Writing Tip of the Day: Ask

I just had an interesting Skype chat with Jodee Redmond. We were talking about how shy we were/are in the real world, but received a bravery boost when we began freelancing. Both Jodee and I brought up situations where we were hesitant to discuss payment options, raises, or asking contacts for work – when we shouldn’t have stressed.

I’m surprised by how many people are receptive to my ideas and suggestions – when I finally get up the nerve to ask. I have never been turned down when asking for a client for a raise, and I’ve landed several projects after cold calling or reaching out to contacts and former clients.

When you ask, one of two things will happen. The other party will say “no”, or, he’ll say “yes.” How will you know if you don’t try?

This writing tips is sponsored by Demand Studios.


  1. says

    I was just thinking about how asking for a job is the way to go. I saw a gig I liked on the leads for today, but the job description had that you needed to be able top come in to their store.

    The topic is something I know backwards and forwards, so I wrote and asked if they’d consider telecommute as an option. They wrote back “Yes!”…we’re in the negotiation stage but who knows? I defiantly wouldn’t know if I hadn’t had the nerve to ask.

  2. Rebecca says

    This a topic I’d like to see you write about more. Although I don’t consider myself shy, I feel uncomfortable trying to sell myself. It’s difficult for me to find that line between appropriate self-promotion and being pushy.

    • says

      It might be helpful to look at the sales process from a slightly different perspective. When you are pitching a client, you are not selling yourself. You are selling a product/service. Don’t concern yourself with the fact that you are the one providing the service and creating the product. Treat the sales process no differently than you would if you were selling something made by someone else.

      If you can sell your own work the same way you would sell someone else’s, then you should have no fear of being too pushy. Most often, salespeople selling their own work undervalue and undersell their product. After all, we are our own worst critics. 😉

  3. Phil says


    One of the biggest problem in sales, (if you’re not in sales, you’re not in business) according to what I’ve read, is failure to ask for the order.

    • says

      Cold calling is certainly not the most fun aspect to the sales process, that’s for sure. I can’t stand receiving telemarketing cold calls at home, and I could never cold call someone else’s home phone number.

      I don’t consider cold calling a business to be as invasive or taboo as calling someone’s home. The key is to be polite, professional, and to get right to the point. Typical scripted pitches are worthless in my opinion. You are more likely to insult someone’s intelligence reading off a script than to have a natural conversation.

      Anyway, cold calling is all about your comfort level. If it is something that you truly do not feel comfortable doing, you can hire someone else to do it for you or continue market your services more passively. It certainly isn’t for everyone. :)

  4. Kathleen says

    I agree with Rebecca. I have “asked for the sale” so to speak and ended up feeling like I was being too pushy. Which probably was the case because I did not get either gig.

    It’s frustrating because I know I have to approach potential clients if I want to get higher paying gigs. I’m just no good at it. Phones make me hyperventilate (literally) so I am pretty much stuck with email or snail mail. Guess I’m hopeless. lol

    • says

      Don’t let yourself be too discouraged! It isn’t easy when you first start reaching out to potential clients, especially when it involves cold calling. Chances are, you will be told no 10 times before you get a yes. The key is to be persistent and keep trying. Trust me when I say that it does get easier with a bit of practice.

      If phones are difficult for you, it might help to practice with a friend or family member before trying to pitch a real lead. Getting used to the phone with familiar voices will give you a bit of confidence for when you try pitching an unfamiliar one. If you give this a try, be sure to ask the friend/family member to try and come up with objections. Write them down, come up with ways to overcome those objections, and try again.

      If you are prepared for an objection, you just may be able to overcome it before you get hit with the dreaded “not interested.” If you are able to overcome all the lead’s objections, and you take the initiative and ask for the sale, you have a very good chance of getting it!

      I hope this was helpful. Like I said before, it might be intimidating now but with a bit of practice you will find it does get easier. :)

      • Anne G. says

        It’s funny you mention practice with family. My kids were picking on me a couple days ago for always saying yes to everyone but them. I have a friend going out of town and I usually watch her house for her, but recently her list of “can you’s” has gotten incredibly long. So this time, she asked me to do her cat’s litter box twice a day during the three days she’ll be gone. Then she said come over and feed him twice a day now instead of once a day and make sure the temperature is warm enough and if not adjust the thermostat. Bring in the mail, etc.

        In the end, I said yes even though I think the twice a day trips are a bit much given my schedule. Meanwhile, my kids are asking why I have no problem telling them NO, but never do it with anyone else.

    • says

      Thanks! Glad you liked the idea. It helps to do the same with objections you come across when talking to an actual lead too. The more objections and rejections you face, the more experience you can gain in overcoming them.

      Remember, objections and rejections are opportunities not failures. You might not meet your goal of landing a contract, but you can certainly learn from the experience and be better prepared the next time a similar situation presents itself.

  5. says

    I agree, it never hurts to ask.

    My very first client wanted me to write articles for the same rate as resumes. I asked him for a higher rate, he didnt budge, so I declined. This was a hard decision considering he was my first client/gig and I didn’t want to risk losing him. A week later he contacted me to do more work AT THE RATE I ASKED. I had an “I’m so happy to be freelancing” moment:)

  6. says

    This is the first time (to my knowledge) that something I said was the inspiration for a post. It’s an honor.

    It’s hard to know what will make a potential client say yes, but my feeling is that you need to connect with them in some way. I was on a job interview once and I started giggling because I was nervous. The person doing the hiring was looking for someone with a good sense of humor, and that was part of the reason I got hired. My previous work experience also made me a good fit.

  7. Tania Mara says

    Sadly, I can’t say I’ve never gotten a “no” as a response after asking for a raise. :( Still, I didn’t lose anything. In fact, I might have lost an opportunity to get a “yes” if I had remained silent. So I’m glad I took the initiative to ask.

    There are too many freelance writers out there who rarely ask anything, because they’re too afraid of the answers they’ll receive. Those who do have the courage to ask are two steps ahead in this game.

Leave a Reply

Your email address will not be published. Required fields are marked *

* Copy This Password *

* Type Or Paste Password Here *

CommentLuv badge