t send the contract with the proposal, as that seems a bit forward to me. Once it’s approved we decide on payment terms, add those payment terms into the contract, then send it over with the invoice.

      Thanks for stopping by and sharing your thoughts 🙂 Best of luck to you and your husband 🙂


    2. Just wanted to pop my 2 cents in:

      My proposal doubles as my contract, so I don’t have to waste time creating a second document. I make sure my wording is as concise as possible to keep things short and sweet, but also ensures that I CMA.

      Great discussion!


  3. Thanks for the great article! But does it really make sense to phone (up to 1-2 hours) before having made sure the budget the client can pay at least roughly matches with the prices I will need to charge?

    I instead tend to check that first (via email) and perhaps afterwards half a phone call – before sending a final proposal.

    Would love to hear your thoughts on this!

    1. Hey Lisa,

      I think that makes a lot of sense 🙂 I tend to take the phone call beforehand, and in the beginning of the convo talk about budget. If it’s in line, then I’ll keep the convo going, otherwise I’ll tell them I’m sorry and wind down the convo. My thinking is if the budget is in line – I’m already on the phone and we can get down to business. If it’s not, then I only wasted a few minutes.

      Sometimes I forget to ask though 🙂 In those cases I usually send a quick email with a really rough estimate and ask if that’s okay, and if it is I’ll send over a detailed proposal.

      Thanks for sharing,

  4. Despite of how much I used to hate selling on the phone, after doing this a long while now, always amazes me how it works like magic.

  5. Great article again! And it’s no problem taking advice from you, because you come accross as very honest and genuine in your writing. But nice to read about your journey nevertheless. 🙂

    When on the matter of phone calling – do you do any cold calling as a way of gaining new clients? This article focuses more on potential clients that have reached out to you by email, if I got it right? I would love to read an article about your take (or view) on cold calling. I think this is a skill I need to be learning.

    1. Hey again, Anita! I’m glad you liked this article too 🙂 Thanks so much for your kind words 🙂

      My view on cold calling is very simple: don’t! Unless you have gigantic cajones of steel and enjoy it for some reason – I’d steer clear. Years ago in times of desperation we tried that among just walking into businesses and pitching them on the spot.

      I learned a lot about rejection lol.

      The ONLY kind of “cold” communication I’d do is email or Facebook – and even then I’d do it in a very strategic way. Perhaps that’s a post for some time down the road too 😉

      1. Email marketing for most on just 2000 leads is about $850.00 per month.. Expand from there and add at least 31cents per lead.. Yes you can research and choose your list from a million or so. Your skills matter here! But does everyone have that cash at hand to spend? ROI is similar to direct mail marketing.. Email is statistically most cost effective… But needless to say to generate 20 calls per day would cost you 20k.. Plus your time..

        I guess my question is really how do you start from scratch and spend that money?
        But most important how do you disregard the cold call..? After all.. It does perfect your pitch when you challenge yourself!

  6. Great tips on how to steer the conversation and make sure you put the client first. Although this is always at the back of my mind, I really liked how you laid out your strategy to make sure everything is open in the conversation and to diffuse any confusion or miscommunication.

    The worst thing that could happen is that the client says all their needs but somehow we miss some items. There’s no harm in asking them for clarification before we assume and get things wrong.

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