Transformative Questions for Leaders
I'll never forget we were at an event and one of the business owners that had actually spoken on a panel at the event was talking to Kyle, you and me, after the event, and he was just talking about his business and we were asking him a bunch of questions and the conversation was moving pretty fast paced. You could tell this guy, actually was quite successful and he was very, very sharp too and he was pretty bold and assertive in the way he was talking, pretty honestly aggressive about the way he was talking about his team, about where his business was at, where he wanted his business to go, and all of these different things. And then he said something to the effect of, like, my team can't handle that rate of growth or something like that. He said something pretty bold, pretty assertive, and I'll never forget, you just jumped in really fast. And I think to a degree, cut him off a little bit, and you said, is that true?
Alex Judd:And and it was, like, his entire demeanor changed. He shifted from his toes to his heels in some ways. Like, he got off of offense, and he literally started backtracking some and started to say, no. It's not fully true that they can't handle it. And then you started to ask more questions.
Alex Judd:And I I thought that was such a powerful moment of, man, the quality of your conversations always reflects the quality of your questions. And one specific question that really kind of in some ways engaged with him in the thought process and belief system that had been driving the trajectory of his business up to that point changed the entire trajectory of that conversation. And out of that, I actually think he left with a different strategy than what he came into the conversation with. That's really what we're gonna be walking through in this episode. We always say that we help leaders build healthy, growing, profitable businesses that don't depend on the owner to create a positive impact.
Alex Judd:And part of that is, man, what is the quality of the questions that you're asking both yourself and others? Because that's gonna impact the quality of the results that you get. So what we're gonna walk through is really a handful of questions that we see ourselves asking business owners and leaders over and over and over again in coaching conversations. These are not theoretically, hypothetically good questions. Like, these are the questions that we see transform conversations and therefore generate really powerful results.
Alex Judd:So let let's start with the one we just said, which is is that true? Kyle, I'd love to for you to add any color you have from just that particular moment if you remember that moment. And then I just I hear you ask this question a lot to people. Maybe give us some understanding of when you use it and why it's so powerful.
Kyle Guemmer:The fact that we work with CEOs and business owners and business leaders, it means we work with a lot of really strong personalities, people who do have strong beliefs and opinions and biases and communicate about those things very confidently. And what I have learned the more and more that I work with these business owners is a principle I use all the time is belief drives behavior, but a part of that and why that principle is so important is the story you tell yourself is is the way that you live. And so he was really not telling me maybe realities of his business. He was telling me a story about his business.
Alex Judd:That's so good.
Kyle Guemmer:And it was really just, is that true? And I think it kind of just story and data are very different. Story is just it's a narrative where data is fact, and that is just a question that can just cause a little bit of a stutter of, like, is this narrative that I'm telling myself, which is driven by beliefs and assumptions and biases that I have, is that true?
Matt Aiken:Mhmm.
Alex Judd:And I think there's something to be pointed out there is, like, we are all operating out of what we think is true. Other like, no one is oh, you know, hopefully, you're you're in a very unhealthy spot if you are intentionally operating out of a lie. Right? So most of us are operating out of what we think is true. It's just what we think is true isn't always what is actually true, and it takes a question to create the time for internal reflection to realize, no.
Alex Judd:That's not actually true. What what would you add there, Matt?
Matt Aiken:Perception is reality. Not saying that there's not truth. Right? But perception is really, really important. And and it's it's a danger if we continue down a path or or it's a waste of time if we continue down a path and we start solving a problem doesn't actually actually exist.
Matt Aiken:And so it's it's an uncomfortable question. I think that's the thing that sticks out is this is a question that is hard to use without a lot of context and confidence. Yes. Or actually, you know what? You didn't have a lot of context from from what that that leader was telling you, but you did have a lot of context in the sense that when someone is so confident, we need to pause and ask is this is this confidence honest?
Alex Judd:That's also one of the I mean, one of the things that's unique about the dynamic that we operate in is he had heard about an hour of teaching from us. And there was a level like, he came up to talk to us, and it was clear that, like, there was a level of respect, and that was why he you know, and and trust in terms of our competency at the very least, that that stuff should all be in place if you're going to ask a person this question. Otherwise, that's probably not gonna go super well. Let me ask you all this. Are there any flags that, like, if you hear people say this, maybe just as even like a a setup for them telling a story, you're gonna counter it with is that true?
Alex Judd:Always, never,
Matt Aiken:any of the any of the, you know
Kyle Guemmer:The absolutes.
Alex Judd:Mhmm. They always do this. I'm not able to delegate this responsibility. We've never been able to do this, so we can't ever do this. Yeah.
Alex Judd:Anything else?
Kyle Guemmer:Yeah. If if people are building strategy and vision out of a narrative and not data and and, again, I'm not even saying this as saying, like, we should make all of our decisions out of data, but it's if the story that was being told was a narrative about things that that were quite nuanced. And so there was a lot of absolute language about things that are a little bit more nuanced, and he was building strategy and vision of how he was gonna move forward in the business based out of that. And so it's it, like, just can be a helpful question in those moments of even for me and how I how I live my own life, like, there are certain strategies and tactics that I choose to pursue based on narratives that I have, and it's like, it's really helpful for me to ask, like, is this true? Because if it is, I'm gonna do this.
Kyle Guemmer:If it's not, I'm going in a way wrong direction.
Alex Judd:Yeah. I I think I I like to ask this question a lot whenever someone presents something as the only option. Like, this is the only way to do this. This is the only way to accomplish this goal. I'll I'll never forget.
Alex Judd:I was on on a coaching call with someone that was just I mean, they had just gotten walloped a few times, and and I think there were a couple of contributing factors to the bad circumstances they found themselves in. They had a really successful business, but they they just kept getting I'm just beat down. And part of that was they probably weren't engaging as much in their own growth journey as they probably could have or should have for the rate that their company was growing. And I sensed a ton of conflict in this person of they felt a need to be the CEO of this business because it was a family business, and and they took it over, and there's all of these expectations associated with taking over this business. And I don't know that they actually wanted to be doing that, but they felt like they had to.
Alex Judd:And they had kinda set out, like, this, like, five to ten year plan of, like, eventually, I'm gonna work my way out of this business. And I I just asked them, well, could you sell this now? Like, it's clear I mean, it's a wildly successful business. Could you just sell this now? And they were very assertive and say they said, no.
Alex Judd:I I can't do that. I have to do x y z first. And I said, is that true? Like, you have to? Like, there you literally cannot.
Alex Judd:And, I mean, what was crazy about this is they spent a lot of time justifying why it was true. Like, I cannot. And and then we start going into, like, man, why does, you know, you keep kinda having these challenges where you feel imprisoned by your business because you literally have imprisoned yourself in your business. And I finally got them to say, it's not true. I could.
Alex Judd:I could. It doesn't mean I'm going to, but it means that I could. And I think the minute that we start to consider, okay. It doesn't mean that we're gonna take other options, but we've gotta consider that are other options. Because if we don't even consider that there are other options, we will experience it as a prison, I think, in so many ways.
Alex Judd:Anything else on that question of is that true?
Matt Aiken:Yeah. I I would say it might seem like an uncomfortable question, but it's such a it can be a powerful service to the person you ask it of. Yeah. I I was I'm, like, over here kind of replaying a couple of recent times. Y'all have asked me this question just in the context of of normal relationship,
Alex Judd:Like, when you say I'm not hungry and I go, is that true? Is that true?
Matt Aiken:And and what's so interesting is I find myself sometimes making statements around people I trust in hopes that they either challenge or help help me think through a statement. Like, I'm I'm talking to myself about I think this might be true, but I'm saying it in in a in a manner of, like, this is true and it's so helpful. It's such a service when when people you know and trust around you just just take a minute and say, is that true? Yeah. Talk about a deep breath.
Matt Aiken:Yeah. Let me think. I I think that is true. Here's what I'm thinking. What do you see?
Matt Aiken:And so it, you know, it's not always a confrontational assertive question. Sometimes it's a it's a really gentle and serving question.
Alex Judd:Yeah. I mean, Ben Ben and Olivia on our leadership team, they ask me this a lot. And sometimes they don't even ask. They just say, Alex, that's not true. And I say, okay.
Alex Judd:Well and I I find myself trusting them so much because what I'm trusting in there is their competency. I'm trusting that they're not just being yes, man, and allowing me to walk to the edge of a cliff knowing that, dude, you're, I mean, you're gonna fall off that thing and just not saying anything. And that that really helps me. I I think another point to hit home on here is I think we we think that effective leadership is getting to a spot where no one has to ask you this question. And, like, I I think we put the expectation of ourself as like, oh, I'm the type of leader that only operates out of what is true a 100% all the time, and no one has to ever ask me this question.
Alex Judd:I would say the minute you're doing that, you have stopped leading. Because in so many ways, leading is like making hypotheses about the world, the unknown world that you're stepping into and testing those hypotheses. And one of the ways we test hypotheses is is basically socializing them with other people. And so the more you lead, the more people you should have asking you this question. And if you don't have people asking this question, that might actually be an indicator that something's gone awry.
Matt Aiken:Yeah. Okay.
Alex Judd:Which one should we jump into next? Let's choose a question that we find ourselves really asking business owners a lot. What do you want?
Matt Aiken:I mean, what do you really want?
Alex Judd:Yeah. The tone makes such a what do you want? What do you want?
Matt Aiken:Yeah. That's right. It kinda goes into this this this story that we're living in is the story we're living out or the story we're telling ourselves is the story we're living out. You know, I I will find myself in a conversation where where again, there's an assertive statement or or there's some sort of circumstance that is that is explained and and that person is either feeling trapped. They're they're living in that only, this is my only option.
Matt Aiken:This is the only reality that experience and and and we just need to pause and say, okay. Well well, what do you want? What do you want to be true? What what do you want this employee to do? What what do you want to be able to say to that person?
Matt Aiken:And just stopping and getting clear on the desired outcome so often reveals, well, the path between where I am and my desire doesn't have any blockers other than me taking the courage to go and and get after that. What what does Brene Brown say? Vision is vulnerable. Right? Mhmm.
Matt Aiken:The moment you say what you want, you're entering into a vulnerable state where you've now said, well, there's a failure. It's not getting what I want. Yeah. Which is not always a bad thing, by the way. But, yeah, what do I want?
Alex Judd:I guess I would like to know from y'all, like, the scenarios in which this question is most helpful for people. I can speak from my own experience because I've had a lot of mentors or coaches even ask me this question in some form or fashion. And oftentimes, it's probably helpful and serves me because I'm avoiding qualifying what winning actually is. This is not like I'm making this hyper conscientious decision. You just get busy.
Alex Judd:And in the process of getting busy, you stop engaging with things that feel uncomfortable. And when you don't qualify what success actually is or what winning actually is, there can be a level of convenience associated with that because then you're also not qualifying what failure is. And so that's why I think that can be a really natural default position to settle into. But what actually happens whenever you do that is not, oh, if I don't qualify what success is and I don't qualify what failure is, you just end up in this spot where you actually kind of question, am I failing all the time? And you never actually know because you haven't identified the parameters of success.
Alex Judd:And so a lot of times when someone asks me this question, they're actually counseling me through having the courage to define what winning actually looks like. And they're also giving me the confidence to know that my vision of success and the calling that God has placed on my heart might look different than someone else's, and that's okay. And they can support me in that and say, dude, you don't have to do what everyone else is doing, and it's okay for you to want what you want in so many ways.
Kyle Guemmer:First of all, you said something there that I wrote down because I was like, this could be another podcast. You said, when you get busy, you stop engaging with things uncomfortable. And I'm like, is that a principle?
Alex Judd:Is that true? There's something in there.
Matt Aiken:I think we could
Kyle Guemmer:wrestle with that. So you said it, and I wrote it down. Okay. Thank you. What do you want?
Kyle Guemmer:Yeah. I find myself asking people this question in in decision making situations, particularly around things that are really emotional because we're dealing with impact driven leaders who love their people and who love their customers and love what they do and are really passionate about it. And when you're navigating through really difficult situations, you are you are juggling all the nuance of that, the emotion that's involved in that for you and for other people. You're you're navigating the ramifications and how that will affect your customers and your people. And there's all of these things that you're kind of, like, playing with and jostling with and trying to trying to make sense of, and you never stop to consider, like, well, what do I actually want in this?
Kyle Guemmer:And so those are the moments that I feel like it can be helpful because then it can draw out what are the emotions that are maybe impacting how you're thinking about this decision, and then we can call those things for what they are and get to actually a little bit of the vision of what are we actually trying to get accomplished here.
Alex Judd:Yeah. And, you know, it's okay to in conversation, if conversation is mutual exploration, it's okay to work through, is this a good desire or a bad desire? Having the desire is just a statement of fact, and then we can talk about, is this a good desire or bad desire? It was interesting. I was sitting down with Jim.
Alex Judd:He's a pastor at the church that I go to and just been an incredible mentor of mine, and Was talking to him recently about the fact that I'm about to take a month off of work. I don't know if challenging is the right word, but it's been a clunky conversation for Aspen and I to work through. I for sure recharge in solitude. And, like, if I go off and, you know, camp in the mountains for two nights, with zero human interaction, that was something that will fuel me for the next eight months sometimes if I do it right. Right?
Alex Judd:And I I do travel some, but but whenever I travel by myself throughout the year, it's always work oriented. And so now I'm taking this month off, and and we've just had conversations around, like, is it okay for me to do that and stuff like that? And I was talking to Jim, and he asked me, well, what do you want? And I I said, like, I I really want to, you know, go just for two nights camping somewhere in the mountains where it's green, where it's cool, and just run a ton and all that. And then I actually asked him, is it okay to want that?
Alex Judd:And and if I was journaling on my own, I could have answered this question, but I didn't journal this on my own. And so it was really helpful to talk to someone about this. And he said, dude, of course, it's okay to want that. He's like, now me telling you it's okay to want that is not your excuse to just go and, like, pull the trigger on it and and just tell Aspen deal with it. He said, like, this is gonna be something you have to work through, but he said, probably be really good for you to ask her what she wants and you to get clear on what you want then and for y'all to bring those two together and be like, how could we collaborate to accomplish all these objectives?
Alex Judd:But again, I think that my predisposition that I see show up with a lot of leaders in personal and in work context is we start to think that desire in itself is bad. Yeah. And the minute you start thinking desire in itself is bad Yeah. You're actually setting yourself up down the road to be, like, actually quite resentful or apathetic, which both are not who you were created to be. Yeah.
Matt Aiken:The way you ask this question can come in a lot of forms. One is as a reaction to someone bringing something to you, like, hey, I've got this thing coming up or or I'm I'm unclear. What do you want? But it's also a really good proactive question. Right?
Matt Aiken:What do you want to be true at the end of this meeting? Like, this is what we teach in operationalizing. Right? Yeah. All we're trying to get to is is that vision, is that outcome.
Matt Aiken:And sometimes it's a very proactive and and curious exploratory question. Other times, it is to to stutter step and pull people out of, an assumption that they might might have. What, like, what do you actually want?
Alex Judd:Yeah. And sometimes you might have to stumble your way verbally through saying what you don't want.
Matt Aiken:Mhmm.
Alex Judd:But I think a good coach and a good leader will always make sure the conversation lands on what you actually do. Yeah. That's good. Like, I I do not want your list of negative things you want to avoid. We can talk about those, but now let's talk about what we are actually for.
Alex Judd:Okay, Kyle, where should we go next?
Kyle Guemmer:Have you told them that?
Alex Judd:Yeah. Okay. I feel like we all kinda like, this was the one that we actually almost missed writing down as a question we ask all the time because we ask it so often. Like, it just as, like, a you don't even think about asking this question. So what is the typical answer to this question?
Alex Judd:No. Yeah. Well, so so why is that the case? Like, so often we're in conversations about challenges, problems, maybe sometimes drama, maybe goals, maybe expectations, all of that. And and then in the midst of all that, other people get involved, and we end up asking the question, have you told them that?
Alex Judd:And then as you just so eloquently said, the answer is often no. Why is that the case, and why is this question so valuable?
Kyle Guemmer:Yeah. So I first wanna preface our job as we coach and serve our customers is to navigate through really hard situations. And so there's some things that they are really, like, lack clarity in that, like, you need to navigate and work towards where it's like, that question won't be appropriate because it's like, well, you don't even know how to like, you don't even have clarity on what to do in this situation. This is more in a situation where this could be as small as, like, spinach in the teeth or as big as they're failing in their role, and I can, like I have a lot of confidence in me being able to communicate that with them communicating it to me. And that's where it's just like really helpful to say, have you told them that?
Kyle Guemmer:Like, because I don't want to engage in gossip, and if they say no, then it's like, well, what do we need to talk about for you to be able to have that conversation? Mhmm. Because you have a very strong feeling about this. I don't think you need my insight potentially in this, or if you do, communicate to me what you actually need because at times, they're looking for validation. At times, we may be looking to avoid, or at times, we may just lack courage in being able to have that conversation.
Kyle Guemmer:And so just asking them that gives us the baseline of like, we're talking about someone in your organization here, or we're talking about a relationship here. You have strong convictions or feelings in this particular area. Have you told them that how you answer that question helps us know how to navigate this situation effectively?
Alex Judd:Yeah. What's the personality type that most needs to be asked this question?
Kyle Guemmer:People who avoid conflict.
Alex Judd:Mhmm. People pleasers, maybe?
Matt Aiken:Yeah. Mhmm. If you have a proclivity to complain, like, you have a predisposition towards verbal processing of frustration, I think it's a good tool for one stutter stepping, you know, have you said that to them? Oh, I would never say that to them. It's like, well, then why are saying it to yourself?
Matt Aiken:Okay? Is there is that goes back to is this true? Like, is this is this actually a deep frustration or a need? But, you know, anytime you got a proclivity to to complain, what are you doing? There's a pride associated with that of like, well, you know, I'm the victim here.
Matt Aiken:And it's like, well, I thought leadership was service. And so the question is, are you you saying this to yourself or are you engaging with this in a manner that is gonna help you get yourself, your organization, or this team member person in your life from here to there. Mhmm. And then you can you can say like, well, I I don't think it'd be wise to say that to them. And then you can go into, okay, Let's test that.
Matt Aiken:Would it be wise? Would it not be wise? What would be wise to engage in?
Alex Judd:Yeah. The skill of going and talking to the person, it is oftentimes not developed in people that maybe the only job they've ever had was they were the founder of the organization, and then they looked up, and now they're the CEO of a 50 person organization or something like that. And maybe that's because, like, they never saw an effective CEO. And and so they're they're not aware of what good leadership looks like, and they think, like, good leadership is just appeasing people or or they maybe have some questions in their head or some doubt or lack of confidence in their head about what you can expect from people. And I think it's why it's so helpful for people that, you know, maybe the the only job you've ever had is the one you're currently in.
Alex Judd:You look up and you now have the title of CEO, but you have no clue how to do it is go around other, like, wildly effective CEOs. And one of the I mean, I have done this. Right? And and one of the things I'll be shocked by is, like, I can't believe it, the stuff they just say. Like, it's like and the thing that will take me two weeks to work up the courage to say, they they will just say it, and and there's no malice.
Alex Judd:They're they just are confident in, like, this is part of my role, and I'm just gonna tell you this, and we're get then gonna move forward. Right? So, like, I think the answer can often be no if we don't feel confident in the fact that it's one of our roles, responsibilities to say things that we see or the things we believe are true.
Kyle Guemmer:Anything that has to do with people is hard. Leadership is has to do primarily and only pretty much with people, and so it's really hard. And it it is really it is it is easy, or there can be a temptation to to be the victim. Well, if these people just could figure this out, my life would be easier. And I think this question kind of just cuts through maybe the victimhood mentality and gets to agency of, like, what is the conversation we need to have here to make you feel confident that you either need to let this go maybe or have a conversation or how to have that conversation in a really productive way.
Alex Judd:Yeah. I mean, in some ways, all the questions we talked about in some form or fashion are agency oriented questions, and it's because I think a lot of coaching a lot of times is rooted around the virtue and value or the fruit of the spirit self control because it's like what reality, this is a conversation between you and I. What else can we actually talk about? You certainly can't talk about other people, like, and how you can control them. We can talk about what can you do, and the thing that keeps us from doing what we can do, the thing that keeps us from self control is lack of agency, the belief that we can't actually do the things that God has empowered us to be able to do.
Alex Judd:Okay. So we've walked through a couple of really valuable questions that we find ourselves using. If you were to give one word of encouragement or challenge to the business owners and leaders listening to this in terms of how do they actually take these practical tools and deploy them in their context, what would the two of you say? Matt, you go first.
Matt Aiken:Yeah. I think challenge yourself to be a curious leader and start using questions and try to use the same question in several circumstances and evaluate the result. Like, this is a skill that we're talking about. Kyle and I have trained. You you have trained.
Matt Aiken:We have trained and talked about and evaluated how did that go? What would have been a question you could have used here? It is something to be honed and developed. It's not something that you are gonna be accidentally good at. You might have a predisposition to it, but pick pick one or two questions, start to use it regularly, and evaluate how did that go.
Matt Aiken:Yeah. Really good.
Kyle Guemmer:Focus less on the questions and that being prescriptive and focus more on the general spirit of the conversation that we're having in the sense of, yeah, maybe these questions are very assertive, and I think there is a balance between being curious and assertive, it's more just the quality of your results will never exceed the quality of your questions. Be curious and start to practice asking effective questions. Maybe not assertive questions, but let me not assume here or let me not just give a statement or a thought here. Let me just ask a question. And I I think as you I think that's a really good developmental skill to have as a leader because good great leaders are great coaches, and great coaches are curious.
Kyle Guemmer:And so start asking those questions. But I think in this general spirit of this conversation, understand the why even behind these questions, and don't be so prescriptive to the the number of questions that we talked about, but more the spirit of why asking questions is helpful and effective in leadership.
Alex Judd:Yeah. Excellent advice. Thanks, y'all. Well, there you have it. Thanks so much for joining us for this episode.
Alex Judd:If you want any of the information or resources that we mentioned, that's all in the show notes. Hey. Before you go, could I ask you for one quick favor? Could you subscribe, rate, and review this podcast episode? Your feedback is what helps our team engage in a sequence of never ending improvement.
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Alex Judd:Hey, thank you so much to the Path for Growth team, Kyle Cummings and the crew at Podcircle, and the remarkable leaders that are actively engaged in the Path for Growth community. Y'all are the people that make this podcast possible. Y'all know this. We're rooting for you. We're praying for you.
Alex Judd:We wanna see you win. Remember, my strength is not for me. Your strength is not for you. Our strength is for service. Let's go.
Alex Judd:Let's go. Let's go.
