Ignore Red Flags At Your Peril. A Cautionary Tale

Caroline Leon
11 min readFeb 20, 2024

“Intuition is a sense of knowing how to act spontaneously, without needing to know why.”
~ Sylvia Clare

I want to share with you a personal story about the worst thing that has happened to me in over 12 years of working online. I’ve decided to share it so that I can glean the learning from the experience and pass that on to you (in the hope that it’s helpful) and also because to write and share about it feels like my best way of processing it.

I’m sure you all know what I mean when I refer to red flags. We often hear the term used in the context of dating and it can also apply when we are choosing which clients to work with.

Google’s definition of red flag is this: “something that indicates or draws attention to a problem, danger, or irregularity.”

If you’re anything like me, you’ve probably ignored a red flag or two as it relates to working with clients and suffered the consequences of doing so. I thought I’d got pretty good at spotting red flags and taking measures to mitigate against them, but recently I messed up big time in this regard.

In the context of this story, my use of the term red flags relates to whether or not a person might be a fit for me and my work. Red flags in this case, simply point to things that indicate that the person in question might not fall into what constitutes an ideal client for me. Everyone’s red flags and ideal client descriptions will, of course, differ.

So it all started when someone completed the application form for coaching on my 1:1 coaching sales page. The next step I take, once someone has filled in the form, is to read the application thoroughly and then decide if I want to schedule a call with that person.

To be transparent, I don’t remember ever not offering a call to someone who has completed the application form. Most people find me through my content, or come from a word of mouth referral and as such, I rarely have calls with people who aren’t a fit.

The way it normally goes is this: the person completes the form, I send my scheduler, the person books a call, we have the call and then we decide whether or not we want to work together. It’s a process that around 60 people have been through since I implemented it 2 years ago and I’ve never had any negative feedback or experiences from it. Until I did.

This particular person found me on Google which, from experience, can mean that they know less about my approach than other warmer leads and can mean that we’re not a fit, but not always.

Usually at this point I do a bit of research, look at the website, check out their social media accounts and get a sense of the person and their business. I do this to ascertain whether or not this is a business owner I think I can help.

In this case, where I ask on the application form for details about “audience”, this person wrote “N/a” and said that they didn’t have any social media channels related to their work. This could have been a red flag (given that I primarily work with “online” business owners) but I have worked with many clients who hadn’t yet got their websites or channels set up so I dismissed it as unimportant at this stage.

Even though the answers were fairly sparse, I went ahead and sent this person a link to book a call. Shortly afterwards I received an email questioning my time slots as they were the middle of the night for her and saying that despite being a night owl, meeting that late would be pretty weird even for her.

Less than 48 hours later, before I had a chance to reply, she forwarded her previous message with a solitary “?”. A personal pet peeve of mine. As a solopreneur, who manages my own inbox, I struggle to keep up with the amount of emails I receive on a daily basis and always do my best to prioritise emails from my paying clients. This means that sometimes it takes me a while to get back to people. Something I value highly is patience and understanding. This was a red flag that I should not have ignored.

Despite this, I followed up with her to let her know when in my schedule the next daytime slot (8am) in her timezone was available. The next thing I know she booked a call at 1am her time, which was very confusing in light of her last message. So, I followed up to make sure that it wasn’t a mistake. She said it wasn’t a mistake and that 1am worked better for her than 8am.

By this point all of this back and forth over email and all of these little niggles amounted to a sense of unease in me, I can’t really explain why, but something just didn’t feel right. I’ve learned, after well over a decade of dealing with strangers on the internet, to honour my instincts when I feel uneasy.

Realising that the only availability I had to work with her, should we get through the work together call and decide to proceed, would mean having ongoing coaching sessions at 2.30am or 8am — both of which she had said weren’t ideal, I decided to email her to let her know, and suggest that as a result of this, I may not be the coach for her.

Several confused emails later (she thought I was trying to change the time of our work together call) and she finally shared that the available time slots of 2.30am or 8am would not be a problem for her. Which left me feeling even more confused as it contradicted what she had already told me.

I’ll be honest. I should have cancelled the call at this point as I already knew deep down that I didn’t want to have it.

So why didn’t I cancel? Well at this point it was just a feeling that we wouldn’t be a fit. I was also in the middle of my CBM launch and onboarding the 2024 cohort and I didn’t have the headspace to craft a message that could explain why I was cancelling the call.

It’s also a really tricky one, how do you tell someone you have a gut feeling that you’re not a fit for each other without offering some explanation? So, instead, I said fine and agreed to go ahead with the call which was going to take place just 90 minutes before my first CBM call of the year, which is a pretty big deal in my calendar!

Then, the night before our session (after I had already gone to bed) this person wrote to tell me that she wouldn’t be putting her video on during the call. When I saw this email on waking, it was like all the red flags converged at once and I just didn’t want to get on the call. It was the hour before my mastermind kick-off call, I was already feeling uneasy about the call and now I wasn’t going to be able to see this person (video is extremely important to me, especially when trying to forge a connection).

So I decided to cancel the call, with 2.5 hours notice. Not ideal I know, but I just didn’t want to get on a work together call with someone I had already decided I wasn’t going to work with.

This was the email I sent:

Hi xxx,

I’m really sorry to do this but I’m going to cancel our call. I’ve made this decision for a few reasons.

Firstly, I have an extremely busy day today as I kick off my group program and the slot you booked wouldn’t normally work for me, it was only available because I opened up more spots to talk to people interested in the group program.

Also having no way of confirming your identity, given you have no website and no social media and now no video, I’m not feeling comfortable about the call.

Finally, on re-reading your application, I’m not sure I’m the best fit for what you need anyway. I tend to work with people who already have a social presence and an audience.

I apologise for any inconvenience.


What followed was a flurry of angry emails.

In which she accused me of being thoughtless, inconsiderate, unprofessional and unethical. She accused me of treating her like an object, tossing her out like trash and described the cancellation as a punch in the gut and said that I had ruined her chances of trusting or opening up to another person online.

She also said in regard to the video that I didn’t need to see her face and that a good coach would do what their client is comfortable with not the other way around.

I was shocked by her response and I genuinely felt bad that she was so upset by the cancellation. But, given the tone of her emails, I also felt somewhat relieved that I had cancelled the call. Now my gut feeling made sense.

I tried my hardest to reply with kindness, stating in my reply: “I’m truly sorry you feel that way, it was never my intention to cause harm.”

And attempted to explain my decision, “When you said you weren’t going to do video, it prompted me to look deeper at your application and my gut feeling was that I’m not the coach for you. For me it felt more unprofessional to waste an hour of your time than to get on a call, knowing already that I didn’t feel that working together would be a fit.”

This just seemed to make her even more angry and she accused me of trying to excuse the inexcusable, saying “you are wrong and you refuse to admit it”.

I’m not going to lie, these emails were deeply unnerving.

I’ve never had someone get so angry at me before and all this was now happening in the hour before my CBM kick-off call, the very space I had wanted to protect, so after she ended an email with the words “spare me any more self-serving emails.” I decided to close down my email and try to gather myself to host the first group call of my yearlong group program. I was genuinely shaken.

After the call, I had lunch with my 6 year old. Normally I rush around trying to clean up and answer emails while he watches a bit of post-lunch TV. On this day, still feeling knocked by the experience, I felt the need to snuggle with him on the sofa. Cuddling with him started to calm my nervous system. I had my phone on the arm of the sofa when I saw a notification pop on the screen saying that this woman had not recommended my business on Facebook. My heart plummeted, I had a spike of adrenaline and I cautiously opened up Facebook.

This is the review that she left (available for anyone who visits my Facebook page to see):

Caroline canceled our scheduled appointment that I anxiously waited a whole week for, just FIVE MINUTES before our call time…. because she “couldn’t find my social media”. 😳
For the record, I have an established writing & consulting business that I keep under my pen name, she never brought up this concern in all the surveys and emails back and forth, she just suddenly decided to treat a new client like trash without any warning or attempt at communication.
Oh and don’t believe the sales pitch about her “compassionate” approach to helping introverted, sensitive service professionals with their online businesses… she is ruthless, money driven, zero compassion, and I felt objectified during the entire onboarding process, right down to revealing my financial information on pure faith to a complete stranger. SO inappropriate… Felt like a slap in the face that she turned out to be thoughtless and unprofessional, unethical “coach”.
Don’t trust the fluff written by her friends in the recommendations… I recommend you run the other way and find guidance for your life/business anywhere else… it wasn’t just a waste of time, it was deeply hurtful and dehumanizing the way she treats people as pure comodities without any respect to them having feelings or schedules of their own. I’m sorry I ever trusted her “pitch” only to end up feeling so violated. 😓

In that moment, I felt devastated. I couldn’t help but feel that all of my years of hard work had been trashed by a stranger on the internet, one I had never even spoken to and all for cancelling a call.

Words like ruthless, money driven, objectified, unethical and dehumanizing swam around my brain. I felt total panic.

I had my second group CBM call that afternoon, so I did my best to put it out of my mind and focus on other things, but that felt impossible.

That night, I couldn’t fall asleep, I kept going over every aspect of her review. Was I really ruthless? How am I money driven? Would it not be more “money driven” to get on a call with someone I didn’t think was a fit? Am I unethical? Is my enrolment process really objectifying? Why had no one else said anything?

You get the idea. I was rattled and it made me question everything.

I subsequently blocked her Facebook profile from my page and reported her review to Facebook. I have no idea if they will remove it but I’m okay with the fact that it may stay there. I felt nervous that she may show up in other places to write bad things about me.

So that’s the bad news.

The good news is that I got through it and within a few days I started to feel better, as I realised that there were lessons to be learned from this experience.

This is what I’ll take from it:

1. If something a (potential) client wants or needs makes me uncomfortable, we are not a fit. Period.
I can’t do my job effectively if I feel uncomfortable.

2. I absolutely reserve the right to cancel a call if something doesn’t feel right and I’ll probably add words to this effect somewhere in the enrolment process.

3. From now on I will read each application for coaching carefully and thoroughly and if in doubt follow up with clarifying questions.

4. I won’t offer a call if it doesn’t feel like a fit or if something doesn’t feel right.

5. I will create an email template for use in these situations. I’ve always struggled a little here because I’ve never wanted to lie and say I don’t have availability if I do but saying we’re not a fit right off the bat can feel a little brutal.

I’m thinking something along the lines of: “thank you for your application, based on your answers, my feeling is that I’m not the coach for you. If you would like me to refer you to a coach who may be in a better position to serve you, let me know”

What do you think? I’d love to know. Do you have a suggestion? I’ll be honest, I find this bit tricky and I am open to ideas.

6. People can say bad things about me without it meaning anything about who I actually am.

And that’s it. Thankfully the worst and only bad thing to happen to me on the internet in over 12 years, so something like this was probably overdue!

I thought long and hard about whether or not to share this story and I decided I would for a few reasons.

I like to be transparent with my struggles not just my wins, a hope that you can gain something from my experience and to remind you of these 3 things:

  • Always trust your instincts, even when you can’t explain them.
  • Don’t work with anyone who expects you to sacrifice your comfort for theirs. Your ability to do good work, requires you to feel comfortable and safe.
  • Don’t stop yourself from showing up for your business out of a fear criticism, you can do your best and still get criticised, the key is you will get over it.

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Caroline Leon

Business Coach helping conscious change makers to build and grow sustainable businesses, using strategies rooted in integrity. https://carolineleon.com