Management Theory, Part 1: Thoughtful Management and a Functional Strategy

Making Purpose

Working toward a long-term goal is a challenging proposition. You need to be able to focus at many levels to answer questions like:

  • What should I do today?
  • Is the work I do this week purposeful to the long-term goals?
  • Am I working towards valuable long-term goals?

These are all ways of asking: Is the work I am doing the right work? It’s the separation of the question “am I productive?” from “does my productivity matter?”

These are the types of questions that make sense for entities that self-determine. A core example is an organization such as a start-up company. What does a company do? What should it do? How does that purpose translate into day-to-day action?

Management in a Company

A typical approach for a company is to separate out the different levels of thought into separate company roles. You have your long-term strategy thinkers (e.g. CEO), the people who turn long-term strategies into concrete projects (e.g. Product team), and the people who turn those projects into day-to-day tasks (e.g. project managers).

As a shorthand, you could define these levels of thought by their time horizons:

At each level of thought, the basic question is the same: How do we get from where we are, to where we want to be?

The role of management is to constantly consider: Am I doing the right work?

Frustrations in Management

Management is really hard. I hear complaints from my friends all the time about their managers and work frustrations:

  • “My manager has no idea what I do, so they set the wrong deadlines.”
  • “I have so. Many. Meetings! I can never get any work done!”
  • “My manager assumes that I’ll always take longer than the deadline, so they ask me how long something will take, and then they tell me they want it done in a shorter amount of time, so I say, okay, I’ll try, but then of course I go past the deadline, so the cycle repeats. I wish my manager would just trust me.”
  • “The scope of my work is always changing, but the deadlines stay the same, so of course I never finish anything by the deadline.”
  • “I have no idea if what I’m doing has any real value.”
  • “I want to be able to choose what I work on, but I don’t want to manage other people.”

My cross-section of experience is skewed: most of my friends are engineers who work in technology, especially software. A persistent issue in this field is the promotion of engineers into management– a field that a given engineer has often not trained for, and may or may not have interest in.

I know of engineers who get “promoted” to management, but find that though they now have the power to choose their work (generally a positive), they now have all this other stuff do deal with (e.g. managing others and internal politics) which keeps them from getting to do the work they’ve chosen.

In the meanwhile, people who may have trained in management (say, MBAs) often have trouble managing engineers. Engineers might not grant respect to someone who doesn’t understand the nuts and bolts of the technology. Managers from outside the field might not know how to scope appropriately.

I believe that many of the problems of management can stem (ironically) from a lack of intentionality. The role of a manager is to be thoughtful on behalf of the organization (“Am I doing the right work?”). But frequently, this is not how managers perceive their own roles.

A good manager, a manager of people has a duality of roles. Both roles are goal-oriented and thoughtful. A manager in an organizational structure asks: “Am I advancing the goals of my organization?” A manager of fellow humans asks, “are my people deployed appropriately for their skills, growth, and satisfaction?”

These vital questions are often subsumed by the trivial: “Is my team meeting stated deadlines?” “Are we following protocol?”

These are symptoms of the “what gets measured, gets managed” adage. A manager is typically deemed successful if their team produces work reliably, to spec, within budget.

It is easy to see the value of management in this light, because it is easy to measure the success or failure of these goals. But management is a human problem, a squishy problem, and a problem of purpose.

Successful execution of a project should be the natural result of a functioning team. A functioning team is a team of worthwhile individuals, given purpose. A good manager helps the managed team by helping them understand the context of the challenges they’re given, and then getting out of the way.

We’re All Adults Here

I’m a firm believer in intentionality. I don’t think it matters if you have scrum every morning or never; if you enter tickets in a fully-defined Jira system with set levels of difficulty, or you exchange tasks on post-its on the wall. You could have meetings every day of the week, have a meetings-free day, or have no meetings at all. With thoughtful execution, any of this could work.

There’s only one thing that matters: do you know why you’re doing what you do?

Thoughtless management looks like:

  • A manager who top-down assigns work and deadlines without discussion with the individual who does the work
  • Endless meetings full of status updates where many of the people in the room either already know each other’s statuses or don’t need to know
  • Endless cycles of manager-managee deadline negotiation, where the managee inflates the time required because they already know the manager will increase scope and/or ask for a tighter deadline
  • Teams that don’t trust each other to get their work done, or are afraid of asking each other for help, or are afraid of saying they’re behind schedule
  • Manager’s job is nagging managees into doing work/moving work tickets around in the management system/shepherding meetings

How do you fix this? Take a step back. Cancel all the meetings, and use that time to think about what they’re for. The meetings, the management tools, the one-on-one discussions, they’re tools. Tools can be handy, even vital, but only when deployed strategically to work on a problem you understand.

If you’re a manager, but feel like a babysitter, something is wrong. You were hired; your team was hired. You’re in a curated environment where you can presume that everyone present is competent. It’s your job to help bring that competence to light.

A Functional Strategy for Management

My team was facing a number of common problems. There was deadline negotiation along the lines of, “Ok, this week will you be able to finish that?” There was babysitting to the extent of “Did you finish that Jira ticket? Can I move it for you?” Worst of all, we had meetings full of status updates that took so long that nobody could actually improve on their statuses. And nobody paid attention in those meetings; how could they, when the topic wasn’t directly relevant and they were trying to sneak in a bit of work time?

It was bad. My inbox was overflowing with all-hands email and direct requests, all the Jira tickets were out of date, and my team was putting in lots of hours but somehow not advancing critical path. So one morning, I left my laptop full of email on the desk, took a legal pad and pen, and walked up to the quiet workspace on the roof. And I put together a philosophy I could put into practice.

There is no one correct approach to management. What’s important is that your approach is thoughtful and sensible to the managed team. I’ll here present an approach I’ve used. It might work for you, just as any managerial fad approach might work– if you follow it thoughtfully rather than blindly.

Daily Check-in

What it is: A highly structured session towards the beginning of each day where all members of the immediate project team gather in one room to give one-minute updates in the form of: “Since last meeting, I…”, “Today, I will…”, and “I am blocked by…”.

What it is not: A discussion, a time to talk out project vision or details, a time-consuming daily commitment.

Execution notes:

  • As moderator, I would have a teammate time a maximum of one minute per person, with a beeper so they couldn’t go over. This distributes power in an otherwise somewhat dictatorial meeting, and kept things both demonstrably efficient and lighthearted.
  • The meeting would start exactly on time, so teammates who might usually come five minutes late to meetings would be timely here so as not to miss five people’s updates. I would come in with my own update pre-formulated on a post-it so I was free to take notes (which I could use to prioritize my own day).
  • Updates were not discussions. I encouraged teammates to bring note-taking materials so they could discuss anything after the meeting; your one minute is yours alone. Frequently, the team would break into discussion while leaving the room: “You said you were having trouble with X, but I thought we had already…” etc.
  • I would break the no-discussion rule for only one reason: a too-short update. “Yesterday I worked on integrating the web service and I’m doing that still today” is not a sufficient level of specificity to be useful to the team. I would ask what was different between today’s work and yesterday’s, in order to know what work was done.
  • My managers would occasionally drop in on this meeting, and I’d welcome them but hold them to the same rules– one minute, share!

Why it works:

  • There’s no mystery in “what so-and-so does all day” such that X feature isn’t finished yet. You know exactly what they’re doing and why it’s taking the time it does.
  • The team understands each other’s challenges and efforts. This puts them in a better position to prioritize their own tasks and remove each other’s blockers.
  • Doing this daily helps each person set appropriate priorities each morning– often adjusted in reaction to understanding teammates’ priorities.
  • The draconian structure is a way to respect each other’s time. A team of six people will take six minutes and no more– half an hour spread over a week. There’s now no need for status update meetings; everybody already knows.

Weekly (or Every Two Weeks) Meeting

What it is: An open-ended hour for the team to evaluate progress toward goals and re-scope as necessary. Manager seeks input from every team member on their piece of the project, and identifies any issues or unclaimed project pieces.

What it is not: A time to line up who is doing exactly what in the next week/two weeks (team members are adults who can make their own to-do lists). It is also not a status update; you already did this in your daily check-in.

Execution notes:

  • Level of structure will likely vary depending on team dynamics and where you are in a given project– how urgently are deadlines approaching? How much do you trust each other?
  • One way to open this meeting: reiterate upcoming major deadlines (ideally a few weeks out) and ask everyone to take 1–2 minutes to write down any concerns they have re: meeting the stated goals by the planned deadlines.
  • The goal is to create an open discussion: is this product scope realistic? Are we deploying team abilities in a reasonable way? Do we need to move a deadline, or to cut a planned feature?

Why it works:

  • Every member of the team has agency in the process– there’s no deadline by edict, grudging agreement to a given assignment– information is bidirectional.
  • The manager gets regular listening time: is something more time-consuming than expected? There’s no surprise; the manager now has the information needed to make hard decisions about what will be done by when.
  • Each team member sees their work in the context of the whole project and its priorities.

Irregular Onboarding

What it is: A one-on-one meeting between the project manager and any new member of the team to get them excited, invested, and up to speed on the project. Then a follow-up one-on-one about a week later to ensure no missing pieces.

What it is not: An information dump or heavy welcome-to-the-team assignment. The goal is to have the new team member get excited, understand the problem, and begin to think about how they can best add to the project.

Execution notes:

  • Getting involved in a new project is overwhelming. There’s going to be an information dump, but save that for an email after this meeting.
  • Go on a walk or similar, preferably off campus, and talk about the vision. Why are we doing what we’re doing? Is there anything special about the way we’re approaching this? Why are we excited to have this new person on the team?
  • Set the expectation that there will be a follow-on 1:1 at the initial meeting. This reduces pressure on the first meeting.

Why it works:

  • Ideally, each member of your team is self-assigning work. This can only happen if they understand the context of the work and the need for their particular skills. Help them get to that place of understanding.
  • It takes time to really understand a project. In the first week, a new team member should get the space to feel out what the work is, and have time to try a few useful tasks before truly diving in.
  • You can’t know what questions to ask when you’re brand new to a project. The one-week-later follow-up leaves time for the new team member to run into problems, attempt their own solutions, and generally find out what they will need to ask someone else.

Regular Vision-Setting (Weekly or Every Two Weeks)

What it is: Open-ended one-on-one (or up to three-person) conversations between project leads or anyone invested in the project. Air concerns, consider available resources, and reflect on both direction and execution.

What it is not: A scheduled meeting in a stuffy conference room constrained to a particular agenda.

Execution notes:

  • I did a weekly hour-long walk when I was co-leading a project with someone. The two of us got out of the building and started talking naturally as soon as we were outside, ranging from life updates to project direction details. This helped us build rapport and stay human with each other.
  • Make this regular and don’t put it off even if you have no specific thing to talk about. You think about your work project all the time; create the space to let the pieces you haven’t scheduled surface.

Why it works:

  • Distance from the workplace reduces distractions (no emails or interruptions); open-ended conversation leaves room for creative thought. Decompress and let yourself think beyond the day-to-day tasks. Is this the right project? Are you approaching it well? What do you think about but not usually talk about?
  • As a project manager, you are responsible for conveying project vision to your team in a way that makes it executable. For this to work, you personally must understand and buy into the project vision! This is your time and space to do so.
  • Your team will bring up good points in your weekly meeting: why a particular feature might be time-costly, why there’s something important you’re overlooking. A manager is responsible not just for translating a project vision down to team members, but also for conveying team insights back up into the vision and other management. This time lets you adjust plans based on feedback. It lets you ensure your team is heard and understood.

Making Your Own Management System

Hopefully, my strategy helps you think about your own team– their needs, their processes. The way I ran meetings, at one particular company, with a particular team, is not a model to extrapolate to every situation– but hopefully you can use it as a framework to devise thoughtful management where you are.

With the framing I came up with, I can tell you:

  • What I’m doing
  • How I’m approaching it
  • Why I expect it to work
  • How I could recognize if it wasn’t working (“what it is not”)

My approach addresses management according to a mental model I find useful. I expect a manager to have a strategy to help each team member address the following questions:

  • What should I do today?
  • Is the work I do this week purposeful to the long-term goals?
  • Am I working towards valuable long-term goals?

You might come up with different important questions, or different timescales. But the truly key idea is that your team is counting on you to manage thoughtfully.

As a manager, your job is to understand the people around you and their needs as they relate to the company and its goals. Use any system, meeting schedule, or software you like. Just be sure you understand why you are doing what you are doing. Your effectiveness as a manager is directly proportional to the thought you give your team’s projects and processes.