4 Ways to Work With Challenging Clients

Eilis Gregory
5 min readJul 8, 2021

Sometimes collaborating with a client can be challenging. You may have difficulty connecting with them on a personal and professional level. It could be cross-cultural. You are in the US and they are across the pond. Whatever the reason, this may make progress difficult or make the work less enjoyable. There were times I felt undervalued or appreciated because I was alone in a lot of the process. Set adrift with little help. So when the project closes, it was unceremonious or expected. And yes, I know that’s what a job is. But here’s the thing, learning the ins and out the hard way made me resilient and when faced with the same archetype of problems you get better at recognizing and managing them. Here are 4 ways to collaborate with challenging clients:

1. Know Your Audience

This sounds like a given. What I mean here is that you should take the time to do an assessment of your client. Do you know their “What’s In It For Me?” motives? Sometimes it’s obvious it’s getting a project or a body of work done. Other times it’s not clear. Here, it’s important to work on getting objectives and goals written and agreed to. Understanding and delivering on their needs is easier said than done. Get beyond the surface level and take time to hear what they are saying. People reveal through their works or body language a lot of their thoughts and feelings. Sometimes they try to mask it. Dig into that layer (Be discreet! We’re trying to be professional here!). The other part is that you need to build trust in the working relationship. You may be an unknown and to them it’s the same as being unproven (yep….). Showing your capability and flexibility to manage the work will help, especially if you are delivering results. Think of this activity as if it were a Facebook profile but for projects/work. What priority level is this work? Is it mission critical? What are key deliverables that make this exciting for them? Do they have competing priorities? Are they they project sponsor or are they their company’s liaison? These are just some questions to start with. By being able to answer the questions to your list of questions will help guide and navigate the occasional challenging client.

2. Plan with Your Client

One of the key things that makes any work successful is involvement with the client (Unless they explicitly say they prefer not to be). And that will be a red flag. Clients need to be collaborative at the distinct steps along the way. They either need to decide or give feedback so that you can move the work along and ensure it is baseline to their expectation. In the past, I’ve worked with many clients that want to see results but not be a part of it. It’s hard for me to speak to that for all industries, but in the tech industry planning and digging beyond the contract layer is the best working experience for both sides. If you’re invested in each other’s success, the outcome is likely to be positive. Taking the time to meet and plan the work allows both parties to see if there are any roadblocks that need to be addressed early and de-risks what could be major issues down the road. They don’t need to be in the day-to-day, but having the client including in the planning and re-planning allows them to give insight into how the work is being managed.

3. Providing Regular Cadence Updates

Setting up regular one-on-one time with your client may be a part of the contract. And if it isn’t carving out even a quick ten-minute chat, every other week may help build the work relationship. It can provide quick bursts of information. It’s also a good way to gauge their mood and get feedback on if the outcomes are desired. You’ll be able to address issues or manage expectations if there are any concerns. This is the best time to shine. Show the value of your work and the results you and your team have delivered. By keeping the information flowing, you are providing progress on the work, engagement with the client, and consistency. You can find different ways to elevate service. Giving that personal touch by having that one-on-one time allows you to get to know your client better. And hopefully it makes a difference in building the rapport and winning over your challenging client.

4. Bad Chemistry

And of course after exhausting all other efforts… you may come to this realization. Unfortunately, sometimes it is just bad chemistry. For one reason or another, you don’t get along. It could be their view of pets, their work style, and so on. When you realize this is the case, focus your time and energy on the work. You can’t change that there is bad chemistry. I could spend time here talking about ways to build a better relationship. However, sometimes it simply doesn’t matter what you do. They may not like you. And that’s okay. Keep it strictly professional and don’t feel inclined to engage further if it causes more stress. It’s hard to manage work knowing that there is someone that doesn’t like you or what you’re about. It may not even be something you control over. It took a long time for me to let go of that fact and not let it take hold. There are times it gets the better of me. Manage your own feelings because you can’t control the parts you don’t own.

Final Thoughts

There will be times you’ll have a challenging client, whether it’s the work, the personality mismatch, or something else. It can make the work unpleasant. It will be hard to keep your head up. In those moments you have to ask yourself if the work, job career, any of it is all worth it. I understand that it may be very millennial of me. But stress does a lot of unhealthy things. And in the time I’ve been working I’ve had to learn how to manage it. Whether it be through meditation or finding ways to work through the challenges. Whatever it is it’s very personal how you choose to persevere through. I only hope that these four tips help and guide you through those challenges.

--

--

Eilis Gregory

Millennial, Lover of Memes, YA fantasy, video games, and sometimes trying to be an adult.