How To Negotiate Remote Work

Tim Ferriss may be best known for inspiring a new generation of entrepreneurs, but in his book The 4 Hour Work Week, he also lays out an effective strategy for employees to gain leverage and negotiate remote work.

He frames the discussion around the following question:

“How do you train your boss to value performance over presence?”

You need to be able to show them that you get better results outside of the office. This means that not only do you have to get better results, but you also have to measure these results.

Your results should show that your remote work output is higher than your in-office output.


The easiest way to do this is to document some metrics that do a good job of representing your performance.

If you work in customer success like me, this might just be account growth over a quarter - if I can prove that my accounts grew 20% more whilst I was working remotely than in the office, I have leverage. Of course, there’s going to be multiple other variables that impact this metric, but the key is to find the best one and prove you’ve increased performance.

If you’re a mechanical engineer, this might come down to the number of designs per day that you’re producing. If you can prove that working remotely enables you to produce three more designs per day and three hours of additional billable client time, then you have leverage.

If you’re a more experienced employee and a large part of your job involves onboarding new hires, you might mention enhanced productivity in regards to training these new employees and getting them ready to contribute as fast as possible.

You get where this is going. Identify a quantifiable performance related goal that you can measure. Prove that you perform better when working at home. This is harder for some jobs than others, but if you’re in any sort of environment in which KPIs are used, that’s a good starting point.

Keep in mind that having a brag document here might be really helpful, as it’ll easily allow you to showcase your wins and tie them back to you being able to work remotely.

For explanations behind why you work better at home, Ferriss mentions that you could bring up removal of commute and fewer distractions than at the office.

Business Decision

One thing you don’t want to do is present remote work as a personal perk. If your company doesn’t offer the ability to work remotely currently, it’s unlikely that your simple desire to do so will change their mind.

Rather, it needs to be framed as an effective business decision. If your output increases outside of the office and you have hard data to back that up, then that becomes harder to refute than remote work just being a perk you enjoy.

Let’s go back to our example of the senior employee. If that person is able to ramp up three new hires per week working remotely rather than just one (say due to increased focus and limited distractions), then that clearly benefits the business in terms of worker output.

Trial Period

Once you have the data, talk to your boss and outline a revocable trial period for working remotely.

This could be something like working from home Mondays And Tuesdays for two weeks.

Ferriss actually outlines a step by step script you can use in his book - here’s what I took away from it:

Once you’ve hopefully secured your trial period, you overdeliver on your remote days.

You ensure that they’re your most productive days of the week. This might mean having to work extra time in the short run - probably worth it.

Expanding Remote Time

Once your trial is over, set a meeting with your boss to discuss the results of the trial period. Again, have evidence ready and prepare a short one-pager clearly detailing your increased productivity.

Suggest increasing your ability to work remotely to 4 days a week - again, having good negotiation skills here comes in handy as there will likely be minor objections.

Ferriss notes that it’s important to not get overly defensive after an objection.

You want to acknowledge the validity of your boss’s concern - if you don’t, you’re just going to turn this into a battle of ego rather than an actual productive discussion, which is what it should be.

I hope the above also illustrates that negotiating remote is not some binary event. In all likelihood, asking just once and hoping for your boss to allow you to work remotely won’t work.

Rather, it’s a process. You go from trying to negotiate one day out of a few weeks to a few days per week to full time. Each step of the way, you have direct evidence justifying the why behind this change in accommodation.

You’re ready to concede a few days and you realize that you might actually need to work harder on your remote days in the short run.

Remote Work Consequences

Something I don’t see being talked about as much is the downside to remote working.

Often, people will try to use remote work as an escape from their actual job. Somehow they’ll think that just because they’re not present in the office, their life got better (despite having to do the same exact work).

Sure, it might be true you don’t have to commute and you’ve unlocked a new batch of time that wasn’t present before.

But if you didn’t like doing the work in the office, you’re not going to like doing it at home (or in Bali, depending on your inclination to travel).

So be sure to get that part sorted first. Find work you enjoy and then sure, if you work better remotely, use these tips to get you going. But don’t try to use remote work as a band aid solution if you don’t enjoy your job.


Thanks for reading. If you enjoyed this, you might also enjoy my discussion on keeping a brag document as well as my thoughts on skill stacking.

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