How to handle holidays in remote work

Hey,

I'm Sergio Pereira, and this is the Remote Work newsletter 👋

Last week I told you the economics of remote work and what's separating most of us from those fat USD salaries.

Today, I'll write a bit about how to handle holidays in remote work. Once again that was part of a recent conversation, as I tweeted, this Startup Founder is frustrated about holidays in India, where his tech team is based. "Nothing gets done", he says.

I've been part of these conversations more times than I can count, both as a CTO managing remote teams around the world, and as an employee or contractor who enjoys taking time off once in a while. Let me lay down some facts, to start with:

• There's big discrepancies in "holiday culture" around the world.

• Eg1: US work culture is known for taking little time off, with few days per year, and a common frown upon anyone taking a day off.

• Eg2: Europe work culture is known for having 20+ days of vacation per year written in contract, abiding by local labour laws.

• Eg3: India has many festivals throughout the year, but they differ per region and per local culture/religion.

• Eg4: Pakistan has few festivals per year, both each of those are like a full week long.

I could go on and on, but the main point is: Holiday culture means different things in different places around the world.

So, how can we get around this in a remote team, which has team members based in all of those different places??

Having been a remote CTO I've set policies for this, and I usually recommend having a well defined holiday policy, counted as number of days off per year. No one in my teams knows, or cares, about my local holidays in Portugal, I should count them as normal days off.

For some reason, national holiday are so natural for us that frequently we forget to inform our teams. We must do that, though. The same way we'd announce that week off over summer, we must inform about national holidays. Treating those as normal days off is a key step to standardise time off across a team, even if people are in different countries with different amounts of local holidays.

Now, while most people in the office are off on the same day (eg: 4th of July in the US). In a remote team spread around the world is hard to have a single day around the year in which no one works. Conversely, is common to have someone off every week, if the team is large enough.

This is where documentation and async processes come in very handy, as I wrote here. Work should not stop if a team member is out.

And this is where I close the loop on this Startup Founder blaming the holidays in India for "nothing getting done" at his startup. Holidays are not the problem, processes are.

If months go by and there's no new feature in prod, or the ones that go live are full of bugs. Then, let me tell you, there's hard questions to ask:

• Are priorities clear?

• Is the scope of work well defined?

• Is there a capable team to deliver?

• Is there a deterministic process to release to prod?

As a Fractional CTO, I'm a part of this conversations very often and the answer is never "Yes" to all these questions. With this specific Startup Founder, the answer was a clear "No" to most of them, actually.

For the last 8 years I've been delivering software products, and growing engineering teams on a fully remote basis. It takes some efforts to create the right processes, especially when the team spans multiple time zones. But it has tremendous upsides:

• I can hire anywhere around the world

• Time to hire is much faster than if I'm tied to a certain city or country

• Teams have a much more diverse composition

• I can leverage an almost 24/7 operation, given different team members are working at different times of the day

In other news, this week at the Remote Jobs Braintrust, we celebrated Kurian's new job, and we learned from his approach to job seeking, which got him 2 offers on the table. Some key takeaways:

• He understood what applications were generating interviews.

• He was failing most of those, and he understood where he was falling short.

• He built a side project to showcase key experience.

• He started advancing in those interview rounds.

• As a bonus, he used the side project as a lead magnet on Twitter and Linkedin.

This was truly insightful. The recording is available to everyone on the community's Slack and Notion.

At Jobs Copilot, I'm about to launch the Auto-Apply functionality, which will materialise the vision of "getting job interviews scheduled on your sleep". It will be first launched in private to existing customers. Keep an eye on your email, you'll get an invitation from me soon.

Thanks for reading this newsletter until the end. You can read all past editions here. Make sure to share it with your friends and colleagues so they can read it too.

If you're interested in sponsoring this newsletter, send me an email or DM.

Cheers,

Sergio Pereira, 
Startup CTO & Remote Work Lover