Every Question to Ask Before You Roll Out an Unlimited Vacation Policy

I’ve been thinking about implementing this policy for three months. I’ve interviewed dozens of CEO’s who have implemented an Unlimited Vacation Policy to discuss how different companies handle different situations. Next week at the Beyond the Beer Pong and Foosball Tables event, I’ll be discussing the process that I went through to  come up with answers to every Unlimited Vacation Policy question that we could think of. Register for this event at Westland Distillery on October 28!

Why Implement an Unlimited Vacation Policy?

My company is not a tech startup, but because we support hundreds of startups and are entrenched in the startup ecosystem, I gravitate towards and embrace the workplace culture that is on the bleeding edge. I also want to attract employees who thrive in the startup ecosystem and feel like this is one of those things that separate the best from the rest. I also feel that PTO is punitive and traditional vacation and sick leave is even worse. Having an Unlimited Vacation Policy shows your employees that you trust them and allows employees to recharge when they need to. This leaves employees feeling empowered, respected and motivated.

Build With the Long View in Mind

I’m also a firm believer of building the company with the long view in mind. There are no shortcuts when you’re building something that is sustainable. Life is full of changes at each stage of life. When you’re single, there are things that you just want to be able to do and there are fewer commitments holding you back. Once you have children, the world completely becomes different. Suddenly your time off is spent at your kid’s Halloween party, attending parent teacher conferences, staying home with them when they’re sick, or figuring out how to handle summer vacation when they are bouncing back and forth between summer camps. That leaves a person with essentially no time off for actually recovering from working hard and crushing their goals. There are also unforeseen issues that come up in life, ones that no one ever plans for, and I want employees to feel supported in those situations and throughout the various stages of life.

Questions and Roll Play

Here is a list of questions that I came up with. As a team, we spent a few hours (spread out over a week) to discuss and role play the questions.

  • How do you ensure that people don’t take too much time off?
  • How do you ensure that people don’t take too little time off?
  • How do you ensure that people do not become resentful of others who take too much time off?
  • What do you do if your incentives don’t support your goals?
  • How do you ensure that people do not feel guilty about taking time off?
  • What’s a healthy amount of time off to take per year?
  • How much lead time do you have to give in order for vacation to be approved?
  • Should unlimited vacation be tracked?
  • Most unlimited vacation plans have some sort of manager approval step. What systems are in place to ensure there is an equal approval process for each manager to ensure that there is not inequality among teams?
  • If sales people reach their goals they can take off as much time as they like. What about for jobs that are more operationally focused?
  • If you need an extra day to recover from your vacation buffer that it. Nothing sucks more than people that call in sick because they are wiped out, hung over or didn’t rest enough when they took their vacation. Be back in the office when you say you’re going to.
  • Is it okay to just call in sick when you just don’t feel like working?
  • If it just happens to be a sunny day, should you just call in and say, “I’m not coming in”?
  • What if an employee needs to take time off because of something related to FMLA (Family Medical Leave Act)? How does that work with a unlimited vacation policy?
  • How does maternity or paternity leave work with an unlimited vacation policy?
  • Can you take time off if you’re behind on your projects or they are not complete?
  • Do employees feel like they are working all the time even when they are on vacation?
  • Is there a cap on the number of weeks a person can take off at one time? Two weeks? What if someone has something that they would like to take off which is longer?
  • How do you treat existing accrued leave while transition from PTO to unlimited vacation? Payout at termination?
  • How do you ensure that you have a vacation schedule that is fair to all and effective for the business?
  • How can you have an unlimited vacation policy for hourly employees?
  • How do managers arrange with their teams to take time off?
  • The hiring process needs to weed out people that don’t align with our core values and how we operate with a unlimited vacation policy.
  • Is the client or customer suffering?
  • What if I want to take time off but my manager doesn’t approve?

Unstructured or Guidelines?

At the end of our discussion, it was clear that expectations are set and guidelines are in place. This helps people understand what is considered to be acceptable, aligns with our core values, and allows employees to show they really care about their coworkers and the company.

What other questions would you ask if you were implementing an unlimited vacation policy?

Can a woman have it all?

“You have a condition that usually only occurs in people over 60,” my doctor said as she typed in her lap top. “Have you been under a lot of stress lately?”

Hmmm, does she mean balancing the needs of my family, and my growing business?
Or does she mean the PTA meeting I skipped so I could meet a writing deadline?
By “stress” could she mean the lists that don’t get checked off, or the emails that don’t get opened, or the dog that doesn’t get walked?
Which stressful event was my doctor alluding to, and how could I answer “yes” without shouting, “Isn’t every working mother- are you crazy?!!”

“You know,” she continued, “You will probably get this again if you don’t do something about your stress level.”

Shingles. That’s what she diagnosed me with. Shingles is this terrible burning sensation that attacks the nerves underneath your skin until you eventually erupt into mischievous oozing bumps. Awesome. I’m a therapist. I preach self care. I believe in balance. I teach people how to take care of themselves. And I have a stress-related, immune deficiency condition that no 38 year old should get.

Wake up call.

Come-to-Jesus moment.

Time to take some things. Off. The. Plate.

So, when Marissa Mayer of Yahoo announced no more working from home, I paid attention. When Facebook’s COO Sheryl Sandberg told American women to “Lean In”, I listened.  What are the women at the top saying about their positions, their work-life balance? What are they saying about their priorities? How do they balance it, and what are their secrets?

Turns out, they probably experience the same things I do (with the caveat of being paid just a tad bit more- wink).

Erin Callin, former CFO of Lehman Brothers before the crash, recounts in her New York Times piece this weekend that “Work always came first, before family, friends, and marriage- which ended just a few years later.” She goes on to say, “Until recently, I thought my singular focus on my career was the most powerful ingredient in my success. But I am beginning to realize that I sold myself short… there were diminishing returns to that kind of labor.”

Though admired by many young women who see Mrs. Callin as a hero and an over-comer of the gender barrier, she is fraught with regret.

University of Michigan business professor Marina Whitman, a full-time professor and a corporate executive says in a recent CNN article by Todd Leopold, “I think this thing about ‘can women have it all?’ or ‘can’t they have it all?’ is kind of a silly argument. Yes, you may have it all, but not all at once.”

And what about Marissa Mayer banishing the working-from-home flexibility? She certainly has gotten a lot of back lash. Some of my working mother buddies say she ought to be ashamed of herself. But it has got me thinking that maybe “working from home” for the working mother, is just playing into the illusion that women really can have it all. That there is some ideal out there that a woman can be at home with her smiling contented children, while sitting at a desk with phone in hand, lap top open while climbing the corporate ladder. Maybe we’ve bought into the illusion that we “should” be able to do it all. Maybe we think, “if only my work schedule was ‘flexible’ then I could make that PTA meeting, I could take that work call while mixing the baby formula,” or in my case, I could schedule myself to being two places at one time and be half committed to both. Ugh.

So what did I learn from Shingles? Well, for one thing, I’m taking the Sabbath. I’m working my tail off Monday through Friday 8:30 to 3 until Sweet and Sassy get home from school. I’m shutting my lap top until they go to bed at night, and I’m wearing them out on Saturdays with chores, sports and lots of family fun. I schedule a date night with Mr. Dashing and make deposits into the marriage bank account. Come Sunday, I don’t return e-mail, I don’t write blogs, I don’t do anything that could remotely seem like work. I go to church, I go out to eat, and I read for FUN (not for work.) Then I try to catch up on some Duck Dynasty, which really puts me into relaxation mode, because I’m pretty sure they haven’t worked a day in their lives, unless you count catching bull frogs as work.

Everything has a price tag. Everything worthwhile requires sacrifice. Some of us choose work, some of us chose family, and then the crazy ones, like me choose to work out the balance of both. The sacrifices I make as a working mother are continual and on-going. The fact is, if I throw the soft ball with Sporty Spice, then I’m not going to get that blog post done. And if bring home work to do, I won’t be available to hear mini-Taylor Swift’s original song on the piano. What am I going to forfeit? What am I going to give up? Something has to go, which one will it be? I’m the last to cast a stone at working mothers’ choices. But I’m the first to say, life is about choices, and values, and about consciously making those choices according to your values. Could I be further along, higher on the ladder, with a broader following if I chose to spend more time at the office? And if I spent more time at work, would Sweet and Sassy be as well adjusted and fantastic as they are now? I wonder. We make choices, some good, some bad. But most times we don’t know they’re bad till we feel the pain of them. Like the pain of Shingles. I didn’t know I was burning at both ends until I actually felt the burning.

My prayer is that you won’t have to.

This  is a guest post written by  Michelle Hollomon.  Michelle is a Counselor and a Coach, author of God Unwrapped, and host of Relationship Coach Radio. You can find out more about her at MichelleHollomon.com.

The glorification of busy.

always-open-closed11Has anyone ever qualified a question with the following: “I know you’re busy, but…”?

This happened to me the other day, and I had two immediate reactions.

My first reaction—> I was glad they recognized my schedule was packed with busy and important things.
(Confession: that observation made me feel important and popular).

My second reaction—> I was frustrated that my busyness made them think I wouldn’t have time for them.

Too often, I over emphasize my busy schedule.
When people ask me “How are you?” usually my response includes something along the lines of “Good, I’ve been staying really busy, etc etc etc.”
We live in a world that masters the glorification of being busy.
While busy seasons come and go, defining myself by my busyness will communicate that I’m unavailable.
So even though I desire for others to know that I am always open, my actions show that I am closed.
What would it look to communicate a more open and flexible schedule?

I’ve set a new goal—> To stop defining myself by being busy, and to be more approachable and flexible so people don’t begin conversations by first acknowledging my limited availability.

That’s been on my mind this week…I’d appreciate any feedback or suggestions you all might have!


Compartmentalization is overrated.

workA while back, I learned the importance of creating boundaries between my work and personal life.  Those boundaries helped to compartmentalize my life, which had its benefits.  I kept my work life separate from my personal life.  And there wasn’t much crossover.

Working at thinkspace has shown me that I actually need less compartmentalization.  A healthy level of balance can still be maintained without strict boundaries.  In a recent conversation with a coworker, he expressed his strong dislike for the idea of work/life balance.  He argued that the work/life balance concept creates a delineation that doesn’t need to be present.  It usually generates a “clock-in” and “clock-out” mentality.  To compete in the Social Era, that mentality needs to take a backseat to generating value and relationships.  With Value driving the car and Relationships as the copilot, crossover (once was seen as a negative thing) is now welcomed.

In an article in Forbes, Ryan Blair explains a  “pro-compartmentalization” strategy:

“Pretend as if everything you’re dealing with in your life is a room where you have to walk in and solve an equation on a white board. You have a countdown clock with less than an hour to get the problem solved, or take a single step in the right direction, and then shut the door and go into another room equally as important. You spend your entire life going from compartment to compartment.”

While I appreciate what Blair is getting at, and while it may be helpful for some entrepreneurs,  his “one room at a time” strategy is limited.  Every area of our life is hard wired to every other area.  Therefore, there will always be some rooms that I simply can’t “shut the door” on.  Plus, there are some rooms that will always take up more than just one hour of my time.  To take part in meaningful projects, conversations, and interactions, rooms should be inviting.  A countdown clock may be strategic, but it is not inviting.

In an article called “The Fallacy of Compartmentalization,” Jonathan Fields shares his opinion on why compartmentalization is overrated:

We talk about things like our work life and our home life as though we can somehow slip out of our skin and assume another identity when transitioning between them.  However, trying to compartmentalize the various parts of life can take a significant toll on our effectiveness across the board.

How about you?
Are you pro or anti-compartmentalization?
How do you make sense of balance in your life?

Q: Can we really just forgive and forget? A: Yes and no.

headshotsEnter [what’s been on my mind]

Much of last week’s media focused on Lance Armstrong and Notre Dame’s Manti Te’o, and on more than one occasion I heard reporters ask, “Is America able to forgive and forget?”

Blink [see a new perspective]

There is no weakness is forgiveness.  More often than not, it is the strong who are able to forgive and the weak choose to remain resentful.  In regards whether or not America can forgive Lance and Manti, I think the answer should be and has to be “yes.”  While the truth of the matter is that Lance and Manti both got caught in lies, there is another truth present: I am a liar, too.

Don’t get me wrong, I try to be honest.  Honesty and trust are two things that I not only value in others, but also in myself.  But there are times when I have been caught in a half-truth (which is just another way to say “lie”) which I explain away saying “Oh, that was just a little white lie.”

Lance and Manti are liars.  So am I.  And if America is honest (since we are discovering that the truth will come out eventually), then we all have to admit that at some point in our lives, each and every one of us has told a “Lance.”  Or told a “Manti.”  In other words, we have told a lie.  We may console ourselves by saying our half-truths aren’t anywhere near as severe as the lies exposed last week, but I don’t think it’s a good idea to line-up lies on a sliding scale of comparison.

In resonating with Lance and Manti, it makes it a bit easier to offer them forgiveness.

Shift [try it out]

But while I argue for forgiving Lance and Manti, a part of me has a hard time with the statement “forgive and forget.”  In some circumstances, forgiveness is cheapened when it is paired with forgetfulness.

What if the If the U.S. Anti-Doping Agency forgave Lance Armstrong and decided to dismiss and forget about his years of drug use?  Pairing forgiveness, alongside the USADA’s ruling that Lance ran “the most sophisticated, professionalized and successful doping program the sport has ever seen” (source), with forgetfulness would undermine the existence of their organization, as well as open the door for other athletes to do the same.

Forgiveness means getting to a point where you can wish the other person well, but it does not necessarily mean that you completely forget their indiscretion.  Moving through the steps of forgiveness can cause a relationship to change – sometimes you part ways, but sometimes the relationship is strengthened for the better.

Listen [hear from our community]

We are all flawed, in some way or another.  Some mistakes and missteps are bigger than others, and our ability after the fact to do or recognize the right thing and course-correct isn’t a cut-and-dry decision either.  It’s hard to see things from another’s unique point of view, and even more difficult to know that our perspective on their actions is, itself, correct or even appropriate.  Best thing I can think to do is stay true to what I believe, understand and stick to my values, and learn from what I see around me (including experiences from other flawed people) to constantly try to make myself better.

-Matt Heinz, President of Heniz Marketing Inc

How’s your [think]space?

Enter [what’s been on my mind]

messy-desk1Does this ever happen to you?  You’re about to start a new task, and you realize you cannot begin until you either

    a) throw away the collection of empty Starbucks cups,
    b) clear away the mound of papers collecting on your desk,
    c) try out a new organizational strategy (apparently the current one is not working), or
    d) all of the above.

For some reason, organization and my [think]space are correlated because in the midst of unorganized chaos, I have a hard time getting any work done.

Blink [see a new perspective]

Maybe I’m not alone in my multiple choice dilemma.

And maybe the best solution isn’t found in either a, b, c, or d.

Your work environment directly affects your productivity, therefore the status of your [think]space should be taken seriously.

Shift [try it out]

It’s not too late to still start off the new year in a more efficient and organized way.  Resources are literally clicks away and readily available to help people like me (and possibly people like you). Innovatively Organized is local productivity consulting firm, and they just happen to specialize in this very topic.  After checking out their website, I already feel inspired and equipped with checklists, innovative ideas to manage my desk space, and ways to handle digital clutter.

Listen [hear from our community]

Coming up next week Wednesday, we have the opportunity to hear from the CEO of Innovatively Organized, Elizabeth Bowman, at one of our Brown Bag Lunch Events.  The event is called Maximize the Potential: Quick Tips to Organize Your Cubical or Small Office, and it will provide helpful hints on how to maximize your desk space and storage.  For more information and to register for this event, click here.


What really happens when you work from home…

Enter [what’s been on my mind]

work_from_homeAs much as I love working from home (on my couch…in my pajamas…), I must admit that when I’m at the office, I’m much more alert and effective.

Blink [see a new perspective]

The article Snack Laundry Lunch Clean Snack reveals a survey with disturbing results: what employees confess they are actually doing while they work from home.  For example, “43 percent of workers say they’ve watched TV or a movie while ‘working’ remotely, while 35 percent have done household chores, and 28 percent have cooked dinner.”  When I work from home, I find that my taste buds are uncharacteristically high-maintenance:  This iced coffee sure sounded good 10 minutes ago, but now I want a hot earl grey tea…and wouldn’t some toasted almonds be a great pick-me-up?…perhaps with a bit of dark chocolate…Is it lunch time yet?…I should probably start something on the stove right now…and take out that chicken to thaw for dinner…

It’s amazing how much time I spend in the kitchen when I work from home.

Shift [try it out]

If you must work from home, establish some boundaries.  Turn the television off, designate your lunch break, clarify when you’re on the clock versus off the clock, and finally – don’t work in your pajamas.  You probably won’t just lie down for a second when you’re in heels and a skirt (or a suit and tie).  But when you wear pajamas, you’re halfway to a nap.

Listen [hear from our community]

At Innovatively Organized, we not only work with busy entrepreneurs who work from home, but my team and I work from our home offices as well.  It certainly takes discipline to set boundaries around your time in order to stay productive when you work from home.  Just because you have a home office, doesn’t mean you should be watching television or doing laundry during the day.  It’s important to set up your home office to operate efficiently and feel welcoming.  This helps you avoid sitting on the couch with a laptop where it’s easy to get distracted.  Also, I’ve found it is important to set expectations and have open communication with family members when you work from home.  If you aren’t used to it yet, the lines can blur easily.”  –Elizabeth Bowman, President & Founder of Innovatively Organized

Innovatively Organized is also hosting an event tomorrow that will give tips for mobile professionals – find out more here.


”We always marry the wrong person.”

Enter [what’s been on my mind]

relationshipsA recent NY Times article asked, “Is marriage headed for an overhaul?”  The author was responding to what experts are saying, that “there is a need to rethink an institution that so often fails.”  Some even suggest that short-term marriage contracts may be the answer.  But does favoring till awhile do us part versus till death do us part offer an answer to the marriage dilemma?  Or does our culture simply misunderstand compatibility?

Blink [see a new perspective]

Maybe marriage’s fatality rate doesn’t stem from commitment issues, but compatibility issues. We have no problem committing to people that we are in love with. But what happens when that love changes? The root of the matter is, for better or worse, can you commit to being compatible with the same person 10 years from now? 20 years from now? Forever? Stanley Hauerwas, an Ethics Professor at Duke University, comes to a similar conclusion:

“Destructive to marriage is the self-fulfillment ethic that assumes marriage and the family are primarily institutions of personal fulfillment, necessary for us to become ‘whole’ and happy. The assumption is that there is someone just right for us to marry and that if we look closely enough we will find the right person. This moral assumption overlooks a crucial aspect to marriage. It fails to appreciate the fact that we always marry the wrong person. We never know whom we marry; we just think we do. Or even if we first marry the right person, just give it a while and he or she will change. For marriage, being [the enormous thing it is] means we are not the same person after we have entered it. The primary challenge of marriage is learning how to love and care for the stranger to whom you find yourself married.”

Shift [try it out]

As busy people, we make commitments all the time. Whether it involves a project, a job, or a person, there are various levels of commitment: informed, interested, highly motivated, as well as uninformed, uninterested, and unmotivated. The bottom line is this: what you commit to matters and how you commit matters. Contracts might be realistic for some matters, but relational contracts might not be the best idea. When it comes to any kind of relationship, commitment and compatibility must be at the forefront of your mind. After a commitment is made, the relational chemistry will most likely shift. Marriage is an excellent example of this, but other relationships – i.e. business partners, clients, customers, friends – change, too. The challenge with commitments is continuing to be aware and intentional with the dynamics within the relationship. People are not contracts, and they must be treated with care. Imagine if you spent the same amount of time and energy that you do with your career as you do with your husband or wife. That kind of devotion could change everything. In any relationship where you go above and beyond, people are bound to notice. And in turn, they will notice if you aren’t going above and beyond.

Listen [hear from our community]

I met my wife in college. When you marry a person it’s not about being perfect and compatible for each other forever. It’s about making a commitment to each other to take that life journey together for the rest of your lives. The stage that we met at in college is way different than the early working years while starting a career. That stage is completely different than the stage when we started to have a family. It’s always changing and people are always changing. The key thing is relationships; it’s about total commitment and putting the energy into the relationship. If you think you just have to put the energy in at the beginning to win the person’s heart you’re wrong. In business, it’s all about relationships. A co-founder  an employee, a customer. A customer doesn’t do business with a company, it’s a person doing business with another person. Once you recognize that it’s all about people you understand it’s all about relationships. Once it’s about the relationship there isn’t anything that I wouldn’t do for a co-founder, employee, or customer as long as there is a relationship. Once it becomes unconditional it becomes special and that’s where the magic is.  

-Peter Chee, CEO and founder of Thinkspace 

Why You Need A Vacation

Tis the season for parties, too much shopping, sweet treats…and the dreaded choice between taking the time to spend with friends and family and getting through that one last project. America is known as the “no-vacation vacation,” as most employees only get a few weeks off per year to take a break and some employers give even less.

But taking a break from work is actually critical to doing well professionally – especially if you’re the entrepreneur type and rarely even take weekends off. There is something to be said for work-life integration – I can’t even remember that last time I took more than 24 hours without doing some sort of “work” – but a true vacation can be critical to our professional and personal health.

According to CNN, stepping away from work can help inspire new creativity. “Detaching from a familiar environment can help get new perspectives on everyday life,” says Adam Galinsky, professor at the Kellogg School of Management at Northwestern University. This doesn’t necessarily mean you need to travel across the world to find new sources of motivation – though CNN highly recommends it. Instead, simply unplugging from work and hitting the slopes – or even just heading outside – can be incredibly beneficial.

A true vacation can also help prevent burnout, which entreupreners experience all too often as they work 80+ hour weeks. In a report by Psychology Today, 76 billing and accounting workers were surveyed about their exhaustion levels before, during and after a two-week vacation. Burnout dropped sharply during the break, according to the report. Psychology Today also noted that previous studies have shown that vacations boost performance and curb absenteeism – which could also translate to increased motivation for those who work for themselves.

As the holidays are quickly approaching, now may never be a better time to unplug for a few days so you can de-stress and personally recharge for the new year.

Did you take a vacation this year (or are you planning to?) Let us know why or why not in the comments!

There’s no weakness in forgiveness.

Enter [what’s been on my mind]

Forgiveness is not a natural human response. At times, it’s even easier to forgive people for being wrong rather than being right. In a competitive environment like a workplace, forgiveness can seem more like a sign of weakness rather than a helpful step towards resolution. With so many reasons of why it’s hard to forgive, are there any arguments that can be made for forgiveness?

Blink [see a new perspective]

Studies completed by the scientific community (such as the Mayo Clinic) illustrate the positive effects of forgiveness. They have found that resentment impairs your thinking and negatively affects your health (i.e. high stress and blood pressure). Therefore, freeing yourself of resentment by practicing forgiveness can actually benefit your health. It also creates a more effective work environment where communication flows more clearly (and without the passive aggressive undertone).

Shift [try it out]

Keep in mind that forgiveness is a choice. No matter how you feel about the situation, you can always choose to move through it and take steps towards forgiveness and reconciliation. A book that I’m currently reading explains this process perfectly:

“You must forgive in order to understand. Until you forgive, you defend yourself against the possibility of understanding…If you forgive you may indeed still not understand, but you will be ready to understand, and that is the posture of grace” Home, by Marilynne Robinson.

This week, do a self-check and ask “Who am I resentful towards?” If a person comes to mind, remind yourself about the benefits of forgiveness, stop defining the situation based on emotion and hurt, and take the steps to forgive.

Listen [hear from our community]

Forgiveness is the choice to not hold the wrong-doer accountable anymore. Holding a grudge only hurts the grudge-holder, but forgiveness frees you up to have more and better opportunities. Forgiveness doesn’t have to mean reconciliation or closeness, although it can in the best case scenarios. Forgiveness means that you give up your right to be angry, bitter or vengeful toward the wrong-doer. The result is peace and personal power.

  1. Identify the wrong that’s been done.
  2. Identify what justice would look like.
  3. Choose to forgive and let go of your right to get even.
  4. Be released of the power that person’s wrong-doing has had over you.
  5. Verbalize well-wishes for the person.

– Michelle Holloman, Eastside Counseling and Coaching