Effective Line Management

This was originally a poorly formatted word doc created when some management peers asked for tips at being effective at managing their reports. A little bit (but not much) tuning later, it's now this. I make no pretense that this is my own work, it's all received wisdom from a ton of different people and sources. 

You just realized you have no idea why your employees care what you think.

Someone put you in charge. Maybe you demanded to be in charge because you kept telling everyone what to do anyway. Maybe you got stuck with it when the last person in charge bailed and you looked like you knew what you were doing. Regardless, you now have humans expecting you to make what they do and why they do it make sense. INSIDE THEIR HEADS. Welcome to management!

A non-made up, very real statistic: Depending on study, between two thirds and three fourths of employees leave their job because of their direct manager. The odds are that over the course of your career, you will be the cause of several very important employees quitting their jobs. Every time you prevent that from happening by better management you're saving that employer a ton of cash, yourself a lot of frustration, and justifying your own existence at that employer. Remember: most management is overhead; only the very best of management starts to add value again. Only people that add value to their teams should be trusted with larger teams, more complex teams, and eventually executive positions. We all know that the valley isn't really a meritocracy, but that doesn't mean we exist outside accountability either.

Hands-on line management is made up of several things:

  • How to cause work to be done at your company
  • What motivates people
  • What prevents execution
  • How to model someone’s behavior so you understand the prior two

Things we're not going to cover here include: budget, pipeline, managing up, politics, managing the HR dept, and many other important facets of being good at managing people.

Causing work to be done

This is mostly company-specific, with a bunch of generalities that are nearly platitudes. You catch more flies with honey than vinegar, etc. Be nice and professional to people, stand your ground when you're right, insist on being treated the way you treat others (and vice-versa), and generally treat people like adults until they convincingly prove they aren't. There's also a whole host of other strategies that are only viable in dysfunctional environments. You should generally learn those as needed and not by deliberate instruction, as they're all disruptive in an environment that can still function positively.

My guiding principle in this, as in all things, is that you should deliberately reject and act away from cynicism whenever you find it. Cynicism is much bigger than just acting or talking cynically. A bureaucratic process where everyone involved knows they aren’t solving a problem is cynical. An approval loop where you don’t actually consider what is being approved and how it changes things is cynical. A promotion process that defines goals that have nothing to do with performance or aptitude is cynical. Cynicism burns people out, it causes bad decisions, and it will make good employees leave. If you spend your time as a manager doing nothing but finding and fighting cynicism, you would have done more good than many achieve.

The Basics of motivation, execution, and behavior

Let’s start with the books

This is your first-tier homework. Hopefully you’ve got a fair number of “how to manage” opinions from your own experience, quite possibly unorganized. With this you begin to make those more clear and to organize them usefully. That said, management books are a lot like self-help books. You may find something that resonates for you, but that’s more likely to be a unique emotional trigger than it is to be something that works for everyone. People are complicated. If there’s any one rule of thumb here, it’s that: people are complicated. The goal here is to give you a shotgun blast of receivable wisdom, and then a dive into the areas that drive human interaction. The most useful manager is one who can understand why someone is going to react the way they will before they know they will.

Managing Humans - Michael Lopp (get the most recent edition, currently 3rd)

This is a series of bite-sized hard-learned lessons, mostly as personal post-mortems for a management interaction that went badly. This book is a chance to learn from (a very smart) someone else’s mistakes. This is an incredibly central work in tech management.

How to Measure Anything - Douglas W Hubbard

This is a strong foundational intro to modern decision science. A major component of management is how to make rational, repeatable decisions based on rational, repeatable estimates. If I could force everyone in a company to read a book, it would probably be this one.

Other suggested topics and works

Decision Theory, Statistical Analysis, Communist Manifesto (only the first half), Capitalism and Freedom by Friedman, pretty much anything in recent macro or micro economics. Every time you read through a few books on a new topic, I suggest you re-skim Managing Humans for grounding. The point of these areas is that you need to be focusing on increasing the depth and complexity of your understanding of certain very complex subjects, namely, group dynamics, how bias impacts decision making, how to make decisions repeatable, how economics impacts your employees and their place in society, how your personal economics lead to different decisions than they would make. The point of all this is to keep your gut feelings connected to the realities that your employees live in, so they maintain confidence in your empathic relationship with them. This is why they will trust you to make good decisions and treat them fairly. Without that why, the only tools avaliable to you are conditioned responses to negative/positive stimuli. That's not where you want to be.

Additionally, you may want to read through some of the traditional/popular “management” books in order to be able to communicate more effectively with management peers and your superiors. This is a dangerous road though, so go into it with an extremely critical eye and an assumption that you’re learning the lingo, not accepting the arguments. You may find arguments you like, and by all means, incorporate them. Just don’t do so solely because these books are popular. Here’s a brief list of such popular works:

  • Who Moved My Cheese? – Johnson
  • Peopleware: Productive Projects and Teams – DeMarco
  • First, Break All the Rules – Buckingham & Coffman
  • Slack Getting Past Burnout… - DeMarco
  • Turn the Ship Around! – Marquet
  • The New One Minute Manager – Blanchard & Spencer


As a manager you have six primary things to worry about with regards to your humans:

  1. Is there something preventing them from executing on the task?
  2. Do you understand how to motivate them day-to-day?
  3. Do you understand how to motivate them long-term?
  4. Are you getting better at managing them?
  5. Can you answer all of these questions about how you handle yourself?
  6. Can you answer all these questions about your boss handles you?

Let's break these down

Is there something preventing your employee from executing on the task?

The possible reasons are:

Knowledge Gap - A knowledge gap means they don't know what to do or how to do it. You can solve this with training, education, hands-on mentoring, conferences, books, etc. If the knowledge gap is extensive, you may need a long-term plan here. This is a gap that you identify mostly by building trust with your employees. If they aren’t afraid to say “I don’t know how to do this” you’ll rarely be burned by it.

Capability Gap - A capability gap means that they know how to do it, but they can’t pull it off. There’s several possible reasons for this (execution anxiety, stress, it’s too complex for their experience level, they just aren’t smart enough on their own for this problem). The fix depends on the cause. You may need to team up with them on this, you may need to partner them on this; you may need to take tasks away from them based on this.

Motivation gap - They don't want to do it, or they don't want to do it to the necessary standard. This is the hardest to solve, but we have an entire section here on motivation. Let’s get to that.

Overall Employee Motivation

This is totally different from how to keep employees motivated day-to-day. We’ve got a whole section for that after this one. This is how you need to keep employees motivated on a big-picture, long term basis. You will eventually need to build and maintain a personal model for what motivates each employee or coworker. To start with though, you should stick to the classic reasons and then modify from there based on your interactions.

If you ask ten different managers, you’ll get ten different responses as to how they model motivation. I prefer to try to stick to Maslow’s Model of Hierarchal Needs and the 4-Drive Model. The 4-Drive is fairly new, and adheres well to the motivations you see everyday in tech and sales. Maslow’s is a classic, tried and generally still true (there’s some debate about whether “internet access” needs its own tier). Neither of these are absolutely correct. They’re models that you should always have to hand to think about why someone is reacting a certain way, or how you might try to predict their reactions to change. Explaining these in depth is well beyond the scope of this document, ample resources exist elsewhere. While I won’t say that you should only pay attention to management texts that reference them, be very critical of management texts that don’t reference well-understood engagement/motivation models.


Maslow’s model can basically be thought of as “people don’t care about the higher-layer needs until the lower-layer needs are met.” This is probably obvious to you, but the model breaks it down well, and it’s a useful touch point. When someone is furious and frustrated and all but yelling at you in a one-on-one, having clear models close to hand is very useful. Think about the interaction you’re having and realize that if your motivations for that person do not resonate to the layer of need that is upset with you, then those motivations cannot affect the behavior.


4-Drive is a model of why people do things, assuming that there are four general reasons for action/motivation. People are rarely so simple as for only one of these reasons to apply at once, but if you can try to think of someone’s personality as a group of people with their own drives, it’s very useful to guess which of these reasons is driving the behavior you’re wanting to change or to reinforce.

As with most other things about managing your team, you need to understand how these things apply to you even more than you understand how they apply to them.

Keeping Employees Motivated Day-to-Day

Keeping your employees connected to their work requires first that you keep them generally motivated, then that you keep them specifically enthused about either the challenge, what the challenge generates for them, or how their performance interacts with their environment.  There’s no one solve for this, but rather an environment of good management will lead to day-to-day motivated employees. Maintain this through a constant lifecycle of positive actions:

Be a good coach

  • Provide specific and timely feedback
  • Balance positive and negative feedback
  • Understand unique strengths/development areas of each team member
  • Tailor coaching to the individual & situation
  • Suggest solutions
  • Have regular 1:1s

Empower execution

  • Do not micromanage
  • Balance giving freedom with being available for advice
  • Make it clear you trust the team
  • Advocate for team with others outside the team

Be a decent human being

  • Genuinely care
  • Be fair
  • Make new members feel welcome
  • Show support in the good and bad times

Be productive and results-orientated

  • Keep the team focused on the results/deliverables
  • Help the team prioritize
  • Remove roadblocks
  • Be clear about who owns what
  • Be a hard worker

Be a good communicator

  • Encourage open dialogue
  • Be available for the team
  • Explain the context
  • Tell the truth - even when the news is bad
  • Be calm under pressure
  • Listen to each team member

Help with career development

  • Provide honest, specific feedback on the next step in team members' career
  • Help team members find new opportunities
  • Talk about all aspects of career development, not just promotions
  • Balance their team members’ and company’s needs

Have a clear vision for the team and a strategy to achieve it

  • Create a compelling vision/strategy
  • Clearly communicate vision/strategy
  • Involve team in setting vision/strategy
  • Build relationships with others to help the team achieve their goals

Have and use skills relevant to the team

  • Roll up sleeves and actually conduct work
  • Understand the challenges of the work
  • Help solve problems based on technical skills

Other important factors

The rest of this is basically “extra credit,” it isn’t something that you need to be focused on to start being a good manager, but it’s extremely useful. If you find yourself feeling that you’re plateauing as a manager or in your relationships with your people or peers, look here.


Clarity of thought and purpose is necessary for really strong management. We’ve all run into an executive who seems to have their shit incredibly together every time they’re asking you something. That kind of clarity just comes to some people. Most of us have to work very hard at it. Mindfulness and meditation are a strong, wide pathway to that clarity. If you find yourself wishing you had more of it, I encourage you to explore both concepts.


Don’t be afraid to run non-damaging experiments with how your people behave. Need someone to get better at telling you when they’re too busy? Start slowly overloading them with stuff that it’s OK if something gets dropped. Need someone to give you better feedback. Illustrate the problem for them with someone else, then push them a little till they are actually kinda mad at you. Use this to help them understand how feedback matters and when they should know to give it to you. Hopefully you get enough accidental experimentation through the vagaries of life in the workplace that you don’t need to intentionally push people for effect, but if not, do so thoughtfully and ethically. People respect being taught careful lessons.


Yes, I am literally telling you to go to therapy. You go to the doctor to make sure your body is working to your expectations. Therapy is exactly the same thing for your mind. In most cases, improving your capabilities as a human improves your capabilities as both a manager and an employee. This is both separate from mindfulness and complimentary to it.


This is not a complete or exhaustive list of what’s required to be a good, or even an OK manager. It’s a primer for where to start, with some pointers on where to go next. For yourself, everyone on your team, everyone you deal with regularly, and your boss, you must always have an expectation of normal behavior, a model for how to engage with and motivate them, and an understanding of what forms of feedback are productive. You also need to still get work done. It’s hard, but ultimately if management is for you, it’s probably the most rewarding thing you can do.