In October 2021, I welcomed my first baby. To prepare for my subsequent parental leave, there were a few things I had to do. 

The most consistent thread that remained in the nine months leading up to my son’s birth was the fact that his arrival factored into every decision at work. If I planned to tackle a new project, it either needed to ship before October, or I needed to coach the right people to take it over. If our team, for example, was moved to a different part of the engineering organization, changed managers three times, and doubled in size, I’d need to decide how to navigate each of these changes with my upcoming leave in mind. (And yes, all these things did actually happen – all within the second half of my pregnancy.)

Before I dive into the nitty-gritty, I want to address a few important points:

• I’m very grateful to work in an environment where my teammates and management chain are wildly supportive. I was able to announce my pregnancy to the team relatively early without any doubts that it might impact my career. (In fact, I was promoted while six months pregnant.)
• I’m one of the lucky few in the United States who has access to six months of fully-paid parental leave. While I was at home recovering from birth and bonding with my son, I missed two full quarters, the end of the fiscal year, and our annual feedback and compensation cycle.

Finding the right mindset

Preparing for leave is an odd experience. To do it well, you have to essentially render yourself obsolete: successfully redistribute each and every one of your responsibilities so that nothing gets neglected while you’re away. 

If you’re already riddled with anxieties about being absent from work for a few months (what if they realize they’re just fine without me?) or imposter syndrome has crept up on you (I’m just one incident away from everyone realizing I have no idea what I’m doing), the thought of deliberately shedding your duties at work might sound like the last thing you’d want to do. 

Unfortunately, if you want your team to thrive in your absence and also have a restful leave, you’ll need to do your best to put aside your fears. “Working yourself out of a job” in this way will ensure high praise for your strong leadership and leave your team in good stead while you’re away.

Identifying your responsibilities

If your work week is anything like mine, each day can vary widely from the next; this makes it difficult to pinpoint everything that needs handing over. To give yourself sufficient time to thoroughly itemize it all (in the least stressful way), conduct an overview of your work life during the course of one whole month, ideally four to five months ahead of your anticipated last day.

When auditing your workload, separate your responsibilities into these four broad categories:

The grind

This includes repetitive tasks that are never “finished”. Tasks like grooming your team’s backlog, triaging bug tickets, interviews, pull request (PR) reviews, and on-call rotations fall into this category.

Hopefully, most of these tasks are already fairly evenly distributed across your team, so your departure will only result in everyone taking on just a smidge more.

However, pay special attention to any grind activities that are either solely owned by you or overseen by a cross-functional (or “informal’) team. Say, for instance, you and another colleague lead up the mentorship program for front-end engineers. In this instance, the best course of action may be to delegate your half of the workload to the co-lead in your absence, or you could find someone to (temporarily or permanently) step in for you.

If you’re the single point of contact for one or more systems that require regular upkeep, you’ll need to recruit one or more colleagues to serve as the new point person(s) in your absence. This means onboarding them to the system and ensuring they have proper permissions to any repositories, deployment mechanisms, etc. Ideally, have them handle one or two tasks related to the system ahead of your departure.

The big projects

This includes multi-quarter (maybe multi-year) efforts either led or contributed to by you or your team. If you’re coordinating these efforts, you’ll need to appoint a new lead. Usually, because these projects involve many people, there’ll be a number of good candidates. Work with your manager to identify the best person for the job, keeping in mind that this might be the perfect growth opportunity for an aspiring leader.

The vision

If you, like me, are the technical lead for your team, you’ve probably put a great deal of thought into technical vision. You might’ve written a few documents outlining your; overall motivations; short-, medium-, and long-term goals; and obstacles that could put these goals at risk.

If any of these thoughts haven’t made it into a written, distributable format, now’s the time to make it happen. If such materials do already exist, comb through them carefully and make sure that their content both reflects the current reality and also covers the team’s technical path well beyond your expected return date. Note, however, that having a strong vision for what your team should work on while you’re away doesn’t guarantee that it’ll happen, but it’ll certainly help keep everyone on track and hopefully inspired!

I’ve (thankfully) never had a shortage of ideas as to what our team might accomplish in the long term. I have, however, sometimes struggled to figure out the (achievable) intermediate milestones and how to adequately prioritize these goals that we’re striving toward.

To ensure that everyone on the team felt confident and excited about their work while I was away, I tailored our roadmap with their input over multiple 1:1 conversations.

The glue

Being “the glue” of the team isn’t as easy as it sounds. This undefined role comes with a myriad of responsibilities, for instance, helping team members out with interpersonal issues, onboarding and upskilling new hires, or improving internal processes. And more. The difficulty is, that these actions are often so elusive, they will most likely only become apparent once you’ve gone. But if you’re actively on the lookout, you’ll likely identify the bulk of them before it’s too late.

When pinpointing these “glue” tasks, decide whether there needs to be an explicitly new owner or if it’s safe to “drop on the floor” for someone else to pick up if necessary. Be mindful that, with this latter approach, the task may just be handed over to a junior teammate who won’t be rewarded for their extra workload. Planning ahead, though not strictly necessary, will mitigate this risk.

A little Marie Kondo

Going on leave is a rare (but welcome) opportunity to reevaluate which tasks you’d like to hold onto and which you’d rather let go of. For the optional responsibilities you’ve accumulated over your tenure at work (teaching, onboarding, mentoring interns, etc.), ask yourself whether you’ll genuinely miss it. If not, recruit someone new to fill that role! Finding someone who’s eager to get involved and excited about the opportunity to grow their career is more likely to bring renewed energy to it while you’re gone.

Training your replacement(s)

Now that you’ve recruited all the right stakeholders, it’s time to bring them up to speed. There are two simple ways to do so:

• Write onboarding documentation; or
• Loop them into any meetings/syncs/code reviews.

If you have a decent runway (two or more months) before heading on leave, I recommend opting for both. If you’re crunched for time, lean heavily on producing thorough documentation. There are two advantages to looping your replacement(s) into your meetings earlier. The first is that you’ll have an opportunity to work with them to craft the documentation together, answering their questions as they organically arise. The second will be the option to help build (or strengthen) their working relationships with existing project stakeholders. 

In my case, with three months remaining before my due date, I made the explicit decision to never be the sole representative for my team in any cross-functional meeting. If someone reached out to get my opinion on something, no matter whether it had an immediate impact on my team’s work or not, I’d add at least one other teammate to the meeting. This way, I’d foster new (or stronger) connections between my teammates and other engineers across the organization, and I’d be certain no context was lost, no matter how small.

I applied the same idea to working in Slack channels. If someone DM’ed me a question I thought was important for my team to know the answer to, I’d cross-post the message into our team’s public channel and respond there. This way, they could get involved with the conversation and the content could be easily found later. 

It shouldn’t be a surprise

I spent the entirety of my pregnancy working from home, with my camera angle conveniently hiding my growing bump. Although the majority of my coworkers were aware I was expecting, others would sometimes forget (I’d periodically startle them when getting up to grab another glass of water).

About two months before going on leave, to try to create more “ambient” awareness of my imminent departure, I updated my Slack name to “Maude (going on leave 10/14)”. This way, anytime someone interacted with me in Slack, they’d be implicitly reminded that I wouldn’t be around much longer. If there was anything they needed me to know or attend to before 10/14, now was the time.

Going out with a whisper and a channel

If you can, spend your last week or two before leave on “standby”. You can help your team triage incoming customer requests, or pick off a few easy bug fixes (less than 50 lines of code) from your backlog. This is your final opportunity to identify any lingering items that might have fallen through the cracks: did you forget to remove yourself from your team’s PagerDuty rotation? Did you transfer your team’s monthly office hours calendar event to someone else?

About a month before I headed out on leave, I spun up a new Slack channel (aptly named #maude-parental-leave) and populated it with a few documents. One such document listed the directly responsible individuals (DRIs) I'd appointed for various projects and efforts in my absence. I included links to our team’s document repository, our team’s roadmap, and a few other important contextual documents. I also changed my profile picture to point inquiring coworkers to the channel.

Once your leave starts, log off. Delete Slack from your phone; stop forwarding your work emails. Allow yourself to pretend that, for the time being, you don’t have a job. Trust that your teammates will do their best in your absence, but know that things will have changed. It’ll be much, much easier to ramp back up when you’re ready to regain an active role at work.