Navigating the Challenges of Difficult Clients

Have you ever had to deal with a pissed off client? Were they pissed off for real reasons, or was it something else? How do you handle it when a client is frustrated for real or imagined reasons? Today we’re talking about how to navigate our way through these situations because how you course correct may be the difference between a client sticking around and a client hitting eject.

My name is Adam Hannemann. Welcome to Ramblings of a Geek. I’ve been in the MSP space for a long time. Something like 25 years or so. I have definitely had more than my fair share of irritated clients. Sometimes they were pissed off for solid reasons, but some were let’s say a bit embellished. It was a thing I was good at dealing with. In fact, a former client used to call me the apologizer in chief.

Here’s the deal. IT support is a tough gig. Things break. Humans running the technology make mistakes. Humans that are end users make mistakes. Technology malfunctions. The whole industry is rife with opportunities for error. Handling these errors and managing your clients frustration is something best prepared for ahead of time instead of reacting to every incident that happens.

Today, I’m going to talk about handling difficult clients. I’ve already covered how to manage clients who don’t follow your support procedures, but now let’s dive into those who cause frustration for various reasons. There are a few types of challenging clients worth discussing:

• The Grumpy Client: Always complaining, whining, or angry.
• The Technically Inept Client: Struggles with technology or refuses to learn.
• The Late-Paying Client: Consistently fails to pay bills on time.
• The Once Burned Twice Shy Client: The client that has had bad experiences before and won’t let it go.
• The Legitimately Pissed Off Clients: Sometimes you drop the ball. They noticed and aren’t happy.

Let’s break these down one by one.

The Grumpy Client

Grumpy clients can be a handful, but it’s important to understand the root of their frustration. Sometimes, it’s not the entire client organization but a few noisy users. Here’s how to approach it:

• Understand the scope: Is this a single user or a couple users or is it more systemic than that?
• Business Review Meeting: Schedule a meeting to understand their pain points. Are there underlying IT issues? Is the business owner struggling with something else?
• Solve the solvable: If there are issues that are solvable get in there and fix the issues. Remove the pain. Remember the fable of the lion and the thorn. Fix the pain if possible.
• Thick Skin: As MSPs, we need to handle grumpiness with patience—as long as it doesn’t escalate to belligerence. If the issue isn’t solvable, will take some time to get solved, or even if it’s external to IT (maybe it’s their culture) having a thick skin helps.
• Ejecting Clients: If the grumpiness is pervasive and you don’t need their revenue, it might be time to part ways. This is especially important if the issue is solvable BUT they’re unwilling to go through the process with you to solve the problem.

For individual users, try to understand their frustration. Maybe they feel insecure about their tech skills. Partner with them to teach and support, and you might turn a critic into a fan.

The Technically Inept Client

Clients who struggle with technology can be challenging, but they also present an opportunity to add value. Here’s how to handle them:

• Target Client Profile: Decide if you’re okay working with clients who aren’t tech-savvy. If so, invest in training and patience. If the vertical you support is filled with non-tech-savvy companies you know what you’re getting into. If that’s not the case, you just need to solve for the “normal” amount of technical ineptitude.
• Patience is Key: The first thing you must do is be patient. Remember, you likely couldn’t do their day-job so giving them some grace for not being super users is smart. This is a thing you should instill in your team as well. I had this coaching conversation so many times in my career as a leader that I’ve lost count. Also, I had a really good elevator pitch about this while working with clients too.
• Training Resources: This is your opportunity to generate content to help your clients out. Create videos, blog posts, or webinars to help them learn. Use AI tools to convert training content into transcripts or guides. The added benefit here is that if you can make this content general enough you can use it on your website, YouTube, and social media channels to help more than just one client out. It also will help drive traffic to your business via SEO and other social reach which may help your sales efforts. Depending on how good at training you get, you could even leverage training as a service that you can use to generate more revenue by putting on training classes for your clients.
• Evaluate Fit: If a client has no desire to improve their tech skills, consider whether they’re a good fit for your business. Ultimately, if you don’t have the patience to push this Sisyphean rock up the hill you may have to eject clients that won’t or can’t get it.

The Late-Paying Client

Clients who don’t pay on time can disrupt your cash flow. It’s important to have a plan to manage this ahead of time. Ideally, you don’t have a bunch of broke clients. I’ve seen enough situations where the MSP almost encouraged clients to not pay because there was no penalty for late payment. Let’s fix that.

• Strong Contracts: Include clear language about late fees and consequences for non-payment. Make it clear that you expect that they’ll pay their bills on time. Not paying = no service and eventual shut off of their cloud licenses and late payments.
• Clear Process: Make sure that you have a defined Accounts Receivable process along with how you handle late payments. I talked about this in a previous ramble about your core processes.
• Auto-Payments: Encourage or require clients to set up auto-payments to make everything simpler. Make this part of your onboarding process and address this in your sales process. In a perfect world, every client would sign up for auto payments. Make this the default option.
• Take Action: If a client is consistently late, stop services until they pay. Be firm but fair. As Brad Gross said in an earlier video, “When one party doesn’t perform under a contract, the other party doesn’t have to perform their end.” Meaning, if they don’t pay, you don’t provide service. The best practice here is to have a solid process for handling late payments.

The Once Bitten Twice Shy Client

This client has had previous experience with MSPs and at least part of their experience wasn’t great. Then they carry all that baggage to your relationship which makes your life more difficult. OR you made a mistake before and you’re paying for your past screw ups.

1. Learn where this stems from: Was it you or was it a former MSP.
2. Address the concern head on: If it was you that made the mistake own it. If it was the former MSP let the client know why this won’t happen with your MSP. Have some empathy for their situation.
3. Prove that their concerns are in the past: Execute on great service and make it clear that the issue won’t come back with you as their service provider.

The Legitimately Pissed Off Client

Sometimes you make a mistake or your service slipped for some reason. Shit happens, and sometimes you’re the one that created the frustrated. What do you do when the cause of their frustration is you?

1. Own the issue: If you caused the problem own it. Let the client know that you know that you caused them the pain and that you are working to solve for it. Do NOT hide or try to ignore the issue away. Especially if many clients are seeing issues. Communicate with your clients. Your clients will (or should) understand that we’re all human and sometimes mistakes happen.
2. Be transparent: Be as transparent as you can. Tell your client(s) what happened, how you’re going to fix the issue, and that you are sorry for the trouble. Careful with your language here. Don’t say things like We’re sorry if we caused inconvenience. You are sorry for the inconvenience. The last thing you want to do is to do the equivalent of telling your spouse that you are sorry that they took the issue that way. You made the mistake. Don’t gaslight your clients (or your spouse for that matter).
3. Solve the problem: The best cure for a mistake is to correct it. Fix whatever the issue is as quickly as possible. If it will take time, give a realistic timeframe and pad it just a little to give yourself some wiggle room.
4. Communicate after the fix: Once whatever the issue is has been resolved communicate again that you believe the issue is solved. Also communicate what you learned and how this will never happen again.
5. Correct your process(es): Here’s the important part — do NOT let this become a repeat thing. Solve the root cause of the problem so it doesn’t continue to come back. Most clients will give you some grace for mistakes as long as they’re not repeated or frequent.

Final Thoughts

Handling difficult clients is part of the MSP role. By understanding their challenges, providing solutions, and setting clear expectations, you can turn frustration into loyalty. Remember, life is too short to work with clients who make your job harder than it needs to be.

Thanks for coming on this ramble with me. I hope to see you on the next one.