Overdeliver Without Overwhelming.

that's a screenshot from an audit I produced last fall

Newsrooms sometimes hire me to produce an audit of their email strategy. They’ll give me logins to their email system and their analytics, and I’ll interview key staffers to understand what they’re doing and where there are opportunities to improve. Then I’ll turn my findings into a slide deck.

When I first produced these audits, the final deck was about 50 slides long. But as I did more of these, and started to identify other areas to cover during an audit, the decks started getting longer. 50 slides became 100, and then kept growing from there. My most recent audit checked in at 206 slides.

As a partner for these newsrooms, my job is always to overdeliver. I want to make sure I give them everything they’re looking to learn — and then some.

But last year, I noticed that when I’d present these longer decks, I wasn’t getting much feedback from the newsrooms. They weren’t asking questions about specific slides or tactics, which seemed odd, since they’d been so curious earlier in the process. What had changed? After I followed up with a few clients, I got my answer: I was overwhelming them with information.

So that became my new challenge: How could I overdeliver without overwhelming?

A few changes really helped. Up front, I started setting clearer expectations for what a client could expect from the audit. I told my teams: This is going to be a lot, and I don’t expect you to do every single thing in here. That freed up the teams to pick and choose what tasks to execute on based on my findings. 

I also changed the structure of my presentations. Instead of one big audit reveal at the end, I started coming to my newsrooms with initial findings — a shorter presentation, about 45 minutes long, to talk through the most important topics, and to get feedback about things they wanted to see more of in the audit. That gave them a chance to start thinking through the big themes of the audit before the final deck was presented.

I changed the structure of the deck itself, adding a section at the start with a list of suggested tasks to prioritize. That helped teams understand which tasks were ones to work on right away, and which were ideas to put on the back burner.

I told newsrooms not to invite their entire team to the final audit presentation. Did the sales team really need to sit through 90 minutes of discussion about email deliverability or growth? No, not really. Instead, I started giving the audit presentation to a core group of stakeholders, and then set up smaller presentations to specific teams (sales, product, editorial) so they could focus on the findings most important to them.

And lastly, I started setting up monthly calls to check in with teams after the audit, to talk through their prioritization list, and to help remove any roadblocks in their way.

I’m still searching for other ways to overdeliver without overwhelming. The audit process isn’t perfect, and there are going to be ways to continue to make it even better.

———

At top is a slide from an audit presentation to an Inbox Collective client.

It’s OK to Fail. Just Don’t Fail to Pivot Away from Failures.

Post it notes on a white board

If you launch lots of new products or features, several aren’t going to work. You’ll be excited about a big new newsletter launch, and you put it out into the world, and the audience just doesn’t like it. It happens!

The truth is: If you’re not failing, it means you’re probably not trying enough new tests.

And it’s OK to fail! The only mistake you can make is failing to pivot away from your failures.

When you fail, move on quickly. Don’t double down on your mistakes. Keep testing, keep trying. The more you try, the better the chance that you’ll eventually stumble into something that truly works.

——

That stock photo of various sticky notes comes via Unsplash and David Travis.

How I Keep Notes With Clients.

that's an example of a notebook + running notes doc

I have a few dozen Inbox Collective clients that I’m working with right now. Some I talk to daily or weekly. Some I talk to once a month or once a quarter. And there are days when I’ll have five or six calls, often stacked back-to-back-to-back. When clients hop on that call, they expect me to be able to pick up exactly where we left off. They pay me too much to be disorganized or unprepared.

Part of my organizational strategy is spending an hour or two every Sunday prepping for my meetings. The other key part are my running notes.

When I’m on my call, I’ve got a notebook where I jot down notes and ideas. I find that I stay more focused if I can write things down on paper instead of trying to type up notes as we go.

And at the end of the day, I go through my notebook and type up the notes in a Google Doc designated for every client. If they’re not a client, I create a new Doc for them — often, I’ll find that a casual conversation might lead to something a few months down the road, and having those notes is a hugely valuable tool. I’ll document everything — the date, who was on the call, updates from the team, ideas we discussed, and next steps. 

What it means is that over time, I’ve fully documented everything I’ve talked about and done with that client. Some teams have been with me since 2019, and I can’t always remember what we might have tried three years ago. In those cases, it’s great to be able to open up their Google Doc and search for a phrase to figure out if we might have tackled a particular issue already.

If you’re holding regular meetings with a variety of stakeholders, you might want to try the running notes system, too. Set up a doc for every team or individual you meet with, and document your notes from the day. That way, when you need to find notes from a conversation, you’re not searching in your desk for that one notepad that might have your notes, or searching through your inbox hoping to find an email that mentions the topic. You’ll have a document of exactly what you discussed, and when.

———

That’s my notebook and a running notes Google Doc, both for WBUR, a client that’s worked with me for nearly three years. At this point, my Doc for them is 44 pages and more than 9,000 words long.

Nobody Noticed.

me, reading my torah portion at my bar mitzvah

I’ve told this story before, but I’ll share it here again.

Two days before my bar mitzvah, I did my final rehearsal at the synagogue. I’d spent months working on my Torah portion, practicing in a language I could read but didn’t fully understand. The day of the rehearsal, I screwed up a line — and completely lost it. I started crying, ran to the bathroom, and locked myself inside.

I was 13 years old, and terrified of screwing up in front of all of my family and friends. And since this was the first of the Oshinsky bar mitzvahs, there were going to be several hundred people in attendance. I was scared of looking dumb in front of all of them.

But the rabbi had good advice. He told me: If you screw up a line, it’s OK! Just go back to the beginning of the line, and read it all over again. Nobody will ever notice.

He was absolutely right. Of the several hundred people in attendance, there wasn’t a single one who spoke Hebrew fluently. (Perhaps a few dozen could read Hebrew, but none could’ve translated what I was saying into English.) Which meant that when I did mess up on the day off, I followed the rabbi’s instructions: I went back to the beginning of the line and read it again. Nobody noticed — mostly because nobody else had spent the previous nine months learning and rehearsing a single Torah portion.

I’ve had the same thing happen when giving a big presentation. I’ll have rehearsed and practiced, but then I’ll flub a line or forget to cover a specific slide. My first reaction is often to beat myself up for making a mistake. But the truth is, only I knew how things were supposed to go.

So when it happens, I let the mistake go, and move on. The truth is, the only person who even noticed was me.

———

That’s a photo from my bar mitzvah, back in May 2000.

Trust Your Turns.

the view from the charlift at Breckenridge, Colorado, in 2021

I’m a pretty good skier on a sunny day. When the light is good on the mountain and I can clearly see the next few turns, I ski with a lot of confidence.

But it’s another thing to ski on a wintry day, when the clouds and the mountain seem to merge into one. When the light is flat, seeing the path ahead gets tricky. On those days, I find myself struggling to maintain control — it feels a little like skiing through fog. A bad turn or two and I lose confidence quickly.

So on those days, I try to adopt a mantra: Trust your turns. I’ve been skiing since I was a kid, and I can get down just about anything. (It won’t always be pretty! But I’ll get down.) And when I tell myself, “Trust your turns,” I’m saying: You know the motion — trust your ability to string turns together, even in low light. Ski just like you would on a blue-sky day.

We all want to be able to clearly see the path ahead. But we can’t always see the next turn — or whatever’s around the next corner. And in times of uncertainty, we can’t just stop and wait for things to clear up. Trust the work you’ve already put in, and the processes you have in place.

Trust your turns, and keep going.

———

That’s a photo I took on a sunny day at Breckenridge in 2021.

Kill Your Darlings.

editing with a red pen

I’m reading Mel Brooks’s autobiography, “All About Me!”, and loved this section about “Young Frankenstein” so much that I’m going to quote it in full. Here’s Mel:

The first cut we put together for a test screening was two hours and twenty-two minutes long. That was pretty long for one of my films. “The Producers” was only eighty-eight minutes. While “Young Frankenstein” ran long, I didn’t want to leave out anything that might possibly catch fire with an audience. I screened it at the Little Theater on the Twentieth Century Fox lot for people who worked on the lot. The theater was packed, and we didn’t get all the laughs we were aiming for. It went well, but not well enough for me. It was just too long.

When the picture was over, I got up in front of the audience and said, “Ladies and gentlemen, you have just seen a two-hour-and-twenty-two minute failure. In less than three weeks from today, I want you back here to see a ninety-five-minute smash hit movie. I want every one of you back!”

Editing was both easy and difficult. Easy because when something was supposed to get a laugh and it didn’t, I simply cut it. Difficult because I was in love with too many moments and had to cut them for the good of the overall film. Sometimes, you have to kill your darlings….

Of course, it was more than three weeks later when I reassembled most of that same audience at the Little Theater. It was actually closer to three months later. But I had a cut that was pretty damn good and wanted to show it. It went like gangbusters! Every single scene in the picture worked. The audience not only laughed their heads off, but there was a palpable feeling of sweet sadness when the picture ended.

I love what Mel describes here: He’s using audience feedback to understand what works and what doesn’t, and then is willing to use that feedback to make his work better — even when it means getting rid of something he’s proud of. Pay attention to what your audience says — they might just make your work better, too.

———

That photo of a red pen comes via Unsplash and Kelly Sikkema.

A Wish for the Year Ahead.

two people cheers with beers

As we wrap up 2021, and look towards the new year, I wanted to say a few words:

It’s been a strange year — another strange year, I suppose. There have been moments of joy, of celebration, and moments of true alarm. I have no idea what 2022 will bring, but at this point, I wouldn’t bet on “normal.”

This moment in time has been strange for every single one of us.

So here’s my wish for the year ahead: Be kind to the people around you. Be kind to the co-worker, to the person in the supermarket checkout aisle, to the flight attendant, to your friends. This is a time of great stress and confusion, and whatever you’re feeling, the person standing in front of you is probably feeling it, too. Try to be slow to anger, even when things aren’t going your way. A little kindness — a kind word, a gesture, a thank you — might mean the world to them.

Here’s to 2022 — a kinder year, I hope, for all of us.

Cheers.

———

That photo comes via Wil Stewart for Unsplash.

Be Your Own Biggest Fan.

It’s not all going to go right. You’re going to make mistakes, and you’re going to do things that you wish you could undo.

And when things go wrong, it’s easy to be your own biggest critic. It’s easy to get down on yourself.

But give yourself permission to make mistakes. When things go wrong, try to pick yourself up. Remind yourself that everyone makes mistakes, and that nobody is going to do the right thing every time. Try to cheer yourself on, and push yourself to do better next time — because you know what you’re capable of, and you know that you can show the world how good you can be.

Whatever happened, happened. Now go be your own biggest fan. 

———

That image of two people celebrating is about stock footage as it gets. It’s by Priscilla Du Preez for Unsplash.

Thinking Add and Subtract.

Two passengers standing near the door of a train in Copenhagen, but it remains closed due to some clever engineering

I just finished “Subtract,” a fascinating book by Leidy Klotz about what humans do when given the chance to improve a situation. He writes that our first impulse is almost always to add something — to take what’s already there and add more to it in order to improve whatever it is. But he suggests that we often forget about another option: Removing elements to better the situation. If we can get to a point where we start thinking about both options, “add and subtract,” Klotz writes, we might discover opportunities that would otherwise be ignored.

Just after finishing the book, I spent a few days in Denmark, and over and over, saw examples of Klotz’s concept in action.

In hotel showers in the U.S., I often get frustrated when water leaks out onto the bathroom floor. But at our hotel in Copenhagen, the hotel had thought of an ingenious solution: Instead of adding some sort of barrier to keep the water in, they’d built the shower floor on a slight angle, to keep the water flowing more easily back towards the drain. In all the showers I took there, the water never leaked out onto the floor.

Or take their beautiful subway system, built in the early 2000s. In New York, lines often form at the entry point to the subway as travelers swipe their cards to enter the station. In Copenhagen, they’d removed those barriers entirely — and replaced them with a handful of check-in points, spread out all across the station, where people could tap their subway card before getting on the train. Even when the stations were busy, I never saw the same chokepoints that I do here in the U.S., since there was no one spot where lines could form.

Once I started noticing the ways the Danes had thought “add and subtract,” I couldn’t stop seeing them around town. Every subway station had added an underground room where someone could park their bicycle, which meant that they didn’t have to carve out space on street level for bike parking. At restaurants, people always paid at the exit, which meant that servers didn’t have to waste time running credit cards back and forth to the table, and could instead of focus on getting food and drink to customers. 

Or how about this: On regional trains in other parts of the world, trying to find an elegant solution to allow passengers to move between train cars, an engineer might add a sensor that automatically opens the door whenever someone gets close to the door. But there’s a weakness of that approach: Often, someone’s standing close to the door not because they want to move to another car, but because the train is full, and lots of people are forced to stand. In that case, the door might constantly be opening and and closing — which is both annoying for passengers and lets in cold air during the winter.

But in Denmark, engineers found a simple solution. They kept that sensor, which is just above the door — but it only opens the door when someone waves their hand horizontally just in front of the door. It’s an unusual motion that someone would only do on purpose, which meant that on the crowded trains we rode on, the doors only opened when someone actually wanted to move to the next car.

I loved seeing the way the Danes had clearly considered all sorts of options — ways to add elements, like bicycle parking, when necessary, and ways to remove elements, like unnecessary bathroom features, when it made more sense. They’d thought “add and subtract” — and built amazingly functional spaces as a result.

———

That’s a photo of the doors on the regional train. Two people are standing right next to it, but because no one’s waving their hands horizontally underneath the sensor, the door remains closed.

You Never Know When You’ll Get the Chance Again.

On Tuesday, I stood on stage in Odense, Denmark, at the 2021 Email Summit, to give a talk in front of a few hundred people. It was the first time I’d been on stage, in front of other people, in 22 months.

There was a moment in time where giving a talk like this didn’t feel all that unusual. I gave a dozen in-person talks in 2019, and had a dozen more planned for 2020. Getting on a plane to a new place — Berlin! Sydney! Montreal! — to talk about email was just something I did.

Since the start of the pandemic, I’ve lost track of the number of talks, webinars, and live interviews I’ve done over Zoom. But I wasn’t sure if — or when — I’d get the chance to do a live talk again.

On Tuesday, I tried to take a moment at the start of my talk to look up at the crowd and remember that feeling I get when I’m presenting. It’s such a privilege to get the chance to share what I’ve learned with others, and while I feel lucky to be able to do so many talks over Zoom, nothing compares to an in-person session.

So I wanted to say thanks to the entire Email Summit team — and to the amazing people I met in Denmark — for giving me that stage, and for the reminder that every opportunity to speak is a true privilege. I don’t know when the next opportunity will come, but I’m grateful to have had this chance in Odense.