How to Have Hard Client Conversations

This blog was originally shared on February, 20 2024. With the relaunch of our website (www.curateimpact.co), we are reposting our blogs on the new website and on LinkedIn.

We’ve all been there. Maybe you’ve just signed on for a new project and the project manager repeatedly calls you late in the evening or on the weekend. Maybe you’re coming up on a renewal and you’re suddenly presented with new, tough contract terms. Maybe you’ve been working with a client for a while, but over time their requests have become demanding, their tone borders on rude, and they only have complaints about your work.

As a freelancer or small business owner, there’s no manager or someone higher up the chain to run interference for you in these uncomfortable situations. It’s up to you to decide to have tough conversations with your clients, ultimately presenting the opportunity to lead to a better working relationship. (Though, a plug for joining the Curate Impact membership community here, where you can find a group of people happy to support you in walking through a variety of freelancer challenges!)

For this blog, we’ll consider when a conversation is necessary, why hard conversations are beneficial, and how to have these conversations, all through the lens of some favorite quotes!

"Oh, I'm fine. It's just that life is pointless and nothing matters and I'm always tired. Also, I can't sleep, I'm overeating and none of my old hobbies interest me." - Andy Dwyer

First, how do you know if a conversation with your client is necessary? Check in with your body and mind like our good friend Andy does above. Do you dread hearing from this client? Do your shoulders and neck feel tense after interactions? Have you been casually looking for opportunities to replace this work? These are all good signs that something is off and it might be a good idea to talk directly to your client about what’s bothering you and what needs to change.

Caveat here that not every client is going to be open to feedback. 95% of the time a conversation is worthwhile, but some client interactions may border on being toxic. If this is your case, it might be best to jump down to the final boundaries section instead of engaging in conversation with the goal of change.

"Most of the trouble in life comes from misunderstanding, I think” - Anne of Green Gables

Second, why talk to your client? Well, if you don’t, then either a) everything stays the same and you continue to be miserable in your work or b) you find new work and leave the client without feedback, which is a lot of effort for you and a little unfair for your client. (Note, there is no secret option c) where everything magically gets better.) It’s worth the effort to offer feedback and to give your client a chance to do things differently. Similar to what Anne says above, it’s possible your client doesn’t realize how their behavior is affecting you without you bringing it up!

Let’s dive deeper into the “how” of hard conversations with three more quotes.

“You’re not mean and they’re not fragile” - Jules Christie

Big thanks to our Curate Impact member Jules Christie (Crafted Leadership) who has given me (and many of our members) in-depth coaching on professional conflict resolution. The framework she shares here is essential to keep in mind when approaching a tough conversation. You are not hard-hearted, cruel, too sensitive, rude, or demanding when you have feedback to share. And your client is (likely) not going to crumble or lash out upon receiving feedback. The dread in your head is worse than how the conversation typically plays out.

“Be curious, not judgemental” - Ted Lasso

It is too easy to go into a tough conversation flinging accusations like knives. However, if we can adopt Ted Lasso’s attitude, a client is much more likely to be receptive to what we have to say. This can look like saying “I noticed you haven’t offered much praise on my work, am I not meeting expectations?” instead of “You don’t appreciate me and everything I do for you!” For more training on this, we recommend Crafted Leadership’s resources.

"You can set boundaries and still be kind, generous, and loving." - Brené Brown

Finally, the result of these feedback conversations should be grounded in discussing boundaries. Going back to examples throughout the post, maybe this is “I would benefit from 1-2 positive pieces of feedback on my deliverables”, or “I will not be answering my phone after 5pm” or “I am unable to sign a contract with these terms.” Boundaries are a way to care for yourself and your business, to ensure you don’t burn out and can do work for the long-term. Similar to our first point, you are not demanding or unreasonable for calmly stating what is and is not feasible for you and your business.

Is there a tough client conversation you need to have? Review the materials above, lean on your community for support, and be brave to discuss issues and offer feedback! It may be a tough 30-minute call, but this is an investment that will make your work life easier for the weeks and months ahead.

“Just Do It” - Nike

Meet the Author: Kaitlin is an operational powerhouse specializing in strategic services, from high-level executive support to backend business process optimization. With a 10+ year track record of successful partnerships with C-level execs/founders/business owners, she's an expert at managing competing priorities, anticipating and solving problems, and increasing operational efficiency. She’s also the founder of Modus Medley, a newsletter for those embracing the blend between fulfilling work and a joy-filled life.

Connect with Kaitlin: Review Kaitlin's service offerings here; connect with her via LinkedIn or email.