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’ve written before that no matter where you are in your career, you’re not behind. Here’s another perspective on that idea, from author and former Forbes publisher Rich Karlgaard:
How we evaluate young people places needless emotional burdens on families and has helped to spur an epidemic of anxiety and depression among teens and young adults. The effort to forge young people into wunderkinds is making them fragile and filling them with self-doubt: It suggests that if you haven’t become famous, reinvented an industry or banked seven figures while you’re still in you’re twenties, you’ve somehow off track. But the basic premise is wrong: Early blooming is not a requirement for lifelong accomplishment and fulfillment.
A few weeks ago, I read an article in the MIT Sloan Management Review, by Jeanne Ross, titled, “Why Hypotheses Beat Goals.” It makes the argument that instead of setting goals, more companies should be willing to make educated guesses about what will happen next — and then try to proves those hypotheses out. As Ross explains:
A hypothesis emerges from a set of underlying assumptions. It is an articulation of how those assumptions are expected to play out in a given context. In short, a hypothesis is an intelligent, articulated guess that is the basis for taking action and assessing outcomes.
Hypothesis generation in companies becomes powerful if people are forced to articulate and justify their assumptions. It makes the path from hypothesis to expected outcomes clear enough that, should the anticipated outcomes fail to materialize, people will agree that the hypothesis was faulty.
Building a culture of effective hypothesizing can lead to more thoughtful actions and a better understanding of outcomes. Not only will failures be more likely to lead to future successes, but successes will foster future successes.
Every place I’ve worked has set aggressive goals, and I still think that should be part of the process at any workplace. But I have been thinking a lot about Ross’ theory in the context of project prioritization — looking at a long list of ideas and deciding which ones to work on next. At some companies, prioritization is driven by “sizing,” which is the process of estimating how big or impactful a particular project could be. Sizing is supposed to ensure that the team prioritizes work that they know will have significant impact. Other companies tend to focus on hypotheses — we think that if we try X, it might result in Y. They still care about the end results, too, and often have data to support their hypothesis, but they’re willing to take on a bit more risk in the process.
There isn’t a right answer here, although my bias is towards hypotheses over sizing. I’d rather spend more time trying new projects, testing new ideas, and analyzing what’s already been done, as opposed to tying up resources trying to project the potential impact of a particular project.
I’m a bit biased for another reason: So often, when I’m working with a team on something brand new, there isn’t a lot of data for us to work off of. How big could this newsletter be? How much traffic could it drive? What will this product look like a year or two out? We might not have the answers — or even be able to make a semi-educated guess! — because we haven’t tried anything like it before. At a company that focuses heavily on sizing, that type of project almost never makes out of the concept phase, since there will always be other ideas that are easier to project in the short term. But at a hypothesis-oriented company, that idea might get off the ground because leadership is willing to try something that hasn’t been tried before, even if it might fail.
In the long run, I think it’s important for teams to set ambitious goals. The real question is: How will you decide what projects are most important en route to those goals?
Sally and I had a moment a few weeks ago. We were out on a weekend night with some friends for a birthday dinner. Our friends wanted to go out for karaoke, and who were we to say no to off-key renditions of Alanis Morissette and Journey? Around 1 a.m., we both started to fade. But I asked if we could stay for a few more songs. “One day,” I told her, “we won’t live in New York, and we won’t be able to do this with these friends anymore. Let’s just enjoy this while we can.”
It’s hard to live in the moment. I know I’m guilty of sneaking a peek at my phone during dinner. I’ll get lost in my thoughts while in conversation with a friend. And sometimes, if we’re out for the night, I’ll catch myself thinking about what I have to do the next day — errands, work — instead of enjoying what we’re up to that night.
I’ve written before that for every stage of life, there’s a Todd Snider song. And here’s the one I keep coming back these days. It’s called “Enjoy Yourself”:
Todd sings:
Enjoy yourself, it’s later then you think Enjoy yourself, while you’re still in the pink The years go by, as quickly as a wink Enjoy yourself, enjoy yourself, it’s later then you think
It helps to take a few moments to remind myself of what I have. Right now, I feel so lucky to have this job, to have an incredible marriage, to have such a wonderful family, to have my health, to get to travel, to live here in New York. Sometimes, it takes a night like the one at that karaoke bar to remind myself: Who knows how long all of this lasts? Enjoy the moment while you can.
When I was in San Antonio, I covered a fair number of Spurs games. Occasionally, I’d wander into the post-game interviews, and try to sneak in a question to Spurs coach Gregg Popovich. Popovich is legendarily cranky with the media, but he’s also one of the most interesting voices in sports — if you can get a peek behind the curtain.
And this week, we got a peek. ESPN.com has a great feature on Popovich, and his secret to building a franchise that has won five NBA titles. The key? Frequent team dinners:
“Dinners help us have a better understanding of each individual person, which brings us closer to each other — and, on the court, understand each other better,” former Spurs guard Danny Green says. On the road, whenever possible, the Spurs tend to stay over and fly out the next morning. “So we can have that time together,” former San Antonio center Pau Gasol says. “I haven’t been a part of that anywhere else. And players know the importance of it as well — and how important it is to Pop.”
Says one former player: “I was friends with every single teammate I ever had in my [time] with the Spurs. That might sound far-fetched, but it’s true. And those team meals were one of the biggest reasons why. To take the time to slow down and truly dine with someone in this day and age — I’m talking a two- or three-hour dinner — you naturally connect on a different level than just on the court or in the locker room. It seems like a pretty obvious way to build team chemistry, but the tricky part is getting everyone to buy in and actually want to go. You combine amazing restaurants with an interesting group of teammates from a bunch of different countries and the result is some of the best memories I have from my career.”
When we saw her, she talked a little about what she learned from the book. She said, and I’m paraphrasing here: I’ve been to a lot of towns across this country. I know our country is divided. But the opposite of division isn’t unity — it’s collaboration.
Dar was talking about political division in this country, but I’ve been thinking a lot about that quote in the context of the modern workplace. So many offices seek to present a united front — a “we’re all on the same page” mentality. But it’s not enough to know what else other teams are working on. The best work comes from getting incredibly smart people in the same room, asking great questions, and looking to discover new things from one another. Or, as Dar once put it: “Where does magic come from? / I think magic’s in the learning.”
That’s where the best stuff happens: When teams aren’t just working in parallel, but start working together. That’s where you go beyond being aligned on goals, and start building something truly special.
I wrote a few weeks ago about the importance of learning to say “no.” Sometimes, you have to say no to ideas — even ones you like — to make sure that you have the opportunity to focus on more important things.
But there’s an key corollary to that concept: Part of learning how to say no is learning when to leave something out of your work.
There’s a wonderful essay from John McPhee, in The New Yorker, about the power of omission. He writes:
Writing is selection. Just to start a piece of writing you have to choose one word and only one from more than a million in the language. Now keep going. What is your next word? Your next sentence, paragraph, section, chapter? Your next ball of fact. You select what goes in and you decide what stays out. At base you have only one criterion: If something interests you, it goes in—if not, it stays out. That’s a crude way to assess things, but it’s all you’ve got. Forget market research. Never market-research your writing. Write on subjects in which you have enough interest on your own to see you through all the stops, starts, hesitations, and other impediments along the way.
McPhee is writing specifically about the process of writing — but his words apply to any sort of work. Whatever you put your attention or your time into, you have to choose what to leave out, what to say no to. What’s left should be what matters most.
Go ahead and write that memo. Make that deck. Put together an ambitious plan, with lots of specific goals, and multiple ways to measure success.
But don’t lose sight of the ultimate mission. So many big plans get derailed because teams don’t know what they’re actually trying to achieve. Your organization may exist to inform or serve your community, or to better connect groups of people, or to make life simpler for your users. Think about your office for a moment: What’s your larger purpose? It sounds cheesy, but every organization should have a mission statement, and everything you do should be in service of that mission.
Now, individual teams are going to to have their own objectives, and will be using several different metrics to measure up against those goals. (At a news organization, like where I work, the editorial, sales, and HR teams all have very different goals, and we’re setting new goals a few times per year.) But where organizations get in trouble is when their teams lose sight of that overarching mission. Teams often make decisions — taking on a new opportunity to make a bit more money, or to add a few more users, or to partner with a third party — that ultimately compromises their ability to serve that larger mission.
Just remember: The plan can be complicated, the way you measure it may complex, and the goals of individual teams may be ambitious. But everything you do needs to be service of that ultimate mission.
What are you good at? Think about it for a moment. What skills do you bring to the table? What are your best qualities or habits?
Then think about your team at work. What is your team best at? What are your collective strengths?
Lastly, think about your entire workplace. What is your organization great at? What do you do well?
Give yourself a second, and really think about your strengths.
Now think about your weaknesses. Think about yourself, your team, and your organization. What do you do poorly? What do you need to improve on?
Now let’s consider one more thing: If you had an opportunity to improve one of these things — to double down on your strengths, or to better your weaknesses — which would you choose?
Many would choose to improve their weaknesses. That’s natural. People tend to focus on their own faults — I’m not good enough, I’m not smart enough, I’m not talented enough — and would love to have the chance to improve.
But my advice would be to do just the opposite: Do more of the things you already do uniquely well. Take the things you’re good at and truly master them.
Imagine for a second that you’re a Major League Baseball pitcher, pitching for a National League team. In the NL, pitchers have to hit, too, and even the best-hitting pitchers are, by any other standard, bad hitters. (Madison Bumgartner, one of the best-hitting pitchers ever, has a career .183 batting average.) Let’s say it’s the start of the offseason. You’ve got a few months to improve as a baseball player before the new season rolls around. So what would you do: Work on your hitting, and try to become a passable (but still poor) hitter? Or would you work on adding new pitches and becoming a dominant pitcher? The answer is easy: You’d work on your pitching. Baseball teams don’t need good-hitting pitchers — they need great-pitching pitchers.
It’s rare to find a true jack-of-all-trades. Most people specialize in just a few things — and that’s OK!
I started thinking about all of this a few weeks ago, when I was talking with a group of news organizations. Many of them were thinking about launching new newsletters, and trying to decide what to focus on. So I asked: What do you do uniquely well? What’s something you do that your fans fans already love? Many of them talked about their coverage of local news or sports or culture — the areas of expertise that their readers, listeners, and viewers rely on them for. That’s where to focus your attention, I told them. Invest in products to serve those audiences, and give them more of the things they already depend on you for.
There’s a great Steve Martin quote: “Be so good they can’t ignore you.” He’s right. Be so good they have to hire you. Be so good that your fans have to pay to get more of what you do. Identify your strengths — and work hard to get even better at the things you do well.
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I took that photo of San Antonio Missions pitcher Simón Castro — who later went on to pitch for the White Sox, Rockies, and As — back in 2010.
Fourteen years ago this spring, I decided that I wanted to go to journalism school at the University of Missouri. It was a fantastic decision for me. I loved Mizzou, and was lucky to make amazing friendships there. But if I were offering advice to high school me, I’d make sure to tell him this:
Where you go school doesn’t really matter. What matters is what you do while you’re there.
I got so much out of my time at Mizzou. I realized early on that I was going to have opportunities to learn new skills and try new things, and I tried to make the most of that. College was a place for a number of firsts: I got my first broadcasting experience, as a DJ with a weekly show on the student radio station. I took classes in photography. I learned how to play the guitar. I took Spanish classes and studied abroad. I joined the student Senate and tried to have a positive impact on student life.
If I were in school today, I hope I’d go even further. I’d like to think that I’d be adventurous enough to try to launch a magazine — an actual print publication that came out a few times per year — or maybe start a podcast with friends. Or maybe I’d go to the editors of the school paper and sell them on the idea that I wanted to launch a daily morning newsletter briefing. I’d hope that I’d be motivated to create new spaces for others to write, publish, and experiment.
And those are the types of projects that you can take on at any school. I’d tell high school me: Don’t stress too much about finding the perfect school. Make sure you know if you want to go to a big school or a small one, a school in a college town or a major city. Know if you want to go to a school with sports (or lots of school spirit), or not. Understand the financial impact of the choice you’re about to make.
Ever since “Moneyball,” baseball’s gotten smarter about statistics. And I loved this story about how one pitcher on the New York Yankees is using stats to improve his performance:
James Paxton is a starting pitcher for the Yankees, not a statistics innovator. But during the 2018 season with the Seattle Mariners, before his off-season trade to New York, he found a novel way to measure his efficiency and aggressiveness on the mound.
Paxton, 30, asked the Mariners’ analytics department to give him a printout of a statistic he was tracking himself: the percentage of at-bats that, after three pitches, were either in a 1-2 count or already completed. He named the statistic A3P— After 3 Pitches — and monitors it often, rather than relying on more conventional statistics such as earned run average or wins and losses.
During a recent spring training meeting, Yankees coaches stressed the need to be aggressive. Paxton takes this to heart: He is among the best in baseball at throwing strikes. In addition to his A3P statistic, Paxton checks on the percentage of first pitches in each plate appearance that were strikes. His goal is to reach at least 70 percent; he was at 66 percent last season, according to Baseball-Reference.com.
“By thinking about this often, and if I can do it consistently, I’m putting myself in a good spot to have success,” he said.
This is fantastic. By giving Paxton the bigger picture — the team wants you to be more aggressive in the way you pitch — and then the stats to match it, they’re putting him in a position to succeed in 2019. And here’s the most important thing: These are stats that he can act on. If he sees his numbers dropping for A3P or first pitch strikes, he’ll know what he needs to do to improve his numbers. (Data that leads to specific action is the best kind of data.)
