Consistently Prepared: Year-round strategies for career growth

Have you ever dreaded writing your self-reflection because you couldn't remember half of what you've accomplished? Or worse, been surprised by the results of your performance review? Maybe you thought you were a shoe-in for a promotion that didn’t happen. If so, you're not alone. The performance review process at many companies is opaque and frustrating, leaving employees feeling undervalued and confused.

Fortunately, there are steps you and your manager can take to help avoid these scenarios. In this blog post, we’re going to talk about self-reviews and how to prepare for them, making your work visible, and how to have an effective ladder-based career conversation. These will help you and your manager put your best foot forward during review season.

About me: I am currently a Senior Engineering Manager leading multiple product engineering teams at Semgrep, an Application Security platform. Prior to this I managed a team of software engineers at Segment and its acquirer, Twilio. While I have only been in engineering management for 4 years, I have had the benefit of seeing how 3 different companies handle career development conversations and calibration.

Who is this for? I wrote this with the assumption that the reader is an individual contributor (IC) software or security engineer, but have also included tips for engineering managers (EMs). ICs may gain insight into how the organizational layer above them operates. EMs may find information that is useful when coaching their team, or applicable to their own career. As a result of my own experience it is tailored for those working at tech companies, but it may be applicable to other industries as well.

I think there is a common misconception, especially with folks earlier in their career, that their manager is going to plan their career for them. While your manager should play an active role, I am a firm believer that people need to be responsible for much of their own career development. Part of a manager’s job, especially for junior folks, is to teach them these skills and help them stay on track.

Career advancement gets less formulaic after the jump from entry-level to mid-level. Learning to do these things independently will help insulate you from bad managers, changes in managers, and will accelerate your own growth. Nobody else will be with you your whole career.

Before we jump into these topics, let’s cover how companies do performance reviews.

Performance review season

This section provides you with an overview of performance review season and calibration. If you already know how both of these work, feel free to skip to the next session.

The companies I’ve worked at as an EM have mostly done full reviews twice a year. Some places do it once/year. Others do a full review once early in the year, and a promotions-only review cycle later in the year.

The typical full review season looks something like this:

1. Everyone fills out a self-review

   1. Use this as an opportunity to create a permanent record of your accomplishments!

2. Everyone asks people for peer reviews

3. Managers fill out downwards reviews for their direct reports. This typically includes a rating (e.g. does not meet expectations, meets some, meets, exceeds) as well as promotion readiness. At some companies this is a boolean, at others it is “yes, now,” “next cycle,” “no.” I prefer the latter.

   1. If you’re a manager, write this as if you won’t be their manager next cycle. Spend time creating a record that your successor can use during their onboarding. This is especially important if someone is on the cusp of a promotion.

4. Managers will meet for “calibration.” During calibration managers will talk about projects, ratings, and promotion readiness for their cumulative reports. Other managers will ask questions, challenge ratings, and try to ensure people are being evaluated fairly. During this process it is normal for ratings to change and for some promotion cases to get rejected.

5. Managers create a promo packet for eligible employees, which is reviewed by engineering leadership.

6. There may be some additional steps that can also affect ratings and promotions.

If you don’t know how performance reviews and calibrations work at your company, ask your manager. If they don’t know, make sure they figure it out. Unfortunately, the extent to which your manager understands this process and how well they prepare can have a major impact on your compensation and career.

I am fortunate to have worked for managers that were very transparent about how calibration worked, even when I was a mid-level security engineer. When I became a people manager and attended my first calibration, there weren’t any big surprises.

My process

1. Fill out a deconstructed career ladder with individuals on my team (discussed in detail later in this blog). This takes place prior to review season.

2. Review self-review, peer reviews, and other documents

3. Write downwards review

4. Ask my manager to read over my reviews and ratings

5. Prior to calibration I create a “cheat sheet” for everyone that reports to me. It has short descriptions of projects, answers to questions I think I might get, supporting information, and metrics.

   1. If they’re up for promo, I have examples of how they’re already demonstrating their ability to operate at the next level. This is based on a deconstructed ladder for the level they would be promoted to.

Manager tip: Calibration Cheatsheets 📝 In my experience, the cheat sheet has been somewhat overkill—I don’t get asked about half the stuff I write down. But, at the same time, I often have pre-written answers for questions which means I don’t forget things and I can answer quickly and confidently. These things matter. Managers that stumble over questions and don’t have examples are less likely to have their ratings and promo cases stand up to scrutiny.

Yes, the cheatsheet is an extra thing to prepare during a time when managers are incredibly busy. But, I am confident that the cheat sheets have helped people on my team get recognized for their hard work through their performance ratings and promotions.

If you’re a manager and don’t have time to write a cheatsheet, have your downwards reviews handy since this should have a lot of the same information, albeit more verbose.

Manager tip: Gathering support 🙌🏻 If you're promoting someone who has worked closely with another manager (or one of their reports), having that manager ready to chime in can be helpful. Teeing this up can be as simple as messaging them in advance of calibration and asking if they are comfortable speaking in support of your report’s project. 

Now that we’re on the same page about the mechanics of performance review season, let’s talk about how to prepare!

Gathering information year round

Have you had to write a self-reflection, and realized you don’t remember what you’ve worked on the last 6 months? 6 months is a long time, it’s easy to forget things. I tell my team that if it isn’t written down in their “hype list,” it didn’t happen. Of course this is hyperbolic, but it is a good reminder to write down your accomplishments.

What’s a hype list?

A hype list tracks your accomplishments. This list could include being someone’s mentor, features you’ve built, a blog you wrote, or anything else you think is significant. 

Why should I spend my time doing this?

If you spend a little bit of time on your hype list a few times a month the commitment should be low. There will be a time when you need this information, and it is better to capture it when it is fresh in your mind.

A hype list can be used to update your LinkedIn, your résumé, or as part of self-reflections during performance reviews. These give you the opportunity to get recognized for your work and make more money. A hype list ensures you present yourself effectively.

It is also helpful if you get a new manager or need to remind your current manager (or their manager) what you’ve been up to. Your manager has multiple people reporting to them, they won’t know everything you’re working on, especially as you become more autonomous. It is also a convenient place to track documents related to your projects.

I’m sold. How do I make one?

The format I use is simple, it is a spreadsheet with four columns: Month, What, Impact, and Notes. Each year gets its own tab.

What

A project’s name or a brief summary of what you did. Assume the person reading it (most likely your manager) is familiar with what you’ve been working on.

Impact

What was the impact of your work? This column gets people thinking about business impact. A lot of engineers, especially those earlier in their career often think about what they did (e.g. built feature x), and less about why someone asked them to build it, and how it affects customers/their team/the company/etc.

The impact section is also a great place to include a few metrics if you have them. “Built feature x, used by 10% of our customers” stands out a lot more than “Built feature x.” I have another blog from a ~year ago that’s all about metrics if you want to read more on this topic.

Notes

This should include anything you think is important and references to supporting information. It could be a design doc, a retro doc, links to dashboards, or anything else you or your manager might find useful. This section is especially helpful if your manager changes since they will be less familiar with your work—the references in this section will help them gain context. 

It also keeps all these things nicely organized if you need to write about your work in the future.

Frequency

I recommend folks on my team think about their hype list every week, although there’s no expectation that they add something every week. But, it is a lot easier to remember to add things if you think about it regularly. As a project progresses you can update the associated row in your hype list.

You might find that after a few months there are some things in the hype list that are fairly insignificant when compared to other items. Delete rows that you don’t think are valuable. It’s better to write down extra items and prune than to miss things.

Getting Started

The hardest part is getting started. If you don’t have a hype list, consider populating one with your accomplishments since your last performance review (or ~6 months).

You can look through pull requests, project retros, planning docs, calendar invites, etc. to help you remember what you’ve worked on.

Another option is to skip anything earlier than your most recent project, and start tracking things going forward.

The look-back distance is up to you. The further you go back the harder it is to backfill the data, and it is less likely these projects will be relevant. Starting today with no historical data is better than nothing!

Helpful engineering artifacts

Hopefully your company/team already has templates for design docs, project retros, and team retros. If not, maybe that is something you could bring to your organization! I won’t go into too much detail, since each could get their own blog post.

Engineering design docs

Circulating your written plans and estimates for a project helps you build consensus and avoid mistakes later in the development process. I’ve found creating a table like the one seen in this blog to be helpful. 

They’re also valuable assets during performance review season. They help you remember what you worked on, why certain decisions were made, and how plans changed over time.

Project retros

Project retros give you space to reflect on a project. These can be done individually or collaboratively. Prior to working on your retro, I recommend re-reading your original engineering planning doc.

If your company doesn’t have a template, here’s the format I use:

• Intro - high-level overview of the project. This should include a simple timeline and links to relevant docs, like the original engineering doc. I think an appropriate level of detail is something your manager or manager’s manager can understand without much additional research.

• What went well? - which parts of the planning and execution went well and why. 

• What went wrong? - be honest about the things that could’ve gone better. Were time estimates off? Having the aforementioned table helps here. If so, why? Could this have been avoided? Were there any engineering incidents that happened? Did you have trouble working with another team? This section is about getting better, not about casting blame.

• What did we learn? - often includes action items or takeaways for next time.

Project retros are a great source of inspiration during review season. Most companies have a question that asks you to reflect about what could’ve gone better, what are areas you want to improve in, etc. Re-reading retros can help make this challenging section a breeze.

Team retros

We do quarterly team retros using FigJam. This works well for remote teams, and also results in a written record. Similar to project retros, I recommend managers and ICs revisit team retros during review season. 

Weekly notes

Each week I try to write down a few notes about what happened, my interactions with people, what went well, what could’ve gone better, etc. I have a recurring calendar event on Fridays as a reminder. I keep a tab in a spreadsheet for myself, my manager, the folks that report to me, and anyone I think is likely to ask me for a peer review.

I have found this to be helpful when I’m writing my own reviews, having career convos with people on my team, and it is also a nice reminder to give praise or feedback. I have found it especially useful when I’m having an ongoing, and difficult set of conversations with someone. The week-over-week notes make it easier to get the details right.

Some weeks you might not have time, and that’s okay. Some notes are better than no notes!

Getting recognized for your work

Unfortunately, doing the work isn’t enough. People also need to know you did the work. This isn’t about bragging.

• It’s important for people to know what other work is happening at your company.

• It’s important to build technical communication skills for career growth. The more senior you become the more you’ll need to influence people throughout your organization.

• It’s important that people understand your areas of expertise. This can lead to interesting project opportunities and chances to mentor others.

Here’s some ideas about how you can share your work:

• Sign up for demos within your company

• Post in appropriate Slack channels about you’re working on

• Recognize teammates for their contributions to projects

• Write blogs/speak at events. I have two blogs (#1, #2) about how to get started

• Contribute to docs/give trainings (internal or external) for things you helped build

As mentioned earlier, metrics really make these types of communications stand out. “We reduced the amount of customers that abandoned items in their cart” vs. “We reduced the amount of customers that abandoned their cart by 5%, which resulted in an additional $200k in sales last quarter.”

You need to get comfortable talking about your accomplishments. I know this can be daunting for some people, but you need to do it. It gets easier over time. Your manager should also be doing this, but it is more effective if you are both doing it. There may be times in your career where you have no manager, your manager is too busy, etc. so you need to build this muscle independently.

Having people outside your team who are familiar with your accomplishments can support your success during calibrations.

Ladder-based career conversations

Career Ladders

If you know what a career ladder is, skip to the next subsection.

If you’re not familiar with career ladders, they define the impact and attributes of an entry-level engineer, a mid-level, a senior, and so on.

Progression.fyi has a list of ladders across disciplines, although it leans towards engineering. Dropbox also has Security Engineering ladders, which I haven’t seen a lot of companies publish.

Having defined career ladders doesn’t magically make everything fair, but without a career ladder promotions are more likely to be based on time in role, vibes, and people being noisy (complaining about not getting promoted, threatening to leave, etc.). Career ladders allow you to compare a person’s impact and behaviors to a standardized document, which when done correctly should make things more equitable.

If your role doesn’t have defined ladders, that isn’t necessarily a red flag, especially if you’re in a niche role or at a smaller company. Career ladders are a lot of work to build and maintain. You need a certain amount of people in similar roles for the effort to be worth it. If you’re in a position to bring ladders to your org (and your org is ready for ladders), this could be a great career growth opportunity for you.

Having ladder-based career convos

Everywhere I’ve worked as an EM has had ladders prior to me joining. I have ladder-based career convos with the folks that report to me before each performance cycle (twice a year). Having these conversations prior to review time should get you on the same page about ratings and promotion-readiness, and it should make self-reviews and downwards reviews a lot easier.

When I had fewer direct reports, I let people choose if they wanted to have an additional 1-2 convos a year. About half took me up on it. With nine reports, I unfortunately don’t have time to offer this to everyone. Having these conversations more regularly is more important with people earlier in their career since their projects are shorter and they’re generally progressing faster.

Creating a deconstructed career ladder

I’ll use the Dropbox IC2 ladder as an example (check out progression.fyi for other ladders)

1. Map each section (Impact, Ownership, etc.) to a heading in a spreadsheet

2. Under each heading copy the bullet points

   1. If you have more time, each bullet point gets its own row. This will give you a more granular assessment of a given section, but it takes longer to fill out and discuss. I recommend trying this out first, since it is easier to get less granular later.

   2. If you have less time, combine all bullet points into a single row. This saves time, but will result in less nuance.

   3. You could also do a mixture of the two if some sections lend themselves to being combined while others should be separated.

3. This doc should be shared between a manager and their employee. I also add my manager as a backup for when I leave the company.

I recommend keeping your hype list in the same document. Here is a sample spreadsheet using the format from 2a.

Filling out the document

Make sure that your hype list is up-to-date and that both you and your manager know how to fill out the document. Planning docs, retro docs, etc. are all helpful when filling out the deconstructed career ladder.

1. Manager and employee create a copy of the document and fill it out separately

2. Come up with an agreed-upon color system, and rate each cell (see instructions tab of the above screenshot for an example). This is helpful for quickly skimming the document to see how someone is doing at a given level.

3. Add any new supporting work to each cell. 

   1. This should be a delta from the last time you filled out the doc. If this is your first time, pick an agreed upon time (e.g. this past review cycle)

4. When filling out the cells, keep the header in mind.

   1. Maybe there was a project you worked on that went well, but the communication could’ve been improved. This same project could show up as a positive in one section, and as a detractor in another.

5. Copy the information into the shared doc at the beginning of the career conversation. This avoids biasing whoever fills out the doc second.

   1. You can also consider filling out the doc collaboratively the first time to make sure both of you understand the process and ladder categories.

Tip 💡If you're nearing a promotion, I recommend completing a deconstructed ladder for both your current and next level. This is time-consuming, but it can help ensure that you and your manager are aligned on promotion readiness.

You may also discover that you aren't as close to promotion as you initially thought. It's better to identify this together now than to have your promotion case fall apart during calibration.

Reviewing the ratings

Going through the document for the first time may be a little rocky. There are always rows in a career ladder that are a little confusing, and you and your manager may have interpreted some of these differently.

Go through each cell and talk about the ratings and how the projects in that cell contribute to the rating. I recommend periodically alternating who leads the discussion as you work your way through the deconstructed ladder.

Ideally you are in agreement about the rating for each cell at the end of the discussion. If you aren’t, try to resolve this before it becomes an area of conflict in the actual performance review.

If the difference in rating is based on interpreting a row differently, or listing different contributing projects, that is easy to rectify. If you and your manager disagree on how well you are doing in a given category, that can be more challenging. It can be helpful to brainstorm ways to improve in a given category, even if you don’t agree on the current level of mastery.

Manager tip 💡 If there are rows that are particularly confusing, try to contribute changes back into your organization’s ladder. When contributing to your company’s ladder, keep the roles that use the ladder in mind. There might be engineers of different shapes all using the same ladder, and something that is important to your team might not be generally applicable.

After the review

I recommend that you spend time reflecting on the career conversation as well as your team’s roadmap. Select a few areas that you want to focus on improving, you can’t improve everything at once!) Which projects are you most interested in working on? Will these projects provide the growth you’re looking for?

Maybe the areas you want to grow in aren’t related to an engineering project, maybe you want to mentor an intern or speak at a conference. Once you’ve completed this exercise, discuss the results in an upcoming 1:1 with your manager.

Preparing for promotion 

If your manager thinks you’re ready for promotion, ask if you can help them prepare. If you’re a manager that’s planning to put someone on your team up for promotion, consider including them in the preparation process.

Even if you and your manager are in agreement, promotions aren't guaranteed, there are others that need to be convinced.

Even though not getting promoted can be disappointing, it should provide valuable insight into perceived deficiencies identified during calibration. Not only can you work to address these before the next promotion cycle, but it also plants the seed that you might be ready next time, both of which help you get promoted in the future. I’ve seen plenty of people miss a promo one cycle and get it on the next one.

Manager tip 💡  Including someone on your team in the promotion process is easier if they’re more senior. At this point they should be better equipped to deal with not getting a promotion, and should know more about the performance review process since they will have likely seen it at a few companies. It is especially helpful to expose them to this and other processes if they’re someone that is interested in engineering management.

Closing thoughts

Your managers will (hopefully!) guide and support you, but your career growth is largely in your hands. Get in the habit of consistently writing things down, your career depends on it!

This includes:

• Project plans and retros

• Notes about yourself and the people you work with

• Maintaining your “hype list”

This information can be used to:

• Track career progress

• Facilitate conversations with your manager

• Keep your résumé and LinkedIn up-to-date

• Prepare for performance review season

Make sure you and your manager understand how performance review season and calibration works at your company!

Thank you for taking the time to read my blog, I hope it helps you in your own career development. If you have any questions, the best way to reach me is via LinkedIn, please add a note if you send me a connection request.