Two readers asked similar questions about yesterday’s post, “Risks in relationships, rock-climbing, and ratcheting,” on confirming the status of a relationship and how that’s like anchoring yourself while rock climbing.
One reader wrote:

I like the analogy.

Could you give an example of checking in with people and dynamic relationship? Dynamic meaning continuous interaction and keeping in touch? Asking someone how they feel about something is checking in, yes?

Another wrote:

Especially love this article as it applies to many different kinds of relationships. Interesting how communication and constantly working on “the relationship” is vital for all of them. My only question would be the “how” for the anchoring. As in, what passes for helping the dynamic between the two. But I’m sure it’s relative to the context.

Anyway, your article was a nice refresher.

The first context that comes to mind for me is when I’m starting a project with someone. First meetings when we realize we have common interests and start thinking about partnering always sound like sunshine and rainbows before we consider the low-level challenges execution will bring. I’ve learned to pay attention to the person’s interests, experience, whether they’ll stick through challenges or are just dilettantes. In other words, I start itching to anchor and confirm where our relationship stands. I’ll say things like

• “This seems like a project with potential. I want to understand where you’re coming from. Like are we talking about something serious here or just a having a fun conversation?”
• “Have you done projects like this before? It feels big. I want to make sure we’re on the same page.”

The issue is that I’m starting a relationship and it’s developing fast. I don’t know how to read the other person, so I confirm regularly. I haven’t seen signs that people felt I checked in too often.
The next main context is when I’m managing someone in a project. Managers can manage better with feedback, which reports rarely give. I take responsibility for getting it. I say things like

• “I’m managing you how I’d want to be managed, but maybe you have a different style. Do you like this way? Would you prefer more freedom, more instruction, or something else?”
• “Is how we’re working what you expected? Have other managers worked better with you?”

… stuff like that.
In personal relationships, I might say things like

• “I feel like we understand each other well, but I wanted to make sure.”
• “When you said […], I think you meant […]. Did I understand you right?”

Actually, this last question, “When you said […], I think you meant […]. Did I understand you right?” is almost the prototypical confirmation question, so I made it bold. It has a counterpart

• “I said […], but I’m not sure it came across as I meant. Can we review that point to make sure? How did you understand it?”

I suspect most people act as if the longer or more intimately they know someone the better they understand them so the less they need to check in and confirm, not that I’ve researched. I find the opposite, that the more intimacy you have, the more vulnerability you share, meaning the more potential for being hurt, and the more you benefit from checking in. That goes for business relationships as much as personal ones since people feel vulnerable in any of them.
When I’m trying to influence someone, like in a sales context, I generally try to work with their interests, which they know intimately and I don’t, so I find it helps to reconfirm my understanding of their interests as the conversation continues. This also helps them feel understood, which increases my credibility and ability to influence them. It also keeps me from getting distracted with trying to pitch them or convince them logically, which I find ineffective in influencing.
Also, more importantly, as they become more comfortable with me, they’ll change how much they share and reveal more important interests. In these contexts I’ll say things like

• “I understood you needed […]. Is that still the main consideration here?”
• “I’ve been working with the idea that you want […]. It sounds like there might be other issues. Should I start thinking about other things too?”

In general, I try periodically to say things like

• “I just wanted to check in on how things are going. Is what I’m doing working? Could I do something better? Am I missing anything? Are you looking for feedback?”

I don’t claim to be the best at confirming relationships, but I hope the examples above clarify some of the ideas I had in mind. The point to me is not the exact words but the motivation on my part to check in and the sentiment to confirm.