Red Green Repeat Adventures of a Spec Driven Junkie

My Tips on Preparing for Extended Leave

I recently took an extended leave for my new child and I want to help others have a relaxing and peaceful extended leave.

I will share the steps I took for my recent extended leave that helped me enjoy my leave and not panic every time I saw a message from the company.

You will learn steps to take so you can enjoy your extended leave without checking in on work all the time.

This article will take you about five minutes to read.

If you are an expecting father and want tips, check out my tips for expecting fathers article.

George Inness - Autumn Oaks source and more information


Will you have an extended period of leave soon? A dream vacation that you have been looking forward to. Want to make sure you can leave work “at work” and things will run as smoothly as possible without you?

This article explains the steps I took to have a relaxing extended leave from work.

My Experience

For me, I had paternity leave and decided it would be for the full duration of six weeks continuously. I don’t think in the whole time working professionally, I ever took more than two weeks off at once.

This was new territory for me, especially as a manager. These are the steps I took:

  • Have a Timeline
  • Discuss with your manager
  • Get information from Human Resources
  • Have a number two
  • Take Leave!

Have a Timeline

The sooner you start on planning for your extended leave, the smoother the transition will be for you and everyone involved.

This is the timeline I used for my leave:

Eight weeks before discuss with your manager and get information from human resources
Six weeks before have number two with you at all meetings
Four weeks before support number two with your tasks
Two weeks before number two takes care of your tasks
Zero days before Enjoy Leave!

Preparing in advance eight weeks to take a six week leave seems unbalanced. Wouldn’t it be better to just start six weeks before for a six week leave?

You definitely could do that. As I was going on parental leave, the leave would start as soon as the baby comes. One thing about babies, they can come at any time! I wanted to have extra buffer in case I had to leave sooner than planned.

In either case, there are things to prepare within the people working around you.

Discuss with Your Manager

Once you have decided your leave (or have a best guess), discuss with your manager about your leave, especially:

  • duration: how long? from when? (approximately)
  • return: when will you expect to be back at work?
  • protocol: will you do check-ins? how frequent?
  • number two: who?

The last one, having a number two, is especially important. This person will fill in for you while you are out. Having a number two to fill your shoes is important to assign, even if you’re not managing a team..

Main reason for discussing who number two is with your manager is that your manager may be working with this person while you’re on leave. It’s important that your manager feel they can temporarily fill your role.

Get Information from Human Resources

Have a meeting with Human Resources to learn about the extended leave policy. Explain your situation and what options are available. Requirements for those options. Understanding timing for those options (i.e. notification deadlines, supporting documentation required, etc.)

I found speaking directly with a person on this helped me understand my options and what I needed to do for them.

In my case, I had to contact external companies to notify them of my leave. Getting specific steps, dates, and information required from human resources helped. Reading over the company handbook just made me more confused!

Number Two

Once you have discussed your leave with your manager, the next step is to discuss with number two about your leave and the role they will take while you are on leave.

Choosing a number two will be hard as they will be busy with their own work 100% of the time and adding your tasks, however small, will easily be pushing number two to 110%. To understand this better, check out Manager Tools’ episode on Juggling Koan


At the next team meeting, announce to the team who your number two person is and that they will be the person in charge whenever you are not there.

This will:

  • make it easier to act without deciding on who the best person is after you.
  • give you peace of mind the team knows who their next leader is when you’re not there (for any reason).

After announcing to your team, announce to your partners:

  • you will take extended leave
  • who your number two will be while on leave

This will ensure any partners you are working with are aware of your leave and your number two.


Now that you announced who your number two is to your team and partners, grant your number two the same level of access as you.


Any meeting you attend regularly should have your number two attending as well. It’s important for them to attend as it creates awareness for number two and everyone else in the meeting.

It also eases the transition of your number two in attending the meeting to know what’s going on.

Inviting number two to any chat rooms/channels/etc. where you have access and/or given tasks to perform.

Any meeting where you are the organizer should start being run by number two.


Get your number two the same level of system access you have across all systems. Logins, credentials, etc.

This is important so number two can easily complete any tasks you need to do.

Most importantly, have number two test their system access! If they can’t access the system, they will have a harder time completing the task within a deadline. Ensure number two can access these systems!


Create a list of regular tasks the organization expects you to do. Share this with number two and walk them through the procedure.

From the timeline, this would start happening four weeks from the start of your leave.

With the walk-through, number two has an idea of what the task is and completing them.

For any new assigned tasks, instead of “just doing it”, take the task and complete it with your number two. Working with your number two and completing a real task will take longer than doing the task yourself.

Slowing down and completing the task with them will transfer knowledge and fill in any gaps in everyone knowledge of completing the task.

As more tasks come in, let number two complete it on their own with less involvement from you.

From two weeks before your leave, number two should be independently completing tasks.

Ultimately, the plan is for the start of your leave, any of your regular tasks will be done by number two.

With lead time for training and number two to practice on their own, you can guarantee this will happen.

Calm Before the Storm

Ideally, two weeks before your leave starts, number two will have a good handle on everything.

What should you do?

I found creating more documentation for anything that isn’t documented was useful. (i.e. meetings, standards, etc.)

If your number two can handle all tasks, you can help them out by asking if they would like you to do the task instead. (Yes, it sounds backwards, it works though!)

Ultimately, there’s always more work to be done.

Take Leave!

When the big day comes, take leave, simple right??

(Or with a baby, a whole new adventure starts!)

There are small things you can still do to help improve your leave for everyone:

  • clear our your calendar of any repeating events
  • setup automatic email/away messages in your email/calendard/groupware system

Checking in During Leave?

The whole idea of leave and doing this preparation for your leave is so that you will not check in.

At the same time there might be cases you did not think about and/or missed.

I would recommend checking in on your email at most once per week. I did that to ensure an empty inbox when I returned (inbox zero FTW!) and did not miss any larger company duties (i.e. performance reviews).


Taking extended leave is important and will be relaxing when prepared for properly.

Make your leave smoother for everyone by:

  • doing small things like removing repeating events
  • training a number two to do any expected tasks during your leave
  • working with your manager and human resources to understand and decide your leave

Did you take an extended leave recently? Did these tips or something else really help? Let me know! I love to hear what others did.

Also, if you are an expecting father and want tips, check out my tips for expecting fathers article.

Special thanks to the July 2, 2020 Things I Think I Think newsletter from Manager Tools to get me on the right track about taking leave by delegating and succession planning.