Awkward Client Situations: What To Do When Things Get Sticky

No matter how good you are at what you do, or how long you’ve been doing it, awkward client situations happen. I’m talking about things like your client ghosts you, the payment is late, or any other situation where you’re sweaty, stressed out, or full of swears.

In this episode, I’m talking about those awkward client moments when things get sticky and you’re trying not to completely lose your shit.

Before we dive into this episode and talk about awkward client situations, in particular the ones that feel seriously sticky, I want to provide some context.

When you work with clients, there’s a human element. It’s always going to have ups and downs, and tricky and sticky situations happen.

No matter how good you are at what you do. No matter how long you’ve been doing it. No matter how good your contract is. No matter how many times you’ve communicated the thing.

Truth is, shit happens. So there’s no way to stop these awkward client moments from happening completely.

Believe me, I’ve tried. And over the last 20 years, it’s gotten a lot easier, and I’ve learned to stop many of them before they start. But they still pop up from time to time, but the difference is I’m better equipped to handle them.

Part of that has been learning to better manage my reactions and emotions including taking things less personally. Not going to lie, therapy and getting a handle on my anxiety has made things better too.

The other part of it has simply been learning how to navigate these situations which is what I want to get into today. I can’t necessarily help you with the “inside” part of this, but I sure as hell can talk about the fact that these situations are more normal than anyone knows.

Awkward Client Moments: They Happen All the Damn Time

Awkward client moments are totally a thing. This can be everything from “hey, you’re late” to “OMG, I need to fire this client”. Most of the sticky situations we find ourselves in with clients tend to fall into the category of awkward and annoying.

These situations can pop up from the point we have an initial engagement with someone right through to when we finish working with them….or even beyond that point. At every step in your relationship with a potential, current, or past client you may find yourself in one of these situations.

My goal here isn’t to have you stressing out and worrying but rather to equip you with the understanding that this is the result of being in a relationship, even a business relationship.

Like I said earlier, we’re humans, and we’re all imperfect. That means you may screw things up. Your client may mess up. Things may go off the rails, but that awkward client situation isn’t inevitably going to turn into a train wreck.

Every awkward client moment (or potential one for that matter) is an opportunity for us to turn it into an awesome one.

How? We can build better communication skills and have a plan for when we need to do these things.

I know, it sounds way too simple. Here’s the thing. Even though we all communicate with one another all day long it doesn’t mean we’re actually skilled at it.

Client communication is truly an art. And I’ll be the first to admit I probably have an advantage as I’m a natural communicator, I’ve worked my entire career in communications roles. Plus, I’ve worked with clients for over 20 years, so I’ve had a lot of hands-on experience. (And that’s not even counting my years working as a grocery store cashier, that was communications boot camp.) 

Think Like Your Clients to Communicate Better

The good news is that the art of client communication is simpler and easier than most people realize. It starts with understanding what your clients actually want. If you’re able to get into their heads, you’re better equipped to anticipate their needs and cut problems off before they start.

Take for example, when a client is asking about a deliverable. Totally annoying, right? But you need to figure out what’s motivating them. Why are they asking? What information are they looking for?

Maybe they need reassurance. Maybe they’re anxious about their investment. Whatever it is, if you consider that before you respond, that’s going to let you frame things up in a way that allows you to address their concern and put it to bed.

It’s an awkward client situation as we’re sometimes feeling “attacked” by these types of questions. But what if we cut those questions off at the pass?

What if we checked in more regularly? What if we gave our clients more insight into the process.

So many awkward client situations happen because we’re not thinking like our clients.

Honestly, I think a lot of that comes from the fact that if you’re working in the online world, clients are seen as a commodity. Things aren’t client-centric at all. Everything is built around the service providers’ needs as they build their business and meet their goals and the client’s needs are overlooked.

Many of the awkward client moments that are preventable come down to needing better onboarding and project management, as well as ongoing client communications. We assume our clients know things, or that they’ve understood when really, we need to be holding their hand through the process.

I’m not talking about doing their work for them, but rather coaching them along the way, providing context, and keeping an open line of communication. Maybe it’s regular updates by email, or providing clarity on the next steps.

Those small things go so much further than we ever realize. With a little bit of planning and foresight, we can ensure those potentially awkward moments are turned into awesome ones.

But what happens when it’s not a small thing, and that awkward situation is much, much bigger?

When Awkward Client Situations Turn into Downright Awful Ones

Sometimes our awkward client situations are more awful than anything else. So before we get into this, everyone take a deep breath as I remind you all that we’ve all been there.

It doesn’t mean you’re bad at your job. It means you’re human.

I’ve had countless of these situations over the years. Some I could have avoided entirely, and others I never could have ever predicted.

When I think about these situations, they tend to fall into one of three categories: 

• I’ve massively screwed up and need to make the situation right. 
• The client is pushing boundaries, and it needs to stop.
• I really don’t know WTF happened, and still can’t figure it out. 

Let’s talk first about the situations where you screwed up. Mistakes happen, but how you decide to handle them and communicate with your clients is what makes the difference between awkward and awful.

I’ve Made a Mistake

Many times when we make a mistake our reaction is to figure out who to blame. Trust me, that’s not the way to go, if you made a mistake, it doesn’t always matter why it happened, but instead how you’re going to fix it.

Case in point. I could share a million examples, but one that comes to mind is that I sent the wrong information to a key person in my client’s organization. It made my client look bad, wasted a lot of time, and made me look like I was totally incompetent.

There was a series of events that led up to my screw up and I could have easily been like “this is not my fault”, but instead, I identified the problem, fixed it, and then shared how it won’t happen again. The client and I discussed the process and how we needed to update it so that there was no further room for confusion.

Honestly, when I think about times I’ve made a big mistake with a client, I can only think of two times where it didn’t end up with a stronger client relationship. (And those situations fall more in the WTF even happened category.) 

The Client is Pushing Your Boundaries

Next, let’s talk about boundaries. Many awkward client moments happen as clients cross our boundaries.

First thing, you need to ensure your client actually knows it’s a boundary. I could count approximately a billion times I’ve been all fired up as a client was crossing my boundaries but then realized that I did a piss poor job of communicating that boundary, let alone reinforcing it.

For your boundaries to be respected, your clients need to know they exist and need to constantly be reminded.

At the start of the year, our team moved to a four-day workweek, so we take Fridays off. For one of our clients, they’ve had a lot happening, so there have been a couple of Fridays I’ve made an exception.

Our main client has been very appreciative and respectful of the boundary, but then it started to slip a little bit. Honestly, this was my mistake as I made an exception.

I know better, but I did it anyway.

I started to get irritated by the whole thing after two Friday meetings and realized I had to hold the boundary. From there, I proceeded to tell everyone possible that I dealt with that I don’t work Fridays. I’ve since declined two C-level Friday meetings.

Guess what? Everyone is dealing with it, and I’m much happier. Boundary reinstated and I won’t make any more exceptions.

This is just one example, but there are so many ways we miss opportunities to restate or reinforce our boundaries. We shy away from being direct about our communication preferences, working hours, vacation times and so much more.

Honestly, we need to cut this out as we’re causing more awkwardness than needed. I challenge you to consider if you’re being avoidant (I see you my people pleasers) and if that’s what’s really leading to more awkward and potentially awful situations.

You can be clear and kind with your boundaries, and that will go a long way to avoiding situations that make you sweat, stress and swear about your clients.

WTF Client Moments

Finally, let’s talk about the WTF moments. Honestly, there’s no easy solution to these ones as they’re complex, confusing and downright messy. These are not things you can handle with a script or process, but what you can do is figure out a way to communicate clearly and not completely lose it.

First, try to remain calm. I know, easier said than done, but try to avoid reacting in the heat of the moment. Nothing good will come from being snarky or snappy and you’re likely not going to feel good about it later.

This is why I’m a big fan of a cooling-off period. I can think of two or three times where I didn’t do this, and it resulted in me saying things that made the situation worse, and that I regret. I was unprofessional and that just added fuel to the fire.

Next, please know you don’t have to take any abuse from clients. That needs to be a hard line. You can immediately terminate any working relationship for that type of treatment. This is not a squishy boundaries thing, but knowing what your deal breakers are.

One of my hard lines is if someone tries to go after someone on my team. If they have a problem, they’re welcome to come to me, but abusive behavior with a member of my team is completely unacceptable.

Honestly, I’m not big on refunds and dealing with flaky clients, but if anyone crosses a line I will give them their money back and walk away. No amount of money is worth my peace. (And I acknowledge there’s a great deal of privilege in that, but these clients always come at a high cost.) 

Finally, once you’ve dealt with the situation, do a post mortem. Try to figure out what happened. Because the reality is that while these situations can be a WTF, there’s always a lesson that can be learned. What red flags came up? What would you do differently?

For me, I’ve come to recognize a pattern with my WTF moments where it’s a specific type of client or project. So now we completely avoid those types of clients and projects.

It’s really easy to dismiss clients as being bad or from hell, but there’s always been an improvement I can make to prevent those situations from happening in the future. 

Awkward Client Situations: They’re Not Inevitable

Awkward client moments are going to happen, but it is possible to turn them into awesome ones.

After all, you didn’t start a client-based business to be stressed out by your clients, so anticipating the awkwardness and building your communications systems and skills, you’ll be on your way to having more awesome in your business.

Next week, we’re going to talk about the top 10 awkward client moments for a lighter episode to get you thinking about how you can take them from awkward to awesome.