“How many more times do I have to tell you?”
If I’ve said that—or something similar—once, I’ve said it a million times. My kids have heard it. My wife has heard it. The people I work with have heard it. Sometimes I say, “I’ve already said this,” but, honestly, I’m not even 50% sure I have. It just feels like I’ve said it and I don’t want to be wrong.
I don’t like that I get annoyed repeating myself, but it’s the ditch I’ve fallen into 100 times before and potentially 100 more to come. I appear more comfortable in the ditch.
What’s the right amount of times to repeat yourself before you are allowed to get annoyed? How many times do you say the same phrase or offer the same advice? How many memos (that you know won’t get read) can you send about a process, and what level of frustration can you show when someone asks you for the 10th time how to do what you’ve already shown them?
In a given week, I have the pleasure of engaging people in different industries and varied cultures. I love hearing what they do well, what mistakes they’ve made, and how they serve others in their vocation. It’s like a continuous professional development.
But sometimes I hear about ideas that challenge the way I operate and I think, “Yeah, that’s better than how I do it, but I’m not sure I want to change.”


Every few months I head to a nearby Gringo’s Tex-Mex restaurant to get time with Justin. He’s a fellow church member and and one of their VPs of Operations. 11:00AM is the usual call time so that we can talk a while before the lunch rush. Of the handful of restaurants in his area, he tries to visit two a day—so we schedule a lunch a couple weeks out and then confirm the location week of. It’s a good break for me (and Gringo’s has perhaps the most consistent chip quality in all of Tex-Mex).
Having been in the restaurant industry approaching thirty years, Justin has seen it all. Want to know how much they pay for steak, how long they season it, and how many ounces go on a plate for it to be profitable? Want to hear the best (or worst) way to handle customer complaints? Want to know how to train a new manager? Ask Justin.
We cover a lot of ground as we sit in that corner where Justin has a view of the restaurant floor—work, family, faith, food, and failure are usually on the menu. So amidst our discussions of how to slice a lime, video game design, salsa splatter patterns, with his eyes scanning the restaurant for the regulars, he says this about how he trains staff:
“I always tell people like it is the first time I’ve told them.”
Hearing his phrase resulted in a simultaneous recoil and lean-in. I liked what I heard, but I also found myself a little bothered. I think I like reserving the right to say, “We’ve talked about this.” Justin’s principle removes my high ground. I like the high ground.
“If you hire the right people, they’ll catch on,” he explained, telling the story of how this happened to him over the course of several months. By about the third time someone says the same line to you the same way, without any retribution, you start to go, “Crap, I’ve heard this before, haven’t I?” Then you adjust.
This little leadership principle, not even shared with me to try and get me to do it, has left me at a crossroads. Is it a better way, or just one of many ways? Is practicing intentional amnesia more beneficial?

I don’t remember everything, but I remember a lot—more than I’d prefer, actually. I used to think all of that remembering was an asset. I’m starting to wonder at what point it becomes a liability, especially in my relationships. Why does this “say it like it’s the first time” principle semi-bug me?
I think, on one hand, I don’t want to be seen as a pushover—to be taken advantage of by someone who knows they won’t get in trouble if they don’t do what is said. But Justin’s no pushover. You don’t survive (much less thrive) over 20 years in restaurants—an establishment with historically low margins and high turnover—by letting people incessantly bend expectations.
I also spend a lot of time trying to be clear. I say it, I write it, I will ask, “What are you hearing me say?” and I’ll repeat back whatever the person answers. I do research on the three levels of listening and watch body language when someone is in the room with me. I will follow up with written summaries after certain meetings. When we had our staff retreat a couple of weeks back, I wrote the summary on the ride back to the office—and then read it out loud to confirm the staff agreed with what was said.
That’s a lot of “I,” isn’t it? Maybe that’s the real issue.

There’s a slight flicker of enthusiasm being able to put someone in their place by saying, “We’ve talked about this.” When we start repeating ourselves we wonder, “IS ANYONE LISTENING TO ME?” Both of those responses don’t have the other person as the goal but the one speaking—what I say, how I say it, and how I’m heard becomes the goal.
I know some areas exist where failing to listen the first time is a life or death equation, but most of what we common folk train in is not. So why do we—or why do I—treat it like it is?
One likely culprit: my pride.
Answering “pride” on a multiple choice test might not’ve felt like the right answer as I was driving to that lunch preparing for their green sauce. I could’ve answered “excellence” or “accountability” or another word that is more palatable. Coming out of the lunch, though, the word at least needs to be a potential reason.
Why? Because, at least for me, “How many times” focuses on what I’ve said, how someone else has failed, and is a bit self-justifying. It assumes the issue is with the other person and puts me in the better light. But taking the other person and giving them a gracious reminder assumes the best about them—that we believe they can do it and they simply need another reminder.
And we all need that.

But what about you? When is it okay to “How many times?” someone? Chime in below and let us know.





I grew up in a home where my voice wasn't always heard, so when I became a mother, I made it a priority to have open, honest conversations with my children. I wanted them to know they could talk to me about anything without feeling judged or silenced. I've always given advice because I want to protect them, not control them. But as they've gotten older, I've realized that saying "I told you so" can sometimes make them feel like they can't come to me when things go wrong. I'm learning that my children don't have to follow my advice for my voice to matter. I can disagree with their decisions, let them make mistakes, and still be their safe place. My goal isn't to raise children who always listen to me; it's to raise children who always know they can talk to me no matter the situation.
I know God has to teach me the same things over and over again. So, as I learn to live and love like Jesus, I’m learning to extend that same grace to others. I guess it’s why we go over the room rules in kids every Sunday. And why, with my own kid, I’m constantly repeating myself on purpose before she even has a chance to forget. One of my favorite reminders comes from one of my favorite people: “Grown-ups are just taller kids!” We’re all learning!