The Modern Leadership Coaching Podcast

Stop Winging Sessions - The Standard Your Clients Can Feel

Marc & Teresa Hildebrand

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Your client can feel it the moment a session turns into a friendly chat. Marc and Teresa unpack the uncomfortable truth a lot of coaches avoid: improvising might sound intuitive, but it rarely produces consistent client transformation. We talk about the gap between a “good conversation” and a coaching session built for measurable change, and why clients stop re-upping when the work has no clear direction.

We also dig into coaching vs mentoring. If you’ve had success in fitness, leadership, or business, it’s easy to slip into advice-giving and assume your client’s problem matches yours. Real coaching requires a repeatable coaching framework that helps someone find the root issue, name what they actually want, and navigate the whirlwind of distractions and self-sabotage. We share how we use simple pre-call questions to prepare both coach and client, keep sessions aligned to stated goals, and decide whether the real block is an adaptive challenge or a technical challenge.

Then we get practical about skill-building: talent isn’t the point, reps and feedback are. We explain why great conversationalists sometimes struggle as coaches, how staying in a learning environment protects your confidence, and why getting coached yourself makes you better at guiding others. If you want one actionable step to stop winging it, we give it to you: record a session, listen back, and ask for feedback on what you did well and one thing to do differently.

If you got value from this, subscribe so you don’t miss the next one, share it with a coach who’s ready to level up, and leave a review telling us what part of your coaching you want to improve next.

If you want to stop winging sessions and learn to coach at the root level, apply for the next cohort of High Impact Mastery Academy at modernleadership.us/academy and, if this helped, subscribe, share it with a coach friend, and leave a review.

Want to go deeper on what we talked about today?

We put together a short video on how to lead high-stakes conversations without winging it.

Watch it here: https://www.modernleadership.us/mastery


Conversation Versus Real Coaching

SPEAKER_01

So there's a difference between having a good conversation and a coaching session that actually creates measurable change. And I found that most people can't tell the difference, especially when you're first getting started out. That's why today this episode is about the thing that nobody likes to admit, which is that a lot of coaches are improvising their sessions and really just hoping it works. I mean, I've heard this a lot of people just jump onto a call, they haven't planned out the direction, and they just kind of like flow it out. But the truth is that the client can feel that and it's making a bigger difference than you think. So you ready to talk about that today?

SPEAKER_00

Let's do it.

SPEAKER_01

Let's go. So you're listening to the Modern Leadership Coaching Podcast. I'm Mark. Teresa. And this is where we talk about what it actually takes to grow as a coach and leader and parent and spouse. And and and, right? Because the world doesn't need more coaches, it needs more people who can be trusted with this level of influence. So here's the thing some people that I have come across think that jumping into a session and just using their intuition is something that is going to really help their clients. And I have seen some people who can do that, but I've seen most people kind of like not be able to help their client actually have a true transformation, which is why when a client gets to the end of a six-month or a 12-month, they they don't re-up. They're like, hey, this is great. I was just having a lot of conversations versus having a real transformation. Okay, so I want you to think back to the time before you not only got certified, but you had like a standard that you were following, right? I mean, the reason why I say that is because some people who are certified aren't taught a standard, like in terms of ask questions and just get curious and help something arise, like help the client see something that maybe they didn't see before. And that's not what we're talking about here. We're talking about an actual path to guide somebody down. Not that we're telling them to go down there. We saw things in place to make sure that we don't do that. But I'm curious, like before you had that kind of structure or path, I'm curious what a typical session would look like for you. And I'd like you to be honest, especially when we first started out, right? So what what comes up for you?

SPEAKER_00

Yeah. So when I first started as a life coach, I did have a standard. I did learn how to guide a session. But before that, I really wasn't doing that. I was, in a sense, mentoring because what I had experienced, what I had gone through was something that I was passing on to whoever I was helping, right? So I had lost weight, I had gotten into the best shape of my life. People were coming to me to ask me how I did it. So I was like, oh, I'll tell you exactly what I did. And I would give them advice and I would tell them what to meal prep and what exercises to do and things like that. Very similar to your story, right? Because we got started together. But I thought I was coaching someone because I didn't realize the difference between coaching and mentoring. So when I started to go into life coaching, then I saw that there was this rhyme or reason, right? There was this process that you can guide somebody through. That was like a really big eye-opening moment for me because I thought, well, I could still use my experience, but starting off with someone, you really have to gauge where they are and where they want to be. So yeah.

SPEAKER_01

I love it. I mean, obviously, I was there during that story. I was doing something very, very similar, right? And we want to make sure that you don't shame or guilt yourself if you're still doing this, because that's the start, right? We helped out way more people than we would have if we had not done anything at all. Yeah. But I remember, I remember when I was doing this because I was still working full time. So I was working out as an LEPD. And then I would have off days, like anywhere two to three days a week. First day was always recovery, but then I'd have one or two days where literally I would just get on the phone with people for like, I don't know, seven or eight hours. And every half an hour I'd have a new person. And I thought it was coaching too. And I was merely like asking them a couple of questions and then sharing my story, doing like the feel-felt-found model, like all these things that we were taught. And it was connecting with people and people were taking action. And obviously, once they got on board, there were less people that I could actually help with that transformation because it was more of like, we said in the beginning, more of like a monologue. Like, let me tell you all the things, let me tell you all the solutions to your problem. But they didn't know what their problem was. They thought their problem was eating. They thought their problem was they need to lose weight. They thought their problem was the workout that they did.

SPEAKER_00

Because we assume that the the issues that we had were similar to what they had.

SPEAKER_01

Yeah. Yeah. 100%, 100%. So understanding coaching to the level that we do now helps us get to the root of what's actually going on. But that also still not a plan.

Why A Repeatable Plan Matters

SPEAKER_00

Right.

SPEAKER_01

We teach and train a lot of people who are already certified. And I've seen this happen, where what they do is when they get on with a client, all they ask them, they just go through this process every single time of like, hey, what can I help you today? What are you struggling with the most? Now, when you're first getting started, it's important to do that so you can help get to the root of people's problems. And so you get good reps and feedback on how to do that better. But that still doesn't equate to a plan. You have no idea what they want to achieve. If they're bringing up problems today because they're trying to self-sabotage themselves and actually not do the things that they want to do. We started this new program called Meet 10, which is like getting out there and having conversations with people. Do you know how creative our brains can get to self-sabotage that? I need a website first. I need a business card. I need to know what to say. I need all these kind of things before I actually do it. And so it gets really creative on not taking that action. And so we as coaches self-sabotage. So you better believe that our clients are going to self-sabotage. And every time that they that you get on a call, they're going to have a different problem they're dealing with. And they're not going to want to talk about the previous problem because they haven't done anything different. We think about a plan. We think about, yes, having the structure of knowing how to actually get to the root of what people are struggling with, but also having a plan, helping them identify what they want, helping them get out of their way when they navigate the whirlwind, right? Helping to see what they can do differently, but also really think differently, making them aware of those situations, giving them feedback, but also having them reflect for you what's working, what's not working, what adjustments need to be made. And like when you go through this whole process, this is something that we teach in HEMO, when you go through this whole process, you actually have somebody who you can lead to a transformation. And if you don't lead them to transformation, you know exactly the point where they're being held up and you can verbalize that to them so that they can see it. Because the truth is sometimes people see it and they choose not to go down that path. They choose not to get past that. And that's okay. We're not here to force people to do things, but we're here to show them. But having some type of plan like that is really, really powerful.

SPEAKER_00

And one thing that, you know, I was thinking about when you were talking is that eventually that standard becomes something that you use every once in a while. So for example, you've been coaching for a while, you start it off with some type of framework or something to get started and to understand how you can help someone through a session. Eventually you start to develop skills, those things that kind of help you be a unique coach, an expertise or whatever that may be. And then eventually you're not winging it. However, you are coming in with a little bit of a different mindset when you're doing these sessions. And it's just like anything else, like leadership, right? Leadership is taught. There are people who can be naturally inclined to be leaders, but it's the same thing. It's kind of like you learn these things and you learn these skills so that you can develop that expertise.

How Clients Sense You Are Winging It

SPEAKER_01

And at such a critical point, going back to the whole idea of having a toolbox worth of different tools, right? A bunch of different skills. Because in the beginning, maybe you just have a hammer, but then maybe later you get a wrench. You get all these different things, which by the way, generally, two things in terms of how to learn and develop as a coach. Number one is constantly be out there learning to see what other tools, skills, mindset shifts, all that kind of stuff that you could utilize for yourself, you going through that process. And then you can use that to transform your clients. But number two is when your clients get stuck in the beginning, they're gonna get stuck because you don't know it all. They don't know it all. There's a process, there's a learning process, and even as you get older, you're gonna get more developed in coaching. You're still gonna get stuck. Those are the opportunities to lean in and develop a new skill. Those are the opportunities to really say, Hey, this thing is trying to teach me something. What is it? Instead of just trying to use the same old skill that you had over and over and over again, it's time to develop something else. So yeah.

SPEAKER_00

So, you know, we talk a lot about clients being able to actually feel that difference when you're just winging it as opposed to actually having a plan. So, what does that actually mean? How does a client experience a coaching session versus just a conversation that felt good?

Pre Call Questions That Create Direction

SPEAKER_01

Yeah. I feel like this actually takes a little bit of time. So when a client first signs up with you and you're starting to guide them through different things, a lot of times over time, they will start to see the difference between if they're having a conversation with a friend versus if they're being actually challenged by a coach. And when I mean challenge is I don't mean you're challenging them physically or performance-based. I mean you're getting them to see things that maybe they don't spot. You're getting them to see beliefs that are actually holding them back that maybe they didn't know about. And if you're having a conversation where, you know, you're just having a conversation with your friend, which by the way, this is a different conversation when we're talking about coaching. I try to be everybody's friend, but when they pay me to coach them, I make sure I coach them. And if the friend comes up, that's cool. But a lot of times it's the coach who comes up. Did you notice this? I heard you say this. What did you mean by that? And these are all different ways that we utilize to help our clients transform. And over time, you'll notice this after the first couple of sessions, after the first couple of months, the client will start to feel like they're not making progress. And a lot of times it's because they're either just having conversations or they can feel that you don't have a plan on what to do next. Because all you do is you show up and it feels like you're winging it. You're not taking them through different paths, you're not using it as different sessions. You're not doing what we call a reflection session, you're not doing a breakthrough session, you're not doing things differently. It's just the same old, same old of like, hey, what do you want to talk about today? So, one of the things that we've implemented, and we do this a lot with our one-on-one clients, is before our call, we make sure that we ask you four to five questions to figure out number one, based off of what you said you wanted. So you don't differentiate from what you bring something else to the call that is unrelated to what you told us you wanted. But also number two is because we want to know what direction we can actually take you, but also like some skills or something that we could teach you through that process. We talk a lot about the adaptive and the technical challenges. We like to beforehand know some of those adaptive or technical challenges because we have a plethora. I mean, we've been doing this for a long time. We have a lot of teachings and trainings and YouTubes and podcasts and resources and things that we can use. And if I can actually ask you those questions and figure out where you're stuck, where would be the greatest opportunity for this week and what would be transformative on this call, then I can help guide that. And sometimes I teach stuff. Sometimes I ask questions to help identify what's adaptive and what's technical. The client can feel that. They feel that you're like doing this in a working and molding session to figure out like how you can really help them on a deeper level rather than just coming there and go, hey, what do you want to talk about today?

SPEAKER_00

Yeah.

SPEAKER_01

So that's what comes up for me. Anything different for you?

SPEAKER_00

Well, I was kind of thinking when you were talking about you don't want to go in blind. So you do want to prepare and you also want to prepare the client. Like, hey, like this is kind of like the direction that we're going based off of what they really need. Um, so I think that setting that up beforehand during sessions will number one, help you prepare for the session, like you said, bringing up tools or whatever, or I mean, even coaching yourself. But then also preparing the client where it's like, hey, I put this down on paper and this is what we're gonna talk about. Like, I'm not gonna avoid it because there are times where I feel like sometimes the client will avoid certain things because maybe they didn't do the things that they said that they were gonna do. We end a session with, hey, what are you committed to doing for the next couple of weeks or the next week? So I think that's a really great way to keep things in line so that way the sessions can go really smoothly.

Using Research And Outside Expertise

SPEAKER_01

Yep. One more thing came up from what you said.

SPEAKER_00

Okay.

Why Talent Can Hurt Coaches

SPEAKER_01

And that has to do with preparing for the session. I want you to think about this. Let's say you're about to go into a session and you're the client, and your coach jumps on and they're like, hey, you know what? You kind of shared this struggle with me last week. And so I reached out to an expert in this field who also is a coach, and they gave me some different tactics and strategies that I want to bring to you here today because they're an expert in this space. Just think about what it would feel like to know that your coach is going to do whatever it takes to help you through that process, as opposed to just, hey, it's whatever I know, it's whatever is in my brain. One of the things that our clients really love is the fact they get me and you and we think differently. We act differently, we show up differently on calls, we process things differently. And it's really powerful because when I look at something and I'm like, hey, this is what they're struggling with. Like, like this is your area. What do you think? Right. And then sometimes let's actually have her or him wait for you and for your session because that's a really powerful thing related to something you can really relate to, but also help them through. Being able to show your client that you actually have resources, you have things, you actually did research, you took the time. Think about what that portrays when you say that. A lot of coaches are nervous of saying that though. They're like, oh my God, I don't want them to think that I didn't know the answer. And I'm like, no, I'm going to communicate with so many people that they never even had access to to be able to help out my clients as best as I possibly can. And here's the thing that I think people don't want to hear, all right? And that is you could be naturally talented at connecting with people and still not be a good coach. So I'm curious, like, where do you see that happen? I mean, do you see the gap in this space show up? What comes up for you when you hear me say that?

SPEAKER_00

We kind of talked about this earlier, but talent alone isn't enough. And I think that there's a difference between having a conversation with someone and actually coaching them. Someone who thinks they're a great conversationalist, right? Someone who is great at communicating will think that they're just gonna kill it in a coaching session. But there's a lot more nuance to that. And we've talked about it, like how you kind of guide a session, not that we're leading people in a certain way, but they're like guardrails. And I think that just that alone, like thinking, hey, I'm just great at having conversations or I'm great at asking questions, that's great. That's a start, but there also has to be some type of framework, I think.

SPEAKER_01

Yeah, yeah. I feel like there's a bunch of people who are great at conversations that because they're great at conversations, it actually hurts them as a coach. So I think the people who actually talk less are the ones who have the better conversations. Right.

SPEAKER_00

So if talent isn't the thing, what is, right? Because if you always say that like reps and feedback um over raw talent. So break that down a little bit. What does that look like in practice?

Reps And Feedback Build Confidence

SPEAKER_01

Yeah. You know, I also think this has a lot to do with confidence that we bring into session. And the client can feel that just like they can feel if we're winging it. But when we go out there and we don't just think of this in theory, but we actually practice, we take action, we get feedback from somebody who maybe is a few levels ahead of us. This helps us through that process, right? It helps us not only to develop the framework, but maybe different things that we could have used or brought in there. Just like I was saying earlier, I have people that I go to after a session or even before a session where I'm like, hey, this is what my client is going through. What are some ideas that you might have? And they think of things that I would have never been able to think of. But getting that feedback is critical, especially at the beginning phase. Especially at the beginning phase, because you're gonna make mistakes. You're gonna ask the wrong question, you're going to talk too much, you're gonna talk too little, you're gonna not challenge, you're gonna feel like somebody's friend, you're gonna get nervous when they get uncomfortable, somebody's gonna start crying and you're gonna freak out. Like there's different things that we all go through that's a little different in the beginning. But getting that feedback, number one, it'll get you to see that this is just what a lot of coaches go through. But number two, it'll help you so the next time you can show up a little differently. We've been coaching for a long time, but I still find ways of getting feedback, of adjusting, you know, making things better, and finding ways to not only continue to further my confidence, but to continue to help my clients get what they really want. I know a lot of coaches who get to a certain point in their coaching career and they're done learning. That hurts your clients more than anyone, but it also will hurt your confidence because as other people continue to grow and continue to get into other environments and to learn different skills and stuff like that, they raise the value that they bring their clients. So not only is it you having to go through stuff yourself and being able to get out stronger on the other end, but also continuing to constantly learn, to constantly get feedback, it keeps that muscle, that confidence muscle, that growth muscle going and your clients can feel that.

Get Coached To Coach Better

SPEAKER_00

Yeah. And speaking of learning, and maybe this is something we can kind of dissect, is that if you want to stop winging in in sessions, you should have sessions yourself, meaning you should be getting coached yourself because you can put yourself in the shoes of your client. And I think you you learn a lot from that. You learn a lot from other coaches and like their techniques and their style and things like that. But you also can feel how it feels to be in the hot seat. That's one thing that I feel a lot of coaches don't do often enough.

SPEAKER_01

Two things kind of come up for me. Number one is, and this is something that people were kind of taken back from when I first communicated this, but when I went through my life coach certification, it was$18,000. And I thought everybody in there was there to build a business. And more than half of them were there for personal growth so they can get their own level of coaching on themselves. So sometimes going through a certification is actually cheaper than hiring a one-on-one coach because you get so much from that experience. Not only are you learning it, but you're also doing it yourself. You're also getting it done for you, and you have a mentor, somebody to give you feedback, all that kind of stuff. So going through that, I didn't realize that was going to be the case, right? Where, in fact, being a part of that was actually going to help all of them because it's like they had 10 coaches while they were going through that. And the reason for that is because, like you said, is when you're in that environment, it's much harder to not coach yourself when you're in that environment. Yeah. Because you're like, I have to coach myself. I'm learning this, I'm developing it, right? So previously we used to certify people through our mentors program. And we saw people going through the program. They were taking action, they were losing weight, they were feeling better, they were having greater relationships, they were growing their business.

SPEAKER_00

Which is funny because it's not like a weight loss coaching certification. It was just they were going through something, they were developing, and other areas of their lives were being impacted in a positive way.

SPEAKER_01

Yeah. I mean, it's just the whole idea of like managing your mind is really what we do. And when you're able to manage your mind, you're able to manage your behavior. And when you manage your behavior, things change. And so just being in that process helped them grow so much. And then they stopped. A lot of them have reached out to me and go, I don't know what's wrong. Maybe I'm not cut out for this. I'm like, well, you kind of like disconnected from the thing that actually helped you through that process. And it's just what we do as humans, by the way. I've done this too, even with the dad edge. I disconnected for a little bit and now I'm back in it, and now I get to lead it, which is awesome. But at the same time, it was very easy for me to convince myself, hey, I'm good now. But it's one of those things where when you see it, can't unsee it. And you got to figure out, okay, am I gonna put myself back in that environment? Are I gonna do that thing, whatever that next level is, to make sure that I continue to develop like this? We're not saying that you have to do that with us. I just want you to do that with someone. Because in reality, I just want you to feel what it's like to have that kind of environment that you're in, get the coaching you need, and really start to utilize your mind more effectively in all areas of your life. Yeah. Right. So if someone listening right now is still winging it, what's the first thing that you think they should do? If somebody's listening to this and they're like, I need to do something different, I feel like I'm winging it. What do you think that first thing could be?

Record Sessions To Improve Faster

SPEAKER_00

I'm gonna give one actionable step because I don't want to go into a tangent about like all the different things that you can do because I don't want to overwhelm anyone. I just want to give you one thing. One of those things could be to record your session and listen back. I think there's so much power in that because it's not about, oh, I'm gonna feel embarrassed or ashamed listening back to myself. It's really about learning and growing from there. That way you know, oh, you know what? I could have done this in this particular part of the session. Let me see how I can grow through this. Let me see how I can get better at this. So recording a session and then listening back and asking for feedback. If you have someone in your life, if you have a mentor or a coach, have them listen to it too. Be like, do me a huge favor and listen to this and give me some feedback, some constructive feedback. So I think that's one of the things that can really help someone.

SPEAKER_01

Yep. I love it. I love it, I love it. It's kind of nerve-wracking, though, sometimes listening to yourself back. Yes.

SPEAKER_00

Well, I mean, it it is when even I'm listening to our podcast because you're like, wait, I sound like that.

SPEAKER_01

Or YouTube, wait, I look like that. Yeah, okay. Yeah, 100%, 100%. Two things. When you ask for feedback from people, number one, ask for what you did well. Number two is ask for something you would do differently. Okay. Don't just say, hey, give me some feedback on this, because if they're not a coach, they don't understand that you need the positives, the things you did well to repeat and an opportunity for growth, not a hey, what did I suck at? That's kind of like what people think about feedback. But feedback isn't like that. It's like, what did I do well? And what's something you would do differently if you were to redo this, right? And not 10 things I would do differently.

SPEAKER_00

Yeah.

unknown

Okay.

Final Takeaways And Standard Of Care

SPEAKER_01

I know some of our coaches are like, oh my God, can you tell me everything I do differently? And I'm like, no, because that's not how this works. It works one step at a time. So this is what you did well, and this is what you could do differently. So I want to make sure that you got these two things. Number one is the coaches who build something that lasts aren't the most naturally gifted ones. They're the ones who decided to stop relying on instinct and start building something repeatable, something that actually creates a transformation for their clients and helps them solve a problem. And that's what we want you guys to do. Because the truth is, your clients do need more than a good conversation. They're paying for a transformation. They're paying to help them through a problem they're experiencing. And having a standard on how you deliver that every single time is going to be not only powerful for them, but powerful for you too. All right, guys. Thank you for tuning in. Thank you for taking this deep dive. And I just want to say, like I always do, thank you so much for what you do out there every single day. And keep leading from the front. We'll see you in the next episode. Bye.

unknown

Bye.

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