I have this killer client, Yan, who manages a mid-size company that I’ve been working with for years. He’s conscientious, compassionate, holds boundaries, and communicates so clearly it’s like he did it coming out of the womb. When I’m with other companies, I’m usually the one summarizing and paraphrasing confusing ideas, but with this company he is always the one doing it. As a result, his executive leadership team communicates very effectively.

Yan called me recently about one of his workers, a man named Mal. Mal reports directly to Yan and was integral in creating the current plan and direction the company is heading in. He’s a clear communicator and offers challenging opinions with an unflinching straightforwardness and an open mind for exploring other ideas. He’s basically a slightly younger version of Yan in his work ethic and ability to communicate. They have always displayed a hearty, healthy working relationship with equal parts seriousness and playfulness. So, this call was a bit unexpected.

“I’m having a problem with Mal. And just for clear context, I’m in the middle of a huge deliverable for a client and my patience is wearing thin. I’m on edge so I may be more confrontational than normal.”

First of all, A++ to Yan for acknowledging where he is. This little bit of context gives me great insight into how to proceed with him and what filters to put on his words.

“As of late, Mal has been difficult to work with. He’s been pointing out problems and not offering a lot of solutions. While he’s clear to say when he’s not ok with how something is proceeding, he’s been doing it in a way that is fostering a less positive environment. He’s always been the one to voice the idea that’s challenging or difficult, and I welcome that, you know it helps us, but now it seems more out of spirit of assigning blame with no intention of actually working to make the environment he claims he wants. At this point, I want to have a conversation with him, but I don’t want to yell at him, or take out my frustrations on him. He’ll just get defensive, then I’ll get defensive, and we’ll just be mad at each other with no actual solution in sight.”

I asked Yan what it was he needed from me, “Do you want a place to vent, some perspective, or some coaching?”

For me, I often just need a place to let off some steam. The release gives me a chance to clear out the gunk and I can act with a more clear head.

Also, given that I know Mal just as well as I know Yan, I knew some context for what Mal was dealing outside of his work with Yan’s company. If Yan needed some perspective for Mal’s atypical behavior, I could give him a window into some of the other projects Mal was working on.

Finally, if Yan was truly stuck, I could coach him. This would allow him to access a solution he was capable of delivering rather than being prescribed a solution from me.

“I’d like some coaching,” Yan replied.

I asked Yan if this behavior was typical of Mal.

“No. He’ll say the uncomfortable thing, but he’s usually part of the process of determining a solution. But that’s not what he’s doing now.”

“Right, why do you think that is?” I asked

“I’m not sure. I could ask him.”

“That sounds like a great idea. It’ll help you see what else he might be juggling. What do you want at the end of the conversation with him?” I asked.

“I want to know how to support him so he can return to his mindset of positive problem solving,” Yan replied.

“What do you think would happen if you said that to him?”

“Oh, I hadn’t thought to do that.”

Here’s the thing, if you are a caring person, most of the time what you actually want is what you should ask for. In this case, Yan wants Mal to return to behavior he knows is more typical of Mal’s demeanor and how to support him while and until he gets there.

The thing Yan is also gently doing is establishing boundaries about what kind of behavior is or isn’t acceptable within the group. In this group, you are welcome to point out problems, but you must be willing to offer and be part of generating solutions. Otherwise, this is called grown-up whining.

“So what are you going to do?” I asked.

“I’m going to approach Mal, ask for a conversation, and tell him at the start of the conversation that his recent behaviors aren’t congruent with how I know him to operate. I’m going to ask him what’s up and what I can do to support him back to a place of positivity,” Yan summarized.

“Great. I have a challenge for you. Can you find a way to not only bring manager Yan to this process, but also equally overwhelmed Yan? It’s easy to have conversations from a place of ‘I’m your manager’ top-down-ness, but is there a way you can offer empathy and humanity so the conversation is more inviting?”

Yan replied, “Yes. I can definitely do that.”


“One more thing,” I added. “Would you be ok waiting to have this conversation until after this major deliverable is done?”

“Yeah,” said Yan. “It’s due at the end of this week, so I’ll definitely have more bandwidth next week and this will keep until then.”

Wonderful x2.

So, here are the takeaways:

  • Ask for what you want. If you are coming from a place of caring for another human, chances are it’s a good direction to go in.
  • If you’re a manager, bring not only your manager hat, but your fellow human hat to this conversation. This will allow your co-workers to lean into you a bit more rather than act defensively or get worked up about getting called into the principal’s office.
  • Have these conversations when the general stress is lower. At the very least, if it can keep, wait until the pressure is off of you so you can have this conversation with more personal bandwidth and tolerance.

Have at it, lovelies.