Management Problems - From a Manager Perspective

Being a manager myself; I've been both a good and bad manager. However, nothing I ever did seemingly went unappreciated or unnoticed. I have in fact, been an employee more often than not. This isn't really a guide to being a good manager or anything, but I notice a lot and if you are a leader and reading this, maybe take some words of wisdom and self-reflect a bit.

This really is for folks to look at their own boss and make decisions and hopefully learn something new. Not leave, unless it's truly that bad, but rather give the opportunity to recognize it, and learn that as an individual contributor (aka not a leader), that you can in fact have impact.

A lot of us tend to think in authority; I am not one of those. We're all just people doing things, and your job and responsibilities look different than mine. Maybe that's leadership, maybe that's not. I don't view the CEO any differently than I view the intern. Remember that key distinction as you read on.

Being a "good" manager is subjective to the role you're in. For example, a developer manager is going to have different requirements from a say, operations manager, who's also going to be different from a finance manager. Your role, it's objectives and what's needed all play key roles in what type of manager or leader works best for that team.

To take it one step deeper, it also depends on the culture of the company and the team itself. More examples... if you have a team of extroverts and chatty people vs having a team of introverted and "to themselves" people. You might even have a team that's just trying to get through the day, and the leader will need to be fit for that. The company, it's requirements of leaders also play a big role in that as well. Your leader likely has to play two roles no matter where they are; appeasing those above them and helping those under their care succeed.

I bring all this up, because I think being a good manager doesn't just come out of thin air; it comes from being in the right place. If it was ONLY about the qualities, then why can't a manager of a rocket scientist team lead a team of zoo keepers? I know, that's extremes, but it also applies to roles say within a company as I mentioned before. But also, how well do you think some eccentric chatty person who always wants to chat and meet up will work over a team of people that are basically blue collar workers, wanting to get in and get out? There will be a disconnect.

There's also say C-level vs directorship vs management, specific to each company. As much as some would say that's a ladder you climb, each role has a different need for a different kind of leader. You can't just be the best manager ever and hop into the CTO position and expect to succeed. Also though, I would argue that there are some managers that would never make it as a CTO, because of the fit where they are. Maybe CTO somewhere else, but not on this company.

I think this vision I see here often goes well unnoted when people hire for management positions specifically. Like I've seen it where you have a team of 5 people, and they're basically all friends. They work together like they're playing games, but they're highly productive and innovative, then you hire a manager for that team is who kind of a hard head; he's not into games and friendliness, he's about getting the job done and delivering on goals. I've watched managers like that completely KILL the drive on their team. It's not that the manager was a bad guy or a terrible manager... but he shouldn't have been hired for that team specifically. You set him up to fail from the get go.

Most managers really have no clue how they're doing as actual people leaders because their employees never actually send any of that info upwards. They hear complaints, they may get yelled at, they get defensive over things, and they have a lot of surprises and things pop up... but it's not typical that anyone ever says "hey boss, I really don't like that we aren't doing X" or "You know when you do X it really gives the team some crappy vibes."

Even when they do, managers don't often get the problem. You might say complain to your manager about feeling or being overloaded... with what? Are there certain things that might be tougher for you? Do you need help? There's a lot more questions than answers to that statement, but often as employees we're like "I told my boss I was overloaded and he didn't fix anything. He's useless." Obviously we try to dig deeper, but it's not always as clear as it feels to you.

Let's be real; most of the time it's just a bunch of employees over a lunch table complaining about how their manager sucks... but the manager never hears that, so they keep doing what they're doing. Even as an employee, I complain but never bring anything to the table as a solution.

Point being, being a leader is a two way street, and employees need to recognize that too. We can't improve if we don't know there's a problem or we don't understand there's a problem. It's important to give feedback to leaders, and also come with solutions, because often the solutions help us figure out what the actual problem is if you really don't know.

Yes - managers spend a LOT of time trying to figure out your feelings. We aren't you, so we have to figure you out.

Now let's bring up the REAL problem here... that authority can be scary. You know your boss has the weight and power to fire you, and that often sits on your head. You don't want to be too difficult, and you don't want to come off as the negative person. So you bottle it up. Honestly... even the worst bosses, you can at the very least test the waters. Most leaders though, are excited, or at least express interest in some way when you give them feedback, especially critical feedback. That being said, there are a few signs to look out for to make sure you aren't going to risk yourself by going any further -

• They get hyper defensive. Not just "Oh well I did it this way because this." But something like "I would never hurt anyone. I am not targeting people. My boss says this."
• They barely respond. They say they'll make a note and just move past it.
• They immediately start throwing accusations and/or problems back at you. Like in a non-cordial format. You may say "I feel overloaded" and their response is that you have the same load as everyone else. That's not a problem, that's a statement, and what they're asking for is more information. What I am talking about is you tell them about the overload, and they start throwing the last two deadlines you missed at you.

I think a lot of us tend to think more about how others affect us and should bend to our will then the reality of the situation is that we aren't conforming and delivering what our job expects. This is where purpose sets into play. Let's say you work for an operations team that's filled to the brim with requests, escalations, and work that never ends. You as an employee focus on automating things because the work sucks... which is fantastic, but you often miss deadlines, don't communicate well, and take on less "regular" work than others. That my friend, is a you problem, and your manager is there to help, but ultimately it's up to you to straighten that out.

Another way is what I call "comfort feedback." This is where the last point I made becomes a staple. You may have a good manager that pays attention and responds, maybe even acts on everything you bring up. What happens though, is you get too comfortable giving feedback, and you start going unfiltered. What ends up happening is your manager can't always and forevermore address the 11 things you bring up every week, and suddenly you start feeling useless, unheard, and like no one cares. That's not actually your manager's problem; that's you. It isn't that what you're bringing up is invalid, but there's some things that just need to be accepted until we can change something, or if you feel that strongly, you need to take control and do it yourself. A good manager will encourage and empower you to take on challenges yourself.

There's also a group of people you might fall under, which is the "give it to me" crowd. I've had at least one team that's done this; you have articles, the internet, the company offers LinkedIn learning, and there's people galore around the company with knowledge... yet learning is difficult. It's not structured the way you want. You don't understand what to do. They don't give you the time. So when your manager comes to you and is like "so you want to learn this skill? What do you need?" - you have this unrealistic expectation; I need someone to sit with me for 8 hours a day for a whole week. You want company written documentation, playgrounds, and specific books or sites to follow. You want training. I'll tell you in tech... it doesn't work that way. Your manager can literally only give you the time, and maybe direct you to resources or people. Otherwise, it's your drive and navigation that need to go forward. We can't as leaders, typically incorporate learning and advancement into the job directly.

I would also say that when you're having problems or issues at work, the best advice I can give you is to first self-reflect; is this something that you can solve yourself with effort, a mindset, or a change? You at that point become unblocked, it's just however you can get past it and move on.

Half your job as a leader is just simply understanding what's given to you or really vague action items.

From above is one perspective. You may have an employee who is complaining about their pay. You go to your boss and they say "Contact HR" and you're just stuck navigating crap you have no idea how to handle. You flop on a project and your leader wants a retro, wants constant updates, and constantly tells you what your team needs to do and how (despite never doing the job). You get handed like 8 major initiatives that need to be done in the next two quarters, and you know you can't do all 8. You try to set expectations and ask for priorities, and they say some crap like "It isn't an if/or statement, it's an 'and/then' statement. I know you can figure it out." Okay dude. Awesome. Then as you give updates, you gather data that is essential to knowing the status, build a slide for a presentation... and they don't get it. So you have explain it, redo the slide... and someone else doesn't get it. Third time it looks like you've nailed it... except now it's not showing accurate data and everyone thinks we're 3 steps ahead of where we actually are and we suddenly need to speed up the project, but it's what they want to see from now on. Sigh.

Then there are those you lead. You get complained at, you're always the bad guy handing down work, you're always trying to keep people motivated even though nothing seems to work, and you always seem to have pay issues. Often being direct and upfront about the reality of these situations just makes people hate you and become half as productive. If you sugar coat it too much, you become a butt kisser and people stop respecting you. Not only that, but if your team is larger than 4-5 people, everyone wants info delivered differently. You are absolutely screwed no matter what you do... but since you are a good manager and care, you do it.

As a leader, it's a never ending battle of learning how to lose the best way. There's no other way I've experienced it. You might have 5 people, 2 bosses, and company goals, you aren't going to make everyone happy, but you're expected to.

"Where's the 'is it you' part?" - Right here actually. The problem with all that information you get, is a lot of it is feedback you need to use to self-reflect, disguised as demands and complaints. If your team is unhappy, then the first thing you need to understand is what they are complaining about. Maybe it's you. Maybe it's something you could consider doing. Maybe it's something you've always done and now need to change. If your leaders are unhappy, maybe it has to do with the way you're filtering and running projects. Maybe you're not assigning the right people and using the right tools. Maybe it's just that you aren't providing the right updates.

I will say though, while there are situations as an employee/IC that are crappy, management often is always in those situations. Impossible to please everyone, but required to do it. Self-reflection is still key here.

I know I mentioned before that a good fit is needed, but there are also qualities and traits of a manager that often make them good and memorable. Here's a few I've learned from experience, experiencing them, and also included is the poor equivalent.

"In the Pit" - One thing that will kill a leader's respect is being so far removed from the work, that they really don't get it. However, there's also a balance, because if you just put a high performer in charge, they don't actually lead people very well in most cases. The balance is, having enough experience and drive to know how to do the job, without actually doing it on the daily. That's where my "in the pit" philosophy kicks in. If your team gets wrapped up in a project, being able to ask questions, deep dive, and perform work along side them, builds a great sense of comfort that your leader has got this.

• The other side of the coin is where your manager does not care about it, oversimplifies it, or just straight expects things out of you that you can't do. "Work a little harder" or "we've got to meet this deadline" or "just do what you need to do" are all tell-tale signs of a manager who isn't operating well. They lose respect quickly. Often it's not necessarily their fault, but their mindset. These guys often are "company first" guys, which in my opinion isn't right.

"Numbers" - Look. Metrics, performance or not, are a key part of a business and I understand that. C-levels don't really have time, nor do they understand the managers and teams 6 levels below them, so what they need... is well sort of a progress bar. We're 80% complete here. We're 20% here. We haven't started this yet and here's the big blocker. A good manager gets this, and keeps this type of stuff far away from the team. Not the numbers, but the interactions. They don't need to know the slide deck you gave to the CTO. There are certain metrics that you as a manager may not agree with, but you fudge around and stand up for your people for. You get it. These are people, not "resources." You should treat them as such. The numbers are what keep you aligned to everything, but they are not the end all be all of your mission.

• Man have I worked for "number" managers before. It's miserable. I personally have a moral compass that puts passion and compassion above all. So if I am in support, it's whatever makes the customer happy. If I am Ops, I make sure we do it right in the right way, even if it's not as fast as you'd like. I also keep all the issues, cultural and procedural at the front so we can move faster. This mindset, almost never works for numbers guys. You didn't close enough tickets. You closed tickets but your rates aren't good enough. You missed too many SLA's. It's the definition of going from Bob Johnson the support guy to employee 546 in department CBD.

Military Leader - These are the guys that are so up front and clear about everything. Some of my favorite managers operate this way. They don't want to talk about all the minutia of it, they just know X project needs to be done by X date, and we need someone to work on it. They never sugarcoat or hide anything, and often they know how to do the job better than anyone else.

• I think everyone at some point has the opposite. The guys who's afraid, so he individually talks to folks and doesn't give everyone the opportunity and he fears management because he doesn't want to sound dumb. Yeah... that was me once.

"Open Book" - This is the type of manager who's just always brutally honest and transparent. This person will not only share the reality behind the scenes, but also tell you exactly how they feel about it. They often feel the need to do this because it creates accountability on themselves... sometimes to a detriment. Often their greatest strength is being able to pull feedback from people, because their honesty tends to create safe spaces for people to thought dump, work through issues, and help solution without feeling like their job is at risk.

• As opposed to the many leaders I've worked with that feel the need to filter everything. It doesn't matter why, just get it done. Often they have intentions behind the scenes, but pitch something very different to you, and in most cases it's very easily seen through. This type of leader often creates places of fear, and operates off of demands, creating extremely nervous or volatile spaces for their employees.

Whether a good or a bad manager, whether or not a good fit or taking the wrong approach, one thing I can tell you about management is that it is in fact one of the most difficult positions out there... especially in tech. You are in between everything, expected to please everyone, and often your efforts never bear any real fruits. You want your team to succeed, but often you have to fight upper management to get there. You also want upper management pleased, but often you have to overwork and filter info to the detriment of your team.

Also as a leader, the thing is everyone sees it. It's difficulty, the struggle, the never ending hellscape that comes with it. Leadership will always preach how difficult it is. The employees will likely feel your stress and losses. Yet... you're on your own. As a manager, you're often isolated. You're probably in a department with 8 other leaders, but they all lead completely different teams, with different roles, and different needs and struggles. You guys may talk about it in forums, or sync meetings, but ultimately it's your team, and you have to decide what's best.

It takes a certain type of person to do this. A high performer suddenly seeing behind the curtain, going from being a winner at life to basically being a pipe and every time you turn around you lose is not a great feeling. Also, those who expect to just cruise through and just "do a job" is something that does not come with the territory.

As a leader myself, which to be transparent, I no longer want to be - I am often in one of three states; cynicism, frustration, or disappointed. Maybe for someone else this job is fulfilling, but for me, it's literally just a pit of loss. I can't win. I can't help, I can't please, I can only lose. Too far out to be an employee and make the same amount of money, but too far in to not feel like garbage all the time. It sucks. There's a chance your leader may feel this way too. You never know the truth.

It's hard out there y'all. Just be nice and treat others the same way you would. Be kind. Spread love.