There will come a point in every freelancer’s life where they will be faced with some hard sells. If you haven’t encountered this yet, let me set the scene for you.

You get this email from an owner with the initial requirements of what seems to be a fun and exciting project. The tone of the email is exciting, ambitious, and eager to be working with you. Towards the end of that email there’s the tease of “and if this works out, it could turn into more work.”

You start to get really excited because it’s a fairly well known company, the project seems like a great one to be a part of, and the idea of more work sounds perfect!

So you reply back and set up a time to talk or meet.

The only thing with this project is that it doesn’t fit perfectly within your service offering. However it’s still very much doable.

You get to the meeting and have some initial casual chit chat before getting into the meat of the project. You both talk about the paths you took to get to where you are right now.

The prospect starts talking about the project that was mentioned in the email. Saying all the right things that seem to be exciting and interesting about the project. You share with the prospect all the great things about you and what you can bring to the project. You share some of your experience in how you can provide the solution to the problem that the prospect is having. Even offer some ideas that the prospect didn’t think about.

Then there comes a point in the conversion where the prospect says something to the effect of…

“I like what you are saying, however we’ve had freelancers before come onto projects with not much success. They’ve come onboard and then it seemed like they got in over their head or got overwhelmed with the work and we had to end the relationship. So even though I’m happy with what you are saying here, I do have some apprehension hiring freelancers.”

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The Trust Factor from a Prospect/Lead’s a few different things happening at this point that should be seen by you as the freelancer.

The obvious is it’s the start of the negotiation from the prospects side to get you to lower your price. Whether or not that’s the intention, a statement like this lends itself to doing just that.

What’s actually happening is that this is the beginning of the hard sell. The prospect is bringing their past poor experiences with others into your potential project. The prospect basically is saying “I don’t trust you very much” without even knowing you.

When it comes right down to it, business is about people and their relationships. If trust isn’t there, then how could either side of this business relationship be successful.

At this point you haven’t entered into agreeing to work together. Yet, there’s been a serious red flag planted on this common ground you both are about to walk on together.


Before we get into trying to handle this and start moving forward again there’s a bit of psychology at play that should be understood.

The prospect has positioned themselves as the one in control of this conversation. They have the wallet, the company, the project, and now have made you want to work with them even more.

WHAT?!?! Yup, that’s what I said. With just a few words, the prospect has made you want to work with them even more so.

Remember how in the first email that the project really didn’t fit the mold to what our service offering is? This is where the pitfall happens. At this point in the game, that early red flag has now been virtually pushed aside and removed from our thoughts.

This is simply because as humans we want to please everyone. We also have this ambition to prove others wrong. So by saying “have some apprehension hiring freelancers” it’s played into your instincts to want to land this gig even more.

The prospect may be completely genuine in the past experiences they’ve voiced. So it’s not like they are lying just to get you to lower your price. However as a smart business owner, they want to not only get the project done, but for the best possible rate as well. (And the timeline hasn’t even been spoken about yet.)

So the friendly cup of coffee you are sharing over a conversation of business has just become a battle field of negotiation over the project.

At this point, it’s time to turn and take control of the situation before it becomes more and more about the past experience rather than why you are here in the first place.

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The best thing you can do is appreciate where the prospect is coming from. But turn the tables back around to why the prospect reached out to you in the first place. Oh yeah, that’s right! The prospect reached out to you, not the other way around. If the prospect has apprehension about hiring freelancers, it can’t be too much since they are looking to do so again.

However it’s not really too wise to stand up, point and say “I call BS!” However this can be accomplished by referencing the person who connected you if that is the case. Or simply by asking the prospect (if you haven’t already) “What was it about me that pushed you to reaching out to me?”

This turns the tables right back onto you (opposed to others) and the positive reasons (opposed to the poor experience).

[Tweet "Allow them to talk about themselves and their feelings/vibe about you"]

You want to maintain the focus and positive energy of the initial engagement that you’ve had with each other so far. By asking this, you are allowing them to talk about themselves and their feelings/vibe about you.

Before you know it, you’ll be squashing that apprehension and the conversation will continue with both of you being excited for the project.

The real selling

Now don’t get me wrong, there will be times when the tables will turn again and again. This is a business conversation after all. You’ll want to try and maintain focus on you and the project as opposed to what happened in the past that you had nothing to do with.

That’s important! You had nothing to do with the past experiences that the prospect had. You weren’t there, didn’t know the past freelancer, and most certainly didn’t make any money from it. So there’s no reason for you to pay the penalty on that if it went south.

By my count so far we’ve received 2 red flags.

  1. The project does not fit the service offering

  2. The prospect is bringing the past baggage into this project

Anytime during this negotiation if the prospect continues to turn the discussion around what happened in the past, that’s just reenforcing that second red flag and may be that flashing sign telling you to step away. As understanding and appreciative that you can be, if the prospect harps on it several times in a matter of minutes, that’s baggage that you’ll have to deal with throughout the entirety of the project.

Think of it like when you are dating someone new. Would you want them to constantly be bringing up how crappy their ex was? Constantly wondering if/when you are going to repeat what the ex did? Maybe even questioning everything you are doing in fear of repeating what their ex did? This is how the project will go as well.

However if you are good and can turn the tables around after that first statement and the prospect doesn’t return to talking about their “ex” you’ll be in the best spot.

Up until now I’ve tried to highlight some of the psychology that’s creates the pitfalls to avoid. However if after that statement of apprehension you’ve been able to turn and keep the table in your favor, the psychology will have turned in your favor.

You are positioning yourself as a professional by keeping the conversation on point rather than a gossip session. Plus you may have explained how other projects you’ve tackled in similar situations as a bit of proof to your expertise and the quality of your services.

This will actually turn the tables in a way where the prospect will want to work with you. Which, if you remember, the prospect reached out to you in the first place wanting to get you to do their project.

This conversation could be about 45 minutes (or so) in and many things have been laid out on the table. It’s time to do some mental evaluation of everything to come up with the next steps. Depending on how the conversation went (hint count the red flags) you may want to move forward with the project or not.


The first thing is that the prospect reached out to you. So you should have the mindset that you are interviewing the prospect, not the other way around.

Secondly, the prospect expressed some aspects of the projects that don’t align with what you offer. It’s not that you can’t do it, it’s just not something you do often and possibly have to brush up some of the skills needed to complete it. (this is a red flag)

Thirdly, this is a fairly well known client. The project seems like a great one and could be a nice piece in the portfolio. Not to mention that there’s the potential for more work after this one.

Fourth, the prospect is carrying baggage of past experiences that could affect the overall project. (this is a red flag)

Fifth, the past baggage is a reason the prospect wants you to come down on your price. This is an easy defend that can be handled by a simple statement.

“I can appreciate your feelings however I was not in anyway involved there so I don’t know what they charged you and for what services. I know the value of what I offer and I know what I can bring to the project by way of my experience and expertise. So that’s why I charge what I charge. I know that you will be happy with what I bring to the project.”

If they are still harping about your price being lowered, then talk about lowering the scope of the project, and keep your price intact.

Lastly, this is a hard sell. With 2 red flags, in my book it becomes a hard sell. Over the course of my career I’ve come to learn that 2 red flags for me are enough for me to pass on the project.

[Tweet "“If it’s a hard sell, let them go” said Brian Clark (@brianclark)"]

How to Avoid The Pitfalls

Don’t get me wrong, I’ve taken on projects like this in the past. More than I care to admit. However I will admit that every time I’ve taken on these projects, it wasn’t what I expected it to be, took up more energy, and pulled away from other projects I could’ve been doing. Often times I was micromanaged due to that lack of trust from the client because of their past experiences.

One thing that I do want to highlight is that every time you say “yes” to something, you are saying “no” to something else. If you are taking on a project that isn’t an ideal fit, remember you may be forced to not take on a project that is.

A worse case scenario is that you are pulling away time and energy from current clients and projects that are your ideal and damaging yourself and business in the process.

These are the things that should always be front of mind when evaluating new projects. The potential of any project is always exciting, but it shouldn’t cloud our judgement. It’s difficult at times to maintain that clarity and focus. However, just as the prospect is running a business and wants you to fit for them, you are running a business and the prospect should be a fit for you.

Building a sustainable business, especially freelance business means staying focused on the long game of the business. So even though it’s exciting to take on new and interesting projects, it’s best to be able to step back and see if it’s really a fit for the long term sustainability of your business as well.

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