Meet Zen Cachola, a senior sales rep at PandaDoc. Zen is at 133% of her sales number, sitting on a beach in Puerto Rico, with five sales days left in the month.

This may sound too good to be true for some salespeople, but taking a vacation without missing quota is possible with good planning and collaboration. 

The good and the ugly of taking vacations in sales

There are 19 to 22 sales days in a month. When you take three to five of them off, you’re giving up 10 to 25% of the time you have to close business and create future opportunities.

Vacations make you happier. They’re good for your health. They align with personal goals and provide you with perspective, culture, and a chance to see friends in faraway places. Vacations make you better.

But they’re really hard to take in sales -- particularly when you carry a monthly quota. If you’re new to carrying a number, learning how to take a vacation can be trial and error.

Below, I’ve outlined nine key strategies for taking successful vacations, the pros and cons of different vacation lengths, and a few tips for managers on how they can help their team take needed time away.

9 keys to taking a successful vacation

These tips were inspired both by Zen’s experience and an email thread on the Modern Sales Pro forum (an exclusive community for sales operations and sales leadership professionals) with Richard Harris of The Harris Consulting Group.

1) Plan ahead with your manager.

Your manager is your partner in success. Work with them to create a plan that makes you both feel confident about the break.

For example, Zen and her manager planned for her five-day vacation 60 to 90 days in advance.

2) Increase activity before you leave.

First, calculate how much activity you need to do to hit your targets. Let’s say it typically requires 20 demos per month to hit goal. If you’re taking a quarter of the month off, ramp up your activity while you’re in the office so you still get those 20 meetings done.

Zen planned 90 days of 2X activity, 2X demo meetings, and 2X closing calls to make up for five days of selling on PTO.

3) Maintain focus.

Increased activity shouldn’t mean a decrease in quality. To maintain the quality of each meeting, Zen worked with her manager to create a unique playbook for each opportunity. They used Zoom recordings to play back, listen, and catch things Zen may have missed during the call itself. Sometimes, if the call went extremely well, they sent highlights of the recorded demo to the influencer to pass around internally. This can expedite the buying process.

4) Do a deep dive on opportunities that need your attention.

Schedule time with your manager to review all of the opportunities in your pipeline and make sure there are detailed notes on each one. If you expect an interaction with the prospect to occur while you’re away (such as a demo or email exchanges), introduce the contact to your manager while you are still in the office.

Prioritize opportunities based on timeline and the buyer's process. Zen explains the strategy that she took: “Any opportunity who gave a zero to 14-day launch date got our attention, whereas opportunities with 30-plus day launch dates received a decision matrix, Proof of Concept (POC), and a guide to key conversations to have internally.”

5) Automate prospecting.

Set up automated drip campaigns to email leads multiple times while you’re out.

6) Don’t use an out-of-office (OOO) message.

An OOO is a blocker to a prospect who wants to engage. Do you want to block a prospect? Instead …

7) Let your manager step in.

Give your manager access to your email account. They can look out for requests from key opportunities and responses to automated prospecting emails.

8) If you feel you have to, check emails on vacation.

Create a time limit and "give yourself permission.” But cap yourself at 30 minutes. This time limit will force you to be hyper-productive.

9) Take your vacations at the beginning or end of the month.

This way you have a full three weeks to focus on hitting your number.

Pros and cons of vacation types

1) The long weekend

After spending four years in closing roles, this has become my preferred way to take time off. Build a vacation around a weekend.


  • You can take a Friday, Monday, or both off, giving you three to four days to get away with only one or two days out the office. This works even better when you can time your vacation around an existing three-day weekend like Memorial Day.
  • You can take a long weekend vacation every month and maintain top performance.
  • It’s easy to coordinate the long weekend with friends or significant others.


  • The long weekend is great for trips of shorter distance, such as Boston to Miami or New York to Austin. Going to Paris for three to four days might result in an exhausting and unfulfilled vacation.
  • If you feel like you need to disconnect, this might not be long enough.

2) Three to five days

Is there somewhere far off you really want to go? Or do you feel the need to truly unwind? Taking three to five days off and using the weekend allows you to travel for five to nine days.


  • You get enough time to go to a foreign country, recover from jet lag, and relax.
  • As long as you work with your manager, this trip shouldn’t hinder your performance.


  • You’ll need to plan ahead.
  • It’s hard to pull this off more than twice per year.

3) The true getaway

Imagine taking off two, maybe three, weeks to travel through India, Japan, or somewhere on your bucket list. You could fully immerse yourself in the culture and disengage from work.


  • It’s a true break in routine.
  • You can cross a dream trip off your list.


  • A break this long can wreak havoc on your performance.

Note: I’ve tried this. It didn’t work for me. I sailed around Croatia while taking 10 work days off. Although it was incredible, and I had excellent support from my manager, my performance declined for two months. My pipeline didn’t go back to its normal size for six weeks.

Some notes for management

  1. Encourage your team to take vacations. If you make your teammates feel guilty when going away, they may not take a needed vacation, and if they do, they may not get the most out of it.
  2. Set an expectation of what proper planning looks like. You’ll need to take the lead on this for less experienced reps.
  3. Can your organization afford to provide reps with a reduced quota one or two times per year? If so, quota relief is a powerful way to improve sales team health.

It may be challenging to take time off in sales, but it’s 100% necessary to live a balanced, fulfilling life. Use these tips to have a great vacation without sacrificing your quota.

HubSpot CRM

Originally published Jun 30, 2017 6:30:00 AM, updated June 30 2017


Sales Strategy