“How was recess today?” I asked Smoke this week, and he immediately started to cry.

Weeks ago, Smoke had complained to me that a friend was bossing him around, demanding that he play with him at every recess, and then dictating the terms of that play. If Smoke put up a protest, if he wanted to play tag with other friends, or if he wanted to be Spider-Man instead of Batman, this friend—let’s call him Boss—would storm off in a huff and declare that their friendship was over.

From what I’ve written about Boss here, I’m afraid that you’re imagining him as a spoiled, insufferable child à la Augustus Gloop in Charlie and the Chocolate Factory, but this is not the case. Boss is small and goofy and full of smiles. Boss, I suspect, senses that that his spot in the first-grade pecking order is tenuous, and so he does everything in his power to ensure that he has a steady companion. Boss doesn’t want to face the recess yard alone, and I don’t blame him for that.

“You’re just going to have to let him be mad at you,” I told Smoke after his initial complaint. I went on to explain what I thought would happen if Smoke took action on his own behalf. Boss would be mad for a while but then he would cool down. After a few confrontations, Boss would learn to give Smoke more leeway.

And then, like any great parent, after delivering my lecture, I forgot about the problem. Smoke didn’t come home crying or complaining, nor did he resist school, and so the issue fell off my radar until I remembered to ask him about it at bedtime this week. This is when Smoke burst into tears. “All he ever wants to do now is push me on the spinners, and then I get sick.”

“Tell him you don’t want to do that,” I said.

“I tell him every time!” Smoke said. “But he won’t let me play something else!”

In that moment I realized what should have been clear to me earlier. It didn’t matter what advice I gave Smoke. It didn’t matter because I was telling him to do something he wasn’t ready to do. He had it in him to tell Boss that he didn’t want to spin. But he didn’t have it in him to hold his ground or walk away, to risk losing a friendship that was probably providing him too with an indispensable measure of security.

“What can I do to help you fix this?” I asked him. He continued to cry quietly and look down at the bedspread. “Do you want me to email your teacher?” I asked.

“Yes,” he replied without hesitation.

I’ve been thinking lately about being assertive and the ideals we set around saying hard truths. So often we hold off on saying what we need to say because we get so wrapped up in the delivery, we think we must be brave and say it face-to-face. Writing it down would be cowardly. Delivering the message through another source would be cowardly. We suffer for the sake of this principle.

Many years ago, I interviewed for a job and got a voice mail from the employer a week later. He left his number and asked me to call him after 10 pm, because that was when he’d be home. I got the message at 6 pm, and so I had four hours to wait before calling him. I knew that I hadn’t nailed the interview, and so I wasn’t especially hopeful, and yet it was hard to settle into my evening knowing I had this phone call to make. I made my dinner, I showered, and I waited until quarter after ten to call him. Our phone call lasted less than a minute—just long enough for us to trade pleasantries and for him to tell me that they had hired someone else.

I hung up annoyed. I felt certain that he had wanted to deliver hard news to me directly on some kind of principal. But there was nothing helpful to me about hearing the news from a live voice rather than a recorded one. I would have far preferred the voice mail rejection to the personal one. He hadn’t spared me anything, but had instead injected some dread into my evening.

I remember this incident often. I remember it every time I need to communicate something difficult and am tempted to lay it out in an email rather than deliver it live. I tell myself that it’s okay to write it instead of saying it, that it’s okay to need a little space and control. I tell myself that the person on the other end might actually appreciate that space as well.

I emailed Smoke’s teacher that morning, and as Smoke left for school, he was hopping up and down, giddy with relief. He would not have to spin until he was sick at recess.

But Smoke’s teacher didn’t see my message right away. At their first recess, Boss did spin Smoke. Once they had settled back in the classroom, Smoke, impatient for the relief he now felt he deserved, told his teacher by himself.

The teacher took Boss aside. All it took was a single sentence: “You need to let Smoke play with his other friends too.” She didn’t shame him or punish him, but he listened. Smoke hadn’t been able to muster the authority he needed, and so he simply borrowed hers. Not only did it work, it spared him the drama of an angry friend.

For the rest of the day, Smoke played with the friends he’d been pining for in the weeks I’d spent ignoring the problem. He came home happy. It had taken two grown-ups and one child to resolve one common childhood conflict. Three weeks ago, I thought I’d teach Smoke how to be direct and assertive, how to take charge of his own relationships. Instead he reminded me how complicated our problems are and how senseless it is to try and solve them on our own.