In this dynamic episode, Nathan Jamail, Owner of Jamail Development Group, shares strategies to empower middle managers. If you struggle with alignment or accountability, you won’t want to miss it.
You will discover:
– How to foster belief in decisions to drive organizational commitment
– Why middle managers need coaching to align vision from top to bottom
– How to coach down to make employees better, not just easier
Episode Transcript
Scott Ritzheimer
Hello, hello and welcome. Welcome once again to the Start scale and succeed podcast, the only podcast that grows with you through all seven stages of your journey as a founder. Throughout your founder’s journey, there are a number of skills that you need to develop that you probably didn’t even know were skills that you needed to develop, things like managing your small team of underdogs in those early days, or leading a leadership team for the first time, or building an elite executive team. But here’s what I’ve found, all of those skills are simply milestones to what I think is one of the most important skills that every CEO needs if they want to scale their business or nonprofit, and that is the ability to make masterful middle managers. There’s only so much that you and your executive team can do, and the bigger you get, the more you’ll recognize the need to learn to lean on and build up your middle managers. Now to help us crack the code for what great middle management looks like is the one and only Nathan Jamail, who is a best selling author, speaker and leadership expert with over 20 years of experience in coaching, cultural development and sales leadership, his insights have impacted top industries including financial services, Tech, military, manufacturing and hospitality. His real world experience spans over 20 years as an executive director, and includes successfully owning and operating seven businesses. Nathan doesn’t just teach leadership and sales. He lives it daily. His high energy, no fluff approach helps leaders and teams drive results, build cultures and master the art of selling. Nathan your book, serve up and coach down mastering both sides of leadership. It highlights the unique role of middle management. So how does leading from the middle differ from the typical experience of a lot of our listeners who are leading as CEOs or founders from the top of their org chart, and what steps can founders take to to help bridge the gap between those experiences?
Nathan Jamail
Yeah, well, first of all, no one chooses and desires to be a middle manager, right? Like no one says, Oh my God, I want to be a middle manager, right? Yet it is the most common leader we have. And that’s why I call it the leader in the middle because I believe a middle manager does exactly that. They manage the middle which means they do nothing great, nothing really bad. They stay below the radar. What I wrote a book on, and what there’s not a lot of books on out there, is, how do you lead people and then follow someone else? Quite candidly, I spent 20 years corporate America and and if we, if we’re left to our own judgment, we tend to do it wrong. And so one of the things that I wrote this book about is how you become a leader in the middle and teach people how to do it at the end of the day, I debunk servant leadership. Scott, I don’t believe you should serve your employees. I believe you should serve your bosses. I believe our job for our employees is to make them better so they grow, they get promoted, and they become bigger better people. Serving up is not like sucking up. It’s about believing in those we follow. And so when I wrote this book, it’s about how do we address the two greatest competitive advantages, speed of change and organizational alignment. I need the founder’s vision to be the same as the frontline employee. And how do we make sure all the leaders in the middle, no, don’t change that view by serving up and believing in those we follow. We keep a constant message, which gives us alignment. The second one is when we work on belief and not buy in, I don’t have to worry about proving something to someone. I believe in you as my leader. I believe in you as the organization. And therefore we go, now realize this, Scott, we’re wrong 80 as humans. We’re wrong 80% of time, and everyone agrees with this. And so my challenge to leaders in the middle is as you want your people to give you grace. Give your leader grace.
Scott Ritzheimer
Hmm, so there’s so much to unpack in that, and I hope everyone listening is ready for about seven hours, because I gotta let No, just kidding, but, but no. So three, yeah, it’s interesting, because, like, it’s not working, like the stats on middle management are atrocious. I think something like 20% feel like they’re supported. 75% of employees think that middle managers are some degree of incompetent. Like it’s it’s really bad. It’s really not working. But the solutions are, are relatively simple. So why is there such a big disconnect here?
Nathan Jamail
I think there’s two. I think you nailed it. I wrote an article on this just the other day. CEOs have executive coaches and every organization focused on the frontline manager, because that’s where the rubber meets the road. The problem is to your point, it’s the two levels up. Let me give you a quick example. If one person messes up, if an individual contributor messes up, you. It’s one one problem. If a leader of seven, the seven people, messes up eight issues. If a leader of a leader, the middle leader, who has eight direct reports and below them have eight another, another eight direct reports, that’s 65 times. Yeah. And so here’s what happens. The CEOs get executive coach, and the frontline managers get training, and those people in the middle, they are that we we assume they know what they’re doing. We assume that they know the business. We assume that they’re good enough, or they wouldn’t be in that role. And here’s the facts, the greatest athletes in the world still get coached every single day, and those who have been doing it the longest request to be coached more often, and we just don’t, we don’t engage. We don’t we don’t focus on the leaders in the middle by making them better. And we don’t have the difficult conversations we want to use words like trust and autonomy and control. You know, listen, you want autonomy. That’s great, but we still have to, I still want you to be the best leader. Quite candidly, as a founder, my name, my reputation, everything I put on the line, depends on the leader who’s above the other two leaders and below me. Yeah, but they are.
Scott Ritzheimer
So, we’ll poke the bear a little bit here, because servant leadership is like it’s it is a closely held belief for a lot of folks, but here’s where I see it go wrong, and you’ve already made this distinction within some of what you’ve said. But when we think about our job as as a manager, as a leader, as the need to make our team’s jobs easier, we’ve missed it right? And I love what you said is our job is not to make their job easier. Our job is to make them better. Would you agree?
Nathan Jamail
I absolutely agree, and I’ll even go a step further. You know me, middle managers think their job is to protect their employees from their bosses and organization. Can you I have four children, 30, 2315, and 13. I’ve been doing kids for a long time, and sounds terrible. I’ve been having kids for a long time and and I’ve been doing this parenting thing for a long time, and here’s what I found, if my wife told her friends My job is to protect my kids from my husband, I’d be like, what? And I don’t think leaders in the middle they don’t do it to be heroic or whatever, or to be malicious. They truly believe that I need to protect them. We only have to protect people from enemies and danger, yeah, and so again, those little things go into the mindset. I’ll give you one more thing that most people say. The founder comes in and says, Hey, we’re gonna start going this direction. And someone in the middle manager goes, Did you see what the founder wants to do? Has he lost his mind? Does he not know what’s going on in the street? And they believe their perspective is more important than the vision. Now, listen, I get it. I said this a minute ago. Founders are getting a little nervous about giving a book to their people called serve up, Coach down, because they’re afraid that they’re telling them to be a yes person. Serving up is not about being a yes person. It’s about training people about belief. It’s about giving the people who you follow the same belief and respect you want those give you last nugget on that. It’s like you round up a teddy bear. Scott and I just won’t shut up. Is part of our job. I’m a father and a son, right? I know it’s a news flash, but you know, all the same things I bitched about my dad doing as a father, I find myself doing as leaders, those who we lead are going to do the same things we do, so we want to demonstrate the right behavior. So great followers become great leaders.
Scott Ritzheimer
Yeah, yeah, that’s so good. So when it comes to that middle manager, because there’s this temptation that, like getting people who are just on board is easier in the short run, right? It leads us to chaos in the long run, because we just all go off the same cliff together. But in the short run, you know, it’s a little easier to have people who just say yes and get along. But that’s not what you’re talking about here. You’re talking about folks who are deeply committed to the vision of the organization and will hold their teams accountable to it. But that creates this really interesting challenge at the middle management level, where they’re not necessarily the ones that were in the strategic planning session setting the goals that they’re now holding their team accountable to. So how do you as for a founder or CEO listening today? How do they support their managers in fulfilling that, in holding their teams accountable and all driving toward the same destination.
Nathan Jamail
Let’s address both of those two separate questions. The first one is, how do I get people to hold other people accountable be committed to a decision they were not a part of? Is that correct? Yeah, let me be clear, and I’ll say it very slowly so everyone can understand, it is not about being a part of a decision. Decision. It’s about owning decision, owning any decision that is given to you. If you want your people to own the decisions which you make for them, we have to own the decisions that are made. We don’t get paid to to give our input. You know, I have a daughter who’s 15, and when she was in junior high school, she used to say, Daddy, I’m worried about what someone thinks, and this person thinks, and they’re always worried about what the other girls and the kids think. And I told my daughter, as soon as you as soon as you stop caring about what the kids think, they’ll start caring about what you think. As business leaders and middle leaders and leaders in the middle as soon as we stop thinking that our opinion matters, people will start asking for it more often. Yeah. And, and the reason why, Scott, if I ask for your opinion and I know if I don’t use it, you are going to be a nightmare to lead, I won’t ask it, because, unless I know I can use it, but if I know that your opinion is purely something that you want to recommend, but does not have to be demanded. I’ll go to you and say, Hey, Scott, here’s what I’m thinking. What do you think? And you’ll say your opinion. I say, Okay, I like that. Let’s go this way and try it. And if I know, when I know that you understand our opinions are not necessary, I’ll want it more frequently. Yeah. Does that make sense?
Scott Ritzheimer
It’s beautiful. It’s really, I mean, it’s so true in so many environments, but really goes right to the heart of the matter in this middle management space. I love it. I love it. Now, when it comes to coaching down the two I have a nasty habit of asking two questions at the same time, so I’m going to do it again. But I but how do you do that effectively? And how do you help your managers do that effectively?
Nathan Jamail
So I think that in my one of my books, I wrote the leadership playbook I start up in the book that says corporate America is corrupt. And I didn’t mean financially corrupt. I meant the fact that we ask our leaders to coach employees, yet we never teach them how to coach now, let’s be clear coaching and you could think of sports. Now, let’s be clear this. It could be dancing, it’s anything that’s that’s it could be acting. It could be golf or football, anything that’s skill based. Coaching and managing contradict each other in five key areas in coaching, if you’re bad for the locker room, no matter how talented you are, they’ll trade you in business, if you can close deals or you have 10 years experience, I’ll tolerate all the shenanigans because I can’t replace your experience. Or, God forbid, I lose a customer, we will sacrifice the very thing we say so important because we’re afraid of losing someone who we probably should not have anyway. In sports, you’re traded second one and and. And coaching, we work with those who deserve the attention. Coaches don’t work with third and fourth string. They work with the first string. And management, we spend time with those who need the attention. Let me give you a perfect example. How many people have you met in business tell you their number one goal is to be so good their boss leaves them alone. Yeah, here’s my question to the boss, if the goal of mine is to be so good that you leave me alone, what’s your value? Yeah. I mean, a coach, a founder pays for a coach. As founders, we we should be willing. We paid for it anyway. We might as well coach them, because it’s free, it’s inherent, it’s our responsibility. You know, there’s a phrase, a famous phrase from Billie Jean, the famous female tennis player back in the 70s. She says, pressure is a privilege. I’ll tell you, leadership coaching, pressure is your responsibility. And so the last two I’ll give you is in management, we avoid conflict, and we don’t do it, by the way, just because we’re afraid of conflict. We don’t do it just because we’re nice. We say that, but it’s not true. We do it because good people are hard to find. We don’t hold people accountable because we’re selfish, because we have to have a difficult conversation. We have to go through the beat down of the process. And by the way, I’m not even talking about just holding bad people accountable. I’m talking even our superstars who who are being successful, but they’re walking, and if we just pushed them a little harder, they would start running and really succeeding. In sports, everyone’s held accountable. In management, we avoid conflict, we hope the problems go away. And the last one I’ll give you is this, in sports and in coaching, the number one job of the coach is to make people better. In business, most of our people are not better, the more experienced, the more knowledgeable, but the weakness is still the weaknesses, the strengths are still at the same level. And my challenge to ever leader is, what if you loved your employees as much as your kids? What if you invested in them as much as you invest in your children and coach them?
Scott Ritzheimer
I love that because, I mean, it starts all the way up at the top of the organization, one of the things that I see, especially for founder, CEOs, and especially because when I work with them, it’s the first time they’re really stepping into that role. They can be intimidated by coaching their executives, but if you don’t set that example at that level, you can’t possibly expect it to propagate beyond that. And so I love that concept. It works at all levels in the organizations. Very, very good.
Nathan Jamail
And Scott, let me add to that, if I could. Yeah, about it. You know, a founder did something most people can’t do. Most people cannot make the transition from a paycheck to profits, and the founder did it. And whatever industry you’re in as a founder, you’ve done something very few can now that same founder eventually, when they get big enough, and they get their private jet, and they’ve got a CEO, and then all of a sudden they’ve got, they hire a CEO, or a high level guy or gal from a different organization, and they start to go, well, they know more about leadership than I do. I don’t care, yeah, coach them. Give them the nuggets you have, because as a founder, you have nuggets you’re not even aware of, because it’s inherently who you are, yeah? And so I I always, you know, I want to pour into my kids. My challenge to us as leaders in the middle and leaders and founders pour into the leader that you are hiring to coach the team, pour into them, yeah, as much, if not more than you want them to pour into their people.
Scott Ritzheimer
Yeah, yeah. Nathan, so good. So there’s a question that I have for you and I ask all my guests, I’m very interested to see what you have to say. So the question is this, what would you say is the biggest secret that you wish wasn’t a secret at all? What’s that one thing you wish everybody watching or listening today knew?
Nathan Jamail
Committed employees follow committed leaders. And I’m gonna clarify on that most of us are not committed to our employees. And I’ll prove it with three simple things that we all can agree with, and we have never met halfway. Scott one, every leader wants a higher industry experience in their industry, because they think they’re going to hit the ground running. They’re not. They’re going to hit the ground walking. The reason we do it because it’s a lower ramp up fast return on investment. And then we don’t to train them as hard. We don’t spend six weeks on board. We want our people to commit and be committed to the program and the vision, yet we don’t spend any time coaching them and make them better. And then lastly, if someone’s got a bad attitude, that’s their fault. If we’re as the founder or allowing them to be on our team, that’s our fault. How can we say we’re committed to people and we want them to commit to us. We want people to join us and give everything they got for three to four years. I’ll tell you this. If you want someone to commit to you for three to four years, commit to them in the first 90 days, and give them everything you can to on, yes, don’t shadow, don’t don’t sink or swim. If you’ve got a turd on your team and they’re bringing down the other people, you need to get rid of them. You owe it to the team, right? Show your commitment, and you’ll get commitment. And I wish it was a secret, but it’s a very big secret.
Scott Ritzheimer
So serve up, sir, Coach down and no turds on the team. That’s a technical term trademark. That’s the missing chapter, folks. So Nathan, this is fantastic. We have scratched the surface of the surface. Now you’ve literally written the book on this. Serve up, Coach down, mastering both sides of leadership. Where can folks find the book? And where can they find more out about the work that that you guys do there?
Nathan Jamail
Man, you can buy the book on all kinds of online retailers, Amazon or target or whatever it may be. You can go to our website, www.nathanjamail.com you can get all the information about the resources we have on from books to workbooks to group coaching, private coaching. And it’s all leadership coaching, employees based and selling skills. And then lastly, I’ll tell you, Scott, if I can entertain you, you can also try my AI. I literally have a AI mini robot, and you can call that number. And I don’t know if you want it, but it’s 848-277-0867, you call me, I answer the phone, and it’s my AI, and he can answer any questions you have.
Scott Ritzheimer
That’s fantastic. I love it. We’ll get the URL there and the phone number in the show notes, so you can check that out. I highly recommend it and the book as well. Had an opportunity to read it getting ready for this episode, and strongly, strongly recommend it. Well. Nathan, thank you so much for being on the show. Just a privilege and honor having you here today, and for those of you watching and listening, you know your time and attention mean the world to us, I hope you got as much out of this episode as I know I did, and I cannot wait to see you next time. Take care.
Contact Nathan Jamail
Nathan Jamail is a best-selling author, speaker, and leadership expert with over 20 years of experience in coaching, cultural development, and sales leadership. His insights have impacted top industries, including financial services, tech, military, manufacturing, and hospitality. His real-world experience spans over 20 years as an Executive Director and includes successfully owning and operating seven businesses. Nathan doesn’t just teach leadership and sales—he lives it daily. His high-energy, no-fluff approach helps leaders and teams drive results, build strong cultures, and master the art of selling.
Want to learn more about Nathan Jamail’s work at Jamail Development Group? Check out his website at https://nathanjamail.com/. You can call his free AI Coach at 848-277-0867. And get a copy of Serve Up Coach Down: Mastering Both Sides of Leadership at https://www.amazon.com/Serve-Coach-Down-Nathan-Jamail/dp/1639015078/ref=sr_1_1