5 min read

Should you keep working with a difficult client?

Find someone who says that they love every client equally and you’ve found yourself a liar — at least, they may lie to themselves. The client-accountant relationship requires a lot of give and take, and some clients are so focused on the take, they forget the give part.


Your difficult client doesn’t have to stay that way. While some cases will definitely fall into the “it’s not you, it’s me” type of soft breakup, others can be saved by stepping back and looking at the situation constructively.

Should you try to save every client relationship? Maybe if you’ve always looked up to Sisyphus. Since most of us don’t see the pleasure in pushing a boulder up a hill, it’s more reasonable to take a look at why your clients are a pain point and assess whether it can be fixed with a change in workflows or the systems you use.


Why is your client a pain point?

There are a lot of reasons a client can be a pain point for you, and it’s important to remember that not all can be fixed. Let’s go over some of the most common examples of pain points that actually have potential fixes.

Poor communication

Radio silence for months on end? Frantic late-night messages asking for up-to-date reports? Only answering one of your asks in your latest email? Michael Scott says it best.

Client communications can be hampered for multiple reasons. In some cases, it actually is just their style of communication. But in others, it can be their circumstances. Business owners have to wear many hats and oftentimes, the communication hat starts collecting dust as they prioritize other responsibilities.

Understanding when someone is one or the other is essential to ensuring you’re not putting in your efforts where they won’t pay off. Someone who’s distant because they don’t value your work likely isn’t going to become a favorite after just a few changes — especially if they still don’t value you. But someone who’s flustered and has their attention elsewhere might just need you to change your approach to communication or document collection to get back on track.

Late getting to requests

What’s worse: radio silence or someone acknowledging your request but never following up? Trick question: they’re both bad.

they are the same picture meme

The reasons someone is late on getting to your requests can be the same as people with poor communication: they’re just preoccupied with other things. But it can also be disorganization or procrastination: they see the request, they know exactly what they need to deliver, but they want to take care of something else first or they’re not in the mood to do it right now. How you approach the situation will depend on the case.

Unrealistic expectations of you (and their business)

To make it in business, you need to be confident — maybe a little too confident. You might call it self-centered or maybe even main character syndrome, but one thing is for sure: these people will not look at themselves as the problem whether it comes to the success of their business or the level of service you’re able to provide.

Even worse is when you have to tell them things aren’t going according to their (extremely ambitious) plans. When the numbers don’t show profits soaring and exponential growth on the horizon, they can get confrontational and potentially believe that it’s not the business that’s wrong, but the numbers.

the books must be wrong meme

These are the clients that are hardest to please. There’s a gap between the outcome you have to deliver, as is your duty as an accountant, and the outcome they want to see. Bridging that gap can seem impossible at times. But not all of them are a lost cause and there are paths to take that can align expectations before you decide to end the relationship.


How to right the ship

Discard that drafted email saying that you need to move on from the working relationship and put a pause on the breakup ballads playlist. If any of the above examples resonate with you, there is a way to possibly turn things around and maybe even turn that “pain-in-the-ass” into the pride of your portfolio. Too far? Maybe, but try these solutions out first before you decide.

The absent entrepreneur

When someone is constantly ignoring your messages and requests, the first question to ask yourself is why. In some cases, a change as simple as how you reach out can be effective. For example, switching your touchpoints to phone calls can put your client on the spot to do what you need and make it tougher to ignore.


If someone is potentially too busy and has been absent for a while, reaching out with a bit of empathy can show your concern beyond just your ability to deliver your services. Asking if they’re feeling overwhelmed can help you diagnose what’s causing the issue and easily segue into whether your method of communication works for them.

Suggestions on how to fix the relationship:

  • Try setting up a regular communication cadence. Having a regular time where you go over specific things that your client needs can show them the value of responding to your questions quickly. Don’t depend on just one medium, text messages or phone calls can be more effective in spurring action.

  • Provide them with your schedule or use Calendly to empower your client to select a time that works for them. Giving your client the ability to choose a day and time to talk can make them feel like communication is their choice as opposed to a task that can be ignored.

The persistent procrastinator

The longer you’re in accounting, the bigger your database of excuses for not following up on an ask in a timely manner. But the big difference between the persistent procrastinator and the absent entrepreneur is that the procrastinator understands why they need to deliver on your asks, they just struggle to find the time or prioritize it.


Rather than changing up your communication styles or frequency, the better approach is to look at how you can make the fulfillment of your requests as easy as possible. You want to make that mental hurdle of doing the work as small as possible so they can’t get sidetracked, or better yet, they know they can get it done right then and there.

Suggestions on how to fix the relationship:

  • Reduce the barrier of entry for document collection. The more of a time investment you’re asking from a client, the more likely they are to ignore it. A change in your technology that streamlines this experience can make them more consistent in delivering your needs.

  • Ask them if there’s a time of day they have the most amount of free time. For example, sending over a request in the morning when they haven’t gotten started on their day yet might help them find a time to follow up on your requests.

The demanding deliverables

We saved the hardest for last. The client who is overly demanding or seeing their business through an overly optimistic lens is difficult to correct. They will require the most time and effort in course correction, because you won’t get a quick win. Instead, it will be a gradual process of aligning and realigning expectations.

Make the time to really talk to these clients and ideally have documents like a letter of engagement that sets the standard of what you can deliver, on what timeline, and why. As for their unrealistic expectations, it’s going to be a process of understanding their long-term goals to identify how you can better serve them.

Suggestions on how to fix the relationship:

  • Realign expectations with your client, ideally with your letter of engagement. Focus on what they can do to ensure you’re able to deliver your service effectively to meet their needs. Be sure to cover turnaround times for requests and what they can do to minimize them.

  • Discuss long-term plans and what you can do to help them achieve those ambitions. Sometimes the friction in a relationship with a client isn’t because of the service you’re providing, but rather a disconnect in your client’s perception of how it fits into the bigger picture. If you can show them how what you deliver will help them on their path, they will be more invested in supporting you in getting your work done.


Can you cultivate a difficult client into a fave?

Tending to clients is like tending to a garden — Sometimes you can save the plants and other times the climate just isn’t right for them to flourish. The difference is a plant won’t blame it on you, tell you about it, and leave a negative review warning other plants to never be planted there.

Hopefully your painful clients haven’t gone so far. And with these tips, there’s a chance you can turn the most critical of commerce curmudgeons into champions of your service. The key is to pinpoint why they’ve become a painful client and how you can work to address it.

It will take time to do this effectively, but time is a finite resource. To deliver excellent service to all clients, start by looking at the tasks you can automate with software like Botkeeper. With powerful AI technology driven by machine learning and input from fellow accountants, you can make account reconciliations, report generation, and more a thing of the past. It’s the kind of efficiency that will make you a hero with all your clients, even the more challenging ones.


Get started today!