Oct 202016

You, Too, Can Take Six Weeks Off

You, Too, Can Take Six Weeks Off

Note:  I have been really quite on OnlyOnce for a few months, I realize.  It’s been a busy stretch at work and at home.  I keep a steady backlog of blog topics to write about, and finally today I’ve grabbed a couple minutes on a flight to knock one out.  We’ll see if this starts me back on a more steady diet of blogging – I miss it!

I’ve written in the past about our sabbatical policy at Return Path, from what it is (here) to how much I enjoyed my own (here), to how great it is when my direct reports have been on Sabbatical so I can walk a few miles in their shoes (here and here).

But recently, a fellow CEO asked me if there was a special set of rules or advice on taking a sabbatical as a CEO.  My quick answer to his specific question was:

Well, first, you and your co-founder can’t take them at the same time. 🙂

But I have a longer list of thoughts as well.  It’s not easy, but as I’ve said many times, it’s important and wonderful.  Some tips:

  • You have to make sure your balance sheet is strong and you’re not raising a round of financing
  • You’re best off doing it a week or two after a Board meeting (and obviously, don’t miss one)
  • You need everyone on your team to know about it and get excited for you!  They will rally/rise to the occasion more than you think
  • You have to do a total disconnect, otherwise it doesn’t count.  Literally turn off email.  But make sure the team knows they can call you if there’s a true emergency
  • Put someone in charge of keeping a running list of things that happened and be in charge of your “re-boarding”
  • Put one person clearly in charge while you’re out, or tell your senior team that they’re responsible for collectively being in charge – either can work as long as you’re clear about it
  • Be prepared to cancel or shift your plans if an emergency comes up before you leave

This last one is important.  I’ve postponed sabbaticals twice, and while it’s been a little tumultuous both at work and at home, it’s been better than going on a sabbatical and interrupting it with work, which I’ve also done.

Speaking of which…I’m coming up on my 17th anniversary, which in our book means it’s time for another one!

Filed under: Business, Leadership, Return Path


Jan 022014


I’ve written a few times over the years about our Sabbatical policy at Return Path, including this post and this post about my experience as CEO when one of my direct reports was on his sabbatical, and this post about my own sabbatical.

People ask me this all the time, so I thought I’d write the policy out here.  This is the language in our employee handbook about them:

You have big dreams. We know. This is your chance to cross something off your life list. Whether it’s climbing Mt. Everest, learning Russian or taking your kids across the country in a Winnebago, we believe in rewarding longevity at Return Path and know that a good long break will leave you refreshed and energized!  As such, you are eligible for a sabbatical after your first seven (7) years of employment; then again after every five (5) years incremental employment. The sabbatical provides you with up to six (6) weeks of consecutive time off provided you have that time off approved by your manager at least two months prior to the start of your sabbatical.

You will be requested to sign an Agreement before your sabbatical: if you do not return to work after your sabbatical or if you leave employment within twelve (12) months of returning to work, you will be required to reimburse all amounts received while on sabbatical.  If a holiday occurs on any of of the days of absence, you will not receive holiday pay in addition to your sabbatical pay.  During your sabbatical, your benefits will continue and you will be responsible for making payments for the employee portion of insurance costs if applicable. The period you are on leave will be counted as employment for the purposes of determining your applicable level of benefits.  If you are eligible and have not taken your sabbatical and your employment with Return Path ends (for any reason), you will not be paid out for sabbatical time not taken.

I also wrote an email recently to someone internally that is worth reprinting here, which is How to Prepare for Your Sabbatical, which is aimed at both the person taking the sabbatical, and the person’s manager:

As the employee:

–          Prepare your team

  • Make sure their goals and metrics for your time out are super clear
  • Make sure they know who to go to for what
  • Set their expectations of management coverage (see below). 
  • Remember that your manager has a day job so you should look to see how your team members can take over some of the responsibilities.
  • Give them stretch goals while you’re out

–          Prepare your individual contributor work

  • Hand off all loose ends with extra details. 
  • Make introductions via email if your manager/team member  is going to have to work with external parties
  • Can be to your team, to your manager, to someone else

–          Prepare your manager

  • Brief your manager thoroughly on everything going on with your team, its work, your individual contributor work
  • Good topics to cover with your manager:Discuss specifics of team and 1:1 check-ins and agree on a plan for coverage.
    • What are the big initiatives that you’ll need coverage on
    • Which team members would you like the manager to spend a little extra time with?  Are there any work you would like the manager to help a particular EE with?

–          Prepare yourself

  • Plan any personal travel early so you get good rates!
  • Figure out how to keep your work and personal communications separate – your email (autoresponder, routing, disabling from your smartphone), your voicemail if you use Google Voice or Simulscribe, etc.
  • Block out two full days immediately when you return to catch up on email and catch up with your manager and team

As the manager:

–          Prepare your team

  • Make sure the rest of your team knows your time will be compromised while you’re covering
  • Figure out what kind of coverage you need (either internal or external) while you’re covering

–          Rearrange your calendar/travel

  • Add new team meetings or 1:1s as it makes sense.  You don’t have to do exactly what your employee did, but some portions of it will make sense to pick up
  • If your employee works in another office with members of his/her team, you might want to plan some travel there to cover in person
  • It’s ok to cut back on some other things a bit while you’re covering – just remember to undo everything when the employee’s sabbatical is over

–          While you’re in charge

  • Surprise your employee with how much you were able to keep things running in his/her absence!
  • Learn as much as you can by doing bits and pieces of his/her job.  This is a great opportunity of the employee to get some value from a fresh perspective.

–          Prepare for your employee’s return

  • Keep a running tab of everything that goes on at the company, critical industry news (if appropriate), and with your employee’s function or team and prepare a well-organized briefing document so your employee can hit the ground running when he/she returns
  • Block out an hour or two each of the employee’s first two days back to review your briefing document


My main takeaway from this post?  I am overdue my second sabbatical, and it’s time to start thinking about that!

Oct 272011

More Than 1/3 of Your Life

More Than 1/3 of Your Life

When I was a kid, so my parents tell me, I used to watch a lot of TV. For some reason, all those episodes of Gilligan’s Island and Dallas still have a place in my brain, right next to lyrics from 70s and 80s songs and movies. I also tend to remember TV commercials, which are even more useless (not that JR Ewing or Ferris Beuller had all that many valuable life lessons to impart).  Anyway, I remember some commercial for some local mattress company which started out with the booming voiceover, “You spend 1/3 of your life in bed — why not enjoy that time and be as comfortable as you can be?”

Well, we humans frequently spend MORE than 1/3 of our lives at work. Why shouldn’t we have that same philosophy about that time as the mattress salesman from 1970s professed for sleep?  Another one in my series of posts about Return Path’s 13 core values is this one:

We realize that people work to live, not live to work

There are probably a few other of our core values that I could write about with this same setup, but this one is probably the mother of them all.  I even wrote about it several years ago here.  Work is for most people the thing that finances the rest of their life — their hopes and dreams, their families’ well-being, their daily lives, and ultimately, their retirement. I think many people wouldn’t work, at least in most for-profit jobs as we know them, if they didn’t have to. And that’s where this value comes from.

How does this value play out?

First, we are respectful of people’s time in the daily thick of things.  We know that society has changed and that work and personal time bleed into each other much more regularly now than they used to.  As I’ve written about before in this series of posts, we have an “open” vacation policy that allows employees to take as much time off a they can, as long as they get their jobs done well. One of the real benefits of this, besides allowing for more or longer vacations, is that employees can take slices of time off, or can work from home, as life demands things of them like dentist appointments and parent-teacher conferences, without having to count the hours or minutes.

Second, an important part of our management training is to make sure that managers get to know their people as people.  This doesn’t mean being buddies or pals, though that happens from time to time and is fine. Understanding everything that makes a person tick, from their hobbies, to their kids, to their pets or pet causes, really helps a manager more effectively manage an employee as well as develop them. And as Steven Covey says, it’s important to “sharpen the saw,” which a good manager can help an employee do ONLY if they are in tune to some extent at a personal or non-work level.

Finally, our sabbatical policy — beyond our fairly generous and flexible vacation policy — ensures that every handful of years, employees really can go off and enjoy life. We’ve had employees buy around-the-world plane tickets and show up at JFK with a backpack. We’ve had people take their families off for a month in an exotic tropical destination. We even had one employee spend a sabbatical in a coffee shop learning how to write code (names masked to protect the innocent).

The challenge with this value is that not everyone treats the flexibility and freedom with the same level of respect, and occasionally we do have to remind someone that flexibility and freedom don’t mean that work can be left undone or delayed.  We believe that by providing the flexibility, people will work even harder, and certainly more efficiently, to still go above and beyond in terms of high performance execution.

In my CEO fantasty world, I’d like to think that given the choice, most of our employees would still come to work at Return Path if they didn’t have to for financial reasons, but I’m not that naive. Hopefully by setting the tone that we understand people work to live and not vice versa, we are allowing people to enjoy life as much as possible, even in the 1/3+ of it that’s spent working.

Sep 292009

Closer to the Front Lines, Part II

Closer to the Front Lines, II

Last year, I wrote about our sabbatical policy and how I had spent six weeks filling in for George when he was out.  I just finished up filling in for Jack (our COO/CFO) while he was out on his.  Although for a variety of reasons I wasn’t as deeply engaged with Jack’s team as I was last year with George’s, I did find some great benefits to working more directly with them.

In addition to the ones I wrote about last year, another discovery, or rather, reminder, that I got this time around was that the bigger the company gets and the more specialized skill sets become, there are an increasing number of jobs that I couldn’t step in and do in a pinch.  I used to feel this way about all non-technical jobs in the early years of the company, but not so much any more. 

Anyway, it’s always a busy time doing two jobs, and probably both jobs suffer a bit in the short term.  But it’s a great experience overall for me as a leader.  Anita’s sabbatical will also hit in 2010 — is everyone ready for me to run sales for half a quarter?

Filed under: Return Path, Uncategorized


Mar 262008

Closer to the Front Lines

Closer to the Front Lines

When we started Return Path, we added a little clause to our employee handbook that entitled people to a sabbatical after 7 years of service (and then after every 5 incremental years).  Six weeks off, 3/4 pay.  Full pay if you do something “work related.”  Sure, we thought.  That’s an easy thing to give.  We’ll never be 7 years old as a company. 

Now, 8 1/2 years later, of course, the first wave of people are reaching their sabbatical date.  A couple have already gone (one trip around the world, one quality time with the kids).  A couple others are pending.  Four of us at the exec level are overdue to take ours, and we all committed to take them this year, planning them out so we can back each other up.  My colleague George Bilbrey is in the middle of his 6 weeks off now, and I’m his backup.  And wow – is it a great experience.  Busy, but great.

The reason it’s great is that I am one step closer to the action.  Usually when someone on my team goes on vacation, we just let things run for that week or two.  The people who report into that exec know I’m around if they need something, but I don’t take over actively working with them.  Not so this time.  Six weeks is too long for that.  I’m actively subbing for George.  I’m sitting in his office in Colorado every other week for the sabbatical.  I have weekly meetings with his staff.  I’m working with them on their Q2 goals (for added fun, we’re even working on George’s Q2 goals!).  I’m attending meetings that George usually attends but that I’m not invited to.

The insight I’m getting into things in George’s area of the business is great.  I’m learning more about the ins and outs of everyone’s work, more about the team dynamic, and more about how the team works with other groups in the company.  Most important, I’m learning more about how George and I interact, and how I can manage that interaction better in the future.  And I’m making or suggesting some small changes here and there on the margin.  Hopefully I’m not messing things up too badly.  Otherwise, I will hear about it in 3 1/2 weeks!

I strongly encourage everyone who is a Manager of Managers or higher in their company (especially if that company’s name rhymes with Geturn Fath) to use any vacation of someone on their team as an excuse to really substitute and get closer to the front lines.