Tag: lessons learned

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Ask Your Dumb Questions.

That's a photo I took of then-University of Missouri pitcher Ryan Clubb, I believe taken in 2009.

Sports writer Joe Posnanski went on the “Two Writers Slinging Yang” podcast with Jeff Pearlman last week, and he told an amazing story. It’s a story about the time Posnanski, then a young sportswriter covering minor league baseball, had the courage to ask a dumb question of Billy Williams, a Hall of Fame outfielder who was then a minor league baseball coach.

As Posnanski recalls:

So I was sitting next to him, and we were talking a little bit. I don’t even know exactly what pushed me to do this, but I had been dying to know something. I turned to him, and said, “Mr. Williams, can I ask you a question?” And he said, “Yes.” And I said, “What is the difference between a curveball and a slider?”

And as I asked the question — I was probably 19 years old, 20 years old — there were some snickers in the press box, as you might imagine, from people who had overheard. And Billy Williams took my notepad — I had a skinny reporter’s notepad — he took my notepad and took my pen and started to draw the difference between a slider and curveball. And for the next 10 or 15 minutes, he just gave me this masterclass on the difference, how the curveball breaks this way, and the slider breaks this way, but there are different kinds of sliders: This is [Bob] Gibson’s slider, and this is Steve Carlton’s slider, and he would draw that, and this is Tom Seaver’s. He would go through all of that for different players. It was awe inspiring to be getting this lesson about something so basic from one of the best to have ever played the game. 

And at the end of it, he said, “And by the way, don’t let these guys get you, the ones that were laughing. They don’t know the difference either.”

It’s a wonderful reminder: There are things that all of don’t know, but might be too afraid to ask. Why? Because simply asking the question might make us feel like we don’t belong in the room. 

But it’s OK to ask! Be curious, and be willing to ask the questions you need to ask to get smarter. Often, you’ll find that others are more than willing to share what they’ve learned. You just have to be willing to ask the right question first, even if it feels a little foolish.

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That’s a photo I took of then-University of Missouri pitcher Ryan Clubb. I have no idea what pitch he was throwing in this photo.

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Be Unusually Transparent.

that's me giving a talk in 2019

Just because I have expertise in the email space doesn’t mean I have all the answers. Clients are constantly challenging me with ideas or strategies that I haven’t tried, and I don’t always know how they’ll work when we roll out these concepts in the real world.

These clients are paying me to give them good advice, and that’s easy to do when I’m proposing that they implement email best practices. But how do you advise someone on a strategy you can’t guarantee will work?

I’ve found, over and over again, that the only way forward is to be as transparent as possible. I’ll tell them: “I haven’t tried this strategy yet, but I like the concept, and I think it’s worth testing this out! If it doesn’t work, we’ll quickly move on to the next thing.”

Or: “I tried something similar with another client recently, and it didn’t work out. Now, that’s a different client with a different audience, and if you want to test it out anyway, you should go for it! But there’s no guarantee that this will work.”

Or: “To be honest, I have no idea how this will work! But let’s try it together and see what happens. If it doesn’t work, we’ll stop the test and try something else.”

It’s a good thing to be able to say, “I don’t know.” Be unusually transparent with your teams, and make sure you set the right expectations for any project. If you do, everyone usually goes into it with the right mindset — and even if the idea doesn’t work out, they understand that what they were trying wasn’t a best practice but a test, and tests often fail.

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That’s a photo from a talk I gave in 2019.

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Are You Optimizing For Just One Thing?

gymnast in mid-routine

There was a fascinating story in The Washington Post this week about men’s gymnastics, and how the University of Minnesota — which has had a men’s gymnastics team for 118 years — has decided to cut that sport at year’s end. The move will save the university $750,000 per year.

Wrote Liz Clarke:

Minnesota’s decision — combined with Iowa’s plan to drop men’s gymnastics and two other sports — is the latest blow to the dwindling ranks of Division I programs, leaving just five Big Ten schools with men’s teams and 12 in the nation. And it’s part of a larger pattern at Division I colleges and universities across the country, where “nonrevenue” sports are being dropped in the name of fiscal responsibility.

At a university like Minnesota, there are only two sports that make money: Football and men’s basketball. Those sports fund the rest: Softball, hockey, and so on.

But I think what we’re really seeing here is what my former boss, Dao Nguyen, used to warn me about: The danger of optimizing for just a single metric.

What the University of Minnesota — and so many other universities that have cut sports — is doing is making all of their decisions around a single metric: Profit or loss. Sports that make money can stay. Sports that lose money, even a small amount, are expendable.

But there are other ways to measure success for a college athletics program. You can look at the obvious metrics of success: Wins or losses, championships won, or Olympians produced. You could look at the engagement of the community with these sports: Attendance, or tickets sold. You even could look at less obvious downstream metrics of success: How much of an economic impact will these scholarship athletes have on their state over the course of their careers? (A study of previous athletes might help a university understand the long-term return on their investment.)

There’s a lesson here for all of us: If profit is the only goal, then you’re only going to work on things that make money. But there are other ways to measure success. Make sure you have a few metrics in mind so you can optimize for the things that matter — and not just that which produces the highest immediate return.

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That photo of a gymnast participating at the Singapore 2010 Youth Olympic Games comes via Flickr and is used via a Creative Commons license.

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How to Make An Introduction.

a handshake

One of my absolute favorite things is getting the chance to connect two people who don’t know each other — but who I know are immediately going to hit it off. In a typical week, I’ll make a handful of these intros, so I’ve had quite a bit of practice in getting it right. Here’s what I’ve learned about making an introduction that leads to impact.

Step 1 — Reach out to both parties and make sure there’s mutual interest

You’d be surprised how often an intro shows up in your inbox with no previous warning! When those arrive, you often feel like someone is imposing on you, even if that’s not their intent.

But there’s a simple fix: First reach out to make sure each person is interested, understands the nature of the intro, and has the time do so. Is the person you’re being connected to looking for professional help? For a a 20-minute call? For a reference or advice? You’re setting up a blind date here, so it’s up to you to make sure each party is interested and excited to come to the table.

Step 2 — Follow a simple formula for the intro

Here’s what every one of my intros looks like:

here's what one of these emails looks like

Keep it brief, be positive, and make sure each party leaves feeling like you’ve presented them in the best possible light. If there’s a small point of connection that might spark a conversation — say, there’s a mutual friend in common, or they both have a shared interest — mention that to help them kick off the conversation.

One more thing: Make sure you’re introducing them at the right email address. Maybe this person wants to be connected via their personal email, or maybe this is for business and they want an intro at their work email. Double check to make sure you’re introducing them in the correct space.

Step 3 — If you’re the one being introduced, bcc the person who introduced you!

Here’s how I typically reply to an intro: “Thanks, Person Who Introduced Us, for making the intro! I’m moving you to bcc to spare your inbox.” It lets them know you’ve taken the reins here, but also keeps them from having to witness two people make plans on a lengthy email thread. This person’s taken the time to make an intro for you — the least you can do is keep them from receiving a dozen extra emails in the process.

And that’s it! Connect with both parties, make the intros, and make sure you get moved to bcc. Do that, and you’ve just made a proper digital introduction.

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That photo of a handshake comes via Sincerely Media and Unsplash.

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You May Have to Say No.

stop here

An unusual thing has happened in the second half of 2020 for my consultancy: I’ve started turning away work.

When I started this business, if a client approached me and I thought it was a good fit, I almost always said “yes” to the work. Even as I took on additional clients, I kept saying “yes,” since I still had a manageable workload.

But as 2020’s progressed, and I’ve learned more about what each client needs, and how time-intensive some of these projects are, I’ve gotten more selective about saying “yes”. I know that saying “yes” to a project I don’t have the time for is even worse than saying “no” — because it keeps the client from finding another partner to take on the work they need done.

I hate saying “no.” My default position is “yes” — I like trying to find solutions, and I like trying to help. I especially hate saying “no” to exciting projects. But sometimes, “no” is the right answer.

And even when I say “no,” I try to be transparent about why I’ve said so, and when I might be able to work with this client. A few clients have asked if they can sign on to start working with me a few months down the road, and we’ve set up a schedule that works for everyone. A lot of these are businesses that have been around for years or decades — turns out that waiting another 60 or 90 days to get started isn’t that big of a deal.

Other times, I’ll recognize that the client needs help ASAP, and I’ll pass along the lead to another consultant or freelancer who I think can help. If I can direct them to a good partner to take on the work, that’s still a fantastic outcome.

I know as the business grows, I’ll have to be even more selective about what I say “yes” to. Taking on new clients? Launching new products? Hiring staff for Inbox Collective? These aren’t questions I can easily say “yes” to. I need to continue to be honest with my partners — and myself — about what I can truly do, and do well.

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That photo of a traffic signal comes via Kai Pilger and Unsplash.

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It’s Not Worth the Fight.

Two people fencing

When I was younger, working as part of a larger newsroom, I had a bad habit: I always wanted to win.

This wasn’t about getting big projects done on behalf of my team. These were moments when I got hung up on some petty issue, decided someone was in my way, and that I needed to show them not just that I was right, but how right I was.

Why? Stubbornness, mostly. These were fights over tiny issues only I’d noticed. I wasn’t fighting over worthy causes — I’d found a few molehills, and decided to defend them like mountaintops.

But as I’ve gotten older — and in particular, ever since I started running my own business — I’ve learned that I need to give up on most of these fights. It helps to have a great support system that I can turn to when I’m feeling stubborn to remind me to ease up and move on. But it’s also just a matter of time: I can’t afford to waste time on these trivial issues. (I mean this literally: I bill by the hour. Losing a few hours over a silly fight is a money-losing cause.)

When I start to get stuck on one of these fights, I try to find the path of least resistance. Is there an easy way out? Is there an alternative solution? Is there a way for me to communicate clearly and quickly what needs to get done so we can all move on? I try to find the path, and then I get back to work.

At the end of the day, the work is more important than being right. It does you no good to go looking for the fight. Find the way forward, and keep moving on to bigger things.

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That photo is of a fencing match, and it was taken by Micaela Parente for Unsplash.

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In the Moment.

The longer this pandemic goes on, the more I’m realizing that, maybe for the first time in my life, I’m truly living in the moment.

Right now, I’m on a big road trip west. It’s the last road trip I expect I’ll take this year. There’s a lot of big work coming up, but nothing huge to look forward to. Usually, I’m too busy thinking about what’s next to focus on what’s happening right now.

But all that’s changed.

Here in September 2020, I’m trying to make the most of the moment, thinking about what I want to do today or tomorrow, but not much further than that. Usually, this is the time of the year when we’d be making big winter plans. We aren’t — anything beyond Oct. 1 feels too far away to plan.

Instead, I’m thinking about what books I want to read this week, what podcasts to listen to, what friends I might like to see (from a distance). I’m trying not to look too far ahead. This fall and winter, I expect, will be a little surreal. I’m going to be do my best to take it day by day.

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Be Silly.

Carl Reiner died this week. He was 98.

When I think of Carl, I think of his friendship and partnership with Mel Brooks — in particular, their work on the “2000 Year Old Man.” I remember listening to those records as a kid and being amazed at how funny they were. It was just two comedians having a conversation, but those records always made me laugh. (“How many children do you have?” “I have over 42,000 children. And not one comes to visit me.”)

What amazed me most was how silly they were. I think the “2000 Year Old Man” was the first time I realized that adults were allowed to be silly. Until then, I thought that was something only kids could be. I still tend to gravitate towards people who are silly — silly people have such amazing energy, and bring a sense of joy and wonder to everything they do.

The more I watched from Carl — from “The Dick Van Dyke Show” to “The Jerk” — the more I saw that silliness and playfulness in everything he did. As I’ve thought about him this week, it’s the quality I keep coming back to.

Thanks for the laughs, Carl. And thanks for teaching me to be a little bit silly every day.

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You Smug Assholes.

At The New Yorker, we had an inbox where readers could write to us with questions, comments, or concerns, and I made it my mission to check that inbox every weekday. Some days, it took me five minutes to go through and reply to all the emails. Sometimes, it took me an hour. But I always made time to reply.

Why? The New Yorker couldn’t exist without its readers. Revenue from readers — subscription revenue, plus revenue from events like The New Yorker Festival — is what allows that newsroom to keep publishing. So the thought was simple: Readers are what allow us to do our jobs, so we should always be making time for them.

I’ll never forget an email I got in 2019. The subject line read, simply: “You smug assholes.”

I replied to just about every email in that inbox, and many of those conversations were tough ones. Just from the subject line, I knew a little about what I was getting into with this particular email.

The reader had a few issues: They were upset with the magazine’s politics, they were having trouble with their subscription, and they had a few questions about our editorial process.

Over the course of a few emails, I answered their questions one by one, and checked in with certain editors so I could offer an informed reply to certain topics. I helped troubleshoot their subscription issues. And slowly, the tone of the conversation began to change. I tried to do my best to listen and to ask. I tried to do my best to help.

And by the end of our thread, this reader wrote back to tell me: “Thank you so much for your help. I love The New Yorker, and can’t wait to be a subscriber for years to come.”

Over the course of a few emails, we went from “You smug assholes” to “a subscriber for life.”

It’s a reminder for me, especially now: Don’t be afraid to have a difficult conversation. Listen to the people around you, and make sure you’re opening up channels to hear from all sorts of voices. Make time to listen, learn, and ask. You never know where those conversations might lead.

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That photo at top, titled “Day 52/366: 2/21/12 – New Yorkers”, by memsphere, is licensed under CC BY-NC-SA 2.0

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The One Thing I Truly Believe.

Every Thanksgiving, I write a blog post called “The Things I Believe.” And in it, I write the same thing: “Over the past year, there are certain things I’ve come to believe hold true. I know that my beliefs will continue to change. I know that I will change. But here, this year, is what I believe.”

I think being willing to change your beliefs is an amazing thing. It signals that you’re listening and learning. It says that you’re willing to grow as a person.

I know that in my life, I’ll continue to change and grow. But there’s one thing that I truly believe, one thing I don’t believe will ever change, and I think it explains a lot about who am I am and why I make the decisions that I make:

I believe that life is about the people you surround yourself with — the people you care about, the people you love, the people you stand up for. I believe that nothing is more important those relationships.

It’s not about money, or fame, or accolades. It’s about people.

It’s why I try to make things that are open to as many people as possible. It’s why I block out time every month for new conversations. It’s why I share what I’m learning with the people around me. It’s why I make time for birthday cards, anniversary texts, and regular catch-ups.

I’m not perfect at this. I know I can do more to build new and stronger relationships, and I know I need to more.

But this is what I believe: These relationships matter. Putting others first is what this life is all about.

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That photo of one of Pittsburgh’s many bridges was taken by Willie Fineberg.

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