The Art of Eliminating Risk

Train Tracks

Have you ever had to ask for permission to do something you really wanted to do?

Say you wanted to try working from home once a week. Or you wanted to make a lateral move within your company to dabble in a different kind of role. Or you want to rearrange the furniture in your place even though your significant other wants no part of it.

It can literally be anything.

If you’re like most people, you probably don’t even ask half the time because you’re afraid of getting turned down. Some brave souls do work up the nerve to but then don’t go about it as effectively as they could.

Not as effective: “Boss, can I work from home one day a week? I promise I’ll be really good! Pleaaaseeeee!!!”

There’s a much better way. It’s going to involve a fair amount of mental work, but it’ll really help you get the confidence you need to ask and make it virtually impossible to be told “no.”

Taking a Tip from Sales

I don’t work in sales, but here’s a secret: we’re all salespeople.

When it comes to our careers, we are our own agents. And that means it’s our job to advocate for our advancement and compensation. Which means we have to convince others to give us more responsibilities and more money over time.

Convincing other people to part with their money? That’s sales, baby!

And there’s one concept in sales that lines up perfectly with the kinds of requests I mentioned at the start of this post: eliminating risk.

When my wife goes to Old Navy to buy a new pair of jeans, she’ll try them on, walk in them, and ultimately decide to keep a pair (or two). Then she’ll come home and put them on again (indoors only, of course!) and walk around and ask me what I think. The labels will still be on them. She’ll hem and haw and think about it for a few days.

Eventually, she goes back to the store, shows her receipt, and gets her money back.

Taking out her credit card and buying the jeans is a trivial thing because she knows she can come back and return them.

She is taking on zero risk.

By making shopping a no-risk proposition, they’re tipping the scales in favor of making the sale.

Sure, some people will return the items, but a lot of them will wind up buying something else while they’re there. The important thing is that they’re making that  decision to pay an easy one.

Free Magazines!

Have you ever gotten a great deal on a magazine subscription? The kind where you get three or six issues for free and all you have to do is provide a credit-card number and then remember to cancel before the free offer expires?

I love those! All I do is put a reminder on my calendar to shut off the subscription before that trigger kicks in and I’m good to go. I love me some free magazines.

But I know a lot of people that stay away from them because they feel it’s sneaky. Also, they worry that they won’t remember to cancel and then they’ll be upset when the bill comes.

This is an example of a company trying to minimize the risk while creating a system that will get them some paid subscribers. There’s no risk as long as you play by their rules.

There’s a little more risk here, but nothing crazy.

What you Should Do

Keep these examples in mind when you’re brainstorming your request or your pitch. What you have to figure out is how you can frame it (and fair warning: it might be a lot of work) so by the time you finish your pitch, the other person just has to say: “OK.”

Think about that though: it’s not easy.

You have to make a good case while also addressing any objections they may have about your idea (again, that’s all sales). The goal is to leave them with no unanswered questions or doubts. And for the tiny bit of risk that might still be there (eliminating 100% of the risk is really hard), you have to put some kind of money-back failsafe-equivalent that allows things to go back to the way they were without anything getting broken.

Working From Home

Tim Ferris goes into great depth on the subject of working from home in The Four Hour Workweek. It’s been a while since I read it, but as I recall he talks about minimizing risk quite a bit.

The way you’re supposed to pitch this is as a great idea that will be beneficial to everyone (with numerous points on why that is) and as a temporary experiment that is in no way permanent.

Your boss will get updates periodically about how it’s going from you and from other coworkers and when the trial version is over, you’ll meet to discuss if this is something that can work more permanently.

You run through all the risks, how you’ll address/minimize them, and then highlight the positives (I’ll be able to work more! I’ll be more effective! I’ll be so happy that I’ll be more enaged and effective! You have an extra desk that another employee can use!) that will come of it.

At the end of the day, all the boss has to say is “OK,” because he’s just conceding to a temporary test that has a lot of potential upside. The biggest “fail” of the proposal would be that it didn’t work out as well as you pitched it and that everything will just go back to the way it was before.

No harm, no foul.

That’s the art of eliminating risk: doing a whole bunch of work so the other person simply has to say “OK.”

It’s important to put yourself in the other person’s shoes to really think about what kinds of objections they might have and how you can solve for them.

My advice? Start with something small. Before you go into the really big asks, it’s better to get your feet wet with something relatively simple. Maybe you have something you have to go to during work hours and you want to leave early on a certain day.

Easy enough, right? Pitch it to your boss by telling him you’ll come in early to cover the work, lay out all the projects you’re on and their status (to show everything is on track) and that you’ll be on email after your event to make sure nothing has gone wrong. Oh and of course you’ll be on your cell phone just in case.


If you’re a developer and you want to try a different technology you’ve never used before (maybe it’s a new javascript library or something else entirely). Chances are you can just do it and not ask, but if you do, you can frame it like so:

I’ll build this project in a way that makes it easy to fall back to the way we typically do this, so if we run into some unexpected bumps in the road, it’ll be pretty easy to fall back without losing any time. And since I really want to experiment with this technology, I’m willing to work on it outside of work hours to make it work. Either way, at the first sign of trouble we’ll be able to fall back. No harm, no foul.


Now go try it!

And if you want to read a great book on sales, check out Spin Selling by Neil Rackham: it’s a fascinating read that’ll give you a nice head start on building your sales/persuasion skills.

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