Roundup: How to Spot a Problematic Project Before It Begins

There are myriad ways a new opportunity can turn into a nightmare project. It takes experience to spot a problematic client before a project begins.

Micromanagers. Never-ending delays. Stultifyingly complex or boring work. Incommunicado clients. Scope creep. Late payments. (Or worse, no payments.) Know-it-all clients who don’t trust your expertise. In-over-your-head demands.

There are myriad ways a new opportunity can turn into a nightmare project. It takes experience to spot a problematic client before a project begins, but it is possible to sidestep disasters when you know what to look for. Four members of our successful small business owners panel are sharing their best advice for spotting a “problem” client before getting sucked into their vortex. Plus, we added our two cents on how to handle these kind of prospects.

Built for owners

Jennifer Matthews

What I Do:

“Communications strategy, including project planning and communications audits. Plus, writing and editing of:

  • Internal communications like training materials, conference scripts and change communications
  • External communications like magazines, annual reports, brochures, books, fundraising documents, executive speeches and presentations and websites.”

Red Flag Alert:

“Clients who don’t have a clear sense of their needs often aren’t ready for you. And clients who are really hesitant about your hourly rate may not be the right fit.”

Our Two Cents: When They Want the Lowest Rate…

When you’ve sussed out that a client is simply shopping around for the lowest price, respectfully declining is a no-brainer.

But if the client owns or works for a non-profit organization or a small- to mid-size business with limited resources, their price concerns may be more understandable. If the client appears to be a reasonable person, it might be worth considering the work if:

  • Their budget isn’t absolute highway robbery, i.e. $20 to write a 1,000-word blog post
  • You have time in your schedule and it seems like you could knock off the project fairly quickly
  • The work is something you haven’t done before or in an industry in which you’re trying to break in

Tim Dolan

What I Do:

“Kickframe is a new type of consulting and training firm built to serve the need that organizations have for a specialized digital strategy partner that is independent, agile and experienced. Kickframe helps organizations become better digital marketers.”

Red Flag Alert:

“When I work with a client, I am invested in their success (beyond the success of the project). It is important to me that the person who I am working for is someone that I am motivated to help succeed over the course of the project and their career.”

Our Two Cents: When You Don’t Like the Client or the Work…

If you’re committed to the financial success and growth of your business, you’ll no doubt find yourself gritting your teeth behind a polite smile with certain clients. You might also take on projects that require regular brisk walks around the block in order to stay engaged with an extremely dull assignment.

Working with people who rub us on the wrong way and projects that we don’t necessarily believe in are part of paying your dues as a small business owner until you can afford to be more selective. They can also be great motivation to market your services and send cold pitches to better clients in every spare second. Working on drumming up good-quality clients is part of running a business!

Note: There’s a difference between abrasive and abusive; annoying and intolerable; boring and against your values. When you’re confronted with an opportunity that you’re inclined not to take, ask yourself if you can stomach the project because you need the work – or whether your time would be better spent working on your business. Sometimes the answer will surprise you.

Andrew & Jess Campbell, Workshop Training, Speaking, Writing, Project Management

What We Do:

“Andrew’s focus is on training and skill development in communications; Jess does project management and freelance writing.”

chase dreams not payments

Red Flag Alert:

“A major one for me is lack of detail. This client can be challenging if what you develop isn’t what they had in their mind. It means a lot of back and forth on something that no one ends up really happy with. Sometimes, though, these can also go the other way when you produce something that is exactly what they wanted. It’s impressive and both of you are thrilled right away. The interesting part is figuring out which it might be early on.”

Our Two Cents: When The Client is Vague About the Project…

“We need some freelance writing/design/web development support. What are your rates and when are you available?”

While it’s exciting to see inquiries in your in-box, this kind of vague request is a red flag. It’s reasonable for a company to avoid going into detail in a preliminary email, but if they’re asking for price and availability right off the bat, there’s a good chance they’ve sent this request to a pile of people.

A good best practice is a short response thanking them for reaching out and suggesting a phone consultation so you can understand their needs and create a customized quote and timeline. If you don’t hear back, you can move on to better clients. And if the call goes well, you can prepare an estimate or proposal that outlines exactly what you can provide and how much it costs.

Paul Russell

What I Do:

“I’m a writer and communications consultant specializing in both corporate communications and marketing. I have extensive experience working in the human resources (internal communications) and financial services (external communications) areas.”

Red Flag Alert:

“Two things I’ve learned:

  1. Be wary of clients who got your name off of the internet and know nothing about you. They are usually fishing for something cheap and who knows if they will pay. Word of mouth (where a client has heard about you from someone else) is golden.
  2. Avoid ‘bidding’ on jobs whenever possible if you compete on quality and not price. I know I’ll never be the cheapest option, so bidding for me has been a waste of time.”

Our Two Cents: When You’re Constantly Bidding (and Losing) on Work…

It makes sense for consumers and businesses to shop around for the best overall candidate for a job, but if you find yourself losing out on bids, there are few things you can do to get out of this cycle.

stand tall
  1. Improve your proposals. How do you submit a quote for a job? Email, Word, Excel? A less-than-professional-looking bid can make a poor first impression and eliminate you from the running at first glance. Estimates and proposal tools (like FreshBooks’) provide a sharp format that allows you to enter important components like an overview, scope, timeline, pricing and even a place to enter samples or photographs of your work. A comprehensive, well-written bid can make all the difference.
  2. Target a different clientele. Whether it’s high-priced government contracts you’re missing the mark on or low-balling clients whose main concern is getting the lowest price, if the bidding process is not working for you, consider re-examining your target market. You may not be qualified (yet) for those big jobs and you may be over-qualified for those small jobs that are more hassle than profit. What kind of work are you most skilled at and most passionate about? What type of client needs your unique expertise? Once you’ve defined your ideal client, go after them by:

about the author

Freelancer & FreshBooks Customer Heather Hudson has been a freelance writer for more than 17 years. As a small business owner, she understands the triumphs and challenges of life as an entrepreneur. And as a longtime FreshBooks customer, she’s always looking for ways to work smarter, not harder. You can learn more about her work at