Do small favors, ask for big ones

There’s a scene I love in the Amazon original series Red Oaks.

It goes like this: David, the young tennis instructor protagonist, has agreed to play doubles with the country club president Doug Getty under the false pretenses that he’s Doug’s nephew (rather than his instructor/employee). They win, which earns Getty “a case of Bordeaux and bragging rights”. Afterwards, David interrupts Getty to complain that he’s being underpaid for the subterfuge. 

Getty: (annoyed) What?

David: I want a hundred an hour, not 50.

Getty: (bemused) I beg your pardon?

David: I want a hundred.

Getty: What do you mean, a hundred? You agreed.

David: Yeah, to be your doubles partner, not your nephew.

Getty: Oh, so it’s more to be your nephew? I didn’t realize that. What the hell do you care? You’re never going to see Marty or his smiling kid again.

David: Well… I don’t like lying.

Getty: (inhales cigar) Hmm. But you’re okay with extortion?

David: 100 is fair.

Getty: (smiles, shaking head) But shortsighted. (Getty pulls out a wad of cash from his back pocket and hands it to David)

David: What do you mean?

Getty: Well, you could have left here tonight with something a lot more valuable: Me owing you a favor.

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A few months ago I wrote some advice to the oblivious early-twenty-something version of myself, and this is effectively part 2 in that series.

I remember being a new grad in the workforce wondering how exactly I was supposed to interact with the intimidating & powerful people around me (my boss, my VP, the founder of the company, etc) and mostly failing in my attempts to impress them without being annoying. So maybe this will help someone out there do better. 

The lesson of the scene above is that games of reciprocity are constantly being played being people, including between powerful and non-powerful people, and you can really screw yourself if you misunderstand how to capitalize on your positioning.

In Red Oaks, David lives at home and works a summer job to make ends meet, whereas Getty makes more than a million dollars a year and has lots of social prestige. Getty isn’t exactly David’s mentor but he holds significant financial and social power over him. 

Up until this point in the series David has been performing a series of small “favors” for Getty. They aren’t all technically “favors” since they include things like showing up on time for work and being an effective tennis instructor — things for which he is of course compensated. But showing up and doing your job without hand-holding still counts as adding value; people who can’t do that take time and effort to replace. Additionally, he’s done Getty a few bona fide favors such as temporarily fabricating his identity and helping Getty win a tennis match.

All of these fall into the category of “small” favors. It’s important to remember that non-powerful people are by definition only capable of giving small favors. David can’t hook Getty up with a business deal or introduce him to somebody really important. But he can do small things every day to make Getty’s life easier, and make it up in volume.

Where David screws up is by trading all of his deposits of small favors for a very measly small favor in return. A pittance! Getty is a multi-millionaire; he does not care at all about a few hundred bucks. He’s also someone who was positioned to radically transform David’s life — had David waited, and kept doing more and more things to help out Getty, he might have been able to ask for something massive in return. But, alas.

Is the lesson here is not to go through your professional life with a mental ledger of who-owes-what and to be incredibly calculating and tactical in all of your interactions with others? No. 

Instead, the lesson is to understand what value you can provide to other people, and to be smart (both in timing and magnitude) about the value you ask from them in return.

For example, say that you’re a new entrant into the workforce at some company. Basically, you’re a grunt. You only have the ability to add small amounts of value at a time, but you can do it over and over and over again, like one of the workers[1] in Warcraft 3.

“Off I go then!"

A good example is the job of entry-level sales rep or SDR. Every call you dial or email you send adds a minuscule amount of value to the business, but you can do each of those tasks dozens or hundreds of times per day. That’s not an insult — that’s the job. There’s dignity in that job.

(Sidenote: This is one reason that it can be dangerous to read “The Four-Hour Workweek” at the start of your career. In most grunt jobs, responsiveness and availability is how you add value [instead of solitudinous deep work], so throwing on an e-mail auto-responder to prevent interruptions can be self-defeating.)

What the grunt should remember is that in the course of performing this work, he or she is accumulating small little piles of goodwill with surrounding important people (boss, boss’s boss, etc). The key thing is to let that goodwill compound for a long time  — not exchanging it for small trinkets — to instead wait to cash it in one day for something big that only an important/powerful person can grant.

The nuance is not whether to advocate for yourself — you should — but how often to ask & what to ask for. Most people know a squeaky-wheel coworker who is constantly advocating for themselves; constantly pushing for raises or better assignments. These folks do get ahead, but only for a while. They tend to top out when the important people get tired of constantly having to think about them and their needs.

So here’s my gruntly advice: Give. Give away value, give away credit. Do it at high volume, especially towards important people — make their lives easier, and make them look good. And don’t feel like it has to be big, heroic things… a steady, reliable drip of small to medium sized things will do (remember, you were hired to do gruntly work in the first place).

And then wait. While you’re waiting, think about what you really want, something HUGE, something that’s almost scary to contemplate, and wait for an opening to ask for it. Don’t be a squeaky wheel in the meantime, just produce. Then shoot your shot.

I can’t tell you how many times one of our portfolio founders has said “such-and-such employee worked their butt off for years, did their job and rarely asked for a thing, and then when they asked for [an international assignment / a VP title / to leave and found their own startup with us as advisors] we were really excited to make that happen for them”. That’s how you make the system work for you.

[1] Astute readers will note that this is technically a peasant, which is different from a grunt, which describes something else. It felt rude to call my readers “peasants”.