Selling to friends (and telling crushes you like them)

I was chatting with a friend of mine the other day, who remarked:

I’ve got a question for you… I’m working at this company where I get a referral bonus for new hires or new customers, and when I told some of my coworkers that I was friends with the CEO of [Company], they said that I should try to get them to sign up.

…and I was like “whoa, that feels really aversive”. So I was wondering if you have any tips on selling to your friends.

Turned out this is a question I had pondered before, myself. Specifically, last October I found myself puzzling over the question:

“Why was it easy to ask friends for money when I was starting Complice, but not now?”

Fortunately, most of the conversations in which that had happened were recorded in the form of chat logs, so I was relatively easily able to investigate the question framed as such. First, I made a list of relevant factors that were different at the nascent stages of my company versus several years in:

• in 2013 it was kind of an exclusive offer: you couldn’t just decide to sign up without me contacting you… and I was only looking for ~10 people to start. Not only that, but if I hadn’t messaged them, they probably wouldn’t have even known that it was happening… so there was a sense in which I was giving them valuable information. Whereas now, many of my friends have heard of Complice already.
• I was offering a ~discount: I originally thought the price would go up by a factor of 2-3 after the initial cohort. It ended up going up a little.
• at the time, I was in it for information, rather than money: I was pretty clearly looking to test my lean startup assumptions, more than I was just looking to get rich off them. The answer to “would they pay” was more valuable to me than the few hundred dollars of cash I made in that phase.
• I needed to ask my friends: at that stage, I had no product or website (not even a name) so the only way I could get customer validation was to approach people directly and explain the idea.
• it was more clear that it was a general goals process rather than a productivity app: Complice currently looks a bit like a todo list app (and it is, but also not!). Having someone pitch you their todo list app out of the blue is maybe annoying? Having some one ask you “would you like someone to check in with you daily about your goals?” feels more inviting, maybe.
• I was inviting them to join “a core group of people who are committed”: that sort of thing is exciting! Not everyone will want to join a particular small, committed group, but probably most people like to get an invite to such a thing.

So many reasons!

Note that these aren’t answers to “why did it work?” It worked because I have cool friends who are willing to invest money in promising bets to improve their lives. I guess to some extent also it worked because the interaction was non-awkward, and that was facilitated by the features above. But the questions we’re interested in are

1. Why was it non-awkward then?
2. Why would it feel awkward now to just message people directly and pitch them on Complice?

What’s awkwardness?

Awkwardness occurs when someone does something that’s inappropriate for a given social context, whether due to a slip (eg they accidentally say something that they hadn’t intended to say) or due to a lack of shared understanding of what the social context is.

In this fantastic Steven Pinker talk, which I’ve quoted before, Pinker describes Alan Fiske’s Relational Models theory, which posits that people use four basic models for organizing their relationships: Communal Sharing, Authority Ranking, Equality Matching, and Market Pricing. He then goes on to say:

Now [the previous examples] are cases where everyone knows which relationship types are enforced. In cases when relationships are ambiguous, a divergent understanding can lead to an unpleasant emotion, that we have a name for: awkwardness.

One of the examples is how at a cocktail party, you might go up to your spouse and eat a shrimp off their plate, but you wouldn’t do the same with your boss (at the very same party). Check out the whole talk for more.

So it seems that some sort of relationship mismatch that sometimes shows up when a friend is trying to sell something to another one of their friends. This isn’t exactly news—Pinker notes later in the talk, “It’s a well-known bit of conventional wisdom that good friends should not engage in a major business transaction, like one of them selling their car to the other.” Negotiating is appropriate for a Market Pricing relationship, but can put a strain on a Communal Sharing relationship.

And this is a large part of what’s potentially happening when people try to sell things to their friends (anyone who’s lost a friendship to a multi-level marketing scheme definitely knows this can be tense). So we can basically accept that as a default, and focus on the “why was it not awkward in this case?” question.

(Re: defaultiness… it’s worth noting that I have a bunch of friends who do manage to mix payment and friendship reasonably effectively, and that this seems to produce lots of awkwardness at the start but I can imagine it becoming more comfortable over time. Examples one and two)

To do that get more clarity on this question, let’s look at another awkward-by-default situation, and what can be done to make it non-awkward.

Other awkward-by-default situations

One that my friend brought up in this conversation (and compared it to the selling thing) is the issue of “telling a crush you like them, and if it’s not reciprocated, it poisons the friendship”. I noted that I had successfully experienced that (from both sides) and had it go fine. (I’ve also heard several success stories from other people.)

In these situations, what seemed to make a difference is that it was shared not with the expectation that the feelings would necessarily be reciprocated, and furthermore that even if the feelings weren’t reciprocated, then having common knowledge of one party’s interest will still be valuable—ie it’s mostly not held as having a downside.

This is in contrast with when the sharer is thinking of it as a bet: “either they’ll like me or they won’t, but it’s worth the cost of finding out” or (even worse) as a dream: “surely they like me [and I’m not even going to imagine the world where they don’t]”

Instead, in the non-awkward case, the person is presenting their crush with an opportunity: “I would be open to doing this other thing with our friendship if you would!”

Another factor I think is often relevant is communicating clearly and specifically. If you just say “so btw, I have a crush on you,” that can leave a non-reciprocator feeling awkward because they don’t know what that really means, or how they’re supposed to respond. Whereas if the person adds “…to be more specific, you’re a special person for me, and I get little fluttery feelings sometimes when I think of you…” then that helps a bit. Even better is to further append “…and I’m also enjoying our friendship as it is, and am fine with it if you don’t feel that way.”

This of course presupposes that that you are in fact fine with that. If it’s not, then whether you lie and say it is or not, you’re probably going to have a bad time. But this post can’t help you in situations where you’re not fine with the friendship staying the way it is. You have a different problem there. (This blog post might help though.)

Conclusion: Make it about information

So what do we find when we look at these two examples together?

I originally had several bullet points here, but literally all of them could be summarized as “make the conversation be about information”.

• it’s important to be okay with a “no” = care about what you learn, not how they respond
• it’s way easier in the validation stages than when I already know I have a decent product & pitch = it’s non-awkward when I’m looking for information, not money
• it’s non-awkward when it feels like an opportunity, rather than a demand = it’s non-awkward when I’m offering you valuable information
• it’s easier when you’re making an exclusive offer = it’s non-awkward when I’m offering you valuable information

The few other factors end up being not that relevant without this. It would still be pretty awkward if I were to message my friends and just offer them a discount (which is one of the other “differences” I noted in the first section) without any of this other stuff. It would still feel “salesy”.

By contrast! I had a fair bit of success posting to Facebook last fall:

“If you’re thinking of signing up for my productivity app Complice but haven’t yet, comment below. I’ll give you an additional week of free trial if you let me watch (via screenshare) & take notes while you sign up (I’m trying to improve the onboarding experience).”

This is a discount of sorts, but more importantly it’s about information again. If I had just posted “If you’re thinking of signing up for my productivity app Complice but haven’t yet, comment below. I’ll give you an additional week of free trial if you sign up this week” …then I might have gotten a few signups, but it would have felt ickier.

Because with it being about information, their implicit obligation to me is fulfilled as soon as we’re done that initial call. I’ve gotten the value I was asking for from them. Otherwise there’s potentially a weird pressure on them to actually subscribe at the end of their slightly-longer trial. And I think people would implicitly anticipate this being true, well before it actually happens.

So if you’re trying to communicate something that has the potential to be awkward, make the interaction about sharing information (both directions) rather than about achieving a particular outcome.

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