Collecting Payments & Cattle Prodding: Lessons from the trenches

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  • Post last modified:February 10, 2021
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When I first got started freelancing, I was constantly getting ducked when it came to clients paying.

Chasing people for money sucks. At 19, I didn’t have a good way of getting money back. Ultimately I would end up eating the cost, and moving on.

I didn’t know what else to do… head to the nearest Gold’s Gym and hire a ‘debt collector’? It crossed my mind more than a few times.

As I became more comfortable in negotiations involving money, chasing clients has – for the most part – become a thing of the past.

I suspect two things changed to make that happen; both hurdles were essential to growing myself from freelance, to consultant, to now with my little marketing agency, and – looking back at the article as I write this intro – I realize they both came from within.

It has far less to do with anyone else’s behaviour and much more to do with your own behaviour.

First, I stopped misdiagnosing someone ducking a payment

When you’re first getting going in the free market, every project is the project. You don’t have a pipeline of new projects coming in and every project completed is another chunk to put towards rent.

It’s a great goal to have, but it’s not how things will play out. You are now a business and you need to do business things.

In business, you learn that most sales happen after the 5th, 6th, or 7th+ follow up. Most people give up after 1 follow up, but I’ve seen the number 6 cited as the number of follow ups needed to secure 40% of any number of projects. In other words, any less than 7 follow ups all but guarantees that 60% of your sales efforts will fail.

From the above linked article, I’m pasting the following:

How many follow-ups will it take to get a response from your buyer? Maybe 2 or maybe 12. Heck it might be 20 spread over a year until they are faced with year-end taxes or some other life event that spurs a decision.

Nancy Bleeke

Up until now we’ve been looking at things through a sales lens, but the same can be said for following up on outstanding invoices.

You don’t really have any idea where their head is at, or why they haven’t responded. They might might be out of office, they might be busy with something else, they might need to speak to a boss, or any number of other things… they might’ve already submitted your invoice to their Finances department and are expecting to hear back in a few weeks, the cheque might already be in the mail!

You have to give people time to get back to you, and that takes a level of persistence which is totally acceptable, but that you’re not comfortable with.

It’s normal. Don’t feel like you’re being annoying… they’re not noticing that… that’s just how you’re feeling about you. Get over it. You need the money. It doesn’t need to be a big thing, or emotional… you just need the money.

So follow up, be polite, keep it friendly. Don’t assume they’re missing your calls or not responding to your dm’s for a reason (“The message was marked as ‘seen’ 12 minutes ago!” 😡 ), they’re probably just busy doing business things.

Your little slice of work on the project might be over and done with but maybe they’re trucking on with tight deadlines, and things are moving in that direction. Business takes time to come to fruition.

Eventually, with good sales habits, and good follow ups, you will learn the importance of deal flow and having a pipeline of projects coming in; and of being busy at all stages of the pipeline.

Side note to freelancers looking to go full-time:

I learned the concept’s of ‘deal flow’, and the importance of a project pipeline from Warren Buffett’s letters to Berkshire Hathaway’s shareholders when I was first learning about business, which blew my mind, inside out.

They are highly recommended reading to all freelancers looking to go full-time. They are chock full of Mr. B hammering home the fundamentals of business and will serve you well as you grow and need to make larger and larger decisions.


Secondly, I started following up like a Bloodhound

When you’re first getting going in the free market, you’re typically coming at it from a puritan perspective. You have a skill, you have spent years honing that skill, and now you want to go through life exchanging your skill for money.

It’s a great goal to have, but it’s not how things will play out. You are now a business and you need to do business things.

And part of being a business is ensuring you get paid. Since we know that – more often than not – the client isn’t necessarily unresponsive because they’re hiding from you, but more likely because they’re busy with other stuff.

In this case, it’s perfectly normal to send a follow up every 3-5 days. In some cases I’ll do so daily.

Let’s take a look at how to hound a client without going down the rabbit hole of blame

Recently, I had a situation on the Codeable platform – where I drum up work when my team and I aren’t particularly busy with client work – where a client got cold feet at the finish line, but was nervous to say so.

We’d already completed a (small) task consultative where we hopped on a call for a couple hours and ironed out the details for some work he needed done.

Here’s a brief run down of how those follow ups went.

(Name’s have been changed to protect the innocent! 😂 )

Hi Amy,

It’s been a couple weeks since I heard from you, so I’m checking in to see if this is still in the works.

If so, do you have an idea of when you’d want to start?

In either case, I have a task for you – can I get you to come mark the phone call task as “Complete”? This just tells Codeable I’ve done my job on that, and allows me to get paid.

Hope you’re having a great start to your year!

Talk soon,

Message sent January 5

No response. I was gone for a few days, and when I got back, I followed up again, a little more aggressively.

Hi Amy,

I haven’t heard back from you on this, so I’m going to assume you’ve gone in a different direction or your priorities have changed.

That’s totally okay, but I still need you to swing back onto Codeable and mark our Consultation Task as completed so that Codeable knows the phone call happened and that you were happy with everything.


P.S. Let me know if I can be of help in the future; I’d be happy to work with you again.

Message sent January 15

Nothing. Three days later I follow up again. This time I address the elephant in the room.

Hi Amy,

Can you mark our Task as complete?

This allows me to get paid for the call we had together.


Message sent January 18

Tada! I receive a response. The client apologized for the delay and says she’s “OK to proceed with the initial quote,” alluding to a second project we’d been discussing. Following that, she asks, “Should I still mark the consultation task as complete?”

Here, the goal is to strike while the iron is hot. I respond a half-hour later:

Hi Amy,

No problem – I totally understand. Nice to hear back from you!

So yeah, feel free to mark the Consultation as complete (nothing will change here in the Workroom, we’ll still be able to chat, etc.)

[…message continues…]Message sent January 18

After a short back and forth, I submit an updated Estimate for the second Task on the 25th and… she ghosts on my again.

I continue my follow ups in the same order, starting with the opinionated email from before…

Hi Amy,

I haven’t heard back from you on this, so I’m going to assume you’ve gone in a different direction or your priorities have changed.

Feel free to mark the Consultation task as Completed when you get a chance.

Let me know if I can be of help in the future.


Message sent January 25

Shortly after, I got paid. 🎉

Lesson? Never under estimate the power of persistence.

It’s a little bit like cattle prodding 🐄. … your intention is to be constantly prodding with small follow ups, in order to stay top of mind.

The above example is by no means an outlier, or the only one I’ll have this year. They’re just busy.

I’m okay with that. I’m totally okay with that; it’s a part of doing business.

Once you internalize that the market’s not against you, it’s just got a lot of moving parts and you’re in charge of all the pieces in your little part (your business). When it comes to sales? You’re the guy. When it comes to finances? You’re the guy. When it comes to Quality Assurance? You’re the guy. When it comes to Project Management? …

You’re getting the picture…

The point is, follow ups are the life blood of your business. Enjoy them.

And I’m not talking about “check ins”… no one likes a check in. We’re talking about conversations, and following up to get a sale, drum up business, or get you paid.

How these have transformed my payment collection process as a freelancer, consultant, and SEO agency

The main tenets of my approach to getting paid involves follow ups, and to get myself there mentally I had a couple mental hurdles to grow past:

  1. Not blaming the client for anything – Once I’ve stepped back and realized that there are a lot of moving parts to business and that they’re probably just busy, or it hasn’t become a priority for them here & now, and that it’s just a part of the process, I can clearly see that my time would be better spent by letting go emotionally, sending a quick follow up & getting on with my other tasks.

    This was a little bit hard for me in the early years which were hand to mouth for the most part. Once I realized my goal wasn’t to get paid today, but to get paid every week, or every month, then I was allow to zoom out, focus on the bigger picture stuff, and follow ups just became another friendly touch point with my business.
  2. Being persistent – No longer tied up to the emotionally charged, “no, fuck that… they owe me!” (which is ego-driven bullshit), It boils down to ‘you don’t need to be mad to be owed’.

    Getting paid is a part of business, and it takes effort; it’s not personal. Just know what you’re owed, and follow up politely until you get paid or they say no, or the line goes dead.

    Remember to frame ‘getting paid’ as a necessary piece of the puzzle. Don’t make every interaction about getting your piece of the pie, but make sure it stays a relevant topic so that when you decide that the rubber has met the road and you don’t want to move forward until you get paid, there’s precedent.

It’s worth mentioning here, that I’m not talking about dealing with a client who is actively refusing to pay… That falls under a totally different category.

Don’t blame the client for not wanting to pay, it’s natural

Paying people is painful. Now I’m not saying it’s normal to refuse to pay for products or services, but what I’m saying is it’s understandable why paying someone your hard-earned money gets glossed over for other, more pressing issues.

Let’s face it, when your brain is faced with paying someone money, or doing something else, most people would prefer to not have to pay.

And you may be different… Maybe your personality wouldn’t be okay with that, and that’s cool, but you’re in the free market now, and can’t expect the World to adoopt your Worldview as its own.

I understand this concept of not-paying temporarily feeling better than paying, and I allow the client to go through that a few times before I tighten the screws. In the mean time, I communicate what’s left in terms of their responsibility and in doing so clearly communicate that I’m not going away, without having to resort to saying it outright.

Be polite and persistent, this should not be an emotional endeavour

Follow up constantly, but never getting pushy. Follow up, follow up, follow up. Until you hear, “I’m not paying,” always assume the client intends to pay.

I always assume that he will – in good faith – pay for the services rendered… most business owner’s don’t want to rip people off. Mostly, when a client isn’t paying you, it’s because he or she is just busy with other, more prying, more-important-to-them issues.

And therein lies the crux of the issue.

When it’s your money… owed to you… you’re thinking about you. And your client isn’t thinking about you. They’re thinking about them.

It’s not that they want to rip you off, it’s that they’re busy and being pulled in different directions. In fact, you’re the only one thinking about you. So that’s your role. You respresent you.

And that’s why following up is essential. You are your own representative. It’s egotistical to expect someone to schedule paying you into their busy schedule – yes, even if you’ve already completed the work! – and if you instead re-frame that so that it’s your job to ensure the pending payment stays top of mind, you’ll find that very often they eventually come back to you and say “Hey, ok sounds good. Thanks for sending this over. I’ll get you paid today.” as if it’s not three weeks late and sure enough you’re paid an hour later.

That’s what business looks like, and when you realize that, you’ll find that non-paying clients seem to fade away because your professionalism denies the opportunity.

I hope that helps you understand my approach to following up as a freelancer, but if you have any questions don’t hesitate to ask in the comments below.

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