Why Middle Managers Struggle—And How to Set Them Up for Success

You can't skip your, the person who reports to you and tell the person two levels down how to do their job or judge the quality of the work. You have to work with the person who works for you to judge the quality of their work. That's very frustrating for a lot of managers who move up and all of a sudden all the skills they have, their domain expertise, all of a sudden their domain expertise is nowhere near as valuable as many of the other skills.

I'm your host, David Rice. My guest today is Chris Williams. He is a leadership advisor, content creator, and a former VP of HR at Microsoft. We're gonna be talking about the transition to being a second line manager, the challenges that come with that, and how organizations can better support them. Chris, welcome!

None of it reflects the hard problems you face when you're trying to, if you have to lay people off, if you've never had to sit in a room and lay people off who are great people, who have done nothing, but be the wrong guy on the list. Have you really lived as a leader? Have you really lived as a manager? So that's one of my first things. My biggest problem with LinkedIn is that you can't swing a dead

cat without hitting somebody who calls themself a CEO coach. Everybody wants to coach the CEO, right? As if that's the hardest job in the world, so.

Now, the great thing about being a line manager is that, you essentially advise employees on something that you have skills at, that you are a proven performer in that arena. You're in a good position to advise a lot of times, but when it comes to being that second level manager, that transitions a lot harder because it's not quite intuitive.

It's not the lessons that you need to learn or the lessons that you lead, you need to learn aren't exactly a part of your sort of standard manager onboarding process in most cases. So I'm curious, what do you feel like needs to change most for companies to help these professionals thrive essentially?

When you move to be that person's manager, not only are you one level removed from it, but it becomes to the point where you cannot. Advise, right? You can't skip your, the person who reports to you and tell the person two levels down how to do their job or judge the quality of the work. You have to work with the person who works for you to judge the quality of their work.

That's very frustrating for a lot of managers who move up and all of a sudden all the skills they have, their domain expertise, whether it be, in programming or finance or whatever it is, all of a sudden their domain expertise is nowhere near as valuable as many of the other skills like getting to people to work together. Communicating objectives across things being clear and concise in your communication.

There's a whole bunch of things that are more important as a second level manager than you were as a first level manager. But to answer your question, one of the problems I see, and one of the reasons why this is the core group of people who I really like to focus on, is that companies don't know how to help those people. It's particularly easy to teach someone how to be a manager 101. There's a bunch of, there's a lot of literature out there. There's a lot of courses you could take.

There's a lot of training you can do about how to delegate better, how to do a bunch of those things better, but the kinds of things that you need to be good at as a second and above level manager are things for which there's not a lot of literature out there and there's also not a lot of experience out there.

So you'll find, for example, the people in HR frequently can be helpful, or the leadership training can be helpful because they too are managers of people and they can help you manage people, but manage managers, there's just not as many of them and there's not as much experience around them.

I think companies, one of the things that I, and this almost sounds self-serving, but one of the things I think companies should be really open and willing to do is to support these second and above level managers with people, with coaches, advisors, consultants, whatever it is, with some resources to provide them the ability to ask questions and get honest feedback and be stupid or what. One of the problems you get as you move up in an organization is mentorship is hard to find.

If you're a second level manager going to your VP and saying, geez, I don't know how to deal with this guy who works for me, makes you look like an idiot, right? It makes you look helpless. So you don't wanna go to your boss's boss or whatever and be vulnerable and be the kind of person who can't get stuff done. And you can't go to your peers because they're often in competition with you. You can't go to your employees and ask them an opinion 'cause they're the problem, right?

So having somebody to talk to, somebody to work with, a coach, an advisor, or somebody is frequently incredibly helpful.

Again, that sounds like I'm advertising for my own business, but it's the kind of thing that I think companies can do more of and should do more of.

They are deeply dependent upon what their business is and how it works, and who the personalities involved are, and often the technology that's involved. And so it's a really very custom problem. I have this problem, I don't know how to deal with it. What should I do with it? There's no book that's gonna fix that. There's no quip on LinkedIn that's gonna help you. What you need is someone to be able to say, Hey, here's my problem. What do you think? And explore options and figure out ideas.

Figure out how to make this work and have it really helps to have somebody say, been there, done that. Got the T-shirt, right? Be careful, don't say this 'cause that'll upset a bunch of people, that kind of thing. I've found that what really works, and it's very frustrating for me as somebody who creates content and wants to impact a whole lot of people, it's very frustrating. But for me, one-on-one is what works. Working one-on-one, that's where I find I have the most

impact, the most effect, and frankly, it's what I enjoy doing the most because I get the most impact and the most change and the most effect.

You have to translate that, that high level objective into the pieces that actually matter to get done. And that level of translation is really complicated. And it also isn't helped by the fact that you can't go to that frontline person and scream the strategic objective at them 'cause it doesn't help. They don't, I, how do I, how do I motivate our customer base to do it? That doesn't help me. I need to know, should I get this project done like this or like that.

So a huge portion of what middle management is translating requirements. From the vague to the specific, right? And deciding what is noise and what is not, and what to bother your employees with and whatnot. So there's this huge filtration process that you've gotta be just incredibly facile at. And also communicative, right? You gotta be really good at communicating these kinds of things in a way that people can hear them. It's very underestimated how incredibly hard that job can be.

on, and I think it's in many ways just cutting, 'cause cutting feels good to cut.

And lay out some of the strategic challenges that their group, their organization, their company is facing, and talk about the difficulties that they as a manager have in executing against those strategic priorities. And people can understand that sort of the very large scale. Hey, we've been asked by the corporation to implement this. Build this product or whatever, right?

And you can explain to people, then that means we need to do this and this and this, and here's this team over here doing this, and this team over there doing that. And if you lay that out in a particular way, people suddenly get a respect for, oh, I see you are managing this whole project. I didn't understand what that part of it was. So there's an opportunity for you to be more open and honest about what goes on.

But what's absolutely crucial in those sessions is that you also be really vulnerable. This is hard, right? Or, I'm getting a bunch of pressure from the CEO to do this, which I know is really hard. Or to be open and honest with those people because most people are smart. They can smell you when you're making stuff up.

So you have to be honest about, hey, I know this is hard and I know this may be an unbeatable goal, but we're gonna work our best to see if we can get there, or those kinds of things. Be open, honest, and vulnerable with them, 'cause if you're

not, they'll know it. They'll smell it.

How can we help these people look at these challenges in a different way?

Some people like feedback to be very careful and thoughtful and gentle. And they need a little bit of stroking before they get some negative feedback. Other people, if you give them that kind of feedback, they will not hear you and you practically have to scream the feedback, stop doing that, or but if you do that to some people, they will cry, right? So you can't do that. You can't forgive everybody the same kind of feedback all the time. You can't assume that some people are good writers.

Some people learn through watching videos. So every single person, regardless of age, regardless of generation, I know people who are terrible at picking up new technology who are 25 years old, and I know people like myself who are approaching 70 who pick up new technology all the time. So you can't make generational stereotypes. What you have to do is look at that person and decide, oh, I see you are one of those people who likes harsh feedback.

Doesn't hear me unless I'm talking quite directly at you. Will never open my email. Only hears it when I send you a text, right? If you treat each one of your employees that way with the, whatever the world they live in is, you suddenly realize that generational stereotypes don't mean anything. And that's the whole work from home thing, right? There are some people who would. Absolutely love to work from home. There are other people for whom the office is a sanctuary. Their home is a nightmare.

They wanna get to the office because it's quieter and they can focus and whatever because they got kids running all whatever it is, right? There are other people for whom the office is a scary place that's 45 minutes away, and the commute drives me nuts, right? So those people could be 25 or they could be 65, who knows, right? You have to treat everybody as an individual. And the cool part is the sooner you start to do that, the more effective your relationship with them will be.

The more respect they'll give you, the more open and honest your conversation can be, and the better your relationship as a manager and a leader will be. The generational stereotypes thing just chaps me. Partly as an older person being stereotyped, as you don't understand new technology. I'm working with an AI startup right now. Okay. A friend of mine and I have developed a really cool leadership AI startup, which we could talk about at some other time.

We're using AI agents in ways that people haven't seen before. But I'm not, I'm a boomer. Boomers can't even open their phone. Yeah. No, I'm pretty good at opening my phone. Ask my wife.

question is because a lot of middle managers, second line managers, they're expected to grow their influence, right? As you, the more time you spend on the role, influence plays a big part in your success, and one of the reasons is it helps you work cross-functionally.

This is such a big thing that we always talk about now, but when you work in a culture that doesn't necessarily support cross-functional work because a lot of companies like to talk about it, but the actual logistics of supporting that and not keeping things siloed, it's more complicated than just saying, we're gonna work cross-functionally. It doesn't come naturally, but you're still expected to grow your influence within other departments.

What advice do you have for a middle manager who's in a situation where they need to build influence and create more credibility for themselves, essentially?

I just wrote an article for Business Insider about this recently, which is that all these people who were being labeled as under performers, their biggest problem, their largest problem, is that they weren't known in the organization. That when the meeting got together and they tried to pick out who we're gonna get rid of on this list of people, the people who got rejected first were the ones who obviously had blown something up or had some terrible performance problem.

But the next people on the list were the people who, when you brought up their name, people went who? So what you need to do as an individual is make connections across the organization. And the thing I keep telling people is whether or not your organization wants you to work cross-functionally, there's nothing preventing you from having an association cross-functionally.

There's nothing preventing you from giving a, if you work in the product development side of the business, there's nothing preventing you from having lunch with an HR person or a finance person or a marketing person or whatever. And I love to tell people the way you do that conversation is you sit down with 'em and you say to the finance guy, I don't even understand how you guys do what you do. How do you guys come up with these complex reports? How does that work?

When are you guys supposed to do them? How does that, how do the upper management react when you do those things? Don't you get some pushback when you try and push down on people with it? How does this ask them a million questions about their job?

And I have never met someone who, when you start asking good, genuine questions about what they do for a living, doesn't just light up and want to tell you it really gets to me like this and I, eventually you've gained a relationship with someone over in finance and then you've gained a relationship with someone in marketing and sales and whatever, and they will introduce you to somebody else.

And so when the time comes for some thing that blows up, you are required to cut 10% of your organization. You got somebody in finance to go to and say, wait a minute, how does this really work? And what does that look like and how do I make this work? And. Or when that round table discussion is happening and they're trying to lay off the under performers, everybody will go no. Wait, not Chris. I know him. He is a good guy.

Just because the organization doesn't want you to be, working together between each other doesn't mean you can't have a relationship with that person. Doesn't mean you can't know who they are. By the way, the other thing is it's really hard to hate people one-on-one. The finance people are always going, ah, you can never trust the product people 'cause of whatever. And if you have a relationship with one of those guys, one of the finance guys is going and go, no, wait a minute.

I know some of those people, they're not doing that stuff or whatever. So it's really hard to have a negative relationship when you've got a one-on-one connection with somebody.

There's this shift, to new working models where whether it's hybrid or remote, and it's something that a lot of people in HR have been navigating, but now there's this kind of move to push people back in. And I'm curious how you're advising clients to adapt to the new working environment because many seem to really struggle. I don't know if return to office orders are helping anything really.

I think one of the problems is that business is tough and things are hard to do. And if your business is in any way struggling, you rush back to the things you've always done, and one of the things people have always done is be together in an office. So that feels like the thing to do. I also think, as a complete subtext to all of this, it's important to note that Jamie Diamond's Company, JP Morgan is one of the largest investors in downtowns and office spaces and shopping malls and whatnot.

Jamie has a slightly vested interest in making sure that downtowns and office complexes thrive. So there's a reason why Jamie's not just talking about office culture. He's talking about needing to prop up the office class, a office space market. But in any case, the underlying problem is that if you are a manager who is focusing on how the work gets done and not what the work is getting done, you're focusing on the wrong thing.

It's not about where somebody does it or whether they do it in the nude, or whether they do it standing on their head or none of that matters. What matters is the work getting done and is the work quality of the work getting done?

And again, this is one of those things that mattered before Covid and it matters just as much now, which is if you were a kind of manager who wasn't focusing on results, who was monitoring people's keystrokes, or whether they were taking too long of a smoke break or one of those kind, you were not actually managing to the business results you were managing to, the symptoms of business results.

And if somebody is remote, and you should certainly be able to tell whether they're getting the work done or not. And if you don't, then that's your problem. You as a manager need to figure out what are the requirements for this job, what things need to get done, what is the appropriate time to get them done in? And if they don't meet those requirements, that's the discussion you should have. Not about where you're doing it, it's about you're not getting it done.

So I think one of the things that has. Return to office is an easy whipping post upon which to hang your poor management hat on. Gosh, I mixed as many metaphors as I could there, but it's an easy thing to say, oh, I know what'll solve it. Let's all get back in the office and so we'll all get back in the office. Everybody will be miserable again and the performance still won't improve. What are you gonna do then? I'm gonna blame something else. Middle managers I know.

I'll fire all the middle managers. That'll do it.

In the process of doing that compensation analysis and revamp, we talked with some of the world's leading compensation experts and time and time again they said, the most difficult thing to do in a compensation system is to make sure that you monitor the result that you want, not the results you think you want. Because as you see, for example, it's very common in sales circles. For example, if you give people a payment, a commission based on the sale, right?

People will sell stuff that people don't want just to get the sale, even though the return will come back later. So then you have to, oh wait, no, we got a credit for the return. Or you'll get these stupid behaviors where people rush orders through at the end of the quarter and then have no orders for the beginning of the next quarter, and then rushing through the end of the quarter. So compensation systems are exactly the model for that.

The minute you set out some objective, people will figure out a way to gain that objective. You have to make sure your objectives are clear and related to the business at hand. Really relatable to the business, as you said, mouse movers and key twiddles to make it look like I'm busy, right?

And also somebody's gotta monitor it, right? So I think there's a level of mixture in it. Some folks are getting a little nervous. And I think wanting to figure out, like they wanna open another door if nothing else, just to see like what a, what's on the other side. And also, a lot of these folks are overwhelmed right now, right? State of the world kind of thing.

People are asking a lot of questions and they've got a lot of people in their face asking 'em the same questions about ai and they don't know. It's interesting timing because I think a lot of people are thinking like, I gotta figure out what that next thing is. But there's a level of we're not there yet, though. We've got time.

It's gonna be a while before this thing just completely, it's like I, I was saying to somebody on a podcast just last week about, I saw this study from MIT and this guy was like, his management expert was like, there's no meaningful work that a human being does that AI is ready to replace it this time, or will be probably for the next year or two. I think for that generalist crowd, that's a good thing to keep in mind.

Like you're still going to have to be there to manage the thing and monitor it. What is it saying, is it actually put, are the outputs good? They've got a little time, but they should. It's on everybody's mind.

Whatever you do in order to differentiate yourself from the mid that is being automated behind you, right?

The one thing I would say is it's not a particularly talented storyteller and it can't add human value to it. That's where you can thrive,