13 Principles for Becoming the Boss Everyone Wants to Work For (And Escaping “Mid-Level Manager Hell”)

Intro

Last month I wrote an article titled “Why Choosing Your Boss is Probably Your Best Career Strategy”. The key point was that a good boss matters far more than almost anything else in your career if you’re trying to optimize for the best balance of personal happiness + career success. For example, I know many people who have better titles + make more money than me but are far more unhappy because they work for jerks/tyrants (which is a tradeoff I don’t consider worthwhile).

Since writing that piece, I’ve had readers reach out with some legitimately great questions. Questions that I’m not sure I have the full answers to. Questions like: “What are the signals that someone is (or is not) likely a great boss?” or “How do I become the manager everyone wants to work for?”.

I am going to take a stab at answering those here. In full transparency, I don’t claim to have the “right” answer. I’m still relatively young in my career, and it would be silly of me to pretend that I’ve somehow “discovered the true secrets of effective leadership”. There are many men and women far more qualified than I to speak effectively on that subject. What I can share are a few of the principles I’ve observed from leaders that I’ve personally worked for who are (A) people I deeply respect, (B) people I would work for again in a heartbeat.

I hope these are helpful to any reader who is either looking for a great boss to work for or is looking to become a great boss themself.

But First…Why Should I Care About Being a “Great Boss”?

Before we dive into the principles, we need to talk for a moment about why this even matters. The most important reason for wanting to be known as a great person to work for is perhaps a selfish one: It will personally benefit you professionally and financially.

Here’s what I mean: when you’re a great leader you will attract (and keep) star talent around you. People want to work for the best. And talented people are more aware of this than anyone else. More talented people on your team = your team is going to be much more effective at building/doing great things = you’ll reap the benefits of being someone who is highly productive.

Something that is counterintuitive for many first-time managers is understanding how they are evaluated (and compensated). Most people are promoted into leadership roles primarily based on their excellent work as an individual contributor (IC). But the moment you become a manager, this changes. As a leader, you are no longer primarily judged on your individual ability, but rather on the output of your team.

This point is more important than it seems. For example, I know many engineers who were excellent at building/coding things themselves, got promoted as a result, and then have really struggled in their career ever since because they can’t give up their tendency to want to do everything themselves (since they were a great IC!) and the overall team’s performance flounders as a result (meaning that they as a manager now don’t get recognized/rewarded).

The rules of the game have changed, and they can’t figure out why they’re not winning. They’re stuck in “mid-level manager hell”.

This is a mindset shift that took me a while to understand when I first became a manager. I felt guilty for not doing as much of the “direct work” as I used to. But the role of a manager is fundamentally different. Its goal is to get a collective group to produce more than the sum of their parts. Once I understood this, things in my career started to progress rapidly.

This is why having “stars” (people even smarter/brighter than you) on your team matters so much. You want stars because stars are (A) more productive/talented, and (B) easier to manage (e.g., they require much less hand-holding). These are people who are going to maximize the output of the team, which is going to get you the high marks you’re looking for as a manager. It sounds a little selfish, but it’s also the truth.

This is fairly common sense when you put it in other scenarios. For example, what football coaching job would you rather have? Leading a team with a bunch of highly skilled players who understand at a deep level how to play the game, or leading a bunch of scrubs/rookies who have to be told what to do at every point?

It is not only more enjoyable to lead a group of people like this (no one likes babysitting), but will also free you up to work on things that are important (ex: long-term strategy, important but not urgent projects, etc.). AKA you will work “on the business” instead of “in the business” every day. And that is a recipe for quickly rising up the company ladder.

How to be a “Great Boss” (and escape “mid-level manager hell”)… 

So how do you attract “stars”? The simple answer = you need to be someone that others will fight to work for. AKA, being known as a “great boss”.

I’ve had the opportunity to work for some amazing bosses throughout my career, and have noticed some common leadership traits they’ve all shared. I wanted to list those out here. It’s certainly not an exhaustive list, but these have been invaluable to me as I’ve made the transition from “high-performing individual contributor” to (hopefully) being a “manager everyone wants to work for”.

Let’s dive in.

 

#1: Develop an instinct for finding / hiring the right people

You first need to find + hire star talent.

Mark Zuckerberg (Facebook’s CEO) once said that his personal framework for hiring someone is (A) someone he would enjoy spending time with socially, and (B) someone he would feel comfortable reporting to if their roles were reversed.

I find that to be a wise maxim when evaluating candidates.

Note: If you can’t find someone you’d truly hang out with socially, you at least want to work with someone who you deeply respect.

Personally, I also look for someone who is smart, gets things done, and has extremely high integrity (in addition to Zuckerberg’s items above).

You can always trust your gut on this. If someone’s resume seems amazing, but you have some misgivings about them on a personal level, you should trust that instinct. It’s rarely wrong.

If you want to go into depth on all the tactics of how to recruit/hire star talent, check out our article on recruiting like a pro.

#2: Don’t be afraid to be the “dumbest person” in the room

Remember the story of Henry Ford. You don’t need to be the subject matter expert in everything. But you need to be an expert in knowing “where/how” to get the answers. Remember that your primary value as a leader is harnessing & synthesizing the collective intelligence and skill of the team, not any individual brilliance you may have.

Note: You do (and should) develop some expertise on your own. Your team needs to know they can look up to you for guidance/direction on thorny problems (e.g. how to break a problem down into manageable parts, how to communicate their findings in a clear way, whiteboard a solution with them, etc.).

The Henry Ford principle is not an excuse to say “I’m a “strategy person” and I don’t need to deal with the details. That’s baloney that is parroted by people who are too lazy (or too afraid) to get their hands dirty and learn some of the details themselves.

#3: Delegate like crazy

Delegation is not an act of laziness. It is how you get work done as a leader.

Good delegation makes your team feel empowered. No one enjoys being an “order taker”. People (especially talented ones) want to be entrusted to make their own decisions, be creative in coming up with solutions, and getting credit for what they do. Your job is to give them that opportunity.

You need to avoid the trap of being a manager who is really just a “highly effective individual contributor who happens to have people reporting to them on the org structure”. That mindset is what keeps many talented people stuck in “mid-manager hell”.

A few quick tips on delegation:

• You have to learn to trust your team. It can be hard for many first time managers to delegate because they worry the job won’t get done right. This fear is what usually leads to micromanagement. You have to believe in the stars on your team, and then give them the trust to get things done without your direct supervision. It’s hard to let go, but you need to.

• One of the main challenges you’ll face is “workload management” (making sure that everyone has the “goldilocks principle” of the right amount of work to do). You need to avoid the risk of over-delegating too much work to some folks, while starving others of meaningful things to do. If you don’t both the work product and team morale will suffer. Use regular check-ins and an “open door” policy to keep a firm pulse on the workload level of your team and balance accordingly.

#4: Always Explain the Why (Set the Vision)

Never just assign a task, even a seemingly trivial one. Help your team understand “WHY” they’re being asked to do this and how it fits into the bigger strategy and purpose.

If your team understands the role they’re playing in the organization and why it’s critical, it will make them feel more valued and trusted.

• Bad Example: “I want you to do a marketing sizing analysis of the # of Dental Offices in the USA. Can you have that done in 2 weeks?”

• Better Example: “I want you to do a marketing sizing analysis of the # of Dental Offices in the USA. The reason this matters is because (A) we need to provide Wall Street Investors with an understanding of how much sales runway we have over the next few years so they can confidently continue to invest in our stock, and (B) it will help us know if we need to quickly identify a new industry to sell into. These are 2 critical inputs to the long-term strategy we’re developing. Can you have that done in 2 weeks”

Notice how the second one clearly links the ASK (Marketing Sizing the # of Dentists) to the WHY (the impact this information will have on the strategy).

Too often I see managers make the mistake of only delegating out tasks. It’s always worth it to explain the why.

Side note: I’ve noticed that the best leaders also take the time to set a clear vision of where the team is going long term, and what everyone is going to be working on for the next year (+ why those are the projects being chosen). This has the benefit of helping everyone understand what’s coming around the corner and builds a sense of trust as a team (people like being “in the know” and having input into what the team is going to work on)

#5: Protect your team from meaningless busy work 

Make sure your team is protected from just doing mundane/ thankless work. People need to feel like what they do each day is actually meaningful.

There is no way to completely eliminate 100% of the mundane “paperwork-esque” tasks in any job. They are in many ways necessary evils. But you need to be vigilant that this takes no more than 10-15% of your team’s overall time. Your job as the manager is to shield the team from requests (even well-meaning ones) that are really just low-value contributions.

Otherwise, your team will start to feel like they’re living in a Dilbert Cartoon and will start looking for the exit.

#6: Run Really Good Meetings 

Nothing quite sucks the soul out of a team like having to attend a lot of absolutely terrible meetings. Fortunately, there is an easy solution to this as a leader:

First – really limit the number of meetings your team has

Second – make sure that the meetings you *do* need to have are world-class

If you’re new to running meetings (or want to uplevel your game), I’d highly recommend checking out this series of articles:

1. The True Cost of the Dilbert Meeting
2. What to do Before the Meeting
3. What to do During the Meeting
4. What to do After the Meeting

#7: Give Your Team Credit

It costs you absolutely nothing as a manager to express gratitude and give credit to your team. But it has an enormous return.

Many of us have unfortunately experienced the opposite of this. If you’ve ever worked for someone who seemed to always take credit for your work, you can probably remember the mounting frustration and resentment that built up inside of you. You also probably remember the relief it was to finally “quit that boss”. No one likes a “glory hog”.

Your team wants (and deserves) to be recognized. And they’ll be loyal to leaders who provide that to them. Former U.S President Dwight D. Eisenhower once captured this principle perfectly when he said:

“Leadership consists of nothing but taking responsibility for everything that goes wrong, and giving your subordinates credit for everything that goes well”

If you are wondering how to better share credit/gratitude with your team check out this article.

#8: Take Care of Your Team (Financially)

Perhaps the most important way you can say thanks is to go to bat for your team members when Year End Reviews come around. Your team needs to know that you’ll be championing for their financial futures and career development to reward them for the good work they’ve put in. This is the ultimate form of credit.

Get this right and your team will run through a brick wall for you. Get this wrong, and you’ll create a culture of resentment that will end up in high employee turnover.

As an example, my brother just left a prominent local tech company that was notorious for its subpar promotion process. Despite being a top performer by every metric he was denied a promotion for 2 years in a row because the company was extremely sparse in handing out pay changes or title increases. He (and many other folks) started to leave in droves out of frustration that their work wasn’t being recognized.

Contrast this with the time one of my former managers once surprised me with an “off-cycle” promotion and pay range simply because he felt I deserved it. When I learned that he had pounded the table for me to get what he felt I deserved to senior leadership I felt an enormous sense of loyalty and gratitude to him as a leader and mentor.

Note: You also need to get compensation right when you first hire someone. Never try to nickel and dime somebody on salary or equity. Compensation is the worst-kept secret in the business world. Your team is going to find out how they are paid relative to their peers (both in and out of the company). It’s only a matter of when.

You may save a few $’s upfront, but will ultimately spend far more than that when you ultimately have to replace someone who leaves because they know you were underpaying them. It’s also toxic to your reputation. You don’t want to be known as a “Scrooge”

I’ve found that paying new recruits above market value (sometimes as high as I can get them) may cost a little more initially, but pays itself off ten-fold in terms of reduced turnover costs, higher culture/morale/productivity, and increased trust in me as a manager.

#9: Communicate Clearly

I once worked for an executive leader who was (in)famous for sending long rambling emails at 4-5 am in the morning. These epistles wouldn’t be directed at any one individual, but rather the entire leadership team. It was more like reading his scattered consciousness than receiving any clear direction. They were extremely disorganized, had no clear action items, and we’d often have to have a separate meeting afterwards just to try and decipher exactly what “the boss” wanted.

Worst of all, these messages would sometimes be very emotional / attacking and the team’s morale suffered as a result. It was a miserable experience for everyone involved.

Don’t do that. When you communicate to your team, do it clearly, concisely, and orderly. They’ll appreciate it.

And please for the love of all that is good in this world, stop stressing out your teams with cryptic Slack messages!

#10: Enforce a good work/life balance culture

People crave work/life balance. But despite a lot of promises from companies, they rarely find it.

But now that you are the manager, you can change that. You are the pacesetter when it comes to the work/life balance culture of your team. No one will believe you when you say they should relax and spend some time with their families if you are always the one sending emails/Slack messages at 11pm each night, working 12 hour days, etc…

But if the team sees you actually using your PTO, logging off at a reasonable hour, refusing to respond to non-urgent messages until the next business day, etc… then they’ll start to follow your lead.

Be the pacesetter on this.

#11: Listen to your team’s ideas

If your team sees you regularly asking for (and then implementing feedback) they’ll trust you as someone who actually listens. Newsflash: people like working for leaders who listen!

One way we’ve established this culture in my current team is the use of a “Kaizen Idea” section of our weekly huddle (Kaizen = Japanese term for “continuous improvement”).

This means that at the end of each of our standup meetings I solicit any “Kaizen” ideas from the team on how we can improve. Ideas can range from something as trivial as the types of snacks we stock in the team fridge to the types of projects our team will tackle next month. No topic is off limits.

We write down the ideas, and then I earnestly try to implement as many of them as possible. The result has often been a culture where ideas are welcomed (and soon start being suggested outside of our official “Kaizen” discussion). It’s been a wonderful addition to the team culture.

Warning: If your team gives you suggestions and you fail to act on them, they will eventually stop giving them to you (as you’ve broken their trust that you will actually implement their ideas). There will of course be some ideas you can’t implement (ex: giving everyone weekly raises). But try to say “Yes” far more than you say “No” (explicitly or via your inaction).

#12: Give (and Receive) Hard Feedback to Your Team

Something I have appreciated about every great manager I’ve had is their willingness to “coach me up”. A good boss should also be a good mentor; someone who is invested in telling you the things you need to do to elevate your game so that you can thrive in your career.

You need to be willing to do the same thing for your team, even when it means telling them directly about areas that they can improve on. That can be a hard (and somewhat scary!) thing for anyone to do (especially new managers).

The secret to this is trust. I once asked an experienced leader (who oversaw an organization of thousands of people) what his #1 piece of advice to a young manager would be. His answer has stuck with me ever since:

“You need to ensure that your team knows you love them. Because if they know you genuinely care and are invested in their best interest, you can say anything you need to them. Even the hard things. They will be willing to accept this because they know the blow is coming from a friend, and not an enemy”

If you want specific advice on how to give feedback, check out our article here.

Tip: A great manager doesn’t just give feedback, they also ask for it in return. In all of my 1:1’s with my team, I usually end by asking “what can I do better as manager for you?”. I usually ask my team member to tell me at least 1 thing that I should START, STOP, and CONTINUE.

When you show your team that you’re willing to take (and act) on feedback they give you, they’ll return the favor when it’s your turn to give it to them (again, this helps build on their trust in you as a leader)

#13: Be an advocate for your team (even when they leave you)

Ironically, if you have hired the best people there is a good chance they will ultimately receive some “godfather offer” opportunities elsewhere.

Don’t fight this. Instead, let them know that if/when that day comes you will be there to advocate for them again. They should know you’ll be their very first “letter of recommendation” and will help them build a career. Be your team’s biggest cheerleader.

My experience is that leaders who have this reputation of helping others along in their own careers never have a hard time finding replacement star talent (remember that people talk, and all-stars will let other all-stars know about you)

Interestingly, I’ve noticed that leaders who openly help their best talents get opportunities elsewhere often find that their stars usually stay far longer. You “keep more that which you are willing to let go”

Conclusion

There are almost certainly more principles about being a “good boss” than the 13 we’ve covered above. But I think this is much like a starter pack for learning how to transition from being a great individual contributor into being a great leader.

Becoming a great leader is the key to escaping mid-manager hell. And more importantly, it’s also one of the most fulfilling roles you’ll ever have in life if done well.

My favorite quote on this concept comes from HBS professor Clayton Christensen who said:

“I used to think that if you cared for other people, you need to study sociology or something like it. But….I [have] concluded, if you want to help other people, be a manager. If done well, management is among the most noble of professions. You are in a position where you have eight or ten hours every day from every person who works for you. You have the opportunity to frame each person’s work so that, at the end of every day, your employees will go home feeling like [they] are living a life filled with motivators.”

That is certainly a mission worth pursuing to any current (or future) manager out there.