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5 Types of Customers That Will Suck The Life Out of You

At a small software company you can’t afford customers that chew up support time with questions that you have already answered on your website, damage your reputation on Twitter, forums and review sites, or call you up at 5 A.M. on a Sunday.

We all have our fair share of crazy customers. But after you waste hours and dollars on the first one, you realize spotting such people early on is crucial.

You can tell if a customer is potentially crazy the first few times they contact you. Just watch out for the red flags. Here are my top 5:

Red flag number 5: The “A.S.A.P. syndrome”

We do live in a fast-paced world, but small software business is like any other small business. You wouldn't expect someone at the local cafeteria to pick up the phone in the middle of the night and fulfill your custom order for a basket of buns, would you? Then why would anyone expect an immediate response when they have difficulty following the installation instructions for your $30 software? I don't really know. Maybe some people expect anything on the internet to happen in a split second, maybe they are really pressed by their boss, maybe they think software can only be sold by large corporations and therefore live support is mandatory, maybe they are simply a jerk.


  • The customer sent a number of letters within 2–4 hours. Usually the letters will be with escalating urgency.
  • Use of my favourite phrase: "please respond asap"
  • Contacts you through multiple communication channels (e.g. Facebook, then email, then your website)

Here's an example:




Hi there it seems that im having trouble following your installation instructions.

Please respond asap


Following are 2 letters asking if I'm available and if I received the first one. This happened within 4 hours.

Even if there was a problem within the documentation, I don't think that being unable to install our software is so urgent. (We don't sell pacemaker software.)

Why this is a potential crazy customer

If you're not offering live support and you happen to respond instantly, this type of customers might assume you're available for a personal chat. And that's when questions start flowing in. It's happened to me a lot in the past. I even invented a rule to prevent people from thinking that I will reply immediately.

Red flag number 4: Constantly finding “bugs”


  • They keep checking up on things, e.g. Running other 3-rd party software that finds problems on their system
  • Rushing into conclusions–if they can't find feature X, this must be a bug. Or, if they have trouble using the feature, this must also be a bug.
  • Generally agitated
  • Reporting that your software “stopped working”

Here's an example:

I would appreciate your help once again. Only now I found out that some features in your software are not working.
[A “bug” report]

Please run <other_software>. It found a lot of errors on my system. I guess they are related to the problem described above. Please fix it asap.

The problem was with their system, not with our software, as I suspected initially, and the customer confirmed 2 letters later.

Why this is a potential crazy customer

Although this type of customers are not aggressive, they are so concerned with every detail that they will flood your inbox with questions. Moreover, trying to replicate their nonexistent bugs will waste your time.

They might even start relying on you to fix any irrelevant issues they have, claiming your software is causing them.

Red flag number 3: Demanding customizations upfront

Usually customers of this type have a lot of pre-sale questions. They worry if the software is a perfect fit for them. If it happens that it isn't, they want to know if it can be modified. Being the sales person in this situation, you try to be friendly, answer all their questions and show your understanding of their needs.


  • Extensive due diligence
  • Refusing to read your FAQ even after you point them to it several times
  • Even:

  • Demanding that you customize the software for them before they purchase (so that they are certain it suits their needs)

Here's a short story that illustrates this situation: Customer wants to use our software, but is uncertain how and if it can be customized. I explain at length that this is off-the-shelf software and describe the controls for customisation that it includes. In the end, I advise them to try out the demo version and see if it suits their needs.

Here's their reply:

Hello can u help us installing the free version so we can chk how is Ur software working with our system and once we find it is perfectly ok we shall proceed it with Ur professional purchase and u can then install that for us as well..


I point the customer to the documentation, but they say they are scared to perform the installation themselves. So, I kindly propose to help. After all, we do provide free support for installation and some customers are really not that tech-savvy. I decide that showing the customer great service is another selling point for me. Why not help them?

I receive the following letter as a response:

Ok u can install the free version for us so we can demo it with all what best u can from ur end changes,, if i like it i will go ahead with it

Now I think to myself: “Does this mean that I'm allowed to install the free version for them?”. I was patient and trying not to judge, but this triggered my “Crazy customer” detector. Still, I install our demo software and let them test it.

Instead of a “Thank you” letter, I receive this:

Hello few things are missing
[A list of 15 customizations that I (supposedly have to) custom code for them. Not a word about “compensating me for my time”, except, of course, purchasing a license.]
If above u can confirm u can customise for us,we will go ahead with buying ur premium version

I explain politely that this is a free support service and I could help with some of the customizations, but if they want bespoke software they have to hire a freelancer. They never replied.

Why this is a potential crazy customer

It's difficult to determine if the customer is just performing due diligence, or they are trying to get something for nothing. But if they request custom work and don't mention paying for it, this is a huge red flag. Imagine what will happen when they have that precious license. They'll stick it under your nose and rub it all over your face. It will be like they own you.

Red flag number 2: Acting like “The Boss”

I will not even talk about how offensive it is to be treated by someone as their employee, just because they deposited a whopping $80 to your bank account.


  • Acting arrogant and/or talking in a demanding tone
  • Offering to pay for your time, so that you can do what they want
  • When they purchase your software, they immediately have a list of complaints, “issues” and customizations
  • They never say “Sorry”, because it's never their fault

Here goes another story:
Customer has a plethora of pre-sale questions, which I answer. They buy the software. We resolve several issues and in the end I help them with a small customization. And that's when it gets interesting. Instead of thanking me, customer accuses me of modifying other bits of software on their system. Of course, I did nothing of the sort and so I say to them. Three angry letters later, the customer realizes that I wasn't the one who caused them trouble. Of course, they weren't sorry.

Their letter looked like this:


I did not hear back from you yesterday. (I did reply within our support hours, but it seems that the customer expected me to be available round-the-clock.)

The issue we had with the other software has been resolved. Please do not do anything with this file, or any other file apart from your software as I have spent money having things customised and dont want that to be affected. Everything is currently working as it should apart from a couple of minor issues being dealt with. (Oh, so somebody else is working on their system, too. What a surprise!)

[Following is a list of things that they want me to custom code.]

Can something be done about this please.

Please come back to me as soon as possible.

Thank you

This was the moment to stop being too nice. I said that our free support service is limited to fixing bugs, helping with installation and answering questions. We currently don't offer customization of our software.

My mistake was to lead this person to believe that I will do anything they want. I should have noticed their attitude upfront and act a bit more reserved.

Why this is a potential crazy customer

The boss is always in control. The boss expects you to get the work done A.S.A.P. The boss tells you what to do next. If you allow a customer to treat you like this, you're in for an explosion the moment you try to say “No”.

That's why this type of customers must know what they can expect from your service, preferably, before they purchase.

Red flag number 1: Sending veiled threats

You might say that people trying to threaten you is not a warning sign, but a complete deal-breaker. Sometimes this is true, but there are a number of reasons for people to act out: they might have had a bad day, they might be afraid you won't help them, and so on.


  • Always in a hurry.The customer wants the job done so much and so quickly, that they won't agree to wait.

Here's an example:
Customer wants me to fix something which is supposedly caused by our software. However, someone else is working on their system at the same time. I reply that I'm going to wait for the other person to finish their work. If the problem persists, I will look into it immediately. I also point out that other issues might arise in the meantime and it's more efficient to address all of them at one go. Customer doesn't want to wait and replies with a veiled threat that they will request a refund and buy our competitor's software.

The letter goes like this:

[Description of the problem again]
also my other developer said the following;

""Hi , I tested it, and sadly the error still there.
[Description of the problem]
If you buy it reciently, and you can request a refund, I recommend to buy , wich have a lot less problems, and in my opinion is prettiest.
Although i dont agree.. i do like your software better.. hope you can fix this other issue.. and i hope these bugfixes will make their way into your newest versions of your software.

Why this is a potential crazy customer


p>Today it's a veiled threat, tomorrow it might be a request for a refund or a direct threat to badmouth you in public. If they really didn't want to use your software, they would have asked for a refund right away. They wouldn’t take the time to email you. Of course, you can't fire a customer because of one crazy letter.

Where is the line?

There is a thin red line between the “being helpful” zone and the “bending over backwards” zone. Stay in the first one and you'll have happy and thankful customers. Move over to the second one and you'll have crazy customers. So, don't let your customers force you to do anything. Pay attention to the early warning signs and trust your “gut feeling”. If you don't like the way a customer is treating you, try to remind them of the terms and limitations of your support service. (Be sure to have them written on your site.) Don’t rush to write people off. Sometimes they are trying to get their job done, just like you.

About the author Gergana Dimova

I use my non-magical persuasion methods to help small business owners, digital agencies, entrepreneurs and consultants get more leads and sales. You can learn more about working with me here.

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