Conversation Secrets from the first date front lines.

First Dates and Freelance Writing Have a lot in Common.

I’ve done a lot of both and know they are stressful. You know what i’m talking about. You are on the first date, you don’t know what to say, they are staring at their phone and you are losing your mind.

The same is true with a client. You sent them a great proposal but they are late getting back, they aren’t sure about the price or they have no clue what they really need.

First Dates and Freelance Writing are Different to.

The difference between first dates and freelance writing is that a lot can go wrong on a first date, but you still get a second date. In freelance writing, if you get one thing wrong, you won’t get a response to your proposal or get booked.

(Want To Skip That And Increase Bookings? Here)

What is the key thing most freelance writers get wrong? Freelance writers don’t know how to start a conversation.

Image courtesy of Unsplash


Simple. The way the game is being played has changed. It used to go like this:

-You sent in a proposal

-The proposal would list what you would do and what it would cost

-The client would choose what they wanted

It no longer works that way. Freelance writing is different than it used to be.

Why? We have entered into the Conversation Economy.

The Conversation Economy

Experienced freelance writers lose gigs to beginners because new freelance writers grew up in the Conversation Economy. Are you afraid you don’t know how to speak with clients today? Do you feel that you have the knowledge and skills to complete the job but don’t understand what to say to clients?

Don’t worry. Beginners have internalized the key practices to start and continue conversations. We are going to take their knowledge and use it to our benefit.

If you do not know how to:

*Start a conversation

*What to say

*How to keep the conversation going?

Then know this. I’ve shared key tactics culled from natural conversationalists to start and continue conversations with clients. That means you will get the attention of people you have never met, have nothing in common with and want to work for. Master these tips and your freelance writing work will multiply.

Conversation Tactics:

-A Quick Start Guide to Start and Carry on Conversations-

-Succeeding in the Conversation Economy and getting work as a freelance writer is easy.

To succeed-You must change how you communicate in your first interaction.

-For freelancers, your first interaction is the proposal.

Want to increase new clients’ responses to your proposal?

You should. The more willing a client is to respond to your proposal the greater your chances are at booking that client. A key to the conversation economy is master conversation control to create response to your proposals. To help you I’ve included three easy to implement tactics that transform boring proposals into conversation starters.

Each step is easy to implement, won’t take away from the main message of your proposal and makes a client want to follow up with you.

1)Open the proposal with the client’s name:

-Most freelance wriers fail to include the client’s name in a proposal. This is a mistake. Including a client’s name while freelance writing will catch their attention.

This works if you are bidding from a job board (like Upwork) or sending in a project proposal with someone you’ve marketed to.

Psychological Tip:I used to be an entertainer. A large part of my show was built on audience participation. I would bring people on stage who had no experience with crowds and hated public speaking.

To overcome the anxiety of being on stage, I would ask the participant’s name and then introduce myself. This put the volunteer at ease by removing the mental barrier people have about crowds and public speaking.

This works similarly for clients.

Using your client’s name in the proposal removes psychological barriers to hiring by opening up the client to hearing what you have to say.

2)Speak normally:

-Everyone hates lingo in freelance writing. Don’t use it. Using lingo and buzzwords makes you sound like everyone else. Lingo and buzzwords are the white noises of the freelancing world.

Don’t be white noise. Don’t be a freelance writer caught up in sounding smart. If you want a client to start a conversation with you, find a way to translate lingo into everyday language.

Example:Instead of saying, “I’ll optimize click through conversion,” say, “I’ll get more readers to join your mailing list.”

Ask yourself this: Why does one sounds better? Simple, social proof!

Think about it. Freelance writers are skilled in communicating. Prove this by speaking to your client about what they want on the level they want it.

Speaking normally has a key effect. What is it?

Speaking normally humanizes you.

-This is important. Most proposals are template proposals.

Clients hate that.

If you send a client a personalized proposal in readable language, you come across as human.

Coming across as human removes the stigma of budgets, money, and deadlines, and puts the focus on service.

3)Acknowledge their needs:

-This goes back to my first date comment.

The worst first dates happen when the date only talks about themselves. The same is true in freelance writing.

Successful freelancer writers don’t talk about themselves. Successful freelancer writers talk about what a client needs and how a client can get that result.


Clients come first.

You mention their name first; you write so they can understand their project at its most basic level, and you talk about their needs, wants, and results.

Once you have covered all of that, you introduce what you can do to achieve it. Use testimonials to provide social proof and authority, and talk about how you would fit into their project.

4)Remind them to contact you:

-Most first dates don’t lead to second dates because they fail to ask for a follow up. The same thing happens in the freelancing world.

In the copywriting business we call this a Call To Action.

The CTA is where you ask the reader to take the next step. They give you an email address, fill out a form, make a phone call, etc.

CTAs work when they position the reader to take the next step, the next step is easy to take, and you show them exactly how to do it.

Great CTAs remove barriers for people to say ‘No’.

You can increase proposal response with a CTA.

Two CTA Tactics: I’ve found effective to create proposal-based CTAs are:

1)Offer value in a follow up.

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

2)Ask for the follow up.

Personal Preference:I prefer asking for a follow up over offering an exchange. The exchange can work, especially if the client feels like you are trying to start a conversation and supply value to the project. I like the follow up more.

A good follow up feels like a natural extension of the conversation. A value based offer feels like you are trying to extend the conversation.

Key Takeaway

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

Originally published at on January 4, 2017.

Originally published at