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Expanded Skills

The 4 Critical Levels In Your Career

And no, it's not tied to a corporate ladder.

Since leaving the corporate world more than 6 months ago, I’ve had a lot of time to reflect on what career progression means.

Intuitively, most of us know that career progression is not linear. 

Yet, we struggle to articulate exactly what changes as you become “more senior” and more importantly, what adjustments you need to make. 

You probably encountered the following (unsatisfactory) definitions of what it means to be “more senior”, which all contain some grain of truth.

  • You become more independent and require less oversight
  • Your responsibilities and scope increase
  • You’re expected to have more expertise
  • You’re expected to “lead” probably without direct authority, be a “force multiplier,” and have a bigger impact (I’ll refrain from using a 10X engineer reference here)

If this definition and the advice surrounding this were all we need, there wouldn’t be that many people struggling to progress and hitting “terminal level” would there? 

The Peter Principle partly touches on the underlying issue. Still, it doesn’t fully explain why a top performer at the prior levels can suddenly fail to be effective and struggle to recover. It’s also no coincidence that career stagnation usually occurs at “terminal level” at the top of the individual contributor band, right before the management track begins.

It boils down to going through a major transition from individual contributor to manager because the rules of the game have changed. 

The additional responsibilities and skillsets required to manage people present are challenging and present a learning curve, but that’s not the most important point. Instead, internalize that you cannot do more of the same and expect to succeed when making the transition. 

A common trap is to do what got you success so far but with higher quality, faster, and more consistently, but the rules of the game changed, so you need to do different things better, faster and more consistently.

To be clear, promotions earned within the ‘4 Career Levels’ should be celebrated and can come with significant rewards. The issue occurs when we overly rely on a corporate career model to guide our career progression and wonder why we’ve hit a major plateau.

Introducing The 4 Career Levels

The 4 Career Levels are grounded on the premise that the rules of the game significantly change as we ascend to the next level. It’s considered a major inflection point and requires a recalibrate of what we pay attention to and how we operate day to day. What’s considered optimal before no longer holds true. 

Level 1: Individual Contributor (IC)

The table stakes here are mostly around completing your tasks with increasing levels of quality, consistency and speed. Building on this foundation, your individual throughput matters a lot. Find good benchmarks for what quality work looks like and figure out how to reproduce that consistently. Speed will come with time and should be optimized after crossing the required quality and consistency thresholds.

When starting out (i.e. new grads, entry-level), there’s no need to overcomplicate things. In fact, it can be detrimental since you won’t have peace of mind until you get the tasks you’re assigned under control. 

When in doubt, review your output vs. the benchmark and see what improvements you can make to 1) quality 2) consistency and 3) speed, in that order.

Keep in mind adding predictability to your project(s), and in turn, the existing workflow (e.g. overall SDLC) will be viewed in a very positive light by those at the Manager level. You are taking a massive weight off their shoulders and the good ones will in turn, thank you for it (or at least give you more freedom and autonomy).

Level 2: Manager

Here comes the first major transition. Within the industry, you’ll find a fair amount of content regarding the IC to Manager transition since most will realize something significant has changed when transitioning from not managing people to managing people.

Unfortunately, we tunnel on “people management” as the be-all and end-all. That’s why a lot of “new manager” content centers around topics such as delegation and better communication. A common trap is to end up as either a more efficient IC or, worse, stop doing IC work altogether and become a full-time resource allocator. 

We can all recall a particular “taskmaster” archetype that didn’t do anything to improve the work.

A manager’s primary measure is to ensure their team can collectively produce high-quality output consistently. Increasing your own output (or focusing on any one particular individual) is almost never the most optimal strategy for increasing team-level output when you have more than 3 team members. Removing a particular toxic team member is an exception to this rule. 

Instead, consider these alternatives.

  • Removing friction in processes, making tasks in the workflow easier to perform and less error-prone (without risk of burnout and dependency on heroic efforts)
  • Improving standard tooling your team interacts with regularly or rationalizing tools they don’t use to simplify things
  • Guarding what scope you take on and remembering that every “yes” you say is saying “no” to a dozen other things

As a rule of thumb, more of your efforts should be dedicated to working ON the system vs. IN the system itself.

It’s a huge contribution if you can ensure your team’s efforts are aligned with the project’s needs AND strategically aligned with the company’s direction. The Manager of Managers rarely has the inputs needed to know if things are going off course at the ground level. 

Level 3: Manager of Managers

When you are consistently asked to make high-stakes decisions with long-term consequences and never have nearly enough information, chances are you’re at this level. You will encounter a new class of problems beyond the project level where you are the primary decision maker or have significant input. This is why you’re very thankful to Managers who honestly tell you when things are going off-track strategically. 

Here are a few examples that come to mind:

  • Changing the company’s talent management process (e.g. headcount planning, interview process, performance management metrics, rewards & compensation)
  • Division-level funding and scope (e.g. mandate changes across teams in engineering, target setting KPIs / SLAs, in-house vs. outsourcing work)
  • A technology decision that will either trigger a multi-year migration or not 

Everything will be more abstract, and your thinking must adjust accordingly. You’ll rarely be able to examine things at an atomic level (e.g. a task within the workflow). Meanwhile, your decision will have second and third-order effects lasting over a year. 

It’s an art to learn and let go of the minor things at the point even though it’s in our nature to be into all of the details. It’s simply not feasible or practical. Most ascend up to this level by being the most functionally proficient during our days as a Manager and as an IC (and being exceptionally organizationally savvy), but being the most functionally proficient is something we must let go of. Yes, this will hurt your ego. 

Aside from making the best decisions possible with limited information and time, your primary job is to ensure the Managers have what they need, which is almost never coaching/mentorship on technical and functional know-how. Instead, more of your attention is needed to set up decision frameworks to help them arrive at a reasonable solution rather than prescribe the solution yourself.

The decision framework involves:

  • Assess how criticality of the decision
  • Size of the “blast radius” if things go wrong and if there’s enough upside to make it worth shaking things up
  • What data should they collect and where to collect this data
  • How much data to collect and when it’s time to stop
  • Well-defined thresholds for when you should abandon the initiative

Level 4: Executive

If things felt abstract at the Manager of Manager’s level, the Executive ranks take it to another level. Everyone will turn to you for all the most ambiguous yet critical problems within your function, but that comes with the territory of being the last line of defence up the escalation chain. Ironically, you won’t have any peers to help you solve this class of problems. After all, there’s only 1 CTO solving CTO-level problems within the company. 

Your management is a combination of the CEO and the Board, so we won’t be getting any help solving Engineering problems.

Furthermore, all the unresolved issues from the Manager of Managers level will surface and worsen if left unaddressed. For example, if you have trouble dealing with ambiguity, making quality decisions with incomplete information, or building strong relationships with cross-functional partners, expect things to feel challenging. Most of your role is dealing with a more complex version of exactly those things (or they’d likely be resolved at lower levels).   

Additionally, your role is likely a “1 of 1” role, meaning it’s truly bespoke. This is the polar opposite of finding your fit within an existing workflow when you’re an IC or even at the Manager level. It’s safe to assume that there’s no “boilerplate” CTO role and it will be highly dependent on the company’s needs at that time.

For example, the CTO requirements for a late-stage startup will be vastly different than a CTO for a F500 company. 

With the “1 of 1” concept in mind, there’s one statistic from sports (i.e. basketball) called “value over replacement player” (VORP) that’s worthy of consideration. In general, the more senior you are, the more this matters. 

Here’s a couple of the main reasons why:

  • “1 of 1” by definition, means there can only be one, so unlike scaling up a team of developers, it’s not possible to “add more to get more”
  • it’s not only about being “good” (or even great), but being the best fit given the circumstances
  • Being marginally better in, your decision-making, for example, has a significant impact on the company’s performance (contrasting this with one developer being 5% faster than the other)

Although there’s no single playbook for navigating the high career levels, there’s one principle that is helpful to remember.

Higher levels require you to deal with more ambiguity, but will expect you to provide more clarity on longer time horizons.

You cannot go wrong by modifying your game plan and skillset with that principle in mind.

In Closing 

The initial step to progressing within each of the 4 Career Levels is to solve a certain class of problems with more quality, consistency and speed. From there, it’s about solving a different class of problems at the next level and repeating the process. 

This requires an entire book to unpack the topic fully, but this should give you enough to think differently about career levelling and progression.

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