The Best Questions To Ask In A One-on-One Meeting | 688

Your one-on-one meetings are not producing what you want them to. And we are going to discover why that is coming up next.

Welcome to The Chris LoCurto Show, where we discuss leadership and life and discover that business is what you do, not who you are.

Welcome to the show, folks. I hope you're having a fabulous day wherever you are. Here is what we are talking about today.

We are talking about, you've got one on ones on your calendar. You meet with your team members, maybe it's this afternoon, maybe it's tomorrow, and you haven't missed one in months.

You show up, you ask what's on their plate, you ask what they need from you. It appears to be a good meeting. It really does. It feels like, okay, everything sounds right. But six months in, they're bringing the exact kind of problem that they brought to you at the start.

There's nothing, you know, they're not dramatically stuck. They're still competent, they're still reliable, they're still getting things done.

But you keep waiting for a moment where they surprise you, where they, you know, show you that they're thinking about the business differently than they did a year ago. And it's. It's just not coming. It's just not happening.

And quietly, you start to wonder if the one-on-one itself is a problem. Maybe you just need a better agenda. Maybe you need to kind of space them out differently. Or maybe this person just develops slowly.

I want to tell you before we go any further that the meeting most likely is not the problem. The question you're walking in with is.

And when you hear what that means, you're going to understand exactly why these meetings haven't felt productive, they haven't produced growth.

And you're going to know what to do about it as we get through this. But let's kind of set a scene, right?

The Same Meeting Every Time (00:02:04)

So picture your next one-on-one. You sit down, you start the way you always start, hey, what's on your plate this week?

And they tell you, you know, the project that's moving, the client that came up, the task they finished Tuesday, whatever it is. And then you ask the question, anything you need for me?

Well, usually their answer is probably no, or maybe it's something super small. And then that's the meeting. It runs its course. It ends with, you know, it ends on time or, you know, whatever. Nobody walks out unhappy.

But you walk back to your desk, or maybe you're sitting at your desk and something is absolutely nagging at you because you realize you could transcribe that meeting and it would read almost identical to the last one you had with the same person for the last three months.

Right? Different tasks, same shape, same level of thinking. There's no, hey, here's a call I made on my own that I wasn't sure about.

You know, I made this call inside of my team, or, you know, no, here's a conversation I've been avoiding because I'm struggling with this team member and I, you know, I need some help on having a tough conversation.

Or there's no moment where you actually saw how the person thinks to solve problems or issues that they're running into or anything.

Right? It's just what they did. That's it. It's just a list. And it hits you that you've been having this same meeting, every meeting. This is your one-on-one.

Because I've sat across from enough owners and leaders to know that it's a lot of people's one-on-ones right now. Same thing over and over and over again.

How are things going? Great. Or here's a tiny problem, or here's something small, no real big information for you to help them, to grow them, to mentor them, just all is good. Or here's a couple of minor things.

The Wrong Conclusion (Why You Think They've Plateaued) (00:04:08)

So the problem is, is most owners tell themselves at this point, you know what, they're just not developing. They're not, I know, not as fast as I would like them to.

Or maybe I need a different meeting cadence, you know, weekly just isn't working. We're not getting to where I want this to go to. We're not experiencing the kind of deep discussions that I would like to have with this team member.

Or there's the one that quietly settles and over time, which is just some people just aren't going to grow much past where they are, which is just a terrible one.

You don't want to be thinking that because everybody can grow, everybody can be mentored, everybody can, you know, be guided to better thinking. I have yet to find somebody that I would just go, nope, that person just can't grow.

Maybe I've just not met them yet. But I don't think that you've got that person on your team. Right? So from where you're standing, the conclusion kind of maybe makes sense to you.

Maybe it's just they're not developing well and I just need to give them more time or, you know, maybe they're just not going to get past where they are. The crazy thing is you've been consistent every single week.

You show up every week or however often your one-on-ones are and nothing is making sense.

Why is this just kind of like a plateau? Why are we not getting anywhere? Why are we not digging into heavy duty stuff? It's gotta be that this person just isn't growing. And maybe this is it.

The problem is that conclusion is almost always wrong. And if you act on it, you'll probably write this person off as being capped.

All right? You'll stop investing the way that you used to. And we've probably all experienced this to some level in our leadership where we're just like, forget it. I keep pouring into this person or trying to pour into this person.

As a parent, you've probably had that moment when you're frustrated with a kid that's not learning from something. They keep doing the same mistake over and over again and it's just like, forget it.

I don't want to pour anything else into this person. Right. Well, at home, hopefully you go, this is my job. I got to keep doing it at work. It needs to be the same thing. This is my job. This is somebody that I need to pour into. This is somebody.

I need to figure out what's going on. Why are we not getting to where we need to get to?

It's not because the meeting failed. It's probably because the meeting wasn't built to surface the information that you need.

The Real Problem: Your Questions, Not the Meeting (00:06:43)

So here's the problem. What's actually happening? Your questions decide what the meeting is for. So think about what you're actually asking. What's on your plate?

That tends to be something that a lot of leaders ask. And I will tell you, it's just a status question. That's it. It's the same thing you ask.

You're asking what's on their task list. You're asking, you know, a question for them to just list off. Hey, I'm doing this, this and this. I'm working on these things.

And for some reason, as a business owner or as a leader, we get in our minds that if I hear that you're doing a bunch of tasks, everything must be going well. You must be doing what you need to do.

Folks, it's just a status question. That's all you're asking for. You're not asking for deep discussion. You're not asking for problems that they're struggling with. You're not asking for tough conversations that they're not having. You're not asking for more. Right.

What's on your plate? These ten things. Oh, cool. What do you need from me? Nothing. Okay, great job. It's a support question, you know, you're asking, hey, is there anything blocking you?

Or, you know, is there anything that you need me to jump in and help out with? And many people are not going to answer that question with a yes, please help with this.

Or if they do, it's going to be something minimal that they hope doesn't make them look stupid or incapable of doing the job. Nobody wants to answer. And this is because we've not set this up this way.

Nobody wants to answer, yeah, I'm really struggling with something that's going to make me look like I don't know what I'm doing. They just don't.

Because there isn't a trust, there isn't a level of vulnerability. And way too many leaders, and I will tell you this, this is something I've experienced for just too many decades, is when a leader asks somebody, is there anything I can help you with?

They actually literally do come up with something. The response is like, oh, well, just do this, this and this. It's never a real, I'm going to jump in and help you. It is a, oh, well, you got that.

You just have to do these couple of things. I've seen that so many times from team members that are like, well, what in the world? Why did I even come to this?

This leader, right? What's the point of coming to this leader when I don't get any help? So crazy. We're not setting this up for it to be a greatly productive meeting.

And the thing is, it's not, you know, because the team member is really hiding anything. It's because they either haven't been asked properly, and so they're not.

They're literally just answering the question the way it hits them, or they feel like if they answer the question, they're probably not going to get any help.

So here's why this matters so much, right?

A capable person will answer exactly the question you ask them. That's not evasion. That's just how a good team member behaves in a meeting.

You asked me about tasks, so I gave some tasks back. It's dressed up as an update.

Meanwhile, the actual signals of growth, you know, the decision that they made alone or the conversation that they've been putting off or the things they've handled differently or would have handled differently if they could.

All of that stuff does not enter into the conversation. You could rewind the week and get into that. But we're not setting them up for success. It never comes up.

Not because there's nothing there, but because nothing in the meeting, ever asked for it. And that's not a development problem. That's not a team member who can't develop. It's a question gap.

And the great thing is, is that you are the person who can close that gap.

So here's what I've seen over and over again, coaching leaders and owners for decades. A status one-on-one reviews tasks, A development one-on-one reviews judgment.

And the only thing that separates them is which questions you open up with.

So I, I call this, you know, the three judgment questions. And before your next one-on-one, which you might have one soon coming up, you need to know what each one of these questions actually is built to surface.

Right? Because each one pulls on a different thread. Each one's pulling to get different information.

The Three Judgment Questions (00:11:21)

So question number one. What decision did you make this week without coming to me? This is a fantastic question. It's not, hey, what did you get done? It's not, what did you decide on your own?

That's all stuff that again, is not really getting into anything deep. Right? You want to ask the question, what decision did you make on your own that you didn't, didn't run past me?

What's actually happening while the question surfaces? Judgment. Instead of output. It tells you where they're already trusting their own thinking and where they're still not, right?

So if the answer is a long pause, believe it or not, that's data, right? If the answer is a confident story about a real call they made, then that's data as well. Either way, you learn something that a status update never shows you.

Stuff that they confidently did, stuff that they worked on that they weren't confident about, decisions, judgment calls, things that they are doing without you.

This is something that you can absolutely compare to the judgment calls that they did bring to you. And it kind of gives you a baseline. Are they bringing everything to me? Are they bringing the tough stuff to me? Are they making the tough calls on their own?

You know, what are the things that I still need to jump in and guide and direct on?

So if they're bringing you the tough calls for you to give the input, but they're making these calls without you, and they're really kind of, you know, low level. They're not anything spectacular.

Well, then, you know, you've got a problem. You, you now have a different kind of status update. Their status is, is that they're not making the big judgment calls, probably because they either don't know how or they're too fearful.

They're afraid that they're going to mess something up. So it's a powerful question. Start with that first question. What decision did you make this week without coming to me?

Question number two. What's the hardest conversation you've been avoiding? Ooh, this is such a good one. Right? The funny thing is, is it's almost catch 22 one.

If they answer it, great. You've got fantastic information. If they don't answer it and you know that anything is off on their team, then you know that they're choosing not to have that tough conversation, right?

So. And maybe there's just really no difficult conversation that they're avoiding. And it doesn't have to be this last week. It could be, you know, it could be something that they've been avoiding for weeks now, right?

So the great thing about this, it's. It's not asking, hey, how's the team doing? Right? What's the conversation sitting on their desk that they haven't had yet? That. That's what you're asking?

What should you be digging into that you haven't done yet? What?

You know, what conversation is really wearing you out because you know you've got to have it, but you don't know how to have it or you're concerned about having it or you're concerned about the outcome.

Whatever it is, that's what you want to pull from them, right? Nearly everyone has one. You know, maybe it's the. The vendor call that they're absolutely dreading.

Maybe it's the teammate who needs direct feedback that they've been holding off on. Maybe it's the client that needs to have a little bit of pushback on whatever the project is or whatever they're working on, whatever it is.

The question doesn't ask them to report. It asks them to be honest about where they're stuck. And most people asked directly and consistently will actually tell you.

Then again, leader, business owner, you have a phenomenal opportunity to train, to guide, to direct, to help them learn how to make tough conversations for the love.

Bare minimum, do role playing. We just finished up one of our retreats with our Next-Level Mastermind clients. And afterwards, I sat down with one of our coaches and they're asking, hey, I need to run this by you.

Here's the situation, here's the information that I gave. Fantastic information, but they were asking, how could I have done this better? And so I literally, on the spot, role played.

All right, I'll be that person. Let's go. Boom. Five minutes later. Done. Great information, great input. No fear, no concern, no man, this is so weird that we do this.

It was just natural, you know, stuff like that gives you the ability to help them have tough conversations, learn how to have tough conversations, learn how to lead a specific personality style through a tough conversation, know what to expect is going to come back their way.

You know, what kind of pushback are they going to get?

What kind of struggle? What kind of, you know, is it a, you know, controlling person that's going to throw them under the bus? These are opportunities that you have to lead.

So get in there and lead. Ask the question, what's the hardest conversation you've been avoiding? And then, man, enjoy the process because this is where you really get to help a leader grow.

Third question, what would you do differently if you could go back?

So it's not, you know, hey, is there anything you need for me? It's if you could rewind one moment this week or last week and handle it, what would you change?

So what's actually happening when you ask this question? This is the self assessment question. It shows you whether they can look at their own week critically, which is vitally important.

Right? Can they critically look at their own week and find problems, things they do differently, whatever, without you pointing it out first? Right.

Many times a team member is just like, I know Chris is going to point this thing out. I'm just waiting for him to do it.

No, I want the team member to come to me. I don't really have to point anything out with my leaders because they're always coming to me first.

Hey, here's this situation. Hey, I want you to know this. Hey, this happened. It's constant. We are ahead of the game all the time because there's no fear. There's no fear of judgment.

There's no fear of, you know, treating somebody like they're not good enough. There's just no fear. Right? So we communicate early and we communicate often. So when you're not pointing it out, this allows the person to answer honestly.

Right. It's literally building a muscle inside of them to look back on their week and even, especially when you're not in the room, because if they know this is coming, then they'll be practicing this, you know, ahead of time, which means that they're probably going to be able to make some better judgment calls without waiting into the one-on-one.

And, you know, in the early days you'll probably ask the question, you know, what is something you would have done differently if you could have gone back over the week and they'll give you an answer.

Again, another opportunity for you to lead them and guide them to solving that. You know, can they go back and fix it? Is there something else they can do?

Well, the muscle that you're building is that they will start rehashing well before they get to the weekly one-on-one meeting, they will start processing through, because you've worked on it a few weeks, they will start processing through and going, ah, I need to jump on this right now.

So when you get to that one-on-one, after you've coached them for a while, you're probably going to get, well, here's something that I wanted to do differently and I just went ahead and did it.

I just changed this or I had this conversation or I did whatever. And now you see the development, now you see the growth. So three questions.

What decision did you make without me?

What conversation are you avoiding?

And what would you do differently?

Putting It Into Practice (00:19:25)

Every one-on-one that's gone flat is missing at least one of these. And most are probably missing all three. But here's the thing. None of this requires a new meeting.

Not a new hour, not a new agenda, not a new tool. It requires a different opening question. And then go into that meeting and open with that question before the task list, before any status updates, before what's on your plate, before any of that.

Don't have a status conversation, not a, hey, walk me through your week, have a judgment conversation, one that starts with before we do the usual update, I want to ask you something different this week.

You know, prepare them in the beginning. Hey, I want to take a little bit of a turn today, right? I want to ask you something a little different and then ask it. Sit in the pause.

Sit in the pause. If there is one. If they're, if they're having it, they should have to process through this and, and let them think out loud.

Something I say all the time when somebody's having to process and there's just a long pause is I'll say process out loud and I want to hear their process. I'm not going to not because I'm going to correct them on. No, no, that's not correct.

They're processing. So understand they need to verbalize it for a little bit, but just wait patiently, right? I want you to notice because most capable people have been, you know, quietly waiting for somebody to ask them this anyways.

I want you to notice how they respond when you ask, what decision did you make without me? You're telling them you already believe they're capable of deciding things without you, Right?

So they're gonna, you know, most likely they could very well say, well, nothing. I can't think of anything. Give them some time. The goal is, is that we want them to be confident that you believe in them so that they can open up.

This is usually what kind of unlocks that team member. Now, before I let you go, this is usually what unlocks that team member and allows you the opportunity to have one of the best one on ones you've ever had.

Get in there, lead, guide, direct, help them, grow them, develop them. You have the opportunity. Make sure that you don't miss out on it.

Now, before I let you go, I want to make sure you didn't miss something. What we talked about today is real. Ask that question this week. Your one-on-one needs it.

But here's the bigger picture. If your one on ones only ever review tasks, you'll never find out who on your team is actually ready to own more.

And that means decisions, conflict, hard calls that keep landing back on you because you never built a meeting that would show you who could carry them.

That's why I'm addressing on August 6th at 11am Central Time in a free live workshop. It's called Four Steps to Build a business that runs without you. It's not theory, it's the actual system.

The four things that that have to be in place for your team to lead without you in the room.

It's free, it's live. You can bring your questions. Go to chrislocurto.com/build to register. That's chrislocurto.com/build. I look forward to seeing you there.

Well, folks, that's all the time that we have for today. I hope this has helped you immensely. As always, take this information. Change your leadership, change your business, change your life. And join us on the next episode.