Spotting red flags and trusting your gut

Questions to ask yourself when alarm bells are ringing

We like to think that all terrible clients will be immediately obvious to us. They’ll carry a large sign with flashing lights that says, “Don’t work with me,” and toss out rude comments like penny candy during initial meetings. All that will make it easy to, in the words of Nancy Reagan, just say “no.”

Of course, reality is rarely that straightforward. As freelancers, we’re stuck navigating a web of clues, comments, and emails and balancing that against our business goals to decide whether we should work with someone.

Photo by Bernd 📷 Dittrich on Unsplash

The story

I met with Tom (not his real name) in September 2024, a full year ago, which in freelance years is practically a century. He reached out for help refreshing a 150-page website, plus writing ongoing blogs, case studies, bios, and anything else his company might need. So far, so good.

But when it came to the money bit, Tom gave no clues on budget or pricing and was unclear on exactly how much work needed to be done. We closed the meeting with him asking me to send a quote. I followed up by email with some questions I wanted answered so I could send a more detailed quote. Crickets. Red flag #1.

With my patience wearing thin, a few days later, I decided to lob the unclarified quote into his inbox just to clear my to-do list. Still no response. Red flag #2.

Fast forward to August 2025—a year after the quote was sent—when he materializes in my inbox. As he put it, the company wasn’t ready to move forward last year, but now, miraculously, they are. Would I still like to discuss?

Now, the fact that he’d ghosted for a year wasn’t great. But I know life happens, priorities shift, and sometimes emails get lost in the ether. I agreed to a meeting, feeling cautiously optimistic that things could still work out, but also wary of further issues that could arise. Ghosting on its own might not be a deal breaker, but it is a sign to be cautious and even more vigilant.

Questions during initial calls aren’t just about sorting scope

On our call, Tom listed the same Everest-sized pile of content: website overhaul now, regular content for months after. I started asking questions, not only to scope the project but to see what working with him would actually look like.

This is something I’ve learned over the years: questions aren’t just about figuring out the scope of work and delivering a quote; they’re for evaluating how the other person responds. Every answer is an opportunity to assess what you’re being told and watch for any warning signs. The more questions you ask, the more opportunities you have to gather information on the potential working relationship.

So I asked about budget, scope, and content roll-out.

Red flag #3: “I don’t have a budget, but your quote seemed high.” (His words)

Wait, what? If someone doesn’t have a budget, how can anything seem expensive? This is like saying, “I don’t know what’s too tall, but you’re definitely too tall.” And this is especially perplexing when he had my initial quote a year ago and therefore plenty of time to do research or think about what pricing seemed realistic for him. If my pricing seemed high, why not take any time in the last 12 months to do even 30 minutes of research and come up with a reasonable budget?

Red flag #4: “No preference on pricing model.” (His words)

I offered up retainer, hourly, per-piece—choose your adventure—but Tom shrugged off any preference. This, despite having already seen my very clear, very itemized quote and, therefore, having time to look over different models and decide on a preference (again, in the 12 months since that quote was sent).

Red flag #5: “You’re the expert.” (Not initially a red flag, but it’ll come around again)

I asked how he’d like to prioritize and roll out content. His answer? “You’re the expert.” I’m supposed to guide him. That may sound flattering, but when paired with so much ambiguity, it started to feel suspiciously like someone handing me both the steering wheel and a blindfold.

So, with a few tiny alarm bells still tingling in the back of my mind, I sent a revised quote: $4,000 a month retainer, up to 40 hours, payable at the start of each month (like most standard retainer arrangements for real, live working professionals). We’d check in at the end of month one and pivot if needed. (And yes, this quote was less than the initial quote a year ago.)

That’s when the red flags became practically a parade.

Here’s a sample of Tom’s (much longer) email reply:

• “We are not comfortable with a retainer-based pricing model. What we prefer is a content-based pricing approach—per blog, per page, or per deliverable.”

• “The prices suggested in your proposals are on the higher side.”

• “No one has ever asked for advance payments. In my experience, senior writers raise an invoice at the start of the month for work delivered and approved in the previous month. We’re only comfortable working that way.”

Two days earlier, he was a blank slate when it came to payment models and processes; suddenly, he had strict requirements, and—surprise!—mine ticked literally none of the boxes. Individually, his responses may not be dealbreakers, but when he says to my face that I’m the expert and he has no opinion on virtually anything, and two days later takes issue with everything I’ve suggested, that’s a sign it’s how he normally works—saying one thing to the person in front of him and going in a different direction later.

It doesn’t bode well for the future.

How I approach these red flag situations

First, I pause and check in with my gut (which, in this case, was saying “run far, run fast, run like the wind”). But, before making a final decision, I go through a series of questions I’ve learned to ask when a project starts feeling off. Each question is answered using all the evidence available to me.

If you haven’t tried these, you might want to jot them down for future dodgy proposals.

1. Does this client seem to respect how I work? Evidence: He strongly rejected retainer pricing, called my pretty standard payment terms “unusual,” and positioned his (previously unspecific) preferences as standards I should conform to, even after stating that I’m the expert. He’s already asking me to abandon my normal systems. While I won’t share the entire email, it had a tone of “Let me educate you on how this arrangement will work, and what’s normal in the writing world.” None of this seems respectful.

2. Am I being hired as a partner, or just an executor? Evidence (direct quotes): “You will receive a comprehensive brief for every page.” “We will reference government sources—you don’t need to research.” “The key part is the treatment.” He says he wants a strategist, but he really just wants an executor to polish someone else’s briefs.

3. Are my boundaries already being tested? Evidence: He pushed back on my rate without a concrete counteroffer, dissed upfront payment as totally unheard-of (which feels manipulative) and turned from vague to demanding as soon as money was discussed. This feels like him testing my boundaries to see how much I’ll bend to meet his expectations, without him showing any flexibility in return. When things go south (and they definitely will), I’ll be the one doing all the compensating, he’ll be the one doing all the demanding.

4. Could this grow into a fulfilling partnership? Evidence: I’m already frustrated and annoyed (and we haven’t even started). Somehow, he’s come across as uncertain, overly certain, demanding, and condescending, all in the quoting stage. If someone makes you feel incompetent and unseen before you’ve cashed a cheque, it rarely gets better after. And if the thought of emailing someone makes you feel nauseous before work has started, that’s a sign to move along. Nothing about this indicates a fulfilling partnership.

5. What’s my broader context right now? I’m about to start teaching two courses at SFU. I’m also supporting a family member through a terminal illness. Does this gig sound like something I want to pour my precious and rapidly depleting energy into? Reader, it does not. I’d rather spend my time writing this newsletter or walking across hot coals.

6. How do I feel after reading his email? My immediate reactions: This is setting off alarm bells; something feels off; and he clearly has ideas of how this should work, but isn’t willing to state them until he’s criticizing me. This situation feels rigid, not collaborative. I can’t imagine any scenario in which he gets easier to work with once he’s paying me.

My decision

It may come as no surprise to you, but I’m not taking Tom’s project. My bank account may not thank me for this, but my mental health already feels lighter. When I ask, “What price would make this project worth it?” I’ve already quoted that price, and he’s rejected it. Lowering my rate—or bending my process—would only make it less tolerable and make me infinitely more cranky.

The next time an inbox ghost returns from the dead—or a new client throws up red flags—remember: your gut isn’t just noise. Listen in, check your context, ask some questions (based on evidence) and save your best work for the partnerships that actually feel like partnerships.

(Paid content below includes templates for saying no to projects that aren’t a good fit.)