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Hey Dave here from Coaching for Leaders. I get asked a version of this question all the time. What's the difference maker that really helps leaders thrive? And I'm getting this question a lot right now as I talk with applicants to the Coaching for Leaders Academy. Our academy helps leaders thrive at key inflection points, and applications are open right now for new members only until the end of the day this Friday, March 20th. Go over to coaching4leaders.com academy for more details and to apply. The version of this question I'm getting now in relation to the academy is this. What's the difference maker that really helps leaders thrive in the academy? And we always end up talking about that when people apply. But I find that there's an even bigger question behind that, and that question is this one. What is it that really gets in the way of leaders improving? It's not a lack of knowledge, certainly not these days in an AI world. And it's not a lack of resources usually. And it's also not typically a problem with good intentions either, certainly not in the community of people who listen to this podcast. Look, the context of every leadership situation is unique and there are many nuances that come up in our work. But I'm constantly struck by how much is similar across all the leaders I work with. And especially similar is what gets in their ways. That's why today I'm outlining the five things that I most commonly see that stop leaders from improving. These things come up again and again and it's why the structure of our academy is intentionally designed to to help us all transcend these five stopping points. Leaders thrive by creating movement to work through obstacles like these. So let me share the five things that I see all the time. How you can guard against them and how our academy might help. And if you decide the academy might be right for you, go over to coaching4leaders.comacademy to apply by this Friday, March 20th. The first thing that gets in leaders ways most commonly not asking for help My very first job as a full time professional manager, I inherited a team of employees that was really great. Almost all of them, with one exception. There was one person that was, in my opinion, not a very high performer and sometimes didn't meet the minimum standards that we expected in our organization. And yet I didn't really handle it very well. I would occasionally mention something that I thought he could be doing better, he would improve marginally. And then it seemed like things kind of went back to where they were and I didn't really know what to do with that and I didn't see him that often. We ended up working on a staggered schedule, and I kept going back and forth, should I handle this situation? Should I not? What do I say? What do I do? Long story short, this went on for a year, and finally he decided to leave, which I thought was a great outcome, and moved on and accepted a job somewhere else. But he still had a couple of weeks of work left, and I still was frustrated with what I felt like he wasn't doing a good job with in our business. And so I kept going back and forth, should I give him feedback? Should I not? And it came down to the last day of the last hour of his last shift. That was the time I decided to pull him aside and tell him all the things he had not been doing good as an employee for the whole time he'd worked for us. And as you might expect, he did not respond well to that. He got super frustrated with me, as I would have if it had been me in that situation. And I ended up asking him to leave. He stormed out. It was an awful end to a situation that I had mismanaged as a leader for over a year. And as bad as that was, and even in the moment, I remember thinking, boy, I really screwed up. I should have handled this situation better. I didn't appreciate how much I had screwed up until about two months later when some of my other employees who were the high performers ended up finding other positions. And no one ever said anything. But I know now, looking back, that a few of those people who left left because they saw me mishandle a situation and not treat someone well. And when I look back all these years later on that situation, there are some obvious tactical things that I could have done. In fact, almost anything that I could have done at that time would have helped make the situation go better. And if I had just asked for help, it would inevitably have had a better outcome. And so I reflect on it, and I wonder, well, why didn't I ask for help? There's so many obvious things I could have done that anyone would have given me advice on. And the reason I didn't, the honest reason, is I didn't want anyone to know that I didn't have stuff figured out, because at the time I was early in this role, I was trying for a promotion to the next opportunity I knew that was on the table. I didn't want to leave my managers and peers with the impression that I was struggling with stuff, that I didn't know how to do things. The irony Is if I had asked for help, I think they would have actually respected me more. But it didn't feel safe at the time to do that, even though it was mostly in my head. And I say that because we all know that we should ask for help, but we often don't because either it's not safe to do so, as in people will hold that against us, which sadly is the reality in some organizations. More often though, it just doesn't feel safe. It doesn't feel like we should put ourselves out there or ask for help or admit that we don't know something about any whatever that topic is. So if you find yourself in this situation, as I do still today, reminding myself of the importance of asking for help, first step, find someone who is safe that you can ask help of. I think ideally finding someone in your professional, maybe even your personal network that has a similar role that you do, maybe is at a similar place in their career, but who isn't in the politics or the stuff of your organization or industry. So they're invested in you, but not invested in the situation. It's why we build this into the academy and why we bring together leaders from all different industries to work together so that nobody's competing. And not only so that it feels safe in the moment, but that it actually is safe to be able to ask for help. We design asking for help in all of our work in the academy. In fact, one of our key prompts is how can we help today when we start conversations? There's two big reasons that's important. One is it helps in the moment, of course, with the immediate issue. Whatever's happening that's in front of a leader that hopefully we can support them on with next steps. But the second and perhaps even bigger reason is it gets us all used to asking for help and helping us to get better at doing so. Because when we ask for help, we inevitably open ourselves up to learning and opportunities for growth. So that's the very first thing that I see that gets in leaders ways all the time. It's been gotten my way many times. First and foremost, not asking for help. The second thing that gets in our ways, assuming knowledge drives behavior. If you think back to when you learned how to drive a car, I think you'll appreciate this point already. And if your experience was anything like mine and learning how to drive, you had two big components of that experience. One of them was classroom time of listening to an instructor or a video or something that was teaching you the rules of the road and then also being Able to respond back to questions about it and to take an exam and to do the practice work, to eventually be able to sit for the driving exam, which happens in most places. And then there was the experiential part, the behavior change of learning to drive a vehicle, which was actually getting in a vehicle with an instructor and starting off of driving around the parking lot and driving on some deserted roads and then eventually getting to the place where you were driving a little bit more with traffic, and then eventually getting on a highway or freeway and building your skill set with coaching and the appropriate guardrails in order to make sure that that was safe and effective. And you need both in order to learn how to drive a car. Now imagine for a moment they had only had the classroom part. They'd watched all the videos that you'd taken, the practice exams that you went to wherever you took the exam and you passed the exam and you knew all of the rules and the policies and the procedures for driving a vehicle, but you had never actually gotten behind a wheel and driven. You would be very dangerous even if you pass the exam with 100%. And that's because knowledge is not the same thing as behavior. And leadership skills are similar to this. They start with the things we talk about here on the podcast, of course, but they don't end there by any means. Knowledge is the starting point, but it's insufficient by itself. And sometimes the greatest enemy of behavior change is the illusion of it. It's one thing to know an accountability framework. It's an entirely different thing to have the conversation tomorrow morning during your one on one with an employee and to try to bring that accountability framework into the conversation. Sometimes when I'm working with a leader who finds themselves caught up too much in the knowledge part and is, I'll suggest that they actually don't pick up the next book or maybe don't listen to the next podcast episode. Isn't that ironic? But to instead pick something that they've already listened to or read or know and actually put it into practice this week with their team using the same amount of time that they would just acquiring more knowledge. Look, the kind of people who come into our academy are really smart, successful people. In the listener survey we did last year, we found that 60% of listeners to this podcast have graduate degrees. And in addition to the educational work that folks have done formally, so many people are reading books, going to conferences, using the AI tools for support, and tons more beyond that. And what a lot of our members tell me is, you know, I Kind of know what I need to do. I've gotten feedback before. I know that I need to get better in a few areas. And now what I really need to do is to take that knowledge and put it into practice. It's why in the academy, we put almost all of our time and attention on structure and behavior change. Not a traditional curriculum where you're doing a lot of reading and writing, but actually putting the behaviors into practice in the workplace. And by the way, being the most knowledgeable person in the room is quickly not going to be enough anyway. It already isn't in a lot of places, certainly not in this AI world. As things continue to progress, you know what will be competitive, at least for a while yet? Being able to handle complex situations with people. AI may get there eventually, but even in the most optimistic tech roadmaps, not going to be in the immediate short term. And leaders who go beyond knowledge and develop and enhance great people skills in practice are going to have so much more influence. In this AI world. Knowledge is an essential starting point, but it's just insufficient on its own. That's why our academy is focused on putting knowledge into immediate practice, so that we don't get caught up as much in this stopping point of assuming that knowledge drives behavior. The third item that I see get in our ways most often is setting the tactical bar too high. Now, setting high standards is a really important thing for all of us when it comes to the vision we have for ourselves and our careers and our teams and the people who work with us and the goals we set and the expectations for how we show up for each other, ourselves and for others and our organizations. The. Those should be very high standards for all of us. But those things are all outcomes. They're not tactics. And those are very different things. When it comes to getting better at something, our behaviors, we need to actually lower the bar for our tactics. Let me explain with an example. One of our leaders recently came into the academy and said, I want to work on being a leader who appreciates and recognizes employees. And they set that as a standard. That is a high bar, a high standard. I think something that we would all agree with a great goal, no one would argue with that of being an important leadership competency. The temptation, though, is when setting a goal like that is to take on too much initially in tactics. And when I see someone set a goal like that, one of the most common things that they will do is say, okay, I want to get better at appreciating and recognizing people. I am going to work that into every single conversation that I have today. And many people will do a good job at getting started with that. And in fact, we'll do it most of the time in most of their conversations in the first few days that they do it. But something interesting almost always happens. Someone who sets the goal of being better at recognizing and appreciating employees in every conversation gets to the end of the day. And if they had 10 conversations that day and they were successful at appreciating or recognizing people in seven of those conversations, they almost never think back on the day and go, hmm, that was really great. I had a 70% success rate. I talked to so many people today. I recognized and appreciated people. I did exactly what I wanted to do. That almost never happens. Instead, what happens both in that person's mind and in my own, because I've done it too. And in the conversations we have in the academy, when this comes up is the person gets to the end of the day and they say, I missed three people today. And then they say, tomorrow I'll do better. And they go tomorrow, and they attempt the same thing. And maybe they get to six or seven or eight people again, but they missed another one or two. And there's something about the psychology of setting that tactical bar so high, of how we just show up as people. And a lot of us being high achievers and a lot of us having been rewarded for having great outcomes in our lives, of checking the box and getting good grades and all those things that whenever we don't do it perfectly right out of the bat, we criticize ourselves for the things that we didn't do, and we have a hard time appreciating the progress that we're already making. And you know what happens is that people stop pretty quickly, not because they failed, but because they didn't meet their tactical expectation. I wanted to recognize everyone, and I miss two people today and tomorrow I miss someone else. And all of a sudden, we feel like we failed, even though the exact opposite is actually what happened. The way you make sustainable behavior change is by starting small on tactics, Clearing the bar a few times, building momentum, shifting direction as you learn more and get feedback, and staying consistent. So in the academy, we set expectations for our outcomes very high in the visions we write and the commitments we make. But we set the tactical bar much lower, much differently. How low? Five minutes, One action once a day, by design. One of the biggest challenges I have in coaching people is starting small with their tactics, because a lot of us have been socialized to aim High as we should. But we think that means aiming high on every tactical step, which is usually counterproductive in the busy schedules that most leaders have. Instead, start with the tactics being small. Build momentum. Yes, set your expectations high, but start small on the tactics for change. The fourth thing that gets in our ways, and this is a big one, Feeling worse before feeling better. One of our members in the academy right now has the goal of getting a seat at the table. He's been working on being really intentional in recent months, doing what we talked about in the last point, of starting small and getting a seat at the table, both figuratively and literally of getting into conversations that are strategically important to the organization earlier on, because his team tends to do a lot of the execution stuff that comes out of the big picture conversations. And in the past, a lot of things have just been thrown at his team without him having a voice and how they can better execute on the big picture intentions of the organization. So quite understandably, he's recognized having a seat at the table is going to help him and the team and actually help benefit the entire organization. And he's been working on that really intentionally in small steps. And recently by doing that, he uncovered a huge initiative that's at play inside the organization that is going to affect tons of work that his team is doing in the next six months. But he had no idea that it was going on, and his manager had no idea that it was going on. And once they figured it out, things kind of blew up a bit because it was going to be huge implications for work and how the organization does business and how his team is handling things. And as a result, it's triggered a whole bunch of conversations about who was involved and how do we handle this going forward and how do we clean this up and what are we going to do in order to make sure resources are in practice. And the reality is, is that all feels worse. It feels worse because all these things, all these tough conversations, all this stuff that he wasn't aware of before feels a lot worse today. And yet the reality is it's actually way better. And I say that because as we were talking recently, six months from now, this would have still happened. It would have blown up in six months. The difference is by it happening today, by him having gotten a seat at the table and starting to take action on this and being proactive, and he was able to figure out today which would have been a disaster six months from now. And as a result, not only is he doing that proactively, but having really Healthy conversations that have been triggered by this inside the organization. And now he's showing up with a seat at the table in a lot of these conversations and changing that dynamic of how the team works. And it's so interesting because even though that's better, it's exactly where he wants to go. It feels worse in the moment. And that comes to the reality that so many of us run into when we're working on getting better at some of our leadership skills is that something that feels worse is sometimes the best indicator that you're on the right track. And that's why when we get into our commitments in the academy, we plan out in advance. What are some of the things that we're likely to notice when we're on the right track. And as you'd expect, some of those things are positive. Hey, if I have a seat at the table, people are going to invite me to more meetings. I'm going to know things sooner that are happening. All that thing's good. But we also invite all of our members to write down in advance some of the negative things so we know that it's okay when it comes up. And sometimes it's an indicator we're making progress. I'm going to hear about more problems if I have a seat at the table. I'm going to get in some uncomfortable situations if I have a seat at the table. Those are things that are really important to know. Now, let's be real here. Sometimes things get worse and they really are worse, and that's not good. And that's why it's important to do two things in advance on this. First of all, write down for the record, what are the frictions that you're likely to run into along the way so you can anticipate the things that are likely to happen that are the expectations and the expected frictions. But. But you can also parse that from the things that happen that aren't healthy. And then secondly, talk to people who can help you objectively assess what's good, healthy tension and what isn't. It's why we build both into every commitment that every leader takes on in our academy. The fifth and final thing that most commonly gets in our ways is not noticing any improvement. This is a big one. I was thinking about this recently in the context of our kids. Our kids are now 14 and 12 years old. Some of you have listened to this podcast far enough back to remember when they were born. It's been an incredible journey over these years. And every year as parents, we go and take the kids in for their annual checkup at the pediatrician, and they do all the normal stuff. Vaccines, medications, checking, all that stuff. And then they also always do a height and weight measurement. And one of the fun things at every appointment is the doctor will inevitably pull out on the iPad the height chart that both kids have been progressing on since they've been coming to that office since they were born. And we look at how much they've grown in the last year and this past year, like with teenagers now. Wow. It's crazy how much they've grown, like, inches over the course of the year. And of course, that's coming a lot in this next year or two, as well, as they're at this stage of growth. And what's really interesting is they never notice themselves, our kids, they don't notice themselves being any taller. And I don't normally notice on a daily basis. So that if I step back and think about it, I'm like, oh, yeah, wow, he is a lot taller than he was just, like, a few months ago. But I have to really stop and sort of consciously notice that. You know who does notice right away? My parents who live in Chicago. When they see the kids and they only see them a couple times a year, they. They immediately notice. They'll walk into the room, and my parents are like, oh, my gosh, looks like you grew a foot. Because they look totally different from the last time that they saw them. And it's because they have a little bit more objectivity because they are not so close to them every single day. And it's interesting that the same thing tends to happen with almost every leader that I work with. And the same thing happens myself is that I tend not to notice my own improvements as quickly as other people do. And the opposite's true, too, of course. The things that I don't do well, I tend to notice last without objective feedback. And we have it happen all the time in the academy, where we'll be working with someone on something I'm thinking about someone working on, being more concise. And we all see them making some really big improvements on that. And they show up and they're handling things differently, and they're telling stories about how they've interacted, acted differently in the workplace and showed up with their communication. And we all see it in their interactions. And then they'll say something like, I don't know if I'm getting any better at this. And we all look and say, well, yeah, you're getting a lot better at it. We can all See the improvement objectively, but oftentimes the person who has made the improvement is the last person to notice. And when they realize it is when they go back and pull out their vision that they wrote at the start of where they want it to be and compare it to where they are today. And then they'll often say, oh wow, I did change a lot. Because every leader in our academy records at the start what success looks like for each of their focus areas where they want to go, and also records in their write up how they are doing on that today, objectively, what's happening, what, what does the data look like, what kind of feedback are they getting at so we can all clearly see what's most important for each individual leader and also what's improved. And nothing is more motivating than to go back and see how far you've already come on something. So have a practice to record where you are today on your skill set, whatever that is, where you're going, and then some sort of process to check in regularly to see your progress along the way. We do that as a practice in every academy cohort regularly, every 60 days of coming back to make sure we notice the progress that we're making and also noticing the things we're not improving on so we can course correct and also we can keep ourselves motivated consistently. Okay, quick review. Here's those five things again that get in our ways. First, not asking for help. How do you get better at this? Well, find a safe person, someone who's doing similar things but isn't in your world daily. They're a great place to start. It's exactly why one major component of our academy is peer accountability. Partners to help cheer each other on, but also to help each other get unstuck. The second thing that gets in our way, assuming knowledge drives behavior, how do you guard against this? Well, a little less focus on getting more information and a little more focus on real time behavior change. If you have to set aside the book you're about to start and put that same time into implementing one thing you discovered from the last book that you haven't gotten to yet. It's why in our academy we build an entire structure around supporting behavior change. The third thing that gets in our way, Setting the tactical bar too high. Yes, set your expectations, your goals, your vision high as you should. But then when you get to the tactical starting line, begin as small as you can. We build this right into our academy. Five minutes a day, consistency over intensity, building confidence so we get sustainable movement. The fourth thing Feeling worse before we feel better. So normal. We should all expect that when we're learning and growing, some things will feel worse, at least at the start. Here's the key. Just like we do in the Academy, identify in advance exactly where you're likely to run into healthy friction and then have someone who's objective help you determine what friction is healthy and what's not as you go. And then finally the fifth one, not noticing improvement. We're almost always the last to notice when things are working or when they're not. It's why we follow a five step process at the start of the Academy to record our outcomes in detail and also how that compares to current reality. We come back to that every 60 days so we don't miss what's working and what's not. We're entering into our 11th year of the Academy and the one thing that I appreciate so much more today than when we started is the power of bringing leaders together in community with each other. Most of the leaders I work with have good relationships inside of their organization and they're, you know, very immediate industry network. And very few of them have ever built any kind of meaningful professional relationships outside of their organization or industry. Was certainly true for me too when I started this. I think that's a missed opportunity for a lot of us because as evidenced by this list of five things here, finding people who are working at getting better at similar kinds of things you are team leadership, time management, feedback, accountability, change. But who can be objective and not tied into the politics of the organizational stuff can help a lot. It helps a ton in asking for help. It helps a lot when things feel worse and someone can say, yeah, I've been there and you should totally expect that it'll get better if you keep going. And it helps a lot to notice our improvements. The Coaching for Leaders Academy provides structured group coaching to help leaders thrive at key inflection points. Whether that inflection point is a recent promotion or a new team. Or maybe you've got a big new initiative or maybe it's some recent feedback. My job is to help people move through those inflection points and thrive. Every cohort we begin is a small group of six to seven peer leaders led personally by me for every session to help us all move forward. If you're at an inflection point right now, it's the right time for you to consider the Academy. Here's where you need to go. Coaching4leaders.com academy the entire structure of the Academy is there details, common questions and most importantly, the application. It is an application based program and I'm accepting applications right now through this Friday, March 20th. Make sure to get there by Friday to be considered. Again, the link you need is coaching4leaders.com academy or just go over to coaching4leaders. You'll see the Academy button at the very top of the page right there. Until Friday. If you're leading well and learning and growing, you are going to hit inflection points. And you're also going to have the tendency to want to stop when you hit one of these five obstacles. Our job in the Academy is to keep you moving so you don't just survive, but really thrive in your work. Thanks for listening in and I'm back on Monday with the next regular episode.
Episode Title: The Five Things That Get in Leaders’ Ways
Release Date: March 17, 2026
In this solo episode of Coaching for Leaders, host Dave Stachowiak focuses on the crucial obstacles that commonly hinder leaders from continuing their growth. Drawing from years of coaching and community insights, Dave distills his framework into five specific barriers, each illustrated with real examples and actionable advice. He also highlights how the Coaching for Leaders Academy addresses these challenges and creates structures for leaders to thrive at key inflection points in their careers.
[02:40 – 10:30]
"The reason I didn’t [ask for help], the honest reason, is I didn’t want anyone to know that I didn’t have stuff figured out… The irony is if I had asked for help, I think they would have actually respected me more." (Dave, 08:10)
[10:30 – 16:38]
[16:40 – 23:00]
[23:00 – 28:40]
[28:42 – 34:23]
On asking for help:
"We all know that we should ask for help, but we often don’t because it doesn’t feel safe." (Dave, 09:12)
On the illusion of knowledge:
"Knowledge is an essential starting point, but it’s just insufficient on its own." (Dave, 15:50)
On sustainable change:
"The way you make sustainable behavior change is by starting small on tactics, clearing the bar a few times, building momentum..." (Dave, 22:12)
On progress feeling worse:
"Feeling worse is sometimes the best indicator you’re on the right track." (Dave, 26:10)
On reviewing your own growth:
"We're almost always the last to notice when things are working or when they’re not." (Dave, 33:15)
[34:30]
[36:00]
Dave speaks with candor, humility, and warmth—acknowledging his own missteps as well as gently challenging leaders to rethink their approach to growth. The overall tone is supportive, practical, and grounded in real-world leadership challenges and triumphs.
For more resources and to apply for the Coaching for Leaders Academy, go to coachingforleaders.com/academy.