The Unexpected Way to Simplify Your Freelance Sales System

by Michelle Hunter

How adding obstacles boosts your conversion rates and makes it easier for potential clients to say yes to your proposals.

Simplifying Freelance Sales System

At the risk of asking an inappropriate question… how are your conversion rates? Think about your freelance sales system from beginning to end, from first email inquiry to signed agreement and paid deposit. Do people move smoothly from one step to the next or do they get stuck somewhere and disappear? Sales is a frustrating aspect of contract work, but one you can’t afford to ignore.

Back in the day, I worked as an account rep for a large organization. I had a sales quota, a customer list, and a territory. In that role, I learned the subtle art of calculating conversion rates and analyzing a sales system in order to accurately forecast results. See, in that environment, account reps are required to accurately predict how much revenue they will generate in a given time period (month, quarter, year) based on the number of leads they generate and an understanding of their effectiveness.

When I started out as a freelancer nearly ten years ago, I didn’t appreciate the value of what I learned in my corporate life. Rather than analysis and forecasting, I just talked to as many people as I could and hoped for paying clients. Trust me… there’s a better way.

You don’t need to take things to a corporate level, but you DO need to objectively evaluate your sales system if you want to make it simple, effective, and predictable.

  • Do you have lots of inquiry calls and initial consults that go nowhere?
  • Do you spend hours crafting proposals for clients who don’t respond?
  • Do you struggle to quote custom services to a wide variety of clients?

It may seem counter-intuitive, but you can simplify your sales system and improve your conversion rates by removing variables and adding obstacles to your process. You can do less work selling and land more profitable projects simply by saying “no” more often. Not only will you free up time to do more of the creative work you love, you’ll limit your time on the emotional follow-up roller coaster and stop chasing clients who ghost you.

Step One :: Simplify by limiting the number of consult calls.

It’s tempting to speak with everyone who contacts us or expresses even a little bit of interest in our services. I have to admit, a well-written inquiry email is interesting to me even now. I know better, but I sometimes jump on the call anyway.

You might even have a free consultation on your website or as a part of your marketing strategy- allowing anyone with time on their hands to grab a link and put themselves on your calendar to chat. This is an okay strategy when you’re just starting your business. You’ll learn a lot about people and practice talking about your services.

Things should shift when you’re more established. Once you’ve served a few clients and gotten some experience talking to prospects, it’s time to limit your availability. If you’re frustrated by your sales system, you’re likely talking to too many people.

I recommend using an inquiry form with 2-3 questions as a way to limit your availability. The form itself (regardless of the questions) acts as an obstacle. Those who are more curious than serious will hesitate before completing it. More importantly, though, the questions give you a way to filter potential clients and limit the number of projects you consider and calls you accept.

The key here is to align the questions you ask with factors that are important to you. Not sure what to do here? I have a few suggestions…

  • Ask a budget question. Use this question to get an idea of project potential. Does the potential client have enough money to make this call worth your time? Pro tip: Consider asking people to select a range (A to B, C to D, or E to F) rather than simply asking, “What’s your budget?”
  • Ask about goals. Use this question to understand the motivating factors behind the inquiry. Does the potential client have a specific goal in mind? Is this person able to articulate why this work is important to them? Pro tip: Consider asking for a specific number of goals (what are your top 3 goals for this project) as a way to understand motivation and priority.
  • Ask why the person contacted you. Use this question to gain insight into what the potential client values and the interest this person has in working with you specifically. Pro tip: Consider asking directly (“Why did you contact me?”) rather than asking about referral sources or how you were found online.
  • Ask about timeline. Use this question to learn about client urgency and this person’s readiness to get started. Pro tip: Watch out for vague timelines (this year, soon, etc.) as these can be indicators of lukewarm interest.
  • Ask a process-specific question. Use a question like this to gauge the potential client’s willingness to follow your creative process and use the tools you find most helpful in your work. Pro tip: Rather than asking about a specific software (“Do you use Asana?”), ask for the prospective client to share the software solution they prefer and why.

Should you ask all of these questions? Absolutely not. You only want to ask 2-3 filtering questions like these. The key here is to select questions that will help you identify those who are not a fit so you don’t waste your time with a call.

Your goal is to limit your availability and only speak to those who are likely to work with you.

Gut-check time – -> It is perfectly okay to avoid talking to people who are not a good fit for your services. In fact, it’s preferable to say no so you don’t waste anyone’s time and energy. It is not rude or unfriendly or mean. It is simply good business.

Not comfortable adding a form to your website? No problem. You can ask the same questions via email. Simply respond to the inquiry with gratitude and a few questions to help “determine if we should talk.” Trust me, it will only be awkward if you make it that way.

Step Two :: Fill your freelance sales system with questions.

Questions are your friends. Questions are your pathway to a simple sales system and more profitable projects. You want to ask lots of open-ended questions during your initial conversations with prospective clients.

What do I mean by an open-ended question? Questions that require more than a one-word answer are considered open-ended. They require the potential client to open up and share information. They start a discussion. They help you uncover information you wouldn’t otherwise discover. Make it your goal to ask lots of open-ended questions.

Ask questions like…

  • What are your goals?
  • What is most important to you?
  • What will this project mean to you professionally?

Until you feel comfortable with this, you’ll catch yourself asking closed questions. Remember, you can always follow up with “Why?” or, “Interesting… tell me more about that.”

During the consult call (or inquiry call or initial meeting or whatever you call it), you ARE NOT actually selling your services. Conversations like these have only two purposes: (1) determining if YOU want to work on the project and (2) gathering information you will use in the proposal if you decide to write one. This is a mindset shift you absolutely need to make if you want to increase your profitability and simplify your sales process.

Come to inquiry calls with curiosity and confidence. This person reached out to you to discuss a need. You vetted that need by asking a few questions. There is every possibility that the two of you are a good fit… so there’s no reason to be nervous or unsteady. Explore the project openly by asking sincere questions. Listen carefully to the answers you get and dig a little deeper when appropriate. The potential client will feel honored by your interest.

Here’s a little tip to help you master these types of conversations – – > play a game to practice. (Don’t roll your eyes, I’ve done this many times!) Kids are great partners in the game. Ask a kid who loves you (your own kid, a grandkid, a friend’s kid) a few open-ended questions.

Instead of, “How was your day?”  try, “What did you do today?” Listen to the answers you get and ask more open-ended questions like, “Why?” or, “How did that make you feel?” Later, think back on the conversation and challenge yourself to write down the most important points expressed including anything surprising or interesting. Apply this skill to your next conversation with a potential client and you’ll win!

So, by now you might be wondering if there is ever a time for a close-ended question. Absolutely! I’m so glad you asked… keep reading.

Step Three :: Get approval before writing the proposal.

The time for a simple yes or no question is before you write a proposal. You want an indication of interest and commitment at the end of the initial call as a way of limiting the time you spend on proposal writing. You want the potential client to express interest and commit to a decision before you waste your time.

Now obviously, the person you’re speaking with is unlikely to agree to work with you before any details are shared. That’s too much to expect in most cases. However, you can set an expectation that you only prepare proposals for people who are ready to move forward and ask about the decision-making process for this project.

Here’s how I do it…

  • At this point, I’m interested in this project and think we are a good fit. I’d like to prepare a proposal for you, if you’re ready for one. Will you make a decision in the next week or two?
  • If everything looks good with the proposal in terms of timeline and investment, are you ready to move forward?
  • Are you the best person to review the proposal?

Notice these three questions are close-ended. I’m looking for a simple, one-word answer to each of them. Notice as well that these are in a progression. I only ask the next question (or some variant on it) if I get a “yes” to the question before it.

The first question sets an expectation that my proposals are by invitation and are time-bound. If the potential client indicates that they are not ready to make a decision in the next week or two, I don’t write a proposal. Instead, I ask “when do you anticipate making a decision?” I use the answer to decide if I want to write a proposal now or wait a few weeks.

If the first answer is a yes, I ask the second question. This one is a bit nervy, I admit. But, I want to be sure the client is as interested in working with me as I am in working with him or her. The second question gets to the heart of things. I don’t ask for a commitment to terms I haven’t shared yet, but I ask for a commitment to working with ME.

The range of answers to this second question is usually a bit nuanced. Some potential clients practically shout YES or indicate that they are ready to move forward now, without a proposal. (Yes, I’ve actually had that happen a time or two!) In those cases, I write the proposal anyway. I want to be sure we are both on the same page about fees and deliverables before we get started.

Other potential clients give a qualified yes… saying things like “Assuming I like what I see…” or, “If the proposal matches this conversation…” Those are true yes answers too.

But sometimes, a potential client hesitates here. This is an indication that it’s not time yet for the proposal. Often I will step in and say something like, “It sounds like you might have a few questions.” The conversation over the next few minutes is rich with information. Now that I’ve asked for a commitment, I’ve opened the door to objections and true issues. This is sales gold… giving me a chance to put the person at ease (or not) before I spend a moment working on the proposal itself. These hidden objections are the reasons why people disappear after receiving a proposal. Better to deal with them now in an honest and open dialogue. Once we’ve talked them through, I ask the second question again so I can get the yes I need to move forward.

If we make it through the second question with some version of yes, I ask the third question. All I’m looking for with the third question is a personal commitment to receive and review the proposal. Sometimes I’ve gotten to this point without realizing there is a business partner I haven’t met or a committee that has to approve the proposal. If that’s the case, I generally avoid writing a proposal until I can connect with those other decision makers.

Do you see how this simplifies my freelance sales process and limits the amount of time I spend writing proposals by weeding out nearly all the “no” answers? I still get the occasional “no” or “not yet” answer to a proposal. But, those situations are pretty rare and often due to elements I can’t control like a shift in the client’s timeline or complication inside the client’s business.

Focus your freelance sales system on the right kind of “yes”.

By creating obstacles before scheduling a call and asking questions before writing a proposal, you shift the focus of your sales system. Instead of trying to persuade unconvinced people to work with you (a difficult and embarrassing task) you shift your attention to those who are most ready to move forward. You get the same volume of “no” answers… you just get them early in the process and limit the time you invest.

There’s an added benefit to simplifying your sales system in this way. You shine a light on the real limiting factor in your business: lack of quality lead generation.  Want to draw more YES clients into your sales system? We should talk.

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