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The Fine Art Of Telephone Prospecting For Freelancers

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Adapted from The Freelance Designer’s Self-Marketing Handbook by Shaun Crowley

For many people, telephone prospecting can be a painful process. You know it’s a necessary activity—without it, your work will sooner or later dry up.

And if you wait until the long periods of downtime before you pick up the phone, the task is made all the more difficult—desperation is very easy to spot in the voice of a cold-caller.

This article shows you how to gather the courage and the impetus to phone for work, and how to improve your telephone technique for maximum effect.

The introductory phone call

Ask yourself why you find cold-calling a challenge, and you’ll probably come up with one of three answers:

  • “When I cold-call I feel like a pest.”
  • “I don’t enjoy having to sell myself on the phone.”
  • “Being rejected is very de-motivating.”

Interestingly, these anxieties are based on your perception of the call, and not necessarily on the recipients’ experience at the other end of the phone. For them, a call from a prospecting freelance designer may be a stroke of luck, a welcome interruption—not an irritation.

The key to overcoming your fears of cold-calling is to change the way you think about the task.

If you feel like a pest, you’re most likely to present yourself as a pest. If you feel like you’re attempting to ‘sell’ yourself, your recipients will feel awkward and cut you off as soon as they can. And if you feel rejected when a caller makes his or her excuses, you’ll find it hard to pick up the phone again.

Remember at all times: you are not pestering or selling to people, you are offering a valuable service. When you call prospective clients you are presenting them with an opportunity—to improve their website communications, and consequently, to increase sales of their products.

Even if you’re targeting people who don’t have a vested interest in their company’s bottom line, they can still benefit from your phone call. Quality design reflects as well on those who commission it as it does on those who produced it.

Sure, some people you phone don’t use designers, and a tiny proportion of those people may find you a nuisance. No problem, just move on to the next person. Those people who do use designers are likely to welcome your call.

Phone to get to the next stage in the prospecting process
Your ultimate destination is to arrange meeting time with a prospective client. That way you can strike up a personal relationship which will boost your chances of getting work. It’s harder for a prospective client to turn you down if they’re acquainted with you.

If you’re lucky, you’ll arrange a meeting with a contact in your introductory call. But in most cases, your recipients will be busy and unwilling to meet you on a whim. They’ll want to see your work is up to scratch before agreeing to meet.

So rather than try to ‘sell’ yourself on the phone, get their permission to email a link to your portfolio. If you’re pleasant and polite, they will probably say yes. Then you can carefully word your selling message and select your most relevant portfolio links. After all, it’s your work that should do most of the talking.

Indeed, the less emphasis you put on your initial phone call, the less pressurized it will feel for you and your recipients. You can write at your own pace; and your recipients can evaluate your portfolio at their own leisure.

Give yourself a reason for calling
When people receive a phone call from an unknown contact, their first reaction is to think “Who are you?” and “Why are you calling me?”

In your mind, your reason for calling is clearly to drum up new business for yourself. But that won’t persuade your contacts to take an interest in you. You need to tailor your ‘reason for calling’ so it appears more targeted to the needs of the individual you’re calling.

Before you call, do some quick research into the recipient’s company. Is there anything you can lead on? For example, if you’re phoning a marketing executive at an educational publishing firm, you could start your call like this:

“Hi, my name’s Jon Woo—I specialize in designing for educational publishers. So as the biggest educational publisher in Boston, I decided to give you a call…”


“Hi, may name’s Jon Woo—I’m a freelance designer. I notice from your website that your house style is similar to some of the work in my portfolio, so I thought I’d give you a call to introduce myself…”

Tell people about your ‘USP’
In chapter one of my book, I discuss the need to have a clear business offer—a Unique Selling Proposition that sets you apart from your competition.

Your USP can act as the killer punch in your phone call—the ‘Wow’ statement that convinces prospective clients that you are worth investigating.

Before you call, write a brief list of points associated with your USP that you can refer to when the opportunity arises. When a prospective client responds positively to your pitch (“Sure, I’ll be interested in checking out your portfolio, send me a link…”), you can whet their appetites further by revealing your trump card (“Great, I’ll email it to you now—oh, and by the way, I also offer free design consultation—would that be of interest to you?”)

Demonstrate your uniqueness and you’ll leave a lasting impression on recipients as they browse your online portfolio.

Find out recipients’ design needs
Use your phone call to find out about your contacts’ business set-up by asking open, exploratory questions such as: ‘”How often do you use freelance web-designers?”, “What kind of situations require freelance web-designers?”, and “What kind of design works best for you?”. There are several reasons why you should do this.

First, the information you elicit from your introductory call will help you to select the right portfolio pages to present in your follow-up email, and to select the most persuasive features and benefits to highlight (we’ll focus on this later).

Second, if the recipient isn’t interested in your offer, their feedback as to why they aren’t interested is valuable. Record all objections. Later on, as you inspect the contacts in your area, you may find patterns emerging—maybe a sign that you need to adjust your business offer.

But the most important reason for asking questions in your opening call is because it’s an effective cold-calling technique. Exploratory questions quite often open up a need for your service. Sometimes recipients can talk themselves into a positive response. You’ll often find that people start off on the defensive, but as they relax into conversation, they uncover obvious needs for using a freelance designer like you.

In many cases, you can elicit a positive response with a little gentle probing. Example:

Contact: “… No, I’m afraid we already have a team of designers. But thanks for your call. ”
Designer: “Sounds like a great set-up… what kind of design does your team specialize in?”
Contact: “Brochure and catalog design, mostly.”
Designer: “I see—so you just work on print collateral, do you?”
Contact: “No, we deal online too. That’s when we call on freelance designers—do you do websites?”
Designer: “Sure! I can send you some websites I’ve been working on…”

One of the keys to cold-calling is not to give up too easily. Keep your contact talking, and you’ll significantly increase your chances of getting hired.

Say you’ll be in the area
Even if a prospective client appears genuinely interested in your design offer, he/she might still shy away from arranging a face-to-face meeting with you in your introductory call.

One reason for this reluctance could a sensitivity to the time and effort you are taking to visit. This makes for a subconscious feeling of obligation to reciprocate your efforts.

You can soften this by making your visit appear informal and spontaneous. Pick a random day to “visit the area”. Say you’re meeting a client across the road. While you’re in the neighborhood, ask if the contact can spare five minutes for a coffee and a chat about his/her design needs.

This works best if you have already lined up a meeting with someone at the target company. Call other people working in different divisions: “Hey, I’m seeing Paul Boodell in European Product Marketing at four… While I’m there, are you free to meet up just before?”

Call as many people as you can
The law of averages states that even if your telephone manner is less than perfect, you will strike lucky sooner or later—so long as you call plenty of people.

Set yourself a target: Tell yourself you’ll phone one hundred people this week. If you’re feeling really proactive, give yourself a target of a hundred in a day!

The more calls you make, the easier it will get. You’ll find your rhythm—after ten calls your pitch will appear confident and natural.

The follow-up

Exactly how you approach your follow-up depends on the kind of response you get in your introductory call. The status of the contact, the likelihood of getting hired, and the level of enthusiasm they have for seeing your work, are all things that will influence the content of your email and how you follow-up on that email.

As a general rule, maintain phone contact with your most hopeful contacts until you get a meeting. For all others, regular email is an appropriate level of contact, so long as the contact has given you permission to email them.

Personalize your follow-up email.
A few hours after the call, send over an email. The email should be personalized to achieve maximum impact:

  • Remind the contact who you are. Don’t let the recipient confuse your email with spam before he/she opens or reads it fully. Be clear that you have already spoken to the contact, and that you are following up on the phone call as requested. Do this in your subject line, and in the first line of your body copy.
  • Remind the contact of your most relevant offer. Refer back to the contact’s needs (you should have recorded these in a spreadsheet after your phone call), and say how your design offer responds to these needs. To keep your email short and punchy, link to the relevant pages of your portfolio, where each aspect of your service is explained in detail.
  • Flatter the contact. You want your contact to warm to you, so be polite. Thank the contact for taking the time to talk to you. If you can, subtly acknowledge your appreciation of the contact’s business needs. This will help present yourself as a smart and respectful professional.
  • Include relevant links to your portfolio. Make it easy for the recipient to go straight to the page of your portfolio that will interest them most.
  • Say what happens next. Make sure the contact is aware of how you intend to follow-up. Say you intend to call the recipient on a certain day to gauge their reaction and arrange a meeting. If they know you are going to call, they may evaluate your portfolio with greater urgency.
  • Sign off with your USP. As a final reminder of your service, leave the recipient with your USP—the one most appealing aspect of your service that others don’t offer. In fact, why not include your USP in your email signature?

From: Jon Woo Freelance Designer
Subject: Following-up on our phone call

Dear Graham,
It was great to talk to you yesterday! Thanks for taking the time to explain your business set-up and design needs.

It’s clear you work to very tight deadlines on a daily basis. To help you achieve your goals, I offer fast turnaround and a free proofreading service as standard.

You asked to see samples of my web- design, specifically in the education sector:
(A website for an English Language Teaching college)

(A banner-ad for a newspaper educational supplement)

Feel free to browse the rest of my portfolio.

I’ll call you Friday to get your reactions (maybe we can arrange a quick meeting at a time convenient to you? I’d love to discuss how I can help you and your team.)

Thanks in advance for taking the time to evaluate my work.


Jon Woo
Need a fast freelance designer?

Phone again to request a meeting
A few days after sending your follow-up email, call the contact again and ask for reactions to the work in your online portfolio. Then ask for a meeting.

If the person likes your work, the chances are that he/she will want to meet you. Even if there’s no work right now, your contact may want to keep you in the book for later on.

Why meet?
Some clients don’t require meeting time with a designer before hiring them. Indeed, if you are offering an ‘international’ service, it’s simply not possible to meet most of your prospective clients. But if you’re targeting companies in the local area, no self-promotion works better than introducing yourself and your work in person.

So why should a prospective client take the time to meet you? There are many reasons you can give, here are just a few of them:

  1. “I also design print collateral, which you can’t judge effectively on-screen.”
  2. “I have more samples to show you that I haven’t had time to upload onto my site.”
  3. “Maybe we can discuss a brief you’re working on at the moment, so I can demonstrate how I would tackle it.”
  4. “Maybe we could integrate my visit into a creative meeting, I can offer some free design consultation while I’m there.”
  5. “I’d like to learn more about the work you do, maybe you could bring some samples to discuss the design and your brand style.”
  6. “I’d like to meet you and your team – it’s always better to put faces to names.”
  7. “I’ll be in the area next week – it’s a convenient time to drop by and see you.”
  8. “I’ll buy you lunch!”

Make contact every six weeks
Some contacts will still be reluctant to meet—maybe because they don’t have any immediate design needs or they are too busy. If this is the case, agree on a good time to call later. As a rough rule, six weeks is an appropriate gap between reminders.

Don’t kick the cat as it leaves
Unfortunately, a tiny number of people will be rude to you when you call. As much as you want to tell the contact what you really think of them, it’s important to remain polite. That person may have contacts with other prospective clients. Reputations can stick.

Keep your spreadsheet updated

Every time to call, email, or mail a contact, make a note of your activities in a spreadsheet. You can refer to your spreadsheet to find out when you should follow up next, and what specific aspects of your service you should highlight when you do.

Shaun Crowley has worked as a freelance copywriter, marketing consultant, and communications manager for a major UK publishing company. He is the author of The Freelance Designer’s Self-Marketing Handbook and 100 Copywriting Tips for Designers and Other Freelance Artists.

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