Breakin’ up is hard to do, particularly when it comes to ending a client relationship. These conversations can be awkward or even emotional, but it’s important to approach to situation directly. Nobody likes to be evaded or have a relationship broken off without knowing why, say our experts. Providing a clear, reasoned argument for why the business relationship needs to end and offering contacts or referrals for companies that you recommend to replace your services can help avoid bruised egos and burnt bridges. These will still be difficult conversations, but here are a few tips to make it a bit easier.

1. The late payer
You’re tempted to say: “We can’t spend any more time chasing your checks and listening to your excuses.”
Instead say this: “I’ve enjoyed our partnership but you’ve been consistently late on payments while we have continued to deliver on deadline. We can’t operate on that financial model so unfortunately we can’t continue our relationship.”
It’s important because: You have made the business relationship equal, rather than creating a hierarchy. You are also not criticizing their operational model or behavior, but simply stating the fact that their payments have been delayed or nonexistent, says Michael “Dr. Woody” Woodward, professional coach and founder of Human Capital Integrated.
What else to keep in mind: The client may respond with “The check is forthcoming.” Great! Let them know that once the payments are caught up, you can revisit the possibility of future engagements. However, do not commit to anything, and know that you’ll likely find yourself having this same conversation with this client down the line.

2. The diva
You’re tempted to say: “You demand way too much of our time and we can’t make any money off of you.”
Instead say this: “Unfortunately, based on the amount of time you need for a project of this scale, we can’t fit it into our workload.”
It’s important because: You make it about your bottom line, your availability, and your business — and not about their neediness. “Business is business,” says Paul Hebert, human resources expert and vice president of solutions design at Symbolist. “Ultimately, if you can’t be profitable with them as your client, you should be able to tell them that you’ve outgrown each other.” Talk more about hours and business and less about their behavior.
What else to keep in mind: In the future, set boundaries with your clients, whether that is a total number of hours you will work in an engagement or specific times that you can be available to them. This can help stave off the Sunday evening work “emergency” from a needy client, or, at the minimum, give you a document to point to that says Sunday evenings are off limits.

3. The family friend
You’re tempted to say: “I would have fired you months ago if I weren’t so nervous about seeing you at Thanksgiving.”
Instead say this: “I need to end our business relationship for these specific reasons but I hope this does not impact or damage our personal relationship. I know this might reflect on our personal lives so let’s talk about it.”
It’s important because: While you typically don’t want to invite long conversation when firing a client, firing a personal friend or family member requires a different etiquette. Since the relationship is not ending entirely, you want to give them the option of airing any grievances and arguments now, rather than at the next family party or other get together, says Jennifer McClure, president of Unbridled Talent.
What else to keep in mind: Establish some guidelines on your relationship going forward, whether it’s agreeing not to talk to mutual friends about the situation or setting a time frame for seeing each other personally. While you are taking ownership of ending the relationship, let them take the lead on how to reconnect on a personal or family level.

4. The jerk
You’re tempted to say: “My people just don’t want to hear you scream anymore.”
Instead say this: “It’s my responsibility to provide you with the best service I can and unfortunately my team and I can’t do that because of the difference in our working cultures.”
It’s important because: The end of the relationship is about your company culture, not theirs, says Woodward.
What else to keep in mind: If your client is a yeller or has a temper problem, be prepared for him to yell in this moment too. There’s also a possibility that he may disparage you or your company publicly. Be ready to counter any arguments, but take the high road and don’t get defensive, advises Woodward. Ultimately, you’ve done what’s best for your and your employees.