Is That Potential Client Really Waving a Red Flag? How to Decide

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which clients to work with

“Is this potential client actually gonna be a problem… or am I just being judgmental?”

Every service-based business owner ever at some point, probably.


No matter how long we’re in the business, while it becomes easier to spot a bright red flag, or a beautiful flowing “ideal client” green flag over the years — there comes the occasional prospect who lieth betwixt.

Is This a Red Flag Which I See Before Me?

Maybe they ask a question like:

“Can you tell me more about XYZ part of the process? We may already have that part completed.”

Or they tell you:

“Well, I worked with another [copywriter/designer/consultant/coach]… but it didn’t really work out. I love YOUR style though, and I think your offer is a perfect fit!”

Or you notice that their sales goals are particularly high for their list and following numbers.

Or that their pricing seems a little out of whack one way or another.

And you wonder… “Is this a red flag?”

And the annoying answer is:

Well, not always.

It Depends…

These questions, statements, and strategic gaps are the particularly tricky type of signal — because they truly could go either way.

And, while they MAY be a warning sign of things to come…

… They may also simply be signs of a client asking the right questions to get their needs met, who hired a subcontractor who truly wasn’t a fit, or who’s setting goals and prices based on insights and tactics you aren’t quite aware of yet.

So your job is to make your absolute best guess.

NO PRESSURE, right?!

We’re Here to Help You With That

But never fear — because #HAMYAW is BACK this week to discuss that age-old question:

How can you find a way to know for sure?

And how do you parse out…

If it’s the client?

If it’s you?

Are they going to be terrible?


How can you tell? And what do you do next?⁣

Margo Aaron and I get into all this AND MORE on today’s episode of #HAMYAW, where we explore this concept of pink flags, including:

  • Is a pink flag always a problem? Or just a problem… for you? Are you being antagonized or just feeling uncomfortable?
  • Our running list of pink flags
  • How to make your best guess to decide to move forward… or turn down the project

Have Any Pink Flags of Your Own?

Head here to check it out and COME TELL US WHAT YOU THINK.

And let us know in the comments…

What are your pink flags?

Did we miss anything in our roundup?

And what’s your litmus tests for proceeding, or hitting the breaks?⁣

Come get shouty with us — and we’ll see you over there.

Write on, H


Wondering what my least favorite Aerosmith song is?


But at least they followed it up with “Don’t Wanna Miss a Thing”. So perhaps there’s redemption in the cards for us all.

Episode Transcript

Okay, wait. Fix it!  


No, (stuttering) to my left. Yeah.  


That was not better at all. Okay?  

Okay, there, it’s modern art.  

You’re killing it, perfect. This is it. Oh, even better. Even better.  

(wheezing) I want to quit. I quit. (upbeat, bass-heavy music)  

Welcome back marketing nerds of the world. It is time for another episode of HAMYAW, and today, we wanna talk about pink flags. Not quite a red flag, not quite a green flag, but something in between.

So a pink flag, especially when it comes to new clients or customers for a new service that you have are moments and phrases and ideas and questions that sort of send up your hackles maybe a little bit but aren’t enough to be an instant no.

The trick about pink flags, folks, is that you have to learn when a pink flag is in fact red, and when it just happens to be a flag that is pink. There are so many different ways to approach having to parse through these kinds of communications and figure out whether a client said something because they’re a bad fit, or because they had a bad experience, or because they’re trying to make their needs known so they can be met.

So, we’re gonna get into what pink flags look like when it comes to clients, how to work with them and dig underneath the layers, and ultimately, how to decide for yourself when the flag is pink, red, or something else entirely. But before we get into that, Margo, talk to me about your pink flags.  

They’re so hard because identifying red flags is hard enough, and then when you get a handle on something, you and I have discussed this many times, a client who is constantly in a rush, and needs something yesterday, red flag, right?

We know that’s gonna be a difficult client no matter what, and you can opt in to dealing with a client like that, or you can opt out, but at least you know what you’re getting into. But with a pink flag, there’s a confusion around whether you are walking into a trap, or whether this person is just a little overwhelmed, and that’s why they’re hiring you.  

Yeah, exactly. I find often pink flags are brought about by people who have had negative experiences with other service providers as well, which is extremely common, and kind of difficult to parse.  

Well, let’s start here. There are certain things that we hear predictably and repeatedly and consistently. All of us, in our businesses, and the discussion of what the red flag, the pink flag, or we’re gonna call it white, no, white is when you don’t do something.  

Green flag!  

Green flag! Green, right. Sports!  

No, no, just a stoplight, but go on. 

I think some of this is about what you can handle, reasonably, so like, what might be a red flag for me, could be a green flag for you. I do wanna caveat this conversation within that, that something that might be a hard no for us could work well with your personality, so know this about yourself.

But there are certain themes that we’ve seen in our career and those careers of those around us, where there are predictable patterns of behavior that lead to difficult outcomes. And the pink is just the indistinguishability of some of those traits.  

Yeah, I love that you raised that point, because a pink flag can be an issue or it can just be an issue for you. So a pink flag might be a pet peeve. So, if somebody’s like, ‘well, I know the sessions are every two weeks, but I want to do two sessions a week because I think I can handle it,’.

You’re like, you have a lot of energy I just don’t have right now. Like that might be a pink flag for you. But before we get any further into the conversation, I want to do a quick list of some general pink flags. So, I think generally, the first one is something along the lines of I’ve been burned a lot of times, can you make this happen for me?  


And the reason that’s a pink flag, and we’ll get more into this in a few minutes, but while some people have had bad experiences, and need to be honest with them in order to grow, that’s what makes that a pink flag. And some people might say that’s a red, because if somebody comes right out the gate being like, ‘everyone else has failed me, will you solve my problem?’, that seems to be a little bit of a warning sign that something else is afoot.

And then the second kind of pink flag, I would say, most commonly, is something like, ‘well, I’m just not really clear on the offer’, when there’s a whole sales page for them to check out. If only there was somewhere for you to go to get this information, but that is also a sign that you may have not explained it well, correct?  

Right, right, so determining attribution of pink flags is important, because there are definitely times where I get off a sales call like, “I botched that.”  


Where I really was confusing, I wasn’t clear on what this is for.  


Not sure they were a right fit, and even if they were a right fit, I didn’t explain it well. And that’s just a part of the growing and learning process. But that’s distinctly different from a program you sold many times, you get on a sales call with the person, they sound great, they seem like they’re tracking with you, and then you get an email afterwards. It’s like, number one, if it’s really long, that’s always a flag for me.  


Number two, if it addresses or asks questions you thought you answered in the call, and then the kicker of ‘well, can you be clear about what I’m getting?’ and I’m always like “what did you sign up for?” Like, what do you think that I do? (mumbles), that was always a weird, weird one.

Can we go back for a second to the one that you said, and I’m going to add to this list about having been burned, and the different ways this looks. ‘Cause, I think there are different ways that people present. They’ll say, “Y’know, I’ve hired a lot of coaches before.” It always results in you having to prove yourself more because of their past experience.  


And the reason that’s a pink flag is if they have sincerely been burned, but still need the service, they’re not setting you up for a gotcha moment, right?  

Mm-hm, yeah.  

They’re sincerely, like, wanting to let you know that this is sensitive to them but they really care. That’s a good person to work with. But if they’re telling you, like, “Tell me why you’re different” then that’s antagonizing, right? Especially if you have a huge online presence or they’ve been following you for a while, and there are things they should know about you.  

Absolutely, and I think that also, the reality is, especially now that we’re getting into, I’ve been in the coaching world for a little while now like there’s a lot of coaches with an approach that doesn’t exactly jive with what the person was initially looking for.

Like I was talking to a client who was in a serious revenue rut, and somebody had told her to do visualization exercises for her target. Which is great, but it’s not necessarily the hard strategy that she would have needed in the moment. 

So those kind off stories, I understand and recognize, because I’ve lived them. You know what I’m saying? Like, I’ve been on the other side of it. But you’re right, where it slips from pink flag into red flag, is when it’s less, ‘Hey, here’s my past experiences, I want to make sure this doesn’t happen again.’ and into “How are you different? Dance, monkey, dance.”  Yes! Dance monkey!

I saw this a lot, not when I was coaching, but when I was marketing, and people would be like “I paid an agency $50,000, then I paid one $20,000. And they did nothing!” and I’m like looking over the contracts, like “well yeah, because you signed a bullshit contract.”  

(chuckles) Congratulations.  

Like using words like, strategy. There’s nothing here, there’s no deliverable. And they’re like, “I just don’t understand marketing.” Then what are you hiring us for? People who have that kind of ignorance and learned helplessness towards what you do, but then expect you to deliver something, that’s where it becomes a huge red flag. And I saw that a lot with marketing, I saw that a lot with like, people who thought marketing was a panacea that could fix a broken business.  


People didn’t read a contract and hired you for copyrighting, and really wanted website design, but didn’t know how to articulate it. This is where we have to qualify our leads better and that’s usually how you get rid of this problem, but when, especially at the beginning, and I put beginning in air quotes, like the first five years or 10 years of sales, you are still getting to know your service, you’re still doing bespoke contracts, you’re still reacting to the market in a way that’s generally positive, but it leads you to some of these circumstances where you’re around people who aren’t necessarily well qualified.

Because you don’t know what you need yet.  

Yeah. Yep, absolutely. So we’ve got the pink flag number one, the horror stories, right out the gate. Pink flag number two is “What do I get?” What would you say pink flag number three is?  

Boundary violations.  

Oh yes, ma’am, tell me more.  

So, if you are, if we have not signed a contract and you’re calling me on the phone, or asking for my phone number, or texting me a lot, or DMing me a lot, like that kind of stuff, it’s a pink flag because some people sincerely, and I think I’m one of these people like we have a lot of feelings, and we have a lot of things to say.  

Me, not at all. (laughter)  

And confuse and blur the line between friend and colleague. And so, that can lend itself to getting access to your time in a way that’s inappropriate, and then starts the foundation of a working relationship off on the wrong foot. Where they think they have access to you all the time.  

Yep, I think that’s really important, as well. And again, I’m with you. Because I’m a talker, I love people in my DMs, I love conversations. Some of you viewers, I’m regular Instagram DM pen pal buddies with, that I genuinely like. But you’re absolutely correct, what has been absolutely beautiful about the clients I work with inside Power Position and all of that is that often when we start working together, they will actually step back from the DMs because they have access to me in Voxer, because they have access to my email, so it becomes less urgent. 

But I have had moments where I’ve been talking to clients and prospects, and all of a sudden, it’s just machine gun fire. It gets to a point where you’re wondering if they actually want support, or if they just want access to your energy.

And they want the attention and the on-command insights, and that’s a pink flag. And it depends so wholly on what kind of person you’re talking to. Because I’m really blessed with great clients and a great community who respects the boundaries, and once work begins, they actually back off because they know there are now parameters. And some of them I have to encourage to use the platforms.

I’m like, “You got Voxer access, I need you to use it.” But ultimately, I think what it comes down to is just being really mindful about being cautious, and being able to spot when it’s crossing the line.  

Yes, and when you’ve been responsible for those violations. 


I think this one’s really important, because I used to bemoan boundary violations, and then not understand that it was me being like, “Call me at this time, here’s my phone number, I’m available all the time”, and then me interrupting my friends being like, “Hillary, listen, I know you’re upset, but my person is calling, and I need to take this.” And then I become their emotional janitor.  


Then I’m like, God, why are they calling me so much?  

It’s the worst. Because you told them to!  

Because I told them to. Watch your behavior. So something, I actually learned this from Tristan Harris, who was one of the Google design ethicists back in the day. He cited a study that said how you respond to someone’s first email sets the foundation from what they expect from you in terms of response time.

So I think about this now with DMs, with emails, with text messages. If it is from a new person, including readers, I will consciously take time, even if I see it coming in, just to set that boundary that I’m doing other things. We’re not doing the IM via email thing.  

Yeah, of course.  

That’s not how this works.  

Yep. I think that’s the other reason for the pink flags. Like, What is your role in this? Why are people reaching out to you? Is it because you’re just that available? Y’know, and I think that can be a blessing, and I believe in access, and that’s why I believe in social media so much.

Evil empire it may be, I think ultimately I love that access and I think that connection is very powerful. But you’re right, you have to look at, is this person violating the boundary because they’re throwing up red flags or because I have created an invitation to do so?  

That’s right, and also, content matters. Are they telling you about business related things or are they trying to become your friend? I think that might be the next pink flag, which is like working with friends, and that thin line of when something goes from friendship to transaction.  

Yep. 100%.  

And what that necessities, what that allows, what the boundaries are on that, how it becomes a working relationship, what you owe them, what you don’t, it’s hard.  

It is, it’s tricky. And that brings us to, as a matter-of-fact, folks, our fourth pink flag which is trying to mess with your process. And this is usually, I would call this more of like, a fuchsia flag, or maybe a maroon, because it’s getting towards the red zone pretty much, but this is a big issue, no matter how high up you get, you’re gonna experience this where you have a client being like “Well, what if I didn’t fill out the intake?” or “Well, y’know, I’m very busy, so if we could just skip this call, do you think you’ll have enough?” 

And that is a pink flag for I think two reasons. Because one, sometimes a client doesn’t need to do those things and you’re like, “Okay, great, you already have this done, this is fine.” But other times, it creates a really tricky relationship where you’re having to fight for your process and your value every step of the way.

Let me tell you, folks, nobody wants to do that.  

Diminish your own value. Like the amount of times that I’ve been like, “I guess I don’t really need to do strategy like that. I guess they do know their avatar. I don’t need to talk to their people.” And then I’d sit down and I try to do their marketing, and I’m like “Uh.”  

I take it all back. I lied to me, I’m the worst.  

Or, on the flip side, adding to your process. Like I had people who were constantly interrupting my process, where I’d be like, “I’m gonna go in the dark now, I’m gonna copywrite, and then we’re gonna review things together.” And they’ll be like, “Can I just see the document?”  


No! You cannot see the document, cause then I get those few like, “I really don’t feel like this is on brand.” Like, “No shit, Sherlock, it’s a first draft. It’s not even what I want to say either!” 

“You have no idea how messy this gets, get out of here.” Oh my god, I’m having flashbacks, because earlier in my career, I had a client who would go into the Google Doc drafts and sit there and watch me work. I’m not kidding. I would see her face in the upper right hand corner of Google Docs and just be like, (deep breath).  

That’s masochism.  

And this was back when there was chat in Google Docs, so sometimes she would chat me and be like, “I don’t know about this” or she’d be like “It’s so cool to watch you work.” and I’d be like “Uh-huh.”  

Is that what you’re doing?  

Dance monkey, dance! But yeah, is that what you’re doing? Well actually, I’ve also had this experience with my mom, where she’s literally sat behind me sometimes and watched me, and been like, “There’s a typo.” She’s British, so she’d be like, (British accent) “There’s a typo. Miss, there’s a typo.” My mom calls me Missy, it’s a long story. 

So, it’s kind of like that feeling. And sometimes, clients know exactly what they need and they’re efficient, if they know what they have is already working, sometimes you can skip steps. But overall, you’re going to get into a situation like Margo described, where you’re gonna be like, “Yeah, I guess, yeah, I guess.” and then you get into it and you’re like, I guessed wrong, and I’ve made a terrible mistake.  

Remember what you’re charging for, like depending on your service offering, there were parts where when the client would ask those kinds of questions, it was clear they were devaluing my role. As an expert in the field, as a fiduciary, as someone who was a trusted advisor, versus a technician.

And so, I would start to question like, “Oh, maybe this 30-day project was only $400. What was the point of that?” You know what I mean? You go down that route, and you open yourself to those kinds of questions. 

Like I would have a request coming in, that was like, “Okay, so we’re not a big company, and I don’t want a big Powerpoint or whatever, can you just make us a logo?” And I’m like, “Sweetheart, that’s why God invented Fiver.” If you want just a logo, then don’t hire an agency, and don’t have strategy, and that request in itself suggests you don’t understand design.

And you’re not at the right stage for branding. It takes a while as a service provider to recognize these things, because sometimes, those inquisitions, and this is why it’s a pink flag, sometimes, if you get enough of those kinds of questions, you go, maybe I invent Fiver.

Maybe it leads your business in a different direction, where you see a certain amount of demand, but if you know your stuff, Hillary and I both know that we need certain things in an intake form, there’s a reason we’re doing it, we’re not making you get on the phone to waste your time, and this is again dealing with horrible stories, the pink flag number one, lot of times when people want to deviate from your strategy and from your process, it’s because someone else wasted their time.  

Yeah, exactly right.  

Cool, so as we think about getting more clients, getting and attracting the right clients, we always want to be mindful of red flags, but the pink flags to look out for are those moments where we’re like “This could be good, maybe, I’m not sure. We’ll go on a date.”  

Yeah, exactly. Go on the date, folks. If it’s not a red flag, and you feel like it’s a pink flag, go on the date, but also, have your “What is a red flag” parameters in mind. What are pink flags to you and what’s going to make them go red and what’s going to make them go green? Or white, which follows the color metaphor a little.  

(laughter) I want to add that the way to really get conclusive on these things is number one, huge amounts of self awareness, and honesty about your own role in some of these flags, and number two, experience. There is just no short cutting. We’d love to give you a four-step process for identifying pink flags.  

We would.  

We would. It’s not possible. Because all of us are different, and you just need to be in the arena doing it over and over and over again, and frankly, getting burned enough times, and hearing stories from your colleagues. So this is why we always encourage creative outlets, creative outlets.  

Yep, creative outlets. Get your iMessage group chat game strong folks, you won’t regret it.  

And just a screenshot of the email.  

Give your iMessage group chat a creative name, screenshot it and send it our way, baby, we’ll do a live review on an episode of the show.  

So, to that end, we want to hear about your pink flags. Tell us, what’s a red flag for you, what is a pink flag for you. How do you determine the difference? Where have you been burned? When were you like, actually, this is something I can work with? I don’t know. 

So, if you liked this episode, please like it below, subscribe to our channel, comment and share it with your friends. I am Margo Aaron.  

And I am Hillary Weiss.  

This has been HAMYAW, and we will see you in two weeks! Thanks for watching!

(outro beat) 

Photo by Juliet Clare Warren

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