Ask this one question to close more freelance sales

September 9, 2010 by Dean Rieck
Filed under: Freelancing 

freelance questionA while back, Mike Klassen, a.k.a. The Magalog Guy, called me to talk shop. We both specialize in direct mail.

I’m a writer who also designs. He’s a designer who also writes. So he’s like my doppelganger. And a fun guy to talk to.

Here’s Mike’s first post for Pro Copy Tips with advice on how to close more sales by asking one powerful question.


One of the major things I had to adjust to when I began freelancing was the fact that I was responsible for everything.

As an employee at just about any company, our jobs often have a relatively narrow focus. If you work in the accounting department, what management is up to isn’t much of a concern, at least in terms of your day-to-day activities.

As a former Microsoft employee, what the legal department was doing, for example, didn’t affect my daily activities as a technical writer.

But, as a freelancer, every aspect of your business is your responsibility. And because of that, you may have to stretch yourself past your comfort zone.

Nowhere is this more vital than closing sales. If sales isn’t in your background – and it wasn’t in mine – convincing someone to sign on the dotted line can be stressful.

In fact, you might even subconsciously avoid getting to that point. That’s where I found myself some time back.

I’m generally a “no pressure” person when it comes to business. I’m not going to push people to hire me. But what I had to realize is that there’s a difference between pushing people and gently leading them to a decision, no matter what that decision is.

Here’s how my conversations with brand new prospects used to end: “If I can answer any more questions or be of service, feel free to let me know.”

Maybe I’d contact them later if I hadn’t heard from them after a certain amount of time, maybe I wouldn’t. You see, I assumed that if the prospect liked what I said, they’d hire me. Isn’t that logical? Did I really need to push them into taking action?

Well, no, I didn’t need to push them. But a business coach gave me a better way to finish a call that helps lead to a next step. It’s a simple question that has lots of power. Here it is:

“Do you have your appointment calendar handy?”

Don’t underestimate the power of that question. Freelancers lose an amazing amount of work by not setting a specific time to follow-up. They approach it like I used to … assuming that if there’s interest, the prospect will call back.

But prospects get busy, or they sense more interest from another freelancer they’re considering. Believe it not, in some cases they can even completely forget about the project if it’s not an immediate need.

By setting a time and date for the next conversation before you finish the current one, you’re setting expectations and helping lead the prospect to the next step in their project process. What the next step might be is totally up to them based on their needs.

If they’re not interested in hiring you, they’ll say so. Or they’ll resist setting up a follow-up conversation, saying something like, “Well, I’ll get back to you if I need anything else.”

If that’s the case, maybe they’re just tire-kickers. It’s still OK to follow-up with them down the road. But based on their response, they’re not going to be someone you focus all your energy on; you’ll move on to better prospects.

If they are really serious, they’re going to be OK with setting up a follow-up call a week or two down the line just to see where things stand. You’re also showing that you’re serious about their project.

And this is where we need to talk a bit about your self-esteem. Beginning freelancers in particular can suffer from low self-esteem as business owners. We’re new to it and tend to think we’re on unequal ground with prospects because they’re the ones who decide whether we get the job or not.

If that’s your mindset, stop thinking that way!

You are a professional. Your time, effort and experience deserve as much respect as your prospect’s. If a prospect wants to hem and haw about a follow-up call, perhaps that tells you all you need to know about what sort of client he’d be. I’m not saying you totally write him off. I am saying that you need to respect your own time and focus your attention on prospects who are serious about talking and working with you.

If the prospect flat-out refuses to set a follow-up time, great! You want a Yes or a No, or a set time to continue the conversation. Not knowing what’s happening next is stressful and terribly inefficient. So a No makes it clear that you can move on.

A freelancer constantly left dangling in the wind by prospects is a freelancer not making as much money as he or she could.

Here’s the bottom line with prospects: Never leave a conversation without both sides agreeing to what the next step is and when it will take place. Your goal as a freelancer is to get to a Yes or No as quickly and efficiently as possible. Waiting around, hoping the prospect will call you back at some undetermined time is not going to put you on the path to the income you want as a freelancer.

Mike Klassen is a former copywriter who now specializes in direct marketing design for magalogs, bookalogs, and other proven direct mail formats.

Related posts:

  1. 7 defensive copywriting strategies to close the sale

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Smart Comments

9 Comments on Ask this one question to close more freelance sales

  1. Paige Jeffrey on Sep 9th, 2010 1:10 pm
  2. What an incredibly useful post. I really mean that. I’m totally the same way – I could see myself saying it as you commented on “Well, if you have any questions, just let me know!” I never would have thought that I’d be shooting myself in the foot with it.

    Thanks Mike! I think you may have just helped me close some of my future sales. :)

  3. Mike Klassen on Sep 9th, 2010 2:00 pm
  4. Thanks, Paige. That means a lot to me. Because of all the folks who help me in my freelance journey (including my business coach who gave me that idea), it’s important for me to pass it on.

    To know that someone else gets something from that advice makes my day.

    Let’s do ourselves proud and close more sales. :)

  5. Dean Rieck on Sep 9th, 2010 2:12 pm
  6. @Mike: This is great advice. But it never occurred to me to not follow up with clients. I use ACT! to track all contacts and opportunities, so when someone contacts me, I schedule a followup. A program like ACT! makes this easy since it’s geared for sales.

  7. Mike Klassen on Sep 9th, 2010 2:31 pm
  8. And that’s where some of us have slipped in the subtleties of follow-up. I knew I should follow-up, and sometimes I would. But I was inconsistent and trying to read too much into the prospect instead of just being sure by asking.

    Prior to now, even using something like ACT wouldn’t have caused me to be direct with a client in terms of asking him/her for a date for a follow-up because I was afraid of “pushing” or assuming that I’d get a call if interested.

    I started my career with a lot of referrals, so “closing” a sale was a skill I didn’t need too often. Most people who called were ready to hire me. I got soft in that area and didn’t have a better appreciation for Sales 101.

  9. Joshua Black | The Underdog Millionaire on Sep 10th, 2010 10:23 am
  10. This is a great tip for people that don’t really want to “sell” their prospect. However, I like to use the old saying that the only reason to stop folowing up with a prospect is if they are dead, or they tell you tp stop. You never know when someone might turn into a customer down the road.

    There have been people that I’ve been reading for YEARS before I finally pulled the trigger and did business with them, but if I didn’t keep having their message in my ear, I would’ve eventually forgotten about them. Hoever, you’re right on that you don’t always have to waste the time calling them. You can create an email list an follow-up with all the non-takers at once.

    -Joshua Black
    The Underdog Millionaire

  11. Dean Rieck on Sep 10th, 2010 10:36 am
  12. @Joshua: You’re right. But I divide my contacts into four groups: active clients, old clients, leads, and prospects. When I get a hot lead, I call, email, and otherwise stay in touch until I know whether they’ll turn over into a client. If they don’t, they fall back into the prospect category. I have a special email list I use to mail to them 4 times a year just to stay in touch.

  13. Mike Klassen on Sep 10th, 2010 10:40 am
  14. Bob Bly once said the same thing. He was asked how long you should follow-up with a prospect.

    His answer: Until they tell you to stop.

    So I’d never advocate stopping altogether unless they make it clear they want you to stop.

    But what I hope I got across was not being too passive in dealing with prospects.

    And you bring up a good point that I didn’t deal with… getting people on a list.

    It’s not such a bad idea to ask a “not now” prospect if you can put them on your mailing list, assuming you have one.

    I’ve got a guy on my list where we determined he wasn’t really ready for my services yet. But he’s on my list and every time I sent an update, he always writes back to say hello and thank me for whatever info I sent.

  15. Daniel Upton on Oct 6th, 2011 10:47 pm
  16. little late to this one, but thought a newbies perspective may be useful if anyone drops in. I really relate to the point about self-esteem in beggining frelancers and would like to hear from more experienced professionals about how they started approaching prospects.

    I’ve been thinking about my approach to ‘cold calling’ prospects and have decided to take the non-confrontational path. Just an introduction to let the client know what I offer and how to find me if they need my services. I’m not sure if I’m using this ‘planting the seed’ strategy because I think it will be the most effective way to generate business or because it’s less duanting and less likely to result in outright rejections.

    Any thoughts?

  17. Mike Klassen on Oct 13th, 2011 1:50 pm
  18. Hi Daniel,

    I do have some thoughts on this because earlier this year I did a round of very targeted cold-calling.

    A couple of years ago, I took some of my best blog articles and put them into a book that I offer on my site. It’s a free book, but requires a sign-up.

    At 130 pages, it’s got what I feel is good information for direct marketers, which is one of the main groups I work with. It’s information they can apply even if they never work with me.

    When I called these prospects, I simply offered them a book that could help them “increase sales and build deeper connections with prospects and customers.”

    If they were interested, I’d e-mail the book to them and ask if I could call back in a week or two and talk about whether the ideas I was presenting was something they thought would work for them.

    One guy told me how refreshing it was for someone to call and offer him something of value for free, not try to sell when I didn’t have any idea what his needs were at that point.

    What is perhaps even more interesting about this whole thing is that it’s rare I told anyone on that initial cold call what I did. If they took the time to go through the book, they’d know because it ends with what I do for clients.

    So that’s a long story to illustrate one approach to cold calling… offering something of value and setting a time to follow-up. Doesn’t always work. Nothing does work 100% of the time. If it did, we’d all be doing it.

    Daniel, I think your approach doesn’t encourage a dialog that could lead to a sale or at least a stronger connection with a prospect. I was the same way… “Here I am… if you need me, give me a call.” That’s a very slow path to success, in my opinion.