Destination Working, a Win-Win

By Julie Rose | Employee Experience

Sep 09

You’ve heard about Destination Weddings, right? The Bride & Groom choose a location to travel to, along with their guests, to exchange their wedding vows. They say “goodbye” to the traditional home-town wedding and chart their own path to happily ever-after!

Have you ever heard of Destination Working? I hadn’t until I recently talked with Jennifer Dilley at SIVO Insights. Similar to a Destination Wedding, an employee picks a location to visit for an extended time while also choosing to work in that non-traditional location.

I think Jennifer is on the forefront of a trend that will take hold in workplaces today and into the future. Organizations of all sizes and across all industries are needing to operate differently to satisfy the needs of their high-caliber employees. While the idea of Destination Working might be new, the idea of working outside the office certainly isn’t. In fact, 4.8 million Americans consider themselves digital nomads1, able to work from anywhere. Often, that means working from home, which more than half of employees today do at least half of the week2. While this is great for workers, it’s also great for their employers: employees who work from home are more productive3and more engaged4than their office-bound counterparts. If that’s true for working from home, why can’t it be true for other types of remote work?

I recently caught up with Jennifer about her Destination Working experience and what it meant to her. Here’s an excerpt of that conversation:

How did you come up with the idea of Destination Working?

Escaping winter to sun and warm breezes has been a dream of mine since moving to Minneapolis.  Minneapolis has many positives to offer, but winter is a struggle for me. I grew up in the Midwest, so I am used to four seasons.  But winter is different here. Once the snow falls, don’t expect it to be gone until May. Days are shorter too – so it is dark, cold and snowy. Some of the first advice I received after moving here was “Take a winter vacation.” Many others must have received that advice too (laughing) – until moving to Minneapolis, I had never seen so many bathing suits in stores in January!

This idea had been percolating in my head for years. But how to make it work? I knew if I pursued this, it had to work for my employer too.

How did you know SIVO Insights was that employer?

I’d only been working at SIVO for a month when I brought it up to the Managing Partners. Can you believe that?  I’d been an employee for less the 20 business days and I’m like “Hey, would it be okay if next year…” But I felt confident we could have a genuine conversation about the possibility.

See, SIVO’s culture is all about doing what you love. In fact, Marilyn Weiss, SIVO’s Chief Innovation Officer, and Cindy Blackstock, SIVO’s CEO, love this quote from Howard Thurman, “Don’t ask yourself what the world needs. Ask yourself what makes you come alive, and go do that, because what the world needs is people who have come alive.”They live by this tenet; it inspires the best work from each of us. It is the foundation for the unique culture at SIVO.

Tell me about your Destination Working. Where did you go?

My husband and I went to Maui, Hawaii, for two weeks this past February. The first week in Hawaii, I worked remotely and the second week, I took as vacation. Everyone knows Hawaii is a beautiful location for a Destination Wedding; and I can confirm it is an amazing location for Destination Working.

Destination Working is probably not for everyone – tell me about other considerations for people who are thinking this is a good idea for them.

I think it boils down to three critical factors – planning, diligence and awareness.

Let’s start with planning. What does it take to do your job well? For me, I need a phone, laptop and dependable, high-speed internet. When I was booking our condo rental, I confirmed the internet quality before booking and I talked to the owner about my plans to work remotely, letting her know that a good internet connection was critical for me.

Second, you must be diligentabout working. When working remotely, your organization has to trust you. No one at the office really knows if you are on a client call or swimming in the ocean – but youdo. You owe it to your company and your fellow employees to work at your destination just as if you were in the office.

Awarenessis the third factor. Your benefit is getting to work at a great destination; no one else should be inconvenienced. To make it easier for others, I worked 5 a.m. – 1 p.m. in Hawaii to match up with the workday back home. This allowed me to be available to our clients and co-workers when they needed me. Also, when I came back to Minneapolis, I asked the Managing Partners and some co-workers for feedback on what it was like working with me while I was gone. You need to be open to hearing how your experience affected others. Fortunately, everyone agreed it was a seamless experience.

So, did your Destination Working experience go off without a hitch?

Let me start by saying I loved Destination Working and I intend to do it again; but there was one major hitch.

It was Friday, my last day workingin Hawaii. The whole work week had gone smoothly. I had one last client video meeting – the most important meeting of the week. Right then, the power failed in our condo. When you lose power, you lose internet.

This story starts as a nightmare, but pre-planning paid off big time for me! Because the building manager knew me (I made sure to say “hi” the first day and remind her I was working remotely), she understood how critical this hitch was for me. She volunteered another unit with power I could use for the remainder of the day.

We’ve talked a lot about your point of view as an employee.  Is there advice you would give to another manager whose employee asks for Destination Working?

Even knowing SIVO is the first employer I felt comfortable asking for Destination Working, I’ve been surprised at how many others are awed that SIVO would not only agree to, but actually support, me working from Hawaii.

But let’s look at this holistically. Destination Working is a win-win. It strengthened my loyalty as an employee, gave SIVO the opportunity to make an employee’s dream come true, and I think we were both surprised at how physically being in a destination location inspired a higher level of creativity. I’ve heard some refer to this as being in my “alpha state.”

If a manager is reluctant – and the job really can be done remotely — I would ask them to question “What truly is the risk of Destination Working?” In my case, we were talking about five business days. That’s it. Five days is a low investment to engender employee loyalty, increase productivity, and benefit from the recognition of being a modern company embracing the needs of today’s employees.

Where are you headed for your next Destination Working adventure?

I’ve already taken a few smaller trips!  The most recent was a trip back to my home state of Ohio.  Living at a distance from my family, I miss out on many of the smaller moments of their lives.  Last month, we celebrated my mom’s 70thbirthday.  Without Destination Working, I would have arrived late Friday, just in time for her surprise party.  But with Destination Working, I arrived several days earlier; hiding out with my sister’s family, working remotely during the day, and being around to help with the party details in the evening.  One of my favorite moments was driving my niece around my hometown, getting balloons, going to the local bakery; she is eleven and lovingly informed me I was her ‘chauffer and wallet’ as we made grandma’s birthday special.  Destination Working gave me the opportunity to create that memory.

It sounds like Destination Working can be a big adventure, like your Hawaii trip, or something on a much smaller-scale, like your trip back home, and either way, it’s a win-win for you and SIVO Insights!


1MBO Partners: Digital Nomadism: A Rising Trend
2International Workplace Group study
3TED Talk with Standford professor Nicholas Bloom: Go Ahead, Tell Your Boss You Are Working From Home
4Gallup State of the American Workplace report



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About the Author

Julie is an executive with a proven track record for brand building and team building. She is skilled at leveraging disparate resources to unlock new insights and create human-centric strategies. She has held several client service roles in her career and is adept at working collaboratively to set clear goals and deliver on expectations.

  • Awesome post! Keep up the great work! 🙂

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