5 Red Flags to Help Avoid ‘Difficult’ Freelancing Clients
By: Daniel Rosehill
Tags: Writing Tips, Freelance Writing, Freelancing, Writing

I recently wrote about my deliberate decision to be less responsive — about how taking slightly longer to get back to emails and WhatsApps has, in general, made me happier and more productive.

I also described how, unintentionally, my clients’ expectations around responsiveness have served as a filter, or a lead qualification criterion, to enforce during my prospecting and sales process

One that has helped me differentiate between clients I’m likely to have a great time working with and those that ….. let’s just say the opposite. (And to clarify what I wrote in that post, I’m talking about getting back to email in three hours rather than three minutes — but also not in three days!)

As a sort of follow-up to this post, here’s another one that I have been putting off writing for some time. Make that years, in fact.

Because, in truth, I think there’s too much written about Bad Freelancing Clients these days.

Or maybe because there are just more freelancers these days — and, consequentially, there are more bad clients out there than at any point in freelancing history. (If I were to guess, its evolution probably looks a little like the before and after graph of human productivity around the Industrial Revolution.)

Due to the preponderance of client-shamers we witness on many Facebook groups and other online writers’ haunts, I offer this quick guide to spotting potentially problematic freelance clients only with the following disclaimers firmly in mind:

Two Disclaimers About Client-Shaming

Disclaimer 1): In order to optimize our income and our experience (the two are usually directly proportionate!) I believe that it’s important, as freelancers, to make a good faith effort to work with as many clients as possible.

In other words, I don’t recommend throwing every potential client on the trash heap or subscribing to a mentality propagated on many Facebook groups for freelance writers that we should mercilessly “fire” our clients for minor infractions of any of the precepts I have set out below, among many others.

Rather, as freelancers, I believe that we have to see ourselves as service professionals first and foremost and — within reason — it’s our responsibility to meet our clients’ expectations. Not the other way round.

Disclaimer 2): Mathematically, I believe that most clients are good clients. However, I can say with certitude that there are plenty of not-so-great clients out there. And even a few clients that truly do deserve a spot on ClientsFromHell.Net.

A thought on that, though. (If there’s anything worth underlining in this post it’s this!):

Winding up with ‘bad clients’ is actually a sales problem and not a ‘freelancing’ one. Or a manifestation of your random bad luck.

A good lead qualification process, and learning to spot the bad-fit warning signs that I mention here, will greatly reduce your likelihood of winding up with a book of business full of lemons — if not (more ideally) eliminate them altogether.

My biggest regret about freelancing so far isn’t something typical such as wishing I had the temerity to begin charging more sooner or wishing I had the services of a VA to draw upon whenever I needed them.

Rather, I wish that I had realized that I was in the business of sales as much as I was in the business of writing (or marketing) from the very outset.

I’m currently slowly learning to up my sales game thanks to some great books and podcasts and am trying to master things such as setting better prospecting criteria (hint form that experience: funding history and profitability are very important metrics to look at and clients can be a lot harder to work with, and more stressful, when the purse strings are being held unreasonably tightly).

I’m also learning to proactively anticipate potential client objections with a view to resolving them rather than finding myself on the back foot as a client points out a question I didn’t have an off-the-cuff answer ready for.

I can’t emphasize this point enough.

You need to be a good writer / photographer / Wordpress developer to succeed as a freelancer in whatever area you’re doing business in.

That’s a given.

Having a good marketing process and referral system so that some work comes to you helps too.

But — for the 99% of freelancers not fortunate enough to have all of their work come automatically to them all of the time — they also need to be decent to good salesperson, ideally knowing how to be both a good SDR / business developer and a killer closer.

With that out of the way, here are some of the ‘red flags’ that I have come to spot over the years.

Again, I am offering these in a spirit of humility rather than as a vent. (Speaking of which did you know that venting has been scientifically demonstrated to not work?).

Great clients are out there.

It just takes a bit of sales know-how (the positive aspect) and knowing how to spot the dodgy ones (the point of this post) to find them.

Red Flag 1: They Set Impossible Demands Around Responsiveness

Everything needed to be done yesterday? You may be dealing with a client whose expectations around responsiveness are not a match for you.

Tying this back, again, to my first post.

The busier you get as a freelancer, the more two things become obvious:

a) There’s a lot to do just about all of the time. Between marketing yourself, prospecting, administrative work, and …. you know …. actually doing whatever it is that you do for a living. It can be a full and exhausting ride.

b) The better you get at all of the above (generating leads, turning out good work) the more of it tends to land on your plate. The exact mechanism that drives this, beyond you simply becoming more ‘skilled’ and ‘better’ at whatever it is that you do, can involve having a heightened industry reputation, getting your first referrals (and opening up secondary referral networks!), and just getting faster at producing the same volume of work, meaning that more of it gets assigned in closer succession.

Over time, this creates a sort of self-perpetuating dynamic that sees you becoming progressive busier until you either: a) suffer a nervous breakdown from over-work or b) make time for that vacation you’ve been putting off for a year and finally allow yourself to disconnect and recharge. (Note to self: can we please talk about option B, please?!)

As a result, for most freelancers juggling multiple clients (according to research from State of Digital, the average number of clients any freelancer juggles is 14!) being always-available-for-every-client-all-of-the-time is not just an undesirable way to live but, in fact, downright impossible from a simple time management perspective.

A client that seems to expect that of you is therefore implicitly:

a) Assuming that you don’t have many competing deadlines and priorities from other clients to meet.

Which I always find ironic because I think that a fair corollary of this would be that:

b) You’re not … very good at what you do. Otherwise you would presumably have plenty of work and clients to keep you busy.

I find this especially perplexing because in today’s hotly competitive freelance marketplace, one generally expects buyers to want to find good and in-demand freelancers.

Early warning sign: This behavior can be observed at the very earliest stages of the prospecting dance giving you time to decide whether you want to keep the lead moving down your sales funnel or not. You have a call. Can you have another in an hour? Could you be at their office in time for lunch for a face-to-face?

(Note: of course, all this is slightly generalized. There might be rare instances where companies really do need to fly at the edge of their seat for reasons that don’t involve their disorganization. But just as often it’s a sign of systemic disorganization — that will land on your desk as their latest freelancer.)

Red Flag 2: The CEO/Founder Needs to Approve EVERYTHING — All of the Time!

The buck stops at the CEO’s desk. But does every draft need to too?

I’ve encountered this quite a few times when working with smaller startups.

A lot has been written about micromanagement and its detrimental effects on workplace morale.

Clearly, this is not much fun for employees.

But what’s not discussed as much is the secondary effects that this practice has on freelancers and other suppliers of outsourced labor.

A CEO should keep their ears close the pulse of their business — within reason.

I don’t think there’s anything wrong with the CEO getting involved in minute project details when it’s just him and a co-founder currently manning the ship.

Or participating in a kick-off call. Or occasionally checking in to see how your project is going, assessing for alignment with high-level business objectives, and offering his/her feedback upon its progress.

When that same CEO has hired a Marketing Manager, however (along with 20 other people), who in turn hires you — but still feels the irrepressible need to pour over every draft you submit in minute detail and leave his own very personal comments. Well, that tends to be feel very unimpressive to me and doesn’t seem to make for a very agile workflow.

If, in the warm-up process, the CEO doesn’t seem to be able to delegate full stop, then it’s worth taking a careful look at the company’s Glassdoor. (A post on due diligence is coming soon, but I recommend always checking Glassdoor and trying to guess the average employee tenure with some LinkedIn searches to make sure the department you’re thinking about freelancing for isn’t a revolving door. Yes, even if you’re just looking at joining the team externally!)

Is there strong evidence of a dysfunctional and potentially toxic work culture?

Does your point of contact seem depressed and downbeaten and just functions as an automaton doing the will of the founder?

More tangibly: will your payment be held up because the CEO was at CES (a trade show) but the project can’t get signed off on until he or she returns from overseas?

Don’t fall into the trap of thinking that, as a mere freelancer, you’ll be shielded from the craziness and the internal discontent.

More likely, it will simply filter down into your projects — and you might find yourself looking for new clients in very short shrift.

Early warning sign: The startup has a dedicated marketing manager but the CEO is instantly looped into the first conversation you have. You’re initially flattered by the CEO choosing to become personally involved in the process. You might not be when he/she also has to sign off on every single project deliverable.

Orange-Red Flag 3: They Mention Upwork or Fiverr….. A Lot!

Using Upwork judiciously. Ok in my book. Outsourcing every possible project to marketplace freelancers? Potential warning signal.

Upwork has gained deserved notoriety among the freelancing community as a race-to-the-bottom marketplace filled with exploitative clients hoping to find developing world freelancers for rock-bottom prices.

For those of us facing developed world costs-of-living, I don’t believe it is either sustainable or healthy.

There are some good reasons why a company might turn their attention to Upwork the next time they have a gap in their talent pool.

For one, it’s talent network is huge and — if you’ve ever worked the hiring side — you know that you can receive bids within minutes of posting.

Word of it also tends to travel quickly through informal referral networks — such as friends having coffee.

You sign up, post a job, get some bids, and have a freelancer in time for lunchtime. I’ve used it on the buying side and understand the appeal.

This is why I call this an orange to red flag rather than an outright red one.

Because there are legitimate reasons why a company might do some hiring or Upwork or another freelancer marketplace such as Fiverr. Just probably not all of the time.

If —during your prospecting conversations — the client seems to bring up Upwork / Fiverr / some other freelance marketplace an awful lot, then trust me when I say that there’s a good chance that they simply like to do things on the cheap. Yes, all of the time.

And sorry to break it to you, but you’ll probably be next in line.

Early warning signs:

“Daniel, meet our Marketing Manager. She’s based in Tokyo. You’ll be communicating with her through Upwork” (sorry, make that a late warning sign … by this stage getting out needs to be your focus!)

“We use Upwork a lot. Fiverr and Freelancer.com too. Actually, we’re a remote-only team!” (Hint: your point of contact might be a freelancer too!).

“You’ll be filling maternity leave cover on this project for Y. By the way, she’s a freelancer too!”

“We found our previous two writers on Upwork. They were a little expensive.”

Red Flag 4: They Don’t Understand What You Do

Freelance writing ≠ translation service

If you’re dealing with a prospect who doesn’t understand what you do, then it’s very unlikely that by the time they do they’ll ascribe enough value to it to actually pay you a fee that works for your financial needs.

At the very least, this sets you at a significant disadvantage than a client that understands your value proposition from the very outset.

For instance (at least right now) I have chosen to focus exclusively on (ghostwriting) long-form material for my clients.

Blogs and articles (I’m shooting for less); white papers, e-books, books, and speeches (I’m shooting for more).

That’s it.

To make this easy to understand, I sometimes say “I will write anything longer than 1,000 words in the voice of your team member — and under their byline.”

Those of you familiar with the writing world know that copywriting — skilled writers, often matured in advertising agencies, or nowadays just as often in digital marketing firms, that specialize in the nuances of writing microcopy projects such as landing pages and advertising text — is a slightly different skill-set. And that (if you’re into calling all written words ‘content’, which I’m not) that ‘content’ and ‘copy’ are not generally one and the same thing.

Some writers offer both. I’m not particularly interested in the former, nor have that much direct experience to draw upon. So I have chosen not to.

Likewise, public relations and content strategy are slightly separate skills. Can I do them with some competence? Yes. Is that what I’m pitching here? No.

Despite my marketing communications being pretty explicit about all of the above, I still occasionally find myself talking to prospects who think that I:

Offer a translation service.

Am a social media writer.

Will help them write their next newsletter.

In general, I have found that trying to reeducate these prospects on the market, and on what I do, is a futile endeavor.

If they don’t get what you do period, my recommendation is to move on and save your time and energy for somebody that does.

So long as you are reasonably clear on what service(s) you do offer — and it’s a defined and recognized skillset — you will not struggle to find those that do get you. You just have to get out and find them first.

Early warning signs: Clients has never worked with an ‘X’ before (write/photographer/Wordpress developer) but somehow seems to think they have an encyclopedic understanding of how the industry works and what services you should offer.

Red Flag 5: They’re Happy to Pay Your Rate… But Only For ‘The Very Best X’….Ever

When only the very best ever will do …. nothing might.

I have no issue with clients attempting to set expectations about the standard of work they will deem acceptable.

They’re looking to spend their limited company (or personal) funds after all.

However:

a) Budget and expectations always have to be roughly commensurate. When working with startups, this has a habit of being the elephant in the room. Likewise, companies have to be realistic about what they expect for a given budget — and as freelancers, we have to be proactive about helping them set those.

b) Telling a freelancer you haven’t worked with yet that you’ll be only happy with “the very best” piece of web content/photographs/Wordpress site that has ever been produced in the history of the world in return for your rate is …. well, kind of offputting.

Believe it or not (despite the foregoing!), I have worked with more great clients than I have with rotten ones over the years.

The onboarding phase — when you’re in the formative phases of learning their business and the industry landscape — is a particularly telling one in this respect.

And this is where you will often spot a client that is shaping up to be a ‘bad fit’.

(Note: although, in general, I’m not into corporate jargon, and in fact try to resist using it, I’ve actually come to like the term ‘good fit’, because, as it says, sometimes that’s the best and most diplomatic way of describing a business and a freelancer whose unique needs, preferences, and — say — expectations regarding responsiveness are simply out of sync. And, as I think the term implies, that’s perfectly okay!)

If the client is prepared to invest in you for the long term, as hopefully they are, then they won’t be in a frantic rush to see you produce the greatest article that has ever been written as soon as the ink has dried on the NDA you just signed.

In general, I’m happy to work with clients at a modest rate with the mutual expectation that it might increase as I come to learn their business and produce progressively better work.

When expectations and budgets are in broad alignment, neither party feels taken advantage of and it generally makes for a positive and constructive relationship.

That’s a relationship that we can all benefit from.

Early warning signs:

“We can do your rate, but frankly, it would have to be the greatest article that’s ever been written to justify it. Like poetry — just longer!”

“We demand only the very best of the very best.”

“We hired 100 freelancers last year. Only one made the cut and is still with us. You could kind of think of us like the SAS / Delta Force of the startup world.”*

(I pulled this one out of my fertile imagination, but if you ever hear this, please run don’t walk!)

Don’t Be Deterred and Keep Selling

Keep going … even when the going gets tough!

Those are some of the most salient “red flags” I have come across over the past number of years.

A few final thoughts:

a) Don’t be deterred by the red flags and discouraging clients that you will inevitably come across. It’s part of the learning process every freelancer and small business owner goes through and you will get much, much better over time at spotting them before they’re a critical part of your business and you have to look at ways of extricating yourself from the relationship (before it extricates your sanity!).

b) Trust your instincts. “Gut instincts,” it turns out, don’t come out of nowhere. Feel free to nerd up on the science, or let me give you the TL;DR — it’s honed by your past experiences. Think of it sort of like a machine learning algorithm — the more datapoints (freelancing experience) you feed it, the more accurate and reliable it becomes. If every fiber in your body tells you that this prospective client is bad news ….. have some belief in your self and at least consider listening to that instinct.

c) Just as there are nightmare clients, there are dream ones out there too.

If you’re lucky enough to have one on your book of business, my advice (including to myself!) is to do everything possible to keep the relationship warm.

Here, I have a lot of room for improvement. In-person visits are great if they’re in any way feasible for you — even if, given today’s many options for videoconferencing, there’s usually no actual need to do them. Keeping — and upselling — an existing client is generally less work than finding a new one. Simply keeping a face-to-face relationship going can be far more effective than a holidaytime gift. But why not do both?

d) Many problems that freelancers think of as unique problems to their unusual line of work, or their industry, are in fact textbook sales problems that have been covered countless times before by sales educators. Get your hands on some of this material and start upping your sales game. Unless you’ve struck freelancing gold, you’re going to be spending quite a bit of time running classic sales processes.