Project management and estimating are one of the most difficult things a freelancer needs to tackle. We recently hosted a freelance class on project management and estimating.

Josh Ali, a talented IT project manager, led the class. He shared handy tips for developing better proposals. Several questions resulted in one conclusion, “you need to recognize red flags sooner in the project.”

Here’s what we came up with:

1. A prospect’s immediate question, “how much is this going to cost me?”

While we recognize that a budget is necessary, the first few questions should be about qualifications, credentials and project information. Many times this will signify that they are looking for the cheapest option.

2. The customer wants to set a budget or establish a timeline before the discovery meeting (i.e. before setting goals and scope)

Or they ask you to give them an estimate before you have had a meeting to discuss the project; this often signifies that they are shopping and already made their decision, they just want a comparable price. Don’t bother putting the time into building an estimate. Push back that you need a discovery meeting before you can give an estimate.

3. They have a bad reputation

My personal favorite: someone in your professional or social network tells you a disturbing story about when they worked for the customer in the past. This one usually sends me running for the door. If you are in the industry; you likely know others that have done work with them. If your peers are telling you that they are a PITA (pain in the a**) client, expect nothing less. Some companies will continue the project and just add a PITA fee, but trust your gut and know if you should turn down the project.

4. They lack respect

I’ve had meetings where the client would show up in clothes only appropriate for the beach, still hungover from the night before or start scratching themselves like a monkey. This behavior may indicate that they don’t care about a long-term professional relationship. Other indicators are how they talk to you. Calling you kiddo, babe, or telling you about the crazy night they had before are strong indicators that they will treat you poorly.

After the meeting, send them a well-crafted email that you don’t believe that you’re the right fit for the project.   

5. They ask you to discount your rate or ask you to barter.

I get it, we are all looking for a good deal, but respecting someone as an expert should come with accepting their established value. Bartering is tempting but is different than working within a budget where you can adjust goals and deliverables.

Bartering can come in the form of services or products trade but also beware of the dreaded “work for stock” in the company. I have tried it a few times, and it always ended in disaster. Just don’t do it! A company that has good vision and leadership can get the money to pay you.

6. They ask for free work.

It can be a client asking for ad hoc reporting without paying for a consultation or strategy. While you may think this is part of the proposal stage, this is a strong indicator that they are shopping around and plan to walk away with your proposal (i.e., intellectual property). Josh suggested that we start the relationship with open communication and let the potential client know that any work done would be considered intellectual property and that you require payment for the project plan even if they don’t hire you.

7. The customer insists on following a process or methodology that doesn’t fit the project goals.

They’re hiring you as an expert, but if they can’t follow your proven process and expertise, this is a good sign that they don’t respect you as the expert. Expect that this client may treat you poorly throughout the entire project. A good example: They take your work and sending it to all their contacts to have them vote on it.

8. Be leery of working with start-ups

They tend to have champagne taste and a beer budget. Be sure to go through your normal process; proposal, acceptance, strategy, tasks timeline, etc. Do not deviate from your process. Be sure to get money down and don’t work too far ahead. If payments are late, stop the work until payment is made.

9. The customer doesn’t see value in spending time and money to create a strategy before starting a project.

Strategy and planning are essential when building a professional relationship. If the customer wants to jump straight to deliverables, this relationship is likely doomed, as you can’t expect overnight success. Also as a personal opinion, this is usually an indicator that they are hurting financially.

10. The customer demands serious alterations to your contract and Terms of Service document.

Your contract and terms are created from your expertise and experience. If your client has an issue with something that protects you from being taken advantage of, this is a good sign that it will not be a healthy professional relationship. No one wants to be taken advantage.

11. Your gut is telling you no!

As an entrepreneur, you need to learn to trust your gut. There is no one to blame but yourself if you end up in a project gone astray. When you have a bad feeling about a client or project; set a discovery meeting to talk about your concerns. If you still feel the same after a few days, then it’s probably best to let the project or client go. You can always make more money. It’s not worth setting yourself up for failure.

12. The prospect is hard to reach.

During the initial meeting, you should set the expectation of when feedback is needed. If you cannot get input in a timely fashion, you can expect the same during the actual project. Expect the project will get delayed and you will end up eating extra cost or time.  

If you proceed with the project, make sure to set deadlines that will force action or inflict pains to the client for missed deadlines. For example, if the project deadline has been missed, add extra fees to start up again, or we delay the project further until or development calendar is available.


Bottom line–Trust your Gut. We have walked away from six-figure deals because it felt wrong. We have never regretted the decision to trust our gut. You won’t either.

Do share! Have a story or red flag experience? We believe in learning from others and help your freelance peers avoid the same mistakes. Message us at [email protected]