Career Advancement And Removing Walls

We’ve all been there. Sitting at our desks, angrily wondering what’s wrong with our boss that they aren’t seeing what we’re contributing. Why didn’t I get that raise I expected? Why did so-and-so get promoted when clearly I deserved it?

Let’s get a couple of things out of the way:

  1. This post won’t help you if you have a neglectful, spiteful, or prejudiced boss who is legitimately overlooking your work.
  2. This post also won’t help you if you’re actually lazy or unmotivated at your job.

This is for those of us who are hard working, thoughtful, working in reasonably fair and functional organizations, and feeling like we aren’t moving “up” in a way commensurate with the work we’re putting in.

The answer is to ask yourself how many walls you have.

As an individual contributor, you might not even realize these walls are there. Your responsibility is to focus on How you do your work. How do I write this code? How do I design this screen? How do I execute this campaign? The “walls” around you are important: they’re the constraints that allow you to do great work. But someone’s thinking about why you’re doing what you are, how to measure success, what the best tactics are, and who works on what. That’s your box.

At each level up through an organization, one of your walls is taken away. One (or more) of the aspects of your job that used to be dictated to you becomes a concern you’re now responsible for — and that’s cumulative. The higher up you go, the more ambiguity and flexibility there is in what you do.

Your boss is constantly asking herself whether you are (a) interested in making more advanced decisions, (b) able to make more advanced decisions, and (c) mature enough to make the right ones if empowered to. She’s evaluating this all the time, by the questions you ask and the judgements you make.

manager needs to have experience with the kind of work she’s managing, to put her team’s performance above herself, and to have the maturity to make decisions on priorities and tactics that best serve the larger purpose of her team. The first wall that’s taken away is the constraint on how to get the work done. She is expected to make decisions on the scheduling and assignment of work on her team and the process by which her team works. She also has responsibility for coaching her team on their work (thus the requirement that she have personal experience doing it).

Directors are no longer concerned with how to do the work, nor the details of planning its execution, but with balancing resources. A director has lost the constraint of a specific mission and team, and must be able to oversee multiple such configurations, and know how to allocate resources between them to best achieve her goals. She coaches her managers on how to operate their teams, but she must fully delegate the specific tactics, plans, assignments and timing by which the work is done.

Titles start to get very fuzzy and organization-specific at the Vice Presidentlevel in particular, but the next level up of management has lost almost all of the walls that constrain what they do. A VP owns a function within a company, and is trusted with and responsible for everything about how that function operates. She won’t be told where to focus within her organization, what process to use to get work done, or even given much in the way of concrete tasks. She must figure out how, given the goals of the company, to best run her team and cultivate quality in her field. Basically all the VP is told is, “you’re in charge of this part of the company,” and is expected to bethe foremost functional expert on that discipline and how to best operate it.

The CEO is special among executives in that her job is to set the overall direction for the company that everyone works toward, but executives really have no walls left. They have parts of the organization that they oversee, but have to be able to look at the entire market, the state of the whole business, and figure out how to best contribute to its success. They coach their VPs on how to operate and optimize their organizations, and need to know enough to evaluate how the specific departmental functions are performing, but delegate everything about organization and execution. An executive is primarily focused on how the overall system works. She spends her time thinking about how strategy is translated into sets of goals that interact to generate outcomes.

So what?

The dirty secret of advancement is that if you wait for permission to do a more advanced job, you’ll rarely get it. Most promotions happen because someone is already working at level above their official station. When you see someone rocketing up through an organization, it’s typically because they never saw the walls to begin with: they were constantly asking harder and harder questions, advocating for solutions that considered more and more of the big picture, and solving problems nobody asked them to. That doesn’t mean you should be a pest! Seek to understand what’s happening in the larger organization, and look for ways to contribute, not second-guess.


  • Doing an excellent job with your work doesn’t get you promoted. Doing a different kind of work, with fewer walls, does.
  • The best people see through walls, and those who do get opportunities.
  • In startups, these layers are often collapsed and overlapping, which is part of what makes them hard, both to survive if you’re not comfortable without walls, and to survive as a company matures and walls start to appear.
  • If you don’t see why people above you are making the decisions they are, you’re still inside the box.
  • It’s not enough to just act as if there are no constraints: you have to demonstrably use that flexibility to make decisions that help the overall system.
  • We’re all doing, coaching, and delegating. By all means get good at the first, but the second two are what define good leaders.


Kiril Savino

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