Q: I have a long-time friend and professional collaborator, who’s been been acting difficult—disrespectful, giving confusing instructions, unprofessionally scolding, and not responding to requests for clarification. He’s had some business setbacks, and I empathize, but I won’t accept being treated disrespectfully. He’s in his 70s, and I’m concerned about his cognitive skills. What should I do?

A: First off, you’re in a tricky situation. Balancing a professional relationship with a personal friendship—especially when respect is at stake—is no easy feat. Let’s tackle this step by step.

1. Check In, Not Out

You’ve known him a long time, and while his recent behavior has been unacceptable, there could be more going on. He’s had business struggles and is in his 70s, which might be contributing to his erratic behavior. When people feel like they’re losing control in one area, they sometimes try to control others, leading to the kind of disrespect you’re experiencing.

Consider starting with a simple check-in:

“Hey, I’ve noticed some changes in how we’ve been communicating. Is everything okay? I care about our relationship and want to make sure we’re on the same page.”

This opens the door for a more human conversation without making it confrontational.

2. Set Boundaries with Respect

Once you’ve checked in, be clear about your boundaries. Friend or not, no one deserves to be disrespected. Use “I” statements to keep the conversation focused on how you feel:

“I feel frustrated when our communications are unclear or disrespectful. I want to keep working together, but I need to make sure we’re treating each other with respect.”

3. Adjust Your Expectations

Given his age and recent setbacks, his behavior might be a sign of something deeper—emotional, cognitive, or otherwise. While you don’t have to tolerate disrespect, you might need to adapt your approach. If cognitive decline is a possibility, keep your communications simpler and more straightforward.

4. Have an Exit Strategy Ready

If things don’t improve and he continues to be problematic, it’s important to have a graceful exit plan in place. You’ve been loyal, but not at the expense of your well-being. If it comes to that, you could say:

“I think it’s best for both of us if we step back from this working relationship. I’m grateful for everything we’ve built together, but I need to prioritize a healthy work environment.”

Ultimately, you’re not just his contractor—you’re also his peer, and maybe even the one person who can tell him, “Hey, something’s off.” It’s a tough conversation, but you could be doing him a bigger favor than you realize.

You’ve got this!

—Jimi