I’m Dan Oshinsky, and I run Inbox Collective, an email consultancy. I'm here to share what I've learned about doing great work and building amazing teams.
I don’t get worked up much when musicians die. But Guy Clark — a wonderful country singer/songwriter — died today, and I went digging for a great song of his, “The Cape.” Specifically, this lyric:
Well, he’s one of those who knows that life is just a leap of faith /
Spread your arms and hold your breath /
And always trust your cape
I love that so much — it’s so full of hope, isn’t it? I remember hearing that song for the first time years ago, driving somewhere in Texas, and absolutely hanging on to the idea. I wasn’t sure that what I wanted to do was the right thing, but I needed to hear from someone else that it was OK to take the leap anyway. And then that song came on the radio, and I clung to that fortune cookie of a chorus.
I’m obsessed with learning about the habits of people I respect. It’s no surprise, but: Great people often have awesome habits.
Take my favorite sports announcer, a guy named Bill Raftery. If you’re a college basketball fan, you know his catchphrases: “Onions!” “With a kiss!” “Send it in, big fella!” But he’s also incredibly wise. When you watch a game with Raftery, you know that he’s seeing the play happen before it actually happens.
The wisdom isn’t just an act. A few years ago, the Wall Street Journal did a profile on Raftery where they revealed the secret behind his madness: A yellow legal pad stuffed with game notes and scouting reports on every team he covers:
Produced while he watches a half-dozen tapes of each team he’s assigned to cover, Mr. Raftery’s one-page, double-sided reports are written in capital letters and a tiny, crowded scrawl. But his 60-odd team reports are also meticulously structured and filled with countless diagrams, notes on player tendencies, strategic predictions and statistics that could only be the work of a person whose life is set to the rhythm of balls bouncing on wood.
The reports “are like the random etchings of John Nash from ‘A Beautiful Mind,’ ” said Ian Eagle, the CBS play-by-play announcer who has worked alongside Mr. Raftery for years. But, Mr. Eagle added, “because his personality is so strong and effervescent, his basketball preparation often gets overlooked.”
This spring, CBS aired a documentary on Raftery, and they showed off his game notes. I couldn’t believe the detail in them:
If anything, the Journal article understated how in-depth he goes with his game prep. His print is tiny, and he squeezes notes into every square inch of those yellow pages. If you watch a Raftery-called game, he won’t bring up 95% of the stuff in his notes.
So why does he do it?
“I think it takes a lot to know a little,” he said in the documentary. “You try and know everything that they do, not to be a know-it-all, but just to be aware.”
It takes a lot to know a little. How great a motto is that? You study and prep for any situation. Most of the prep work will go unnoticed, but that’s OK. Whatever happens, you’ll be ready.
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That GIF was taken from the Bill Raftery documentary “With A Kiss.’
I was thinking of that today while reading an oral history of Prince’s famous guitar solo at the Rock and Roll Hall of Fame back in 2004. Says Tom Petty (bolding mine):
It’s funny because just a few days ago, he was in mind all afternoon, I was thinking about him. And I had just been talking with Susanna Hoffs of the Bangles — he wrote their “Manic Monday” song. She was telling me the story of that, of how she came to have that song and meet Prince. And I was thinking about him a lot that day, and I almost told myself I was going to call him and just see how he was. I’m starting to think you should just act on those things all the time.
I got coffee the other day with a friend who’s maybe a year out of college, and we were talking about how her work was going.
You know, she said, I just didn’t understand how hard it would be to adjust to working at an office.
And that’s a common sentiment! I know didn’t understand it either when I started my first job. Working at an office is a little different than working a service job or in education. At an office, you have to learn how to operate within a team and what kind of etiquette is required in the workplace.
Here are seven things I’ve learned over the years about being a good co-worker:
Be on time. — Everyone has the one co-worker who shows up 10 minutes late for everything. Don’t be that co-worker. Being on time means showing up at the assigned time if you’re meeting someone in your office, and 5-10 minutes early if you’re meeting someone outside your office.[1. This is really hard to do, and I’m still trying to get better at it myself.] And if you’re late — make sure to send the email 5-10 minutes before apologizing for your lateness.
Prepare people before the meeting. — Nobody should show up for a meeting and not understand what they’re meeting about. Make sure everyone’s on the same page — and has the necessary documents — before they walk into the meeting. And follow up with actionable next steps after the meeting, too!
Respond to emails/calls within 24 hours. — If someone writes in asking you to take a specific action, you’ve got 24 hours to respond. After that window, I find that emails sit in the inbox for days and days, and projects stall. Respond quickly, and you’ll become someone co-workers actually want to work with because you have a track record of getting things done quickly.
Deliver on deadline. — This goes hand-in-hand with responding quickly. Be a “get shit done” kind of person, and be someone who sticks to deadlines. When you find out that a co-worker doesn’t finish their work on time, you might be less willing to work with them in the future.
Send friendly emails. — The occasional “Congrats!” email goes a long, long way towards setting a tone for your work. Send those friendly emails!
Ask great questions. — I love working with people who are curious and ask great questions. They’re people who think critically about issues and can push work in interesting and unexpected directions. I always try to work with people who love to ask “Why?” and “How?”
Be honest. — You can earn my respect by doing the work every day. But you can earn my trust by sitting down to have the tough conversations. If you do both, I’ll run through walls for you. Being honest with someone — even if you’re saying “I don’t know” when you don’t have the right answer — is the first step towards building that trust.
Last year, I wrote down six simple rules for writing better emails. Follow those six rules and you’ll get so much more out of your inbox.
But there’s something almost as important as learning how to write better emails.
Learning when to send those emails.
If you deliver your email at the wrong time, you’re significantly less likely to get a response or the action you’ve requested. And that’s an issue.
It’s why I use the 7-to-7 Rule — I try to send emails only between 7 a.m. and 7 p.m. Why? At my office, most people are at work from 10 to 6. A lot of them are up earlier than that, and checking email. After work, many stop checking email entirely until the next day. So my goal is to send email during that window where they’re most likely to be on their work email and ready to take action on whatever I’m asking.
Does it mean I don’t check email after 7 p.m.? Actually, no! I usually do a quick scan of my email first thing in the morning, and I’ll hop onto email in the hour before bed. The only catch is: I won’t send the email until 7 a.m. the next day.
The secret behind all of this is an app called Boomerang. It works within Gmail and allows you to schedule emails for whatever time you want. I’ve set it up with a series of custom times that allow me to get my email to the top of your inbox first thing in the morning.
So if I realize on Saturday morning that I have something to ask a co-worker, I’ll write the email immediately but schedule it for Monday at 7 a.m. The result? More of my emails get answered at a time that’s convenient for both of us — and when we can move quickly to get the work done.
Boomerang is also great if you’re working with someone in another time zone. My team is doing a lot of work with our office in Sydney, and Boomerang makes sure we get the emails to them in the morning Aussie time — instead of in the middle of the night.
Boomerang’s been a lifesaver for me, and it helps me stick to the 7-to-7 Rule. (Which, in turn, helps me maintain a general sense of sanity.) If you want to give it a try, download it for your Gmail account right here.
My youngest brother graduated in December (congrats, Sam!), and he’s out searching for his first real job. We had a nice talk about it last weekend. He wanted to know: What should I be looking for in a first job?
I think the list of things is pretty short:
1) A great boss
2) A great team to work with
3) The opportunity to take on real responsibility
That’s it.
Great bosses often turn into great mentors. Great teams provide you with the structure to learn how to do great work. And, of course, any opportunity to own a task/project is a wonderful thing for a new hire.
How do you know if you’re coming into a situation with a great boss or a great team? You can always look at their previous output of work. I also think it’s important to ask questions that can reveal how the boss/team will use you. Questions like:
-How does the team work together?
-What types of personalities do you work best with?
-What projects need help right now that I could work on?
-What kind of opportunities for growth do you see for me in this job?
Almost as important as the answers is this: Does your future boss seem invested in you? Do they make lots of time for you during the interview process? Do you get to meet 1-on-1 with the team? How do they describe the opportunities available there? You’re looking for interest, engagement, and positivity. An interview’s like a first date: If the chemistry isn’t there, or if something’s off, you’ll sense it.
It’s funny: Looking back, I wasn’t thinking about any of this when I took my first job. Instead, I was thinking about whether or not the money was any good. (It wasn’t, but I didn’t care — unless I took a job as an investment banker, the money was always going to be lousy.) I was thinking about whether or not it had great benefits. (My first job offered two weeks of vacation. Media companies don’t offer much in the way of vacation because… well, they don’t have to. It’s part of the deal.) I was thinking about whether or not it was the “perfect” job for me. (At the time, I was obsessed with the idea of Google’s 20% time when I really should have been obsessed with working hard and proving that I was capable of taking on bigger projects.)
By accident, I stumbled into a few really good bosses who gave me lots of opportunity. I got lucky. My first job was pretty much exactly what I needed it to be. But I didn’t realize that at the time.
Sam (and others!): Be smarter than I was. Don’t worry about finding the perfect job. Just find the best bosses and the best team you can. It’s the best decision you can make at this stage in your career.
These are two words that people often use interchangeably:
One is “opportunities.”
One is “possibilities.”
As you get older, you learn that there’s a big difference between the two.
Opportunities are the concrete choices you have to make. They come in the form of job offers or acceptance letters from a school. There’s nothing theoretical about them. When you’re presented with an opportunity, you have to make a choice.
Possibilities, on the other hand, are just dreams. Could I move to Bolivia one day and become a goat farmer? Could I quit my job, move to Thailand, and teach ex-pats how to surf? Could I become president of a big company? Sure, anything is possible!
To put it another way: Opportunities are the things that can happen, and possibilities are the things that could happen.
But here’s where it gets important: When you’re young, it’s all possibility. You’ve got dreams and ambition, but not a lot of hard choices that need to be made. As you get older, the scale starts to shift. You’re no longer thinking about what could happen because you have choices that you actually have to make. You’re setting down, you’re starting a family, and you’re thinking about the opportunities that actually exist for you at this moment.
If you’re lucky, when you’re young, you can turn a dream into real work. You’re not tied down by anything — a job, a significant other, a family, a mortgage. That freedom gives you the ability to try something crazy. That’s what Stry.us was for me — a crazy dream that I actually made happen. But as you get older, the windows of possibility start to close. You still try to stay ambitious and idealistic, but you also start to become more practical. You start to make hard choices because you have to, not because you want to.
There’s a difference between “What will you do?” and “What can you do?” So when you’re young, and everything’s still on the table, take advantage of it. Those doors might not stay open for long.
Here’s something that happens at every office: You work hard on a big presentation. It’s got everything a great presentation needs: Actionable advice, clear takeaways, and data to back up your big points. You send out the calendar invite to a large group of co-workers — maybe an office listserv full of people who could use your advice.
Then when presentation time comes, only a fraction of the invited employees show up.
Why? What went wrong?
I’ve been thinking a lot about this problem lately. It’s something we struggle with at BuzzFeed, and something I hear echoed in conversations with friends who work in fields from media to medicine. Why aren’t people showing up for valuable presentations?
Three things are usually at play:
1) No one is holding them accountable — This is the big one. If you’re inviting people on a more personal basis — emailing 2-3 people at a time, or reaching out to folks on a 1-to-1 basis — they know that you personally want them there, and that you expect them to be there. When you reach out to a big team/group/listserv, it’s more impersonal, and people often feel like their attendance isn’t necessary. They also know that if they don’t show up, there won’t be any pushback — you won’t follow up to ask why they didn’t make time for your presentation.
2) They don’t know what’s in it for them —WIIFM isn’t just a silly acronym — it’s also an important part of any good presentation! Every time someone gets an invite to a presentation or a training, they should have an expectation for what they’ll be getting out it. If there’s nothing in it for them, why would they show up in the first place?
3) They don’t believe presentations are valuable — If you’ve been to a handful of sub-par presentations at your office, you’re less likely to think of them as valuable — and much more likely to think of them as a waste of time. And that’s a shame! A great presentation can change the way you work and give you the skills to produce amazing things. In a perfect world, people would LOVE going to presentations — they’re opportunities to make you better at the things you do every day!
So what can you do to improve your presentations? I’d start here: When you send out the calendar invite, let everyone know what they’re going to get out of your talk and why it’s so important. Follow up with people in person to make sure they understand why they should come — and create the expectation that their attendance is important. And lastly: Knock your presentation out of the park, and give them great advice that they can use!
About a month ago, I did something I hadn’t done in almost a decade: I started reading the print edition of the New York Times every morning.
You read that right: A 28-year-old working in digital media actually re-subscribed to the dead tree edition of the newspaper.
And here’s one more confession: I really, really like it.
I like that the paper helps me follow what’s happening in the world, and thanks to my new habit, I think I’m as curious as ever about all sorts of subjects. I love that I’m sending along more stories to friends (via email, of course — don’t worry, I’m not cutting out and mailing stories to friends), and I love the conversations that are coming out of those shared stories.
But most of all, I love the 20 minutes every morning of absolute quiet. The TV isn’t on. I’m not distracted by email, or a video shared on Facebook, or whatever just showed up on my phone. That 20 minutes in the morning where I’m reading the paper is my chance to read, be quiet, and think.
I’ve turned to various things over the years to find that quiet. When I lived in San Antonio, I practiced yoga. In Missouri, I worked out like it was my job. But right now, it’s the Times.
Everyone should have that time during the day to shut out the rest of the world and find quiet. The rest of our days are so hectic, and so full of everything. It’s wonderful (and maybe even necessary!) to have a tool that lets you find that peace — even if it’s only for a little while. Those are the minutes that help keep you sane.
I never thought that peace would cost $9 a week and show up on my doorstep wrapped in a rubber band every morning, but I’m awfully glad that it does.
“So if everybody is essentially doing the same thing, is anybody likely to get ahead?
That quote happens to be about — of all things — the surprisingly high-stakes world of convention center hotel construction. But it could just as easily be about the race to build the biggest car-sharing app (here in New York, I walk past ads for a half-dozen Uber competitors a day) or the biggest social network or the next big whatever. When one company launches a feature, their competitors follow right behind. When someone launches a new app, a thousand spin-offs are sure to come, too.
Everybody is doing the same things. So how do you get in ahead in a world like that?
We live in a world of copycats, but you don’t have to be one of them. Here’s my advice: Don’t follow the leaders.
When others zag, find another path and zig. It’s OK to ignore everyone else — there are thousands of niches out there, and there are opportunities for people who will do stuff that no one else is doing. Let everyone else compete on the same ideas while you compete on yours alone.
I’ve always tried to remind myself: It’s hard to run your own race, but it’s even harder to run someone else’s. So give yourself permission to be different. Your way may work, or it may not — but in the end, at least it’ll be your successes or your failures.
