Making mistakes

Nobody should want to mess up, but at least make adverse outcomes worth it by having a framework to learn and improve. 

Before you write off 2021 as another 2020, remember: There are still 352 days left in the year. We have time to patch this up and make this a comeback year. I won’t add my two cents on the riots at the Capitol, but the embarrassing and tragic spectacle got me thinking about handling mistakes.

Making mistakes

A reality of making many decisions is some will be wrong. Everything can be viewed as an opportunity, and mistakes are no different. Nobody should want to mess up, but at least make adverse outcomes worth it by having a framework to learn and improve.

At Digiday, over a decade, we executed hundreds of events. We were very good at doing events, in large part because our GM, Megan Knapp, built a high-functioning events team. But we also had a big advantage over competitors: We had more opportunities to mess up -- and then correct shortcomings very soon afterwards since another event would always be right around the corner. For competitors with a handful of events, they had far fewer opportunities to commit atrocities -- never try to hold a panel during cocktails, trust me -- and then had to wait far longer to make them right.

Here’s what I found as keys to using mistakes to your advantage:

Understand that mistakes are part of growth. Put aside the Silicon Valley fetishization of failure. Every organization needs to accept mistakes as a necessary part of growth to be successful. Otherwise, you’ll have people who are scared of making decisions, which will slow down anything from happening and lead to all decisions, large and small, going to the top of the org chart. This is doubly pernicious since those at the top often have less access to the data and on-the-ground experience.

Take emotions out of the equation. Mistakes are a lot like accountability: People tend to laud them in the abstract vs in actuality. Emotional responses to mistakes -- on multiple occasions we gave out the wrong awards to people -- often compound the problem by leading to impulsive reactions disguised as rational decisions.

Have a feedback loop. I am a big believer in keystone habits in organizations. One keystone habit we developed early on, although it waned, was after-action reports from events. Every person on the team at the event -- operations, editorial, sales, etc -- wrote a report of five things that went well, five that didn’t, what they did new. The purpose of this was to have an understanding of how to improve from all angles -- and to build the reflex of always thinking of something new to try, if only because you knew you’d need to write something.

Focus on the process. Adverse outcomes happen. That doesn’t mean an initiative was a mistake. The best place to put energy is in the process involved in the decision. Often the right people weren’t even involved who could have steered the initiative to a better place. Just because something didn’t work doesn’t mean it was a mistake to do.

Reward adaptability. I’ve written before about the need for new managers to make decisions rather than bring every problem to group leaders or, worse, executives. Companies get tied in knots that way. One important muscle to build is adaptability and the willingness to take the initiative when things go wrong. We saw that in the chaos of the riot at the Capitol. Quick thinking aides made sure the certified electoral ballots were spirited to safety. Having people waiting around to be told what to do is a recipe for true failure.

Membership mistakes

The pivot to paid is in full swing. For many publishers, moving from an indirect business model (advertising, for instance) to a direct business model (subscriptions) is a painful process. There’s more to do, both strategically and tactically, than simply putting up a paywall and processing the payments. Here are some mistakes we made at Digiday -- and how we adapted.

Getting timing right. The biggest mistake was not moving to subscriptions at Digiday only a couple years ago. We already had a large enough audience and plenty of direct connections, as well as a product differentiated and valuable enough to sell. But we delayed. My fear was we’d hurt the work our “free” content did in order to serve as a marketing and brand engine for our events and sponsor content business. On the flip side, moving to subscriptions too early in a brand’s life stunts its growth.

Treating it like an MVP. Small companies, especially bootstrapped, can’t get too ahead of revenue. There is little appetite or wherewithal to throw people at new initiatives. That means they end up as several people’s fifth job. That’s OK, but a mistake is to allow that to persist for too long. For products to take off, they need people who wake up and go to sleep thinking about making them successful as opposed to being the fifth thing on their ROMP. (I know OKRs are now very popular; we used ROMPs.) Digiday’s membership business took off once it was consolidated and Jack Marshall came back to lead it.

The football phone. Back in the 1980s, Sports Illustrated ran infomercials that ticked through various benefits of a subscription before adding an out-of-the-blue sweetener: a phone that looked like a football. In coming up with a membership model, I was obsessed with avoiding the football phone, throwing everything against the wall -- unlimited access to articles, discounts on events, member webinars and calls, merch, videos of events, early access to podcasts and stories,  a magazine -- and then relying on marketing pushes. Best is to narrow the product to a few core features that are easily understood and valued. Marketing is critical; but it can’t substitute for a tight value proposition.

Getting the tech right. Digiday was mostly a “no stack” media company. We outsourced nearly all tech, standardized on platforms like Wordpress when possible, and relied on services provided by key tech vendors to make up for missing expertise. But subscriptions ties together many different platforms, making the role of systems integration crucial. Too often we were held back from systems not working together, leading to the inevitable finger pointing and investigations as to what went wrong and why. (Once we weren’t putting the paywall up to those whose article limit expired because of a mistakenly checked box deep in our paywall provider’s dashboard.)

Understanding the data. There has never been more readily available data, yet most of us bemoan the lack of true insights it yields. Without a true understanding of what is driving conversions -- not just a signup after 150,000 people got emailed -- held us back. Jack’s take:

For a variety of reasons -- including the need to move quickly with limited resources - we failed to ensure we had robust analytics systems in place early on that served the specific needs of the subscription business. That often led to situations where we were forced to spend inordinate amounts of time manually triangulating between different sources of information to establish what drove a spurt in new conversions or a bad week for churn, rather than simply glancing at a dashboard. This also negatively impacted our ability to spot opportunities, such as identifying churn-risk subscribers and working to re-engage them before they dropped off, rather than attempting to lure them back after the fact.

Some things to check out

  • Tracksmith is one of my favorite brands. As a runner, I appreciate how it found a niche: “serious” runners who aren’t elites or even sub-elites on the message boards but still know what time they need to run a marathon to qualify for Boston. (And they call the Boston Marathon simply Boston.) From a media perspective, Tracksmith does content incredibly well with Meter and even their catalogs. Outside has a profile.
  • The next hot vertical area: blockchain. Blockworks is expanding into news, joining a group of upstarts looking to corner different aspects of blockchain and bitcoin. We had a mistake of our own in this area with a fin-tech brand, but there are several opportunities for new players to emerge.
  • Over at Big Technology, Alex Kantrowitz has a helpful primer on the “alternative” platforms springing up to cater to the Trumpists. The thorny issues of the role private tech companies play in fostering and squelching speech is an issue that will be on the front burner in 2021 — and one that doesn’t have easy answers, despite what people may tweet.
  • Travel & Leisure found a new home with Wyndham Resorts. We’ll see more of these deals as non-media companies find that media is a very efficient customer acquisition and branding tool. What Penn National Gaming is doing with Barstool is going to be a blueprint for many. More on this in the weeks to come.
  • New book: The Art of Fairness by David Bodanis. I believe we’re entering a post-Trump era where we value decency and competence in leaders more than charisma or “vision.” Bodanis writes a counterpoint to those who carry around Machiavelli. For all companies talk about their “no assholes policy,” plenty of assholes seem to thrive in them.