A Learning a Day

I was using Ramp’s app for a work expense recently and realized I’d forgotten to upload the receipt, which normally kicks off an exceptions process.

Except the receipt was already there.

I asked how, and learned Ramp has a direct integration with Toast, the restaurant payment system. Pay with a Ramp card at a merchant on Toast, and the itemized receipt gets attached to your transaction automatically. No photo, no upload, nothing from you.

This is what good integrations do. They take manual load off the user without asking for anything in return.

It’s also one of the hardest things to prioritize when you’re building a product, because integrations like this rarely show up on a roadmap next to the flashier features competing for the same slot.

But the experiences that become invisible, because you made them that easy, are the ones users end up remembering most.

I heard someone recently describe a formative moment from his childhood. Every time something difficult happens to him now, he thinks back to what his mom said every time he told her something bad happened: “Oh honey, things could always be worse.”

He imitated her voice as he said it, and the whole group chuckled.

He said it’s the reason he’s an optimist today, because things could always be worse.

It isn’t a new idea. But hearing the story brought it to life in a beautiful way.

One ideal I’ve found hard to live up to: being consistently loyal to people who aren’t in the room. So much of what we talk about is our reaction to other people, because so much of our life is shaped by them.

Here’s an alternate ideal I’ve found helpful to aim for. With the people you work with regularly, or care about, be someone they know will tell them directly when there’s a problem. So, you never let things fester.

That way, when you do end up talking about them behind their back (and you likely will), the conversation stays focused on getting to the root of the problem.

Often what’s missing isn’t data. It’s insight.

Just as often, what’s missing isn’t good ideas. It’s clarity.

Someone gave me feedback the other day. But they didn’t just hand over comments.

They took the time to understand what I was actually solving for. Then they shared a revised version based on what they thought could help. And they added a short note: no pressure if this doesn’t land, feel free to ignore it, this stuff isn’t easy.

I felt elevated by the way they carried themselves through the whole thing. It was one of those experiences when the exercise of receiving feedback felt like a pleasure.

It made me think harder about how I give feedback myself.

Much to learn, I have.

Time dulls the pain from every wound, especially the emotional ones. That won’t help in the moment, when a fresh wound is still raw. But it gives you perspective.

How many emotional wounds from ten years ago can you even remember right now? Most have faded. You went numb to them over time, and eventually you could smile or shrug about the same thing that once felt unbearable.

Even this will pass.

If you picked up your phone to get one specific thing done, and you’ve done it, put it down.

And just stare.

It’s hard at first. The pull to open it back up is strong, to keep scrolling for one more hit. We love searching for that small comforting hit of having checked everything there is to check.

But it’s worth training ourselves to put it down.

And stare some more.

It’s amazing how many things feel better with a bit more calm, tact, and humor.

The problem is rarely the what. It’s almost always the how.

An idea that we discussed recently that stuck with me: ten extra minutes spent making sure what you send is concise and clear can save the organization two hundred minutes.

The math is simple. Send something vague or sloppy to twenty people, and each of them spends ten minutes decoding what you actually meant.

Brevity and synthesis aren’t just good writing. They’re a form of respect for everyone else’s time.

A good friend put it simply: accountability goes up, credit goes down.

When things go wrong, leaders take accountability. When things go well, credit flows down to the team.

One of the clearest signs of bad leadership is when that relationship reverses.