Ep215 Jack E. Enter - From Doer to Leader: Breaking the Hidden Trap That Derails New Managers

Jack E. Enter 0:00

You've seen it in sports teams. Military thrives on this. The power of the squad or platoon you need to confront the problem employee, but Brad and I will go with you. Everything changes when those magic words, you need to do this, but I will go with you.

Mike O'Neill 0:19

Welcome to get unstuck and on target, the weekly podcast that offers senior leaders insights and strategies to not only lead with competence and vision, but also to achieve groundbreaking results. I'm your host. Mike O'Neil. I coach top level executives on the power of ethical leadership to forge teams to be as united as they are effective in each episode, join me for insightful conversations with leaders just like you providing practical advice to help you get unstuck and propel you and your company forward. Let's get started. Have you ever promoted a top performer only to watch them struggle in a leadership role? If yes, you're not alone. In this episode, I talk with Dr Jack enter. He's a nationally recognized leadership expert about why so many new managers falter and what you can do to stop it. Jack brings a rare mix of military academic and consulting insight to uncover the hidden trap that catches even the most capable professionals off guard. His advice is practical, no nonsense, and he's delivered it with a sense of humor that really makes it stick. As an executive coach, I've seen how powerful it is when new leaders get the right support at the right time. If you're committed to building competent, capable managers, you won't want to miss this conversation. My guest today is Dr Jack enter. He's a leadership expert with more than 30 years of experience, helping leaders navigate the realities of management. Jack brings a powerful combination of academic insight and real world experience, including time in the military higher education and as a leadership consultant to organizations all over the US and beyond. Jack is also known for his practical no nonsense leadership advice, but also for delivering it with a sense of humor that makes even the hardest truths easier to hear, and folks listening in, watching in, will see very soon why I wanted him on the podcast. Jack, welcome.

Unknown Speaker 2:36

Thank you for inviting me,

Mike O'Neill 2:39

Jack. We're going to talk of all things you can speak to I was going to ask if we could focus our conversation today primarily around the notion of new leaders. And I entitled this episode without even recording it from Doer to leader, the hidden trap that derails new managers now in our conversations, we've had a couple of conversations prior to sitting down today, you shared with me how often you've seen that you've been doing this for a long time. What is it about leadership? When people go from being high achievers, but when they get promoted, they kind of hit that wall?

Jack E. Enter 3:23

Well, I think part of it is, is it all comes down to training. Training transforms people, gives them tools to do a job, and we do that at the staff level. We do that operationally. When we bring people in, we think it's our job to equip them, which is another word for training. And we do that well. We do that with obviously specific skills that we know they're going to have to, have to do the job as well as, and this is the most important. We surround them with people who are doing the job, and most staff and operational people are effective, so you have very positive peer pressure, and they're practicing, and modeling is the most powerful form of learning. So we're around people who are practicing, not just in their skills, but their attitude, and they're doing the job, and we have that in that collegial type environment, we tend to be very effective. We also hold people accountable. That's part of the training process that we test them, and if they make a mistake, we we address it, and what we're seeing now is we don't apply those same principles to someone in a new role as a supervisor or manager. So we take all the skills that make us effective operationally and at the staff level, and we don't apply them, uh. For supervisors and managers and so they don't know what to do.

Mike O'Neill 5:05

You know one thing I noted about your background. You have consulted in a variety of industries, but law enforcement is the industry that I've had no exposure with. You shared with me off camera that the issues you see in law enforcement are very similar to the issues that you see elsewhere. But for those who are not familiar with law enforcement and how that process works, give us a little bit of feel for how law enforcement goes about hiring, training and promoting their folks.

Jack E. Enter 5:40

Well, first off there, it's one of the few professions that still does formal training. You go to an academy, and then once you've finished the Academy, which is generally a training format, it's some educational but it's normally tell, see, do, and when you get out of the academy, you're assigned to what they call a field training officer or field training deputy, who is an experienced person, who then says, Okay, we're going to apply this in the field. And so as a result of that, and generally, it runs around six months from the time they join the organization, they're in a constant training mode that is filled with skills based experience number two, they're surrounded by men and women who are mentors, who show us by their modeling how to do this, which is the most powerful form of learning, as well As addressing when they make mistakes and other things. Because, especially given the role of what they're doing in the danger, we try to make sure that they know what they're doing.

Mike O'Neill 6:52

Perfect example, and hope I didn't cut you off there. They're very selective. They go off and they receive highly specialized training in literally, an academy, if you would. And there's at least six months that they are working side by side persons who specifically their job is to assure a smooth transition. They've got others, they got the peer group, and then all of a sudden, they've done this for some time, and they are recognized and they get promoted. What happens in law enforcement when people get promoted more often not?

Jack E. Enter 7:29

It's interesting, for a profession that uses the training module, a model that also imagine a man or woman very well equipped in doing the job. They've been doing the job. Their toolbox is full of well used tools. They're constantly learning from those around them who are effective. Most operational people and staff people, not just in law enforcement, but in the private sector, do their job. So we're surrounded by people who do the job, and we hold them accountable, if, because we have to be our quote, brothers and sisters keeper. Well, when somebody gets promoted at the height of this, they're put in a new position with no training. Generally, they don't have their they've been surrounded before and after promotion by ineffective managers. The modeling is negative, and it's interesting. When you ask people, and not just in law enforcement, all professions, what percentage of your managers or leaders, the answer is 10 or 20% so most of your role models, we know what not to do. But this is very important. We don't know what to do instead. We don't know what this looks like to communicate with people when there's not a problem. We don't know what it's like to address a problem employee and so forth and so on. And so we show up in this new role with with no tools, poor role models, who are going to affect us because we don't know what to do instead and have a replacement behavior. And then on top of that, and this is, to me, the most important thing. For the first time in our careers, the people around us are no longer our peers. Are they? They are our subordinates, and they don't feel comfortable telling you that you're not doing this correctly, or that you're taking this too personal. So we lose the reality that we know about ourselves from feedback from others and and that happens again, not just in law enforcement, in every profession, because this is no longer our peer. This is our superior. And I'm not saying anything to the supervisor or manager. I'm gonna get in trouble. So that silence reinforces this delusional view of how we're doing, you know? But. No one said anything. So we assume we doing well, plus we got promoted, so we must be special. And all of that begins to affect people when they get promoted and they go from effective to ineffective.

Mike O'Neill 10:16

I have seen that in multiple industries. I have had no exposure to law enforcement, and you're just kind of confirming it's true there. It's true across the board. You just mentioned that in promoting folks, we sometimes inadvertently take them from being effective to being ineffective. We have leaders listening and watching this episode, what sage advice do you have for leaders, for helping break this cycle that you have referred to, that you've seen over and over again? What are some suggestions you have for us?

Jack E. Enter 10:55

I think the most important thing, and it's based on the concept that everybody understands leadership, and if you think about it, staff, they understand leadership because they practice it, they communicate with the customer, they address problems. And it's interesting that at the management culture, the number one and number two complaints is people don't deal with issues and people don't communicate. So again, because we've not seen that in the management environment, we saw it in dealing in our staff roles, that the solution to this is ask the men and women that are your former peers to say, I need your help on this. If, if you see something, say something, what the military calls respectful insubordination, that it is everybody's job to help each other, and that includes one soliciting from them. What do you think about this? And when you have multiple people who you ask for assistance and accountability, you will rarely make a mistake, and plus, you have the power of the group to kind of throw you in the ring and keep you there. And they all understand leadership. They all understand the importance of communication everything, but have them help you do it. We are much we are much superior in the in the group, than we are as individuals. Individuals. We become afraid, and so that's why most managers don't make decisions, they don't communicate, because they don't know what to do, and they're terrified, and they withdraw into their office, and that's why they're ineffective.

Mike O'Neill 12:43

You know, as I'm listening to you, Jack, I too, have seen this very thing. Let me see if I understood your guidance to us, and that is to foster environment in the case of a newly promoted supervisor, is that you're encouraging that newly promoted supervisor to go to those that they are actually supervising and say, help me be effective in this role. Absolutely. Okay, absolutely.

Jack E. Enter 13:11

And it plus you're also telling them you're not taking yourself seriously. I need your help. I need your help. And what you're also doing is you're training them to do what you are going to be doing when they get promoted, because you're doing it together. I love the great quote. It's one of my favorite ones. None of us is as smart as all of us are and and you've seen it in sports teams. You've seen it. Military thrives on this, the power of the squad or platoon, and in the same way, we are collegial people, we are relational people. And when we have other people like I said, keep saying, Don't worry about it, we'll help you with this. Or you need to confront the problem employee, but Brad and I will go with you. Everything changes when those magic words, you need to do this, but I will go with you. I can't begin to tell you how important that is. I

Mike O'Neill 14:18

would like to kind of repeat this, because you said something kind of in passing that was, I think, very powerful jack, and that is you're encouraging leaders to one come along side each other, but also leaders to interact with those they lead and ask for their help to be You didn't use the word vulnerable, but if you signal you know what, I'm new at this. I want to be good at it, but I need your help to do so that that is a level of vulnerability, but people appreciate when it's genuine, because that's a sign of leadership. Is it not? Yes, absolutely

Jack E. Enter 14:58

and. Yeah, the what marks the leader is they don't take themselves seriously, and that is not normal human behavior. But you'll find that when you ask people to help you, it just reminds you it's not about you and and think of the natural reaction when you find out you've been promoted before, you're just one of the group, and now you're promoted. It is natural to say, you know, must be pretty smart, and now the problem begins to occur. But what's funny is that pride is also associated with you don't know how to do this, so you ask the men and women around you, and plus they're doing the job, and so you need their input on how to do this job. And my experience is you let them do their job, but by building relationships, you enhance that.

Mike O'Neill 15:59

You know to build on that. The thing that you said, almost in passing that makes this such a powerful thing is not only you encouraging them newly promoted folks to be transparent, but you also said that in doing so, you're modeling what's going to happen when they get promoted, that you are going to reach back. You're going to have their back. And that, I think that's very, very powerful, that I just didn't want that to go missed, that a leader understands that a leader is only leader if they have people to lead. If they're developing the folks that that they are leading, they're going to get promoted. And that's just a sign of leadership, the willingness to invest into those I love that you also said something kind of in passing. I'd love to go back to every organization has them that is a problem employee as a general rule. What do you advise people to do leaders to do when they realize that they have, quote, a problem employee

Jack E. Enter 17:09

again, go back to the other people being impacted by this and verify that what you're seeing is correct, and ask them. What's your advice? What's going on with Roger? Has he always been like this? I've only been here for a week. Is this what he does? And what would you suggest? And the other thing too is, I think when you remind them that it is their job to speak up as well, that they're around the problem employee all the time. And when we remind them, stop them. If you see them going a certain way, if they're if they're way too emotional about this, or they're not doing their job, say something to them, and I will back you up on this, but we have to be and I love the quote our brothers and sisters keeper and and you encourage them to do that as well. And I've had people say, Well, I'm not a supervisor. I said that has nothing to do with a positional rank. It has to do with caring enough about that person and the people of them being impacted to say something.

Mike O'Neill 18:32

So you are encouraging us to involve those you lead to maybe, if you're new to the role, new to the group, go to them to get background. The words you use is, I need your help right by starting that that's yet again reinforcing that, you know, this simple concept we're spending a lot of time on, but it's so foundational. What else about what we're talking about right now that do you want to share?

Jack E. Enter 19:01

I think too, that a leader leads with their people, not over them. And that's the concept that you're doing, that you are saying, follow me rather than go do something. And you and I love a quote I heard one time that basically, the highest compliment you can have is that you are an effective whatever role the organization has. You're very effective at that, and you also happen to be a manager that you don't forget where you come from. You still are involved in the mission or the or the job that is being done, and you still are with them, working with them, that you are constantly engaged in them. Trust is the number one currency of leadership, and you trust who you spend. Time with, and most managers fail to be involved with the people that they're supervising. And as a result of that, they fail because you don't trust people that only show up when you're in trouble. They need a favor, or you're their buddy. You need somebody that always comes and spends a significant time every week, just being with everyone, not just your favorites, but everyone to check on them, see how they're doing, and most of your problems go away when that occurs.

Mike O'Neill 20:38

Yeah, thus far, we've been speaking primarily about those who are newly promoted in the steps that they can take to involve those that they're now managing to involve them. If there's a problem employee issue, let's change the scenario a little bit. Let's say there are folks listening right now, and they have been in leadership for a while. And if we're honest with ourselves, they're taking it maybe a bit too serious. Yes, if they're listening to you and say, you know, I'd like to kind of begin doing the kinds of things, where do I start? How do you answer that?

Jack E. Enter 21:23

All the people that I've seen that have done this well, and they've come from outside the organization, or it's been a while, is they have a systematic approach to talking to each person and getting to know them again, everybody is going to be very defensive when they first show up. And what you do is you address that, say, Listen, I know you're saying, Why am I coming? And say, because I haven't been coming or I don't know people. And if you don't trust me. I understand that you don't know me, but I want to eradicate that, and I want to get to know you, because at the end of the day, you're not a person on an org chart, you're a person. And again, if you don't trust me, I understand that might take some time, but I'm still going to come and check on you once in a while and see how you're doing and and you gather material. Tell me about your family, how long you been here? Where? Where'd you go to school? Were you in the military? If so, what unit? And you get to know them. And as a result of that you know them as a person, again, not as their position on a nor chart and and if they don't trust you, again, remind them I understand that. I understand that,

Mike O'Neill 22:53

but,

Jack E. Enter 22:55

but then you stress at that point, I need you to help me do my job, and I'm tired of sitting in my office. It's not reality. I'm tired of the internal politics and dealing with the problem employee, and I just want to come back out to where people are doing the job. I need this for me.

Mike O'Neill 23:19

Yeah, I love this right off camera. I'm gonna reach for it right now, this reminds me of something I saw firsthand early in my career. It was a supervisor who knew his people very well, but he didn't rely on memory. He literally wrote it down, and when I'm reaching for it, he had literally three by popcorn, yep, yep, and that way, as you begin to do this, you're just kind of capturing that. And if by chance, they mentioned the kids names or a spouse name and you wrote that down, how powerful would it be for a manager who is reacquainting himself with those who he leads to just say how, and mention the spouse's name. How's he or she doing? Or you mentioned that you're going to go on a trip this summer. How did that trip go? Whatever it might be, right? You know, Jack, you mentioned that you've been doing this for a long time, but I know that in your writings, you write that leadership is simple but not easy.

Jack E. Enter 24:33

Would you elaborate on that, please? We intuitively understand it. I we discussed this before I did the Moscow police, I mean, one of the most totalitarian governments in history. And I had never done anybody from a presentation for people out of the country, and I asked them, I said, describe your best leader. And through translators, they said the same thing that i. Heard from Americans, because hardwired in the human soul is an understanding of what it's like to work for a person that you feel safe and you want to come in and work for them, and it's also intuitive about a person that you don't want to go in, because there have they happened to be over you that day. And the point is that it's it's hard when you've not seen it done, and because most of our managers have not modeled we understand the concepts of communication, holding people accountable, the importance of relationships, but we've not seen it done, so it's easy to think about it, but it's harder to apply it when you haven't had that model for you. Just an interesting case study. I have a slide in my presentation of a first line supervisor had 12 employees, and he wrote their names down every Monday, and by the end of the week, he had to scratch every one of them off by spending, think about this, five to 10 minutes that week, saying, how you doing? What's happening with your moms, Alzheimer's and all that. And only then would he be able to line them off, and he did that every week. I've used that slide for 20 years. This is important. I've had people come up me and say, I remember this slide. I heard you speak three years ago, and I tried it and it didn't work. I said, why? I didn't know what to say. I said, Really, yeah, what do you say to people that work for you? And then I started asking them a question. I said, Did anybody ever come and talk to you? Did any of your supervisor managers ever come and talk to you? No, that's why you don't know what to say. But again, leaders create leaders for the future, but since most managers are not leading, it makes it more difficult. And it's also difficult because it's a fearful thing to get promoted and not know what to do, and the natural reaction is fight or flight, that we're gonna get upset with people or we just sit in our office and never come out. That's the easiest thing to do, and that's what most people do.

Mike O'Neill 27:33

So you your expression. It's simple, but not easy, and what you're challenging us to do is be intentional. And by the way, for those who when they heard you say he didn't know what to ask or the like, what might be some suggestions that you would have that would come across as natural from a person?

Jack E. Enter 27:59

Well, first off, I think if we one of the things we do is again when and again when we're supervisor, relationship has changed. These are not the people we work with every day. There's this. The relationship has changed. One of the things that I suggest is to script it out. If you don't know what to say. Think about what you would like somebody to come and say to you, and so you think about, how do I get to know this person? What are some questions I can ask? And most of the effective people that I've known weren't that way when they started, but they learned that from practicing it and then watching what the reaction is and learning from that.

Mike O'Neill 28:48

In keeping with the theme of this podcast, of people or organizations getting stuck, can you think of maybe a real life moment where a leader or leadership team, they kind of almost hit the wall. But what happened, and how did you help turn things around?

Jack E. Enter 29:09

Well, what you what you do is you get out of your office and go and start building trust again with people after they've hit the wall and say, we can't change what happened, but we can change the future. And also, I'm going to need your help and advice on how we can get unstuck on this. What do you suggest? And and again, at the end of the day, it's all about relationships and all, and when you hit the wall, admit you hit the wall and say, how could we have done this better? The military calls it after action. Reports that when you screw something up, what how did, how did we end up doing this? What were the precursors and what could. Could we have done differently? And that, again, is called replacement behavior. What could we have done differently? And you learn from your mistakes, rather than keep repeating them.

Mike O'Neill 30:11

You know, I introduced you as dr, dr Jack enter, and I know you have this advanced degree, but just listening to you, you don't come across as an academic. You're very blessed, and we're blessed not to have to hear all that academic jargon, per se. But what did you learn when you were pursuing your advanced degree that might have really influenced how you go about doing what you're doing? I think

Jack E. Enter 30:37

what you learn is that there were several principles that I was reminded of. I remember we had to read all the leadership books and and diagnose what was the most important thing they had to share. And I remember one. It was there was a book called In Search of Excellence years ago, where they did a study of the top corporations. It was a thick blow, but at the end of the day, it was almost to the point you started laughing reading the stories. They all did the same thing. They showed up at at the workplace, and like Sam Walton, he would show up on the loading docks late at night, when people were loading these 18 wheelers, bring a big thing of coffee and some donuts and sit with them and says, stop what you're doing. How's things going for y'all and then the guy, I remember, it was a major steel plant in the United States, that everybody that worked there could tell you a time at one in the morning or 10 at night that you looked up and here was the head of the organization saying, How are you doing? How's it going? Here. Is this working for you? I mean, what could we do better? And because of that, it showed everybody that the leader valued the people in the organization. Did not see him or her as being better than them, but one of them, and at the end of the day, that's not most managers. Most managers are me people, but the ones that made a difference were the we people that spent time relationally with their people. And as one of the finest leaders I ever met, they asked him one time. They said, how do you give up one day a week, from noon till 2am to go out and talk to your people working 24 hours a day. He said, Because I'm out there one day a week, I have almost nothing to do the other four days a week. He said, Because I trust them and they trust me, I go to them and I learn what's going on in the operational environment, and I help them,

Unknown Speaker 33:07

and they remind me from where I came from. And he said, we're friends. He said, this is, this is always the way you do what you need to do.

Mike O'Neill 33:21

Jack, I was looking forward to having this conversation. I can see why you are sought out to the extent that you are. You do keynotes all over the world. For that matter, the guidance that you are offering us is practical. There have been a number of recurring themes. So thank you for sharing. Thank you. Thank you for inviting me. You bet, as we close, if today's episode hits home, here's your move. Listeners, think about one team member who's great at what they do, but might be struggling to lead. What's one thing that you can do this week to coach or support or better equip them for success. And if you're looking for a system to develop stronger managers and build a leadership pipeline that actually works, visit bench builders.com We'd love to talk to you Jack before we go. What's the best place for listeners to connect with you, to learn more about you and your work?

Jack E. Enter 34:21

My I have a website. It's easy. It's www, dot Jack, enter.com it's got some podcasts I've done before. It's got, you know, where I'm speaking and things like that, and that's probably the best way. And it's also got contact information, and I get contacts, how would you handle this? What would you do on this? And I'm happy to do that, and I've learned so much from other people, and that has been i It's not my wisdom, it is from being doing. This for so long that people come up on the break during the training and say, a lot of them complain, but a lot of them also say, I have a great leader. He does this or she does that, and you go, I never thought about that. That's a great idea. Like the guy with the 12 employees every Monday, and also from going into agencies and organizations and sitting down with people face to face, because I was asked to do that, and I've talked over 1000 people face to face on those issues, what's the best part of working here, the worst part of working here? But what's interesting, the answers from 25 years ago are identical to the answers I got two years ago. So unfortunately, nothing's changed, but the solutions have not changed either. But

Mike O'Neill 35:50

you mentioned that you learned so much from the folks you get to work with. That applies to me. I learned so much from my podcast guest of you in particular, thank you for sharing with us. I also want to thank our listeners for joining us and for the subscribers. Thanks for subscribing, and I hope that today's episode with Jack will give you the clarity, the tools and the inspiration you need to get unstuck and on target. Thank you for joining us for this episode of get unstuck and on target. I hope you gain insights to help you lead with competence and drive your organization forward. Remember, at bench builders, we're committed to your success, your leadership excellence and your strategic growth. If you've enjoyed our conversation today, please leave a review rate and subscribe to keep up with our latest episodes. This show really grows when listeners like you share it with others. Who do you know, who needs to hear what we talked about today? Until next time, I encourage you to stay focused on the target and continue to break new ground on your leadership path. You

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