Preparing your ask, presenting your case, negotiating. Based on FBI negotiation tactics, sales principles, and personal experience. Travel and still come home to a job!
Background:
There's a difference between vacation, and travel. While there's nothing wrong with a vacay (in fact, check out our Guide to Making the MOST out of 3 Vacay Weeks), there are certain trips you just can't squeeze into 3 weeks.
Not to mention, the freedom to take your time, change your plans on the fly, and not be held down by jam-packed itineraries.
"Cool story.. but I have a job"
Sure, instagram reels tell you to quit - but for a lot of you that's either too scary or not an option. How, then, do you go about asking - much less receiving - time off to travel?
Well, here's your ridiculously complete guide.
With years of training & experience in Sales, Negotiation Theory and most importantly getting time off to travel, I've put together the recipe that gives you the absolute best chance of getting on that plane.
The goal will be to get up to 6 months to travel. Usually, this comes in the form of a "leave of absence" or "sabbatical", but we'll also cover the option of "temporary remote work".
At a Glance:
Your Table of Contents
Preparation: - Do Your Homework - Elevate Your Status - Shift Your Mindset (low power distance)
Approaching your Boss: - Timing - Booking the Meeting - Your Opening Line
Presenting your Case: - Presenting your Value - Stating your Loyalty - Honest Statement of Desire - Why you Need it, Why Now, How it Will Help the Business - Make the Ask (with a "How Question" and "Accusation Audit") - How Will you Mitigate your Absence?
Negotiating: - Length (What to Concede First vs Last) - Working Extra - Discretion - Remote Work
A COMPLETE EXAMPLE 🏆
Preparation:
If you want this to work, you have to take it seriously. Come to that meeting over-prepared. Here are some considerations as to how to do that:
📚 Do Your Homework
First, have a good read through your company's HR policies. This might surprise you, but many medium-to-large companies have an HR provision for taking an "unpaid leave of absence". If you're lucky enough to have this, the rest becomes much easier. Most companies who have this in their HR policy tend not to fight you on using it - that's why it's there after all. If they don't - no worries - just keep reading.
Second, make a mental map (or better yet draw one out) of your company's current situation. This will massively help you align with your boss's situation and find a proposal that they'll be willing to accept. Some questions to ask yourself might be:
How is the company doing lately? How about your team? You?
How is your boss performing?
How is he or she evaluated by their superiors?
Where do you rank in seniority among your team?
How many colleagues do a similar role / could cover for you?
How long has it been since your last raise?
How long have you been here / plan on sticking around?
While you may not speak to any of these explicitly with your manager, they'll help you understand how much leverage you have - which in turn informs your presentation (keep reading).
Lastly KNOW WHAT YOU WANT! Do you want 3 months? 6? An unpaid leave / sabbatical? Remote work opportunity for 90 days? Figure out your "ask" - specifically!
🥇 Elevate Your Status
When you go into that room, you want to have a glow around you! That means ahead of your big ask (I'm talking weeks, even months), make sure to elevate your status in your boss's eyes.
"But I just do my job.. what am I gonna do.. promote myself..? How do I 'elevate my status'?"
Good question.
The short answer is, do more of your job. Bear with me: I bet you do a lot more peripheral things within your role that you don't get enough credit for. Am I right? Now it's time to use them.
But how? Well, wrap them up in fancy wrapping paper and put a big ol' bow on them.
Let me explain with an example:
When I used to work as a Financial Advisor at a retail bank, I often got leads passed to me by our bank tellers. In an ideal world, these leads would include complete contact information, a reason for the meeting, a date & time, as well as any helpful notes.
But they almost never did..
Every once in a while I'd ask a teller for more information, or politely urge that they be more detailed next time.
That's it.
Now, unfortunately, on it's own, this wouldn't help me "elevate my status" - and I wanted to go travel, bad! But what if I took this daily part of my job and formalized it, wrapped it in pretty paper and presented it to my boss at our next team meeting? Here's what I did:
I took the things I wanted in a lead, and made them into an acronym:
C - Contact Details A - Appointment Time & Date R - Reason for Meeting S - Some Helpful Notes
I then simply put this on a one-page print-out with a pretty picture of a car and presented it to my team. I asked that they each keep this at their wicket, as a reminder. My boss watched on proudly. In other words, by simply formalizing something I already did, the narrative was now that I had "championed a new Lead-Transfer Process".
Status: Elevated! ✅
Your situation will be unique - but there are always avenues to extend your value, or formalize something you already do. Remember: it's okay to use dorky acronyms, print-outs, etc. to make your contributions memorable. Other options might include:
Hosting "training sessions" for newer staff (on something you're already good at and do everyday)
Organizing a charity drive or team event
Picking up a shift for a colleague
Cleaning out that cupboard, or closet, that everyone neglects but complains about
Don't be afraid to get creative! P.S - If you can, keep a record of all those "shout outs" you get from your bosses and colleagues (via email, say). These come in handy for your travel request but also for future promotion talks!
💡 Shift Your Mindset: "Low Power Distance"
Power Distance refers to how we perceive the difference in authority between ourselves and our superiors. For example, do we dare speak our minds to our boss? Express our disagreement to a parent? Often, this is a cultural phenomenon (Japan: very high power distance, USA: very low), but it can also vary from person to person.
When it comes to asking for time off, though, the reality is you have to shift to a "Low Power Distance" mindset.
In other words, you have to accept the reality that your boss is just a person, too. They are someone who's looking to do their job with relative peace, and who certainly doesn't want conflict with their employees.
If you ask them for time off to travel (appropriately of course, but more on that later), they will not be upset. Much less fire you! They won't even hold it against you. At best they'll understand and give you the "yes". At worst, they'll apologetically tell you it's impossible and send you back to work. At the end of the day, your boss has their own (busy) life, and don't have time to keep petty grudges. If they DO, you don't want to work for them anyway.
So don't be shy.
Approaching Your Boss:
The key to any good presentation is the first impression. Here's how you optimize it:
⏰ Timing
The preparation phase (above) saw you raising your "status" through a variety of initiatives. Once you feel it is at it's peak - say, after a successful project, some recent praise, and/or a well-executed charity event - it's time to strike!
That said, make sure to consider the mental map you made of your business. If, for example, your end-of-quarter is this week, and your boss is evaluated by quarterly performance, perhaps wait until next week - when he's much more relaxed.
Universally though, you can also factor in days of the week and time of day. Specifically, aim for a Friday after lunch.
Why Friday?
For starters, Friday is when most of the week's work and stress is behind us, and we're looking forward to the weekend. In other words, your boss (like all of us) is more likely to have their mind on the "life" portion of "work-life balance" - which will help them empathize with your request.
Why after lunch?
After we eat, our dopamine levels tend to be higher, our cortisol levels lower, and because we're busy digesting, our brain-power is measurably diminished. Sufficed to say, all of these make for a more pleasant, patient boss who's less likely to come up with reasons not to approve your request. Obviously, the same applies to you - so consider eating a light lunch. You don't want to have mush-brain (and the burps) as you plead your case.
❓ Booking the Meeting
But how do you actually book the meeting itself? Do you have this conversation in the hallway, on the fly? Absolutely not.
You want to sit down with your boss, in private, and make a formal ask. In order to do so, you'll need to book a formal meeting. Here's how to approach it, and why:
Chris Voss is an ex-FBI negotiator and author of the best-selling book, "Never Split the Difference". In his MasterClass course, he describes his approach to obtaining "late check out" at every hotel he visits. He states: "I walk down to the lobby, and in a calm, relaxed voice I say: 'I'm so sorry, I'm going to make your day veeeeeeery difficult'"
He goes on to explain that this type of introduction prepares the receptionist's brain for "every possible worst case scenario". Given the vast scope of debauchery that can happen within hotel walls, their imagination will inevitably take over.
Then, when Chris simply asks for late check-out, the request seems comparatively easy, even reasonable, relative to their expectations.
The same concept applies for your boss.
When booking your meeting, send a simple, direct (but formal) email to your boss asking for a meeting on Friday after lunch. Don't be too happy or bubbly, nor rude - but make it serious and formal enough to induce some doubt. Then, when you arrive to your meeting, start with that same phrase:
"I'm so sorry, I'm about to make your day veeeery difficult"
Much like the hotel receptionist, your boss will be swimming in worst-case scenarios. Are you quitting? Have you committed a crime on the job? Broke something expensive? Demanding a raise? WHAT?
This anxiousness will make your ultimate request seem much more bearable.
Presenting Your Case:
The meat and potatoes. What to include in your presentation, and how to structure it. In short, the pitch will cover the following aspects, in order:
Presenting your value
Stating your loyalty
Honest statement of desire
Why you need it, Why Now, How company benefits long term
Make the ask (with a "how" question, and an "accusation audit")
How you will mitigate your absence
At the end I'll include a full example, to see it in action.
😎 Presenting Your Value
Start your pitch with a gentle, but confident reminder of your contributions to the business. Don't be afraid to use exhibits, if applicable. On one hand, this shows confidence and an understanding of your worth which is helpful in negotiation, but also gives the impression that you're about to ask for a raise. Luckily for your boss, that's not the case. What you're asking for is much more reasonable, right?
🤝 Stating Your Loyalty
Now it's time to compliment the business. Describe what you love about your workplace and why you intend to stay long term. This warms up your boss, shows them they're dealing with a dedicated, long-term employee, and perfectly tees up your next two points.
💙 Honest Statement of Desire
This is where you reveal the mystery. You admit, whole-heartedly, that it's been a life-long dream to travel the world. You describe your passion for geography and adventure, and how you find yourself longing to fulfill a long-held goal to explore, before settling down.
📈 Why You Need It, Why Now, How Company Benefits
You need it, because (as per above) you see yourself at this company for a long time, and you don't want to allow resentment to bleed into your daily work life. If this job stops you from living out your dream, it won't make for a happy relationship in the long run. Instead, if you can accomplish this mission, as a result of their blessing, you will return to a company which you appreciate more than ever. And perhaps for-ever. Why now? Well simply put, you hope (and firmly believe - based on the achievements you've just listed) that your contributions to the business will grow exponentially over time. With that in mind, you'll never be worth less to the company than you are today - so it's the most prudent to do this as soon as possible. As you can tell, baked into these responses is the answer to "How The Company Benefits": it does so by retaining a long-term dedicated employee who will owe the fulfillment of their dream to this company. Instead of burning out, growing resentful, or quitting, you will come back rejuvenated and most certainly more mature and well-rounded than when you left. This is essentially a growth and self-improvement exercise!
🙏 Making The Ask (including "Accusation Audit")
Here comes the "and so.." moment, when you summarize everything you've said above into one, final, formal request. Something like;
"And so for all of those reasons, my question is, how can I work with you to make a 6-month leave possible?"
OR
"With all of that in mind, how might we be able to make a 6-month absence happen?"
A couple points about the ask:
Notice the word "how"in both examples. Always frame your ask as a "how" question, as these illicit a feeling of cooperation, wherein the receiver is invited to work with you on a solution. These tend to yield better results - as per Voss in Never Split the Difference.
After you make your ask: shut up. The short silence might feel like a never-ending screech of awkwardness, but as negotiators (and salespeople) know, that silence is key. Don't ramble! Put your ask on the table, then wait for your boss to speak first. Let them process, react, and come back with an answer.
Before you drop your ask, Voss teaches that you should preface with an "accusation audit". According to negotiation theory, when we start by accusing ourselves of everything our counterpart might feel as a result of our ask, it takes the sting out of those emotions. For example; "I know I'm being incredibly selfish, perhaps even naive, and I'm sorry that I'm creating a huge headache for you", makes your counterpart less likely to feel those same sentiments. In fact, they might even defend you! This is based on a theory called labeling, which is explained in-depth in Never Split the Difference.
🔨 How Will You Mitigate Your Absence
There are two parts to this. The first is explaining how you will smoothly hand-off responsibilities to your colleagues / team and how you'll enable them to pick up the slack you've left behind. You'll want to be thoughtful about this. Obviously, they will miss your input (otherwise why are they paying you?) but showing some initiative to leave your team in the best possible spot will go a long way. Perhaps there's something only you do that you'll want to teach a colleague.
The second part is part of the negotiation. It's things you'll do in advance to - at least in part - make up for your upcoming absence. See below.
Negotiation:
To reiterate, anything you offer here will never equal what the company loses in your absence. It doesn't have to. What it does is show that you're proactive, responsible and willing to sacrifice to make this work. It re-emphasizes how much this means to you which in turn breeds empathy from your employer.
Here are some tactics:
🗓️ Length
My first thought is, leave the length for last. If 6-months is what you'd like to have, let that be the last thing you concede. There are other things to offer first. If push comes to shove and nothing else works, then you can pull the silver bullet and offer to shorten the time.
💪 Working Extra
Instead, start with "working extra" before you go. Depending on your job-type there are lots of ways to do this. From "extra shifts", to "working weekends" or "taking on an extra project". There's lots you can offer with your labour to somewhat counter-balance your absence. After all, they pay you to work - so what if you front-load some of that work so you can take time off later?
I personally worked every weekend for two months in order to extend my trip by an additional 3-weeks. Worth, every, second. Often though, your boss - although appreciative - won't even take you up on this offer.
🤐 Discretion
From there, if push comes to shove, don't be afraid to leverage precedent (or lack thereof). This one should be approached delicately, and might not work if you're close with all your colleagues - but bear with me.
To put it simply, bosses aren't just worried about letting you travel, they're worried about what would happen if everyone asked for the same thing. In other words, setting a precedent. If this comes up as an objection, it can sometimes be useful to tell them that.. perhaps.. that precedent doesn't have to be set. In other words, you're willing to include a "shut your lips" clause in the agreement, wherein you won't blab to your colleagues about the special treatment. This one isn't my favourite bit of advice, but depending on how eager you are (and if you're working for a big corporation), promising not to tell your colleagues tends to go over well with some managers. Desperate times and all that...
💻 Remote Work
The last concession, and this totally changes things, is to temporarily work remotely. Obviously this isn't the same as long-term travel - by any means - but if you've exhausted all other options and this is your last move: it at least gets you out there.
Usually, if you're getting to this point, your boss has already told you "no" to all the options above. This, theoretically, should make them more likely to say "yes" here. This is based on the psychological concept of "reciprocity" - the same one that makes us more likely to tip a server $5 after receiving a $0.05 mint.
For that reason alone, it can stand as your last-ditch effort to get out of town, albeit in a different way than you imagined.
Naturally, if remote work is actually your priority, a lot of the same principles will apply. That said, let us know via instagram DM's or email and if there's enough demand we'll write a specific article for Asking to Work Remotely.
🚨 AS A MATTER OF FACT: 🚨
If you still have questions or want some advice on your particular workplace scenario, don't hesitate to reach out at welcome@hangoverseas.net ! ⭐️⭐️⭐️ Here to help. ⭐️⭐️⭐️
EXAMPLE SPEECH
As promised, I'll leave you with a full example of one of the times I did it, incorporating everything we've discussed:
Preparation:
- Do your Homework: I combed through the HR policies at my bank, and found that a "leave of absence" is technically feasible, but is solely based on manager approval. I had work to do. I then mapped out the company situation. The most notable revelations were that a) we were very busy due to a nearby branch shutting down, and b) one of my manager's evaluation criteria was "the flow of promotions within his team" - in other words how much of his staff got promoted vs how much he lost to turnover (this is very typical among middle-managers).
- Elevate Your Status: Once I knew I wanted to travel, I got to work making my contributions known. I started answering every question in team meetings (you know the ones that anyone can answer but no one speaks up), I volunteered for every event and initiative, I put more effort into the treats I brought on colleagues' birthdays, and I formally introduced some initiatives of my own (like the CARS Lead Transfer Process we discussed earlier). I also made sure I was meeting my quota and dressed just that little bit sharper every day.
- Shift Your Mindset: This was a big one. I got to know my manager as best I could by making a bit more small talk than I normally would. This elevated my status but also helped wrap my head around him just being "another person" with feelings and motivations just like mine.
Approaching your Boss:
- Timing: I emailed my manager at 4:30pm on a Thursday afternoon, asking to meet the following day after lunch. My hope was it was enough notice to get the meeting, but not so much that he'd ask to rush it into the end of the day Thursday. Depending on your boss, time it accordingly. We ended up meeting on Friday at 1pm.
- Booking the Meeting: My email was short and succinct: "Hi Jeff, Do you mind if I put 15 minutes into your calendar for tomorrow after lunch? There's something I'd like to discuss. Thank you kindly, Andy" . The goal - as discussed - was to keep him guessing (and even assuming the worst).
- Your Opening Line: When I sat down I started with, "I'm so sorry, but I'm about to make your day veeeeeery difficult"
Presenting your Case:
🎙️🚨 MY SPEECH! 🚨🎙️
"I've been with the company for 2 years, in which I've never missed quota, I've worked my tail off to learn everything I possibly can and move forward in my career, and I've made a concerted effort to do the extra things as well. That includes helping my teammates and championing initiatives wherever I can. At this moment, his brain would immediately have went to the recent initiatives I had strategically undertaken ^ And frankly, I hope to do that here for a long, long time to come. I love our company and I'd consider it an honour to spend an extended career here. Loyalty^ With that said - (because there's always a but) - there's something that's eating at me and I wanted to share it with you. For as long as I can remember, I've had a burning desire to go see the world. As a kid I was glued to my toy globe and dreamed of adventure and exploration. Now that I'm older, and have colleagues who've actually done it, I see the way they come back home: more mature, more centred, armed with fresh perspective and more motivated than ever. Truly, Jeff, I'm dying for that same experience. Honest statement of desire^
If this place meant nothing to me, I'd quit and do it yesterday. But it does mean something to me, and I want to be here for the long haul. On the flip side, I don't want this to become a dream I never fulfilled, and let that resentment seep into my work, or my love for our business.
Now, I know I'm being massively selfish here, maybe even naive. And you must feel like I'm abandoning my post right when we're at our busiest with the other branch closing down. I might even be immature in this regard. But I promise you, I wouldn't be coming to you if I didn't feel very strongly about this. Accusation Audit^
I want my contributions to grow exponentially over time, so in some sense I'll never be contributing less than I am today. That's why I believe now is the best time. Why Now^
You will lose me for a few months, but I can promise you that what you'll get in return is an employee who's a bigger asset than he is today, and who will be forever grateful and dedicated to the business (and leader) that let him live out his dream. What's in it for them^
To sum it up, Jeff, how might I go about securing your approval to take a 6-month Leave of Absence?
Making the ask with a "how" question^
🤫 ***THEN SILENCE UNTIL HE ANSWERED*** 🤫
We ended up negotiating and I offered to train some younger reps, while also working every weekend for 2-months to extend my leave to 6.5 months. This worked for my manager as we were busier now than we were going to be in 6.5 months. (Yes, I got a bit greedy here, but ask and you shall receive!)
I ended up travelling for 6.5 months and saw 13 countries across 3 continents (South America, Europe and Asia). It was worth every bit of effort, that I can promise you!
Once again, if you still have questions or want some advice on your particular workplace scenario, don't hesitate to reach out at welcome@hangoverseas.net ! ⭐️⭐️⭐️ Here to help. ⭐️⭐️⭐️
Comments