Freelancing, just like dating, has changed. You can’t just buy your date dinner and suddenly become the most interesting person they ever met.

When you’re “dating” lots of clients, what can you do to stand out?

You only get one shot. No pressure.

First dates are stressful. Freelancing is, too. You know that date I’m talking about. You’re with your date, and you have no idea what to say. He or she is staring at their phone, and you’re losing your mind.

I’ve been on that date where I struggle to find common ground while I keep shoveling food into my mouth.

The same is true with freelancing clients (minus the food shoveling part). You sent them a great proposal but never hear back.

Relax and breathe… You’re gonna nail your first impression. Design by OrangeCrush

First dates are scary. On that first date, you have one chance to make that first impression. If you don’t do it right, you lose out.

So here’s an example: I was cooking steaks for this girl, dropped one on the ground and was instantly mortified. First impression = dead. (Luckily, the girl laughed and told me she loved floor steaks.)

But, guess what? There’s no room for floor steaks in freelancing! You get one thing wrong at the start and you won’t get a response to your proposal or get booked.

The problem is most freelancers are dropping steak on the floor and don’t even know it. What’re they doing wrong? They treat the client transactionally.

The same is true on first dates. You don’t want to ask your date back home right after the salad course. It’d make them feel cheap.

Stop making your client’s feel cheap, and learn how to start a conversation.

How to up your freelancing dating game

Do you lack the skills to start a conversation with a potential client? Let’s learn how mastering the “Conversation Economy” can get you booked.

Imagine this. You just walked out of a lunch meeting that you worried about for a week. You wrote a great proposal, researched the company and when you showed up you were totally relaxed because you “had it.”

Master the maze of finding your perfect client match. Design by DeanneDesigns

The food was great, and the entire meal you did everything BUT talk about the project. When you went to pick up the tab, the client gives you a nod and says, “Since you’re picking up the contract, we’ll pick up the check.”

They loved you, and you got the gig! Succeeding is really that easy. Once you master it, you will can make even floor steak situations come out in your favor.

Here are the three ways you can start conversations and write proposals that get you booked.

1. Open with your client’s name

You wouldn’t start a first date without learning your partner’s name.

(Actually I did on a bet once. Awful idea.)

Use the client’s name in the proposal to catch their attention and show you didn’t send a template proposal. I’ll floor steak your face if you send a template proposal.

Pro-tip: Using a client’s name in the proposal removes psychological barriers to hiring by humanizing you. The more human you appear, the more you stand out, which makes you more interesting to talk with.

2. Write normally

Ever been in a conversation where you know the person is trying to sound smart? It’s awkward. The same is true for freelancing. Buzzwords and jargon are the weird white noises of the freelancing world.

Avoid them. Don’t be white noise.

Here’s a classic situation I see all the time when coaching freelancers. They’ll want to sound smart and say things like, “I’ll optimize click through conversion.” Ughhhh! If you want to get clients to speak with you, try, “I’ll get more readers to join your mailing list.’

People don’t always speak technical language. They don’t go around everyday talking about KPIs or CTAs or SEO. People talk plainly and respond best when spoken to clearly.

When you communicate simply, clients don’t have to translate your ideas. Your clients will be more comfortable, and they’ll find it easier to focus on the conversation.

Speaking normally humanizes you and makes you stand out from the crowd.

Do you, Client, take this Freelancer… Design by Loresil

3. Acknowledge your client’s needs

The worst first dates happen when you dominate the conversation, and the same thing applies in freelancing.

Successful freelancers don’t talk about themselves. They talk about what a client needs and they can give their client those results.

Here’s how you can put your clients first:

  • Anticipate a client’s needs and give them advice. Most freelancers hoard their ideas. They’re afraid clients will take their suggestions to a cheaper freelancer. Most of them probably won’t (and if they do, you don’t want them as a client anyway). Use your free ideas as currency to yield big returns.

  • Provide relevant testimonials for your client. Don’t waste a client’s time sharing your favorite SEO project when they need a landing page. Most freelancers copy and paste their favorite projects into proposals even if they have nothing to do with a client’s project. Relevant examples show you took time to create your response. 

Pro-Tip: If you don’t have a testimonial that matches the client’s needs include one anyway. Explain how the strategy that made the project successful would apply to their project. Making a lateral comparison creates subtle social proof you know how to not just do a project but also make it succeed.

Make your client fall in love with you. Design by Alice R

4. Remind them to contact you

Ever end a great date only to get busy and forget to follow up? It sucks. The same thing happens in the freelancing world.

Don’t forget to ask for the follow up! Copywriters do it all the time with CTAs.

The CTA is how you lead the client to take the next step. The best CTAs work because they position the client to want to take the next step.

Think about the best date you ever went on. You’ree having a blast and realize you want to see this person again.

All you have to say is, “Let’s do this again.” Here’s how to do it.

You ever start planning your second date in the middle of your first? Usually you mention something you like, and your date  says they’ve never visited/ate/seen it. Next thing you know, you are signing up for a floor steaks cooking class.

The same thing works for freelancing. You provide follow up value to induce the client to want to know more.

Example“I have two suggestions to get your project off the ground immediately. Call me, and I can share them with you.”

This is straight and to the point. The client knows they want to reach out to find out more. Conversation started!

Pucker up, freelance pros! Design by Bluespin

The kiss goodnight

We are entering the Conversation Economy. Freelancers who cultivate social skills will outpace, outwork and out-earn more experienced freelancers.

That second date can be yours with real, authentic conversations.

Got questions about how to to start conversations in your freelancing career? Ask in the comments below.

Jesse Gernigin is a full-time consultant and advisor. He replaced his income working online in 10 months. Now he helps freelancers and consultants learn the key skills to writing proposals that get them booked and booking their schedules full.