How I pitched company paid vacations to my boss.


Let me give you a little background on this post. About 6 months ago, I hatched a crazy ass plan involving employee benefits for our company. You see, back when I was having a bit of a career crises, I was researching small startups that were hiring. (Like I said, crises) Anyways, I came across Buffer and what their employee benefits were. A Kindle? Free MacBook to work on? Working from anywhere and a salary that accommodated that?? I liked these things! But it was one benefit that caught my eye, a company paid vacation. Not just PTO but money on top of that. Halfway through updating my resume is when the idea of proposing it to my boss hit. We had 4 employees, why couldn't we do something similar?


So, I started brainstorming a pitch for a company paid vacation.

Know your audience.

The trick with any pitch is knowing your audience. My boss, while very cool and understanding, needs to see the benefit for him. It's not a bad thing, and you can't get through some of the business world without seeing how something benefits you. So, that's where I began, because most people want to know what they get from it. 

What and who does it benefit?

Coming up with what this pitch benefits is easy. It benefits the company! We have 4 employees, and three of us NEVER check out. I was back to work a week after my inpatient neck surgery and the doctor said 2 weeks minimum before I could go back. For some reason, I thought the entire world was going to burn to the ground if I wasn't there, that's how we function, and it's not healthy! This benefit would help to even back out our work life balance. To receive the funds, we must check out from work. We all would come back refreshed and with new ideas, and that is what all businesses should strive for. 

However, I couldn't think of just how it benefits someone, but who it benefits too. I had to come up with different tiers of people this benefit affected, make definitions of the different terms I was using, and more importantly how would this affect each group. With the extra paid vacations, while I wanted to be fair across the board and give everyone the same amount. It was my boss though, who brought up the fact that I had been working there for 7 years and did a lot. Why does the person under me, who does a fraction of my job, get the same amount? So, I had to change my pitch a little. 

Be adaptable to changing your pitch to meet the demand.

To this day, I am changing little things to make this benefit better. When I first brought it up to my boss, he had questions and I had adaptations and compromises ready for him. I thought of every outcome that would happen and created a list of "if not this, then how about this" ideas for him. If we didn't give everyone the same amount, then how about base it off years with the company? What happens if someone breaks the rule? What happens if they must cancel their vacation because of the company? Being adaptable and prepared is the best way to show you want this to be approved. 

Understand that it may not always be approved.

I have presented things to my boss in the past, that haven't necessarily gone through. The higher powers did not like the ideas, or my ideas were just overlooked. It SUCKS when that happens, but you must be okay with it. You can either let it go, or go back to the drawing board.  Maybe come up with an alternate pitch, that still benefits everyone but might not impact the company as much. 

Now, my pitch went through, but I had an alternate pitch just in case. I understood this grand idea of mine could have tanked, but I prepped in every way possible. Which included scaring the shit out of my boss by requesting a meeting when my employee wasn't there, where I could have his full attention. I had my idea of paying employees to go on vacation. But I also had a backup benefit if you will, allowing them to cash out 80 hours of their un-used PTO at the end of the year. 

Now thankfully starting Jan 1st 2017, I have $1750 to go on vacation with. Hard work pays off, and sometimes so does showing some initiative. Never be afraid to ask for something, but don't forget to put in a little bit of effort.