How to Knock Your Sales Meetings Out of the Ballpark

Did I just use a cheesy sportsball analogy in a headline? What can I say, it scored really high on the headline analyzer and I’m a sucker for high scores.

I don’t know what the analogy means, but I do know that if you learn the techniques in this blog article, you will make more sales as a freelance copywriter.

What is a Sales Meeting?

We’d all love to believe that the excellence of our work will speak for itself, and we won’t ever have to “sell” ourselves as writers. In reality, we all must become salespeople for ourselves in order to achieve success.

Luckily, that doesn’t mean we have to sell ourselves out and become cheap parodies of a stereotypical used car salesperson. In fact, great salespersonship starts with authenticity and genuine caring about the other person, and ends with a win for everyone. So let go of your fear and embrace the sales cycle, at the heart of which lies the sales meeting.

Sales Meeting: Any conversation in which you have determined that your conversation partner may be a good match for your services, and they are interested in learning more about them.

A sales meeting may be in a formal setting in which you and the potential client have agreed in advance that you are going to talk about your services and how you can help them, or it may arise informally out of a conversation that did not begin as a sales conversation.

In either case, learn to recognize when you have entered into a sales meeting scenario, and make the most of the opportunity with these techniques.

How NOT to Handle a Sales Meeting

The first and most important thing to know about sales is that buyers can smell desperation and it smells rotten. The last thing you want to do is make them feel as though you are desperate for their business. The easiest way to avoid giving this impression is to not be desperate for it, and the best way to do that is to have so much potential business in your pipeline that no single piece of business will make or break you.

And the best way to do that is to use the resources in my free ebook.

Some other things to avoid in a sales meeting:

  • The hard sell. Don’t make the prospect feel that you will pressure them.
  • Act nervous. Fake some confidence till you feel it.
  • Talk a lot. My Sandler sales trainer always said, “If you’re talking, you’re losing.” Aim for a 70% listening to 30% talking ratio.

Make Your Next Sales Meeting Your Best Sales Meeting Yet

The best salespeople place a laser focus on learning about the buyer and how they can best help them. To accomplish this, you really only need two things:

  • Killer listening skills
  • Killer questioning skills

Try to spend most of your time listening deeply and actively to the buyer. When you’re not listening, ask questions. Start with the list below, but be aware that you will almost never ask all of them. Listen carefully to the answers and let the buyer talk. You will find that they will answer many of these questions without being asked.

Strategic Questions

  • Who is the audience for your marketing?
  • Do you have persona documents?
  • Where do you see content fitting into your marketing strategy?
  • Where does that content fit in your audience’s journey?
  • What are your biggest challenges to meeting your content goals right now?
  • What would a successful marketing/content program look like to you?
  • How would that help you achieve your bigger goals?

In the course of answering your strategic questions, most buyers will begin to take an interest in the specifics of how you can help them. That’s when you’ll want to explore the scope of the project.

Scope Questions

  • How much content do you want to produce?
  • If the content will include blogging, how many posts would you like to generate per month?
  • How much of that would you like your external resource to handle?
  • How long do you expect each type of content to be?
  • Will you provide access to subject matter experts or other resources, or do you expect your writer to conduct research for each piece?
  • What else will make the process easier for you?

Once you have a handle on the scope of the work they’re interested in, it’s time to cover the nitty gritty.

Administrative Questions

  • What kind of timeline do you have in mind?
  • Do you have a budget in mind?

Many writers, especially in the early stages of their careers, are uncomfortable asking about money. Be aware that business people expect it, and it is a natural part of the exchange. They know you need to get paid. They probably won’t tell you their budget, if they even have one in mind, but it’s important to ask the question anyway. They will give you contextual clues that will help you determine whether they are likely to be able to afford the Cadillac version of your services, or perhaps a pared down version that is easier for them to manage.

Next Step Question

Notice how these questions lead the buyer naturally down the path to considering your services in detail. They also will help you co-design the solution that is the best fit for them and you. When you get to this point, it’s time to ask them what they would like to see happen next. Most likely, they’d like a proposal from you. Whatever they suggest as the next step, make a note and provide them with that next step.

Handling Client Questions

Naturally, the potential client will have questions for you as well. These can take almost any form, but the most common questions are:

  • Can you send samples?
  • How much do you charge?
  • Have you worked in our industry before?
  • What is your process for working with clients?

The best answers to each are:

  • Absolutely. What specific types of samples would you like to see?
  • Once I fully understand the scope, I’ll be glad to send you a quote. (If you have a ballpark pricing guide, you can send that in advance so they have a general sense of your rates, but never attempt to give a dollars and cents answer to this question on the spot.)
  • Whatever the truth is.
  • A practiced overview of your process.


Stay calm, confident, and authentic. Clients will understand if you don’t have answers at your fingertips. Don’t belabor your answers or go on and on. Just stick to the facts and return to your own questioning as appropriate.

Watch the Magic Happen

If you’ve never entered a conversation with the intent to listen more than you talk, then you are in for a treat. I remember the first time I walked out of a meeting in which I had spoken almost not at all. The interviewee was all smiles and warmth, and as he clapped me on the back, he said, “I don’t know that I’ve ever enjoyed a conversation so much,” and then he congratulated me on my intelligence and grasp of the issues. I had hardly spoken a word.

People love to hear themselves talk, and they especially love when YOU hear them talk. Give them that gift, and you’ll be more than halfway to the sale.

Try it, and then tell me how it goes. I look forward to hearing from you.

Fen Druadìn Head
Fen Druadìn Head is an award-winning freelance writer and coach. Her work can be found all over the internet in publications as diverse as Redshift Magazine and Grit. Fen's fiction is represented by Ethan Ellenberg.