Going To Dinner. Early in my career, I was really good… | by Roy Rapoport | Apr, 2026 | MediumSitemapOpen in appSign up<br>Sign in

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Going To Dinner

Roy Rapoport

3 min read·<br>Apr 22, 2026

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Early in my career, I was really good at getting things done. I was also, I now realize, occasionally leaving a trail of quietly damaged relationships behind me — not out of malice, not even out of indifference, but simply because I wasn’t tracking something I didn’t yet know I should be tracking.<br>I’ve been thinking about how to describe what I wasn’t tracking, and the best framing I’ve found starts with dinner.<br>Imagine you come home and say to your partner: “Hey, where should we go out tonight?” One way to evaluate how that conversation goes is purely against its explicit goal: did you agree on a restaurant? Yes or no.<br>But there’s a second dimension that has nothing to do with that question: Is your relationship stronger or weaker at the end of the conversation than it was at the beginning?<br>These two dimensions are independent of each other, and that independence is the whole point.<br>In the best case, you figure out where to go and the conversation was easy and warm and maybe even a little fun. Great. But consider the other combinations:<br>You can fail explicitly and damage the relationship — you get into an argument about Thai food, reach no conclusion, and go to bed annoyed at each other. That’s the obvious bad outcome.<br>You can succeed explicitly but damage the relationship — you push for Thai, you get Thai, but your partner’s resentful because you always get Thai. The goal was met. Something else was spent.<br>And you can fail explicitly but strengthen the relationship — you abandon the dinner plan entirely, stay home, order pizza, and actually talk to each other for the first time in a week. No restaurant selected. Net positive.<br>Press enter or click to view image in full size

Most people intuitively understand this in their personal lives. Fewer people apply it consciously at work — particularly earlier in their careers, before they’ve felt the accumulated weight of relationships that have gone quietly cold.<br>To be clear, I’m not arguing that you should never spend relationship capital. Sometimes getting the thing done matters, and the cost is worth it. What I’m arguing is that the spending should be conscious. You should know you’re doing it, decide it’s worth it, and own it — at least to yourself.<br>And even when you’ve decided the spend is worth it, it’s worth asking: how do I minimize it? Getting what you need doesn’t require scorching the earth to get there. The goal is the best possible ROI on the relationship capital you’re spending — maximum outcome, minimum unnecessary cost.<br>The more senior you get — not in title, but in the sense of needing other people’s willing cooperation to get things done — the more this matters. You can’t mandate your way to good outcomes at that level. You’re working through relationships, whether you’re thinking about them or not.<br>Better to think about them.

Written by Roy Rapoport<br>628 followers<br>·2 following

I have goats. I work in technology. You know most of the rest.

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