How to Sell Problems

Hello! I build IT teams and design IT Systems for startups and nonprofits. I consistently encounter the same problems, so I set out to create a series of guides to help others navigate the IT Ecosystem. You can learn more about my philosphies via my website or via my weekly newsletter.

For 13 years, people have been selling me problems between the hours of 9:00a and 5:00p. I’ve been the personal recipient of tens of thousands of sales pitches over the course of my career — the Mark Cuban of IT — and I’m going to show you how to increase the chances of selling your problem.

But first, I want to share an embarassing story with you.

When Google Pay was released, there was a promotional $30 credit if you completed certain ‘challenges’. For whatever reason, there’s a part of me that loves these things, so I signed up.

Before it ended, I finished most of the challenges except for one that requires buying something from an offer in Google Pay. When I notice a 20% off on Etsy, I thought, “Okay, I recently moved — I can find a bench or something” — and sure enough, after activating the offer and reading the fine print, I found and ordered a bench on Etsy using a card linked to my Google Pay account. A week later, the offer expires without showing as completed and the 20% doesn’t show up.

If this were you, what would you do?

A History of Problem Selling

Humans often require the help of other humans. Whether in the form of direct collaboration, advice, or when something breaks, most will reach out but we’re woefully inadequate at asking for assistance.

In his book, The Laws of Human Nature, Robert Greene outlines strategies ripe for adoption should you be in the business of human psychology or manipulation. At a generic level, his insights provide recommendations that are useful to employ when making requests of others. Because, let’s face it — we’ve all been there.

  • “My mouse is broken.”
  • “The item shipped to me wasn’t the item I ordered.”
  • “Excuse me, I’m just visiting and my parents are trying to meet me but my phone isn’t getting a good signal and I can’t find the place on the map where I’m supposed to meet them 20 minutes ago. How do I get to Penn Station?”

But tell me — why should anyone help you? Put yourself in their shoes — you’re in a support role and upon arriving at work, there is 10, 20, maybe 200 problems sitting in your queue before you even sit down. Which ones are worth doing?

If you’re selling your problem correctly, then you’re offering something in return for choosing it— a hit of dopamine. Helping others is an act of kindness and when people successfully help other people, they receive a little reward to increase our special survival rate.

We need help and they can feel good about giving it, that’s a situational win-win. But when you’re competing for their attention with 200 other people, how do you increase the odds that your problem is the one they focus on fixing?

Generally speaking, there are productive ways to ask for help and unproductive ways to ask for help, but the latter is our default method! For everyone reading this article, that means you’re going to change your default and increase your likelihood of receiving help. Because —

When our request for help is unproductive, we fail to achieve our desired outcome.

In order to become more effective at achieving our desired outcomes, let’s flip the script and look at each of these interactions through the lens of selling a problem.

Effective Problem Selling

Be brief, specific and if you can, state the impact. Just remember, selling problems is all about BS.

First and foremost, this is how you sell problems.

  1. Create a problem statement,
  2. List the steps you took to resolve the problem,
  3. Provide supporting evidence (screenshots/error messages/order numbers), and
  4. Indicate how the problem is affecting your ability to function.

James is an IT Support Technician. He works within a ticketing system that has 25 tickets assigned to him at any given time. The company tracks how fast he closes tickets, the success rate of resolution, and how many tickets he completes in a month. In other words, James is incentivized to resolve as many tickets as possible and he becomes adept at buying tickets conducive to that end.

Alternatively, James has been your friend for years. Outside of work, he has to get groceries, mail a letter to his Dad for Father’s Day, and get his car alarm fixed. He tries to cook and fit in exercise, but doesn’t have much time. In other words, James is busy but you two are friends and as a result of relationship norms, you support each other.

Whether as a colleague or a friend, you need to ask James for help. In the first case, James is incentivized to buy easy problems. In the second, he has competing priorities which reduces the likelihood that he buys your problem. In each instance, how can you maximize the likelihood that he does help and make it worth his while?

As a Colleague —

Technically, James has to help you. But there is helping you and there is “helping” you. Have you ever said, “Gee — Why is it taking this guy forever to fix this seemingly simple problem of mine?” That’s him “helping” you. In other words, you failed to sell him on solving on your problem. He is indicating that he is not buying your problem until you incentivize the purchase.

Hi Buyer,

How are you? I hope you had a good weekend.

I’m reaching out because my mouse doesn’t move the cursor on my screen anymore. I tried rebooting my computer and plugging it into a different port, but it simply isn’t working anymore. If it sounds like it’s dead, could I have a new one?

Thank you,


As a friend —

Hey Buyer,

Long time, no see. What’s up??? Reaching out because I could use your expert computer advice. I need to day trade the opening tomorrow so I can pay my rent and my mouse straight up isn’t doing anything. I plugged it into a different port and restarted the computer — nada. Can I bug you for some help?


In either of the examples above, James can do the following in under 15 seconds.

  • understand the problem,
  • skip outlining troubleshooting steps,
  • prioritize the problem amongst other problems, and,
  • offer a new mouse to fix the problem.

By including a problem statement and steps you’ve taken to the address the issue and how the problem impacts you, you’re showing James that:

  1. Your first reaction to a problem was to try and fix it yourself, and,
  2. You took common-sense steps to resolve your own issue, and,
  3. You trust him to slate your problem accordingly within his list of priorities.

As a result of this, James can skip the mental investment and simply provide a new mouse (dirty secret — IT people have xxtra mice laying around). You’ve reduced the barriers to him buying your problem and thereby increased the chances of achieving your desired outcome at little/no cost to James.

Let’s Review

To maximize the likelihood that you achieve your desired outcome, you will:

  • Craft a problem statement,
  • Include steps you’ve taken to fix the issue and screenshots/error messages of the issue,
  • Briefly state the impact the issue has on your ability to function.

Next, we’ll explore the top three pitfalls of selling problems. For each, I want you to put yourself in the mindset of a buyer. Someone is trying to sell you a set of knives — go!

Help Until Proven Guilty

When we feel guilt, we’ll include a lengthy back story and extraneous details to implicitly justify why the other party should help us or act as a distraction.

It turns out, guilt plays a major role in our decision making processes and the intent here is to weed it out of your sales pitch.

When someone feels guilty, they’ll include extraneous information to mask their request for help or reduce the burden by reframing it as a story, or provide additional information in the hopes that in it, you will find justification to help them. In most cases, this isn’t necessary so let’s look at an example and spot it in our own circumstances.

Hello Buyer,

Three weeks ago, I signed up for Google Pay because I saw the spring promotion rewarding $30 if all of the challenges were completed. I promptly completed most of the challenges but the promotion expired before the last one registered on my account. In fact, it still hasn’t shown as completed even though I know I did everything exactly as was asked. I added the Etsy 20% offer and bought a stool that was over the requested amount using a card linked to my Google Pay account.

I’m not sure how this could happen. I’m trying to figure out how to get the offer to apply and if it’s possible, complete the challenge for the reward.

Thank you for your help.


There’s a few problems with this approach, namely, the problem isn’t clear and the requestor doesn’t seem to understand the problem either. They seem to be asking you to identify the problem and solve it.

If we view this sale through the lens of James, we’ll see that there is a lot of useless information in the request. As a result, James has to expend more time and effort to extract the problem, identify any steps taken to resolve, and understand the impact. This makes it much less attractive to him and unlikely we’ll achieve our ideal outcome.

Guilt is the enemy of brevity. Eschew it.

Righteous Indignation

When we feel righteous indignation, we’ll be confrontational, short of patience, and directive — just do the thing because I’m right!

In the U.S., there is wide condemnation of a stereotype dubbed ‘karen’. Lacking a male equivalent is sexist, but for the purposes of this article, it’s used to exemplify entitlement and lacking empathy.

It is very difficult to sell problems under the guise of forced acceptance and payment. This will immediately put the buyer in a guarded or defensive posture and reflects poorly on the seller. Here is an example:


I downloaded the google pay app and went through all the hoops to get the $30 for the challenge. I even used the etsy offer but it’s been 7 days and it still hasn’t posted a credit to my account AND I don’t even have the reward for completing the offer. When can I expect this to go through?

This seller often provides inadequate information to the buyer and appears confrontational. After a few months of buying problems, James will learn to identify these themes and it will become one of the least attractive problems to buy. Specifically, it requires extended conversations where no amount of apology or restitution will ameliorate the buyer’s righteous indignation.

Sellers who consistently bring these problems to the market lack introspection and may be averse to modifying their sales pitch. If you are overcome by emotion and try to sell a problem via this pathway, your best bet is a follow-up with a level-headed apology to the buyer in the hopes of garnering empathy for your cause.


I recently messaged you about a problem with my Pay app, specifically, not receiving the challenge reward nor an offer discount. When I sent this, I was frustrated with the circumstances and upset that it did not work as expected.

I want to apologize for being impatient with you and ask if you can help me determine where I went wrong in applying the offer so that I can receive the reward. Below are the steps I took.

Step 1, 2, 3

Thank you,


Now the buyer can relate! They too have experienced frustration with technology and can empathize with your emotional reaction. At a minimum, you’ve made this problem relatively purchasable, as it will require some back and forth but in the name of our common enemy — frustrating technology — it’s worth it.


Worst of all, some sellers will try to pass the problem onto another party like a cat laying a dead mouse at your feet, “Here you go! Deal with this!”.

In this scenario, a seller attempts to exercise implicit obligations of a societal, social, or work relationship. It is unlikely they will a find a buyer for their problem because this pathway implies that the buyer must also assume the role of seller — in other words, they have to sell problems to themselves.

Hey Buyer,

Over the weekend, I noticed that the Pay app didn’t apply a credit to my account for the Etsy offer. Can you look into that for me? Needs to get fixed.



Also known as a dead-end approach for buyers, this type of sale looks and smells like a trap. It doesn’t offer any compensation for buying it other than assuming the ownership of something that may never come to a satisfactory resolution.

Nobody likes to take over debt and any follow-ups with an apology will be dubiously regarded as the buyer cannot relate to the level of gall one must possess to attempt this sales strategy. It’s best to avoid this one altogether.

Wrap Up

If we strip away all of the context and emotions, what’s left is a goal we’re trying to achieve with another person’s help.

Let’s look at some new context conducive to problem selling—

  1. An item/service doesn’t meet our expectations,
  2. Text a friend to see them but don’t offer a plan,
  3. Message a support team at work for help with paystub/mouse broken/out of pens.

Without judgement or justification, these examples can be reframed as:

  1. an expectation that differed from reality,
  2. a lack of empathy,
  3. exercising obligations of a societal or cultural role relationship.

Which, in the end, are all excusable or fine conditions for selling problems. But regardless of the circumstances, any sale that aims to be sold must include the following:

  • A problem statement (#2 above — I haven’t seen you in a while)
  • Steps taken to resolve problem (#2 above — I keep forgetting to text)
  • Impact due to problem (@2 above — I am sad and miss you)

And ideally be:

  • Brief (wanna hang??),
  • Specific (out and get lunch at sweetgreen tomorrow? ❤).


Hello, I know why you’re all the way down here. Fine, I’ll tell you.

I messaged Google Pay Support because mky ego couldn’t let it go and I failed to control it. However, I included screenshots of the receipts, charge to my credit card, and the offer on Pay. I specified my compliance with all of the terms.

I was a little indignant, foreshadowing what ultimately came to be — that I would never be passed to someone with authority to reverse the unfortunate circumstances of not receiving recognition for challenge completion. Yet, their inability to close unresolved issues combined with my infinite resolve for stubborness, means that months later, the issue is still in progress.

I haven’t sold my problem yet.

Reach out!

These recommendations are just the tip of the iceberg when it comes to organizational technology postures. Please reach out to me at to discuss more or sign up for my newsletter —



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Dave Bour

Dave Bour

Building IT infrastructure and teams where there was none before. Fitness, wellness, and adventure enthusiast. Engagements at