A few years ago, I found myself totally dreading a client session, which is not normal for me. I love coaching. But I had been coaching Mike for almost five years. Every third Thursday at 10 a.m., like clockwork. And that was the problem: it felt like clockwork.

Mike would show up, talk through a challenge, I’d ask a few questions, and he would leave the conversation grateful. But inside, I had this nagging thought: Are we actually doing anything here? It felt more like a professional friendship than a coaching relationship. We weren’t breaking new ground—we were mowing the same lawn. Safe. Predictable. Comfortable.

That was the moment I realized I needed to rethink what long-term coaching should actually look like.

If you’ve coached someone for more than a few years, you might know this tension. A long-term client is a gift—but it can also become a trap. What started as dynamic coaching can slide into routine conversation. So what do you do when the coaching relationship loses its edge? Let’s explore this challenge so our coaching can remain fresh, powerful, and transformative.

1. Re-Contract the Relationship

When a coaching relationship reaches the point of being routine, one of the most powerful things you can do is pause and re-contract. Set aside a session just to revisit the agreement, which serves as the foundation for the coaching relationship:

• What are we doing here?

• What outcomes still matter?

• Is this still the best structure for our work together?

That’s what I did with Mike. I said, “Let’s push pause and talk about where we are and where we’re going.” Turned out, he’d been feeling the same drift but didn’t want to offend me. While I appreciated his sensitivity, I also assured him that my goal is for him to get great value from each and every coaching conversation, which meant he was encouraged to speak up when things needed to be adjusted. Together, we reset the goals, changed our meeting rhythm, and re-centered the coaching on what mattered most. That one conversation reinvigorated the whole relationship.

2. Shake Things Up

Sometimes the issue isn’t the relationship—it’s the rhythm. Coaching doesn’t always need to be a quiet hour in a familiar setting. Try a walking session. Introduce a new model. Invite your client to bring a stretch goal, or challenge them to coach someone on their team between sessions.

One client of mine had lost steam in our sessions. He was showing up unfocused and eager for me to give direction to the coaching session. My spidey senses told me we needed a shake-up to get things moving in the right direction for him. So I gave him very specific homework: list five things he was avoiding—and then pick one to tackle before our next call. I texted him after making the homework assignment to ensure he knew there was a real expectation. And I texted him again a few days before our session. He actually texted back, listing the five things he was avoiding and indicating that he was trying to decide between numbers 2 and 5 from his list. That little shake-up sparked weeks of bold action for him and completely changed the tone of our coaching for months to come.

Long-term clients often appreciate when you bring fresh energy. It tells them you’re still engaged, still invested, and still pushing for their growth.

3. Say Goodbye (On Purpose)

Here’s a hard truth: sometimes the coaching relationship has simply run its course. It doesn’t mean anyone failed. It means the goals have been met, or the growth has plateaued, or the next step for the client isn’t something you can help with.

I had one client—a sharp executive I’d coached for over two years—who started canceling every other session. When we did meet, it felt like we were rehashing old conversations. So I said, “I think we might be done here.” He jokingly said, “Are you firing me?” While he was surprised, he admitted that he was also a little relieved. We ended with a celebration of the work we’d done and the wins he’d achieved. He still touches base once a year or so to give me an update and to thank me for the value he gained as a client. A clean ending is a gift.

4. Refer or Release

In some cases, it’s not about ending coaching—it’s about getting the client a different kind of help. Maybe they need a coach with a different specialty. Or a therapist. Or a spiritual director. Or a season of silence.

I once referred a longtime client to another coach because the client’s needs had shifted. We’d focused on his leadership of a growing company he’d founded. But when he transitioned to a new leadership role in academia, he needed some things that I felt under-equipped to provide. I recommended him to a coach I trusted and knew could support him in his new role. It wasn’t a loss; it was honoring every coach’s commitment to put the client first. Knowing when to step aside is part of serving the client well.

Long-term coaching relationships only stay valuable when you treat them with intention. Whether you re-contract, shake things up, or bring it to a close, your role is to stay curious, courageous, and committed to the client’s transformation.

Coaching isn’t about tenure—it’s about movement. And movement requires honesty.

So take a look at your calendar. Who have you been coaching for a long time? Is it time to recalibrate? Reignite? Or respectfully release?

Your client might be waiting for you to take the lead.