Take a Fire-Breathing Dragon Approach to Scaring Away (and Attracting) Clients to Your Business

3 smart ways to go about attracting clients to your business | KOTAW Content MarketingWhen I tell branding and content marketing colleagues that I reject more potential clients than I accept, most assume one of three things:

  1. I am independently wealthy.
  2. I married into money.
  3. I am crazy.

I wish one of those were true. But I raised two daughters alone and the only thing crazy about me is the hours I worked to support us.

What I discovered – the hard way, of course – is that bad clients are worse than no clients. Seriously. It’s better to endure the occasional lean month than to work endlessly for soul-sucking, impossible-to-please people. Say yes to the right clients, and serious financial rewards (minus the head-bashing frustration) will follow.

If you’re just starting out on your own or struggling with an existing business, you may find this advice hard to follow.

So let me tell you briefly about my early years as an entrepreneur.

A Diamond is a Girl’s Desperate Friend

Although I’d freelanced for several years, it wasn’t until 2001 that I officially declared myself an entrepreneur. It was a few weeks after Quicksand: One Woman’s Escape From The Husband Who Stalked Her, my first book, had been published and I had to read my copy – and a glowing review by The Globe and Mail — by flashlight because our electricity had been turned off.

I’d spent most of my adult life dependent on paychecks and bonuses. Corporate America had been financially good to me, and I had expected equally reliable – and more rewarding – pay from book sales and a pending movie deal.

Ha! After dropping my daughters off at school and promising them I’d find a way to get the power restored, I drove to the welfare office and picked up an application. I took it home, filled it out and put in the bottom right-hand drawer of my desk.

Please, God, don’t let me have to submit this.

As I buried the paperwork, my hand felt something hard: a box containing a diamond ring.

I took the ring to three jewelers and sold it to the last for a pathetically low sum. But it was enough to pay the rent, the utilities and a month’s subscription to a freelance job site. I kept the welfare application in my desk for one year before tossing it.

Landing Clients and Flirting with Success

It turned out I was really good at attracting clients. I charged rates two times higher than the next best-paid competitor (and 10 times higher than most). And I said YES to anyone who wanted me. My goal was to become the highest earning freelancer on the site within a year. And I met my goal!

But I was unhappy – miserable – because at least 7 out of 10 clients were poor fits. Some were rude, abusive and delinquent in paying my fees. Some were decent people who just didn’t gel with my sense of professional pride or intolerance for micro-management. A few were more interested in me than my work and demanded revisions to prolong their fantasies.

Still, I was afraid to say no. I didn’t have any more jewelry to sell and the thought of returning to the welfare office made me ill. But I started to use slightly more discretion when bidding for jobs. And what I looked for specifically were jobs with serious profit potential.

A few ghostwriting opportunities caught my eye. The ads offered horrible pay and no rewards – “Write my breakthrough business book – a GUARANTEED bestseller – for $1,000” – and most of the ideas were not-so-subtle rip-offs of 7 Habits of Highly Effective People that were destined to sell about 10 copies on Amazon. But some were good – much better than the authors believed – and I offered my ghostwriting services for a discounted fee plus a hefty share of sales.

My instincts paid off, and a couple of royalty checks made it possible for me to take a deep breath and really think about the type of clients I wanted to take on and how to scare off the ones I didn’t.

Hanging Up on Unhappy Client Relationships

It’s not always possible to foresee a bad client relationship. I still get fooled a couple of times a year (usually when my passion for a project surpasses my critical judgment). But I’ve found that asking tough questions upfront is an effective way to sort out the clients who will fuel my creative energies from those who will drain them.

These questions are better asked in person, via video chat or by phone. It’s OK to discuss project parameters and contract details through emails and texts. But, if you want a real preview of a working relationship, you need to hear the person’s voice and gauge reactions in real-time.

Does the idea of asking scary questions scare YOU? Don’t worry. I’ll show you how to act tough without sounding like a bad cop trying to browbeat a murder confession out of a 10-year-old.

But, if you don’t like the answers to your questions, politely bow out. There will always be more clients, and you deserve to work for the best of them.

1. What’s Your Budget?

What’s so scary about this question? It seems about as basic as it gets, right? It’s the way the potential client answers that should make you dance with delight or flee in terror.

If the person immediately answers with an amount that meets or exceeds your expectations, yay! Move on to the next question.

If the person hems and haws and mumbles something about trying to get his mom to float him a loan, hit the disconnect button.

An “I don’t know” is not necessarily a poor answer. I had no idea about the difference between a $500 website and a $5,000 one when I launched KOTAW Content Marketing a little more than two years ago. But I was willing to learn and respected the contractors who explained the difference – without making me feel like an idiot.

A lot of people don’t initially appreciate the expense of branding and content marketing even if it’s broken down to an hourly consulting fee or per word writing rate. If you can make a case for your fees – and the potential client is receptive – see how she fairs with your other questions.

Run, RUN as fast as you can from anyone who answers, “I put all of my money into producing my product. I don’t really have much left for marketing.” This business owner is either stupid, desperate or both. If you really need the gig, draft a short-term contract and get your fee upfront.

I like to ask potential clients what monthly budget they can commit to for six months and to give the question some thought before answering. I’d rather work with a small, realistic, sustainable budget than a big pile of cash the person expects me to double in 30 days. I refer those folks to the nearest casino.

2. What are Your Expectations?

If the person answers, “I want to be on Ellen in three months,” politely say, “Excuse me, did you say your name was Jennifer Aniston?” Dreamers are disasters! They will hurt your pride, your wallet and – if they can get away with it – your reputation. Because, even if you think you could land the client on Ellen in four months or actually book her on the Today show in two, she won’t be satisfied. I recently tried to help the owner of a failing small business land a deal with a multi-billion company and, by the second week, all I heard was whining that it was taking too long.

If the potential client has lofty long-term goals and realistic short-term ones, sign him up! Chances are, you’ll exceed this person’s expectations and make him a client for years.

A client with reasonable long-term goals but without a good sense of what it takes to reach them is worth trying to educate. Few people I talk to understand the power of social media or all of the elements of personal and corporate branding. So I ask follow-up questions such as these:

  • “Social media is the world’s biggest cocktail party, one attended by world leaders, billionaires, celebrities, millions of potential customers and you. How would you behave at this cocktail party – hold up a sign that says BUY MY SCREWDRIVER NOW! or listen to what they were saying and artfully join the conversation?” If the potential client has an AHA moment, consider working with him. If you get a lecture about how many “likes” he could buy for $100, offer a quick “unlike” for free.
  • “If you had $400 to spend on a pair of shoes, would you buy a brand you recognize — Stuart Weitzman, Tory Burch or Kate Spade – or a brand you’ve never heard of and no one is talking about — what would compel you to switch allegiances? And how much time are you willing to spend to grow your company, knowing that these established brands are outspending your marketing budget by a margin of about 10,000 to 1?”

I recently asked both of those questions to an entrepreneur, and they didn’t scare her off. And her answer so impressed me that I happily agreed to take her on. The right clients will respect the questions you ask. Steer clear of those who don’t.

3. How Do You Go About Making Important Decisions?

This is a critical question, and it’s a difficult for most people to answer it. I sometimes hear stories about wedding proposals, which are always interesting but rarely relevant. One person told me about deciding between thin and thick crust pizza! His answer made me hungry but not for his business. So more often, I phrase the question this way: “When you purchased your last car, how did you decide which one to buy?”

Anyone who says he read Consumer Reports, checked out Kelley Blue Book and visited three dealerships before making a purchase two weeks later is a good potential client. Clients who do their research will appreciate that you do yours – they’ll understand that designing a logo involves a lot more than moving images and text around.

Beware the client who buys the first car he likes on the lot, then returns it two days later asking for a refund and then buys another with the same haste.

I like clients who make fast decisions, who trust themselves and my expertise enough to greenlight something I propose. But the ones who say “yes-no-yes-maybe-no-no-no” with lightning speed will cripple your branding and content marketing efforts.

I had a personal branding client who wanted a new website completed in two weeks. I said I couldn’t provide such a fast turnaround but recommended someone who could. I worked with the client on his brand identity, the color palette for the website and the written and visual content. The website was ready to go live in 10 days. Three months of second-guessing revisions later, the website still wasn’t ready and the brand message had taken more beatings than a career boxer.

Successful people make wrong decisions and correct them. But they know enough about themselves and their business goals to trust the decisions they make. People who can’t choose the color of their car – or website – in less than a week are not good clients. Scare them away!

Don’t Wait for Prince Charming

As important as it is to free yourself from unwinnable client relationships, don’t expect a client to fit your needs as perfectly as Cinderella’s glass slipper. Like you, clients are flawed. And that’s OK. People’s quirks keep entrepreneurship interesting and finding creative ways to keep unconventional clients happy will make you better at branding or content marketing.

Don’t let your business dwindle or die waiting for Prince (or Princess) Charming to come. But don’t waste your time kissing toads. Wart-proof your client relationships by asking tough questions up front, and you’ll attract the clients who are right for you.

Now it’s your turn! How do you go about attracting clients to your business? And how discerning are you when it comes to taking on clients? How do you balance the desire to have happy client relationships with the need to pay your bills? Let’s chat in the comments section below! PS: client horror stories are always fun, so feel free to share those with me too! :)


  1. Nataly says:

    Thank you. This is excellent! :)

    I so identified with your story, as I am exactly in the moment when “my electricity is about to be turned off”.

    But putting better in my reality, I came to Bali alone (long, long story), trusting on the idea of starting my freelance writing career, with a little-saved money – that’s over now.

    Still, I do reject clients. And that’s VERY hard and scary to do when you might not have money to eat. The thing is that, even if I have just started (exactly 3 months), I can’t write a 30 pages ebook for 50 dollars.

    The time I would spend writing for almost nothing is the same time I invest in looking for better clients, studying more about writing, blogging and content marketing and focusing on bigger projects.

    It is hard, but I guess it’s part of the process to trust, believe and be persistent. And don’t give up! :)

    Thank you once again for the post. What questions to ask was very inspiring – I just have to send an e-mail now that requires me to ask some good questions ;)

    • Katherine Kotaw says:

      Hi, Nataly,

      I’m thrilled that my story resonated with you.

      And I love the point you made: “The time I would spend writing for almost nothing is the same time I invest in looking for better clients, studying more about writing and content marketing and focusing on bigger projects.”

      Freelancers need to value their time, and I’m glad you figured that out early in your career.

      Keep asking questions — of clients and yourself — until you get the answers you need.

      I wish you the very best,


    • Hey Nataly

      Your candor, commitment and courage are going to be rewarded VERY soon. You are going to enjoy a BRIGHT future on your terms #HUGSS

      Much love

    • Katherine Kotaw says:

      Hi, again, Nataly,

      I saw that my dear friend — and gifted writer — Krithika Rangarajan — replied to your post. If you haven’t already connected with Kitto on social media, I urge you to do so. She’s extraordinarily generous with praise and support, something every writer needs more often than she gets.


    I need to print out this article for future reference!

    You are one of a kind, Kat, for NOT selling your dignity even during the direst circumstances. #HUGSS

    I have a hard time saying NO, so I need to remind myself to NOT give up my long-term happiness for short-term stability. I LOVE YOU SO MUC


    • Katherine Kotaw says:

      Yes, saying NO is hard at first. But it gets easier — and more rewarding — every time.

      If you pay attention to your instincts (and not your fears or insecurities) you will know when to say YES and when to shout NOOOOOOO!

      Not sure? Try a few NOs until the word starts to feel uncomfortable. Because the discomfort that goes along with an ill-advised YES lasts a long longer than the few seconds’ unease in saying NO.

      LOVE YOU, Kitto. And here’s a big YESSSSSSSSSS to your writing future!

  3. Cleone Hall says:

    Hi Katherine, this article was perfect timing for me and bang on. It reaffirmed my choice of letting a recent client go and how I can move forward confidently finding the right business cultures to do business with. I really get the way you write I am so happy I found you and cant wait to read the rest of your articles.

    • Katherine Kotaw says:

      Welcome to KOTAW, Cleone, and I’m so glad my article helped you. It’s hard to say no to instant money, but it’s often the only way to make room for the right clients for you and your business.

      Please stop by again soon. I’d love to hear about your success in saying YES to better clients.

  4. Excellent article, spot on.

  5. What’s Your Budget? -was the first eye opener for me.
    My story is a long one so I won’t go into it, but your article made me truly realize – yes clients are good, but be selective or better yet be honest on that first meeting, show them what they will get and what is a no no :-) hope it makes sense.
    Thank you for this amazing article, it could not have come at a better time when me and my husband are moving to Hollywood to open our photo-studio. Getting clients is never easy, but getting the real good ones who understand the creative process and the talent behind it is the goal. Wish you all the best and hope that we will be successful enough to hire your team :-)

    • Katherine Kotaw says:

      Hi, Lamija, and welcome to KOTAW (and to Hollywood).

      Thank you for the kind comments, and I’m thrilled my article helped you.

      I KNOW you will be successful enough to hire the KOTAW Girl Gang (because you will be selective in choosing clients).

      But, if you’d like to meet for coffee before then, just give me a shout.

      All my best,


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