Red Green Repeat Adventures of a Spec Driven Junkie

My Tips on Returning to Work from Extended Leave

I could not find much information or recommendation around going back to work after taking extended leave. Even after consulting with my favorite (and practical) work resource: Manager Tools.

I share my experience of taking leave and what my work re-entry experience was like and with hindsight, how to improve it.

You will learn steps I wish I knew when coming back from extended leave to help ease the transition back to work.

This article will take you about four minutes to read.

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This is the third part of a series, kind of like a… trinity. :-)

The first helps expecting fathers get ready for the “big day”. Next, I share what I did to have a smooth transition to extended leave.

This article covers my experience returning to work and tips for your return.

My Experience

I went on leave for about two months and did my best to prepare for my extended leave before. I did not want work to meltdown without me during my leave, so preparation was key. This allowed me to leave at a moment’s notice.

That’s exactly what happened, I had to start my extended leave immediately when the baby arrived.

As I prepared well, I focused on my family during my leave and did not have to split my attention with work. The preparation made my extended leave enjoyable.

At the same time, I did check in weekly to clear out my inbox and see if anything crazy was happening.

Nothing showed up. “Oh, I guess they don’t need me at work. OK.”

Due to the timing of my extended leave with the end of year holidays and all the extra vacation time accrued through the year, staying out the rest of the year seemed like a possiblity.

Then, in my inbox, I saw the most dreaded email…


Oh wow, I overlooked that in my preparations. I was not expecting to be out that long. This was something that I never prepared number two for and they would not be capable of doing it, no matter how well they were handling my tasks.


I jumped back into work mode with the “extended leave” brain. (i.e. I was out for so long, I felt like I was coming back from outer space!)

I met with everyone and caught up. It was good seeing everyone again and got updates. Everyone said things were good, that number two did a great job and the rest of the year would be smooth.

Wow - the preparations did pay off!

OK, let’s start those reviews, right?

Not so fast.

I started receiving messages from my manager after-hours about a recently released project when I was on leave. Hmm, this is weird. He usually doesn’t send messages after-hours. Let’s investigate.


Augh - what is going on with this project?!

Fire fighting time!

This was not the way I expected to come back from leave!

Eventually, I figured out things quickly and made adjustments to put out the fires.


Tips from My Experience

Looking back and thinking about it, everything up to my leave was smooth. Re-entry to work was a bit rough. Here’s my suggestion for everyone coming back from extended leave.

Before Re-entry

When you decide your return date:

  • Start getting reacquainted with key system for work. Essentially, do work before you return to work. Your brain is a muscle and it needs training time before it’s at peak performance before your leave. Jumping back in again will be hard. Training beforehand will help.
  • Start rescheduling any recurring events that you may have canceled before leave.
  • Look at work logs and review work delivered.

First Week Re-Entering Work

This sounds counter intuitive, the best approach you can take the first week you are back is to “on-board yourself” back to work, just like you would on-board a new employee. The difference, you know everyone you need to meet.

Specific steps:

  • Make a team lunch with immediate team to catch up on anything.
  • Have 1:1 with everyone on your team, your manager, any partners.
  • Review work everyone did the whole time you were out.

You may be “on-boarding yourself”, you do know key systems and projects. For any delivered projects or even on-going:

  • In the work tracker, review completed, in progress, or upcoming work.
  • Review with your partners what possible upcoming work may be.
  • Review delivered work on production systems yourself, thoroughly. Take it for a test drive, know it inside & out.

Essentially, if anything goes wrong, everyone won’t call number two anymore, they’ll call number one, you!

Since you’re back, you’re well rested, and you can fix problems, fast!


When you have opportunity for extended leave, take it and enjoy it. You should enjoy your leave as best you can without having to think about work.

At the same time, don’t take advantage of the extended leave policy. Otherwise, you are hurting it for all future people.

Your team will need you, no matter how smooth the work appears to be. Number two or the team will be taking on you work, big extra work, while you’re on leave. Another reason to take just enough, because your team will working extra hard the whole time you’re out in keeping things running.

The better you prepare for your leave in advance, the better your leave will be and your re-entry to work.

Don’t forget about company events during your leave. Any major company milestones, team deliverables will have an impact on your return to work.

When you’re returning to work, on-board yourself and get up to speed on everything done.


Taking leave is important for a variety of reasons, returning to work is an important step to completing the leave process.

When returning from leave:

  • Take steps to “on-board yourself” to the team - meeting with everyone and catching up.
  • Thoroughly review any completed or delivered work.
  • Check any major company milestones or events that happened during or end of your leave.

If you are going back to work or returned to work recently, what are your tips? Contact me, I would love to know your experience.