“Would you be interested in running WordPress.com while I’m on sabbatical?”

In honesty, my initial reaction was “No, not really.” It seemed like a lot of work, stressful, etc. But, I named my last team YOLO for a reason: the answer is always “Yes,” because you only live once.

Many teams at Automattic use the “red / yellow / green check-in” as a communication tool. At nearly the one-month mark of running WordPress.com, I can safely say I’ve experienced the entire rainbow of emotional states. Today, I’d like to share a few of my learnings with the hope that they help you during your leadership journey.

Also, one pro tip: don’t open Slack on vacation.

Problem #1: I’m receiving 50x more pings

My former team is largely based in Europe, so their day started much earlier than mine. When I signed on for the morning, I’d usually have a few things to respond to before I dived into work.

These days, I drink from the firehose. I wake up to dozens of P2 mentions, Slack DMs, and other communication threads. I clear them out, and then they just pile up again.

Solution: Delegate, delegate, delegate

Ideally, I’d like to run the business while skiing fresh powder. In order to do so, I need a great team whom I can trust to get the job done.

For our recent efforts, the WordPress.com leadership team traveled a collective 160 hours to meet in NYC. While there, we focused on identifying goals that answered the question: “If we did this in the next 90 days, would it be transformative to the business?” Everyone went home with a specific set of goals they own. Knowing what we’re trying to do and who is responsible for what are two key elements of delegation.

Additionally, I also encourage the team on a daily basis to:

• Actively work together before they come to me. On a soccer field, the team would get nowhere if they had to ask the coach before every pass.
• Come to me with “I intend to,” not “What should I do?” Actively acting on their own and reporting progress represents the highest level of initiative.

Ultimately, I should be the critical point of failure on very few things. When something comes up, there should be an obvious place for it within the organization.

Problem: Something is always on fire

I am a very “Inbox Zero” type of person. Running WordPress.com breaks my brain in some ways because there’s always something broken. Whether it’s bugs in our code, overloaded customer support, or a marketing email misfire, entropy is a very real thing in a business this large.

Even more astounding is the game of “whac-a-mole”: when making a tiny change to X, it can be difficult to detect a change in Y or take Y down entirely. There’s always something!

Solution: Focus on the next most important thing

When dealing with the constant fires and the constant firehose, I’ve found a great deal of comfort in asking myself: “What’s the most important thing for me to work on next?”

Leadership is about results, not the hours you put in. More often than not, achieving these results comes from finding points of leverage that create outsized returns.

At the end of the day, the most I can do is put my best effort forth.

Problem: We’re moving too slowly

By default, nothing will ever get done in a large organization. There are always reasons something shouldn’t be done, additional feedback that needs to be gathered, or uncertainties someone doesn’t feel comfortable with.

If you’ve gotten to the point where you’re a large organization—congratulations! You must’ve done something well along the way. But, remember: stasis equals death. Going too slowly can be even more risky than making the wrong decision.

Solution #3: “70% confident”

I think “70% confident” has been kicking around for a while, but Jeff Bezos articulated it well in his 2016 letter to shareholders (emphasis mine):

Most decisions should probably be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you’re probably being slow. Plus, either way, you need to be good at quickly recognizing and correcting bad decisions. If you’re good at course correcting, being wrong may be less costly than you think, whereas being slow is going to be expensive for sure.

In leadership, I find “70% confident” to be a particularly effective communication tool. It explicitly calls out risk appetite, encourages a level of uncertainty, and identifies a sweet spot between not enough planning and analysis paralysis. Progress only happens with a certain degree of risk.

I’m excited to start sharing what we’ve been working on. Stay tuned for new developer tools, powerful updates to WordPress.com, and tips for making the perfect pizza dough. If you’d like some additional reading material, here is a list of my favorite leadership books.

Original illustrations by David Neal.

Artista poliedrica americana, Mika Cali è prima di tutto una donna con un pizzico di follia che non si accontenta mai e che ha imparato a cogliere le opportunità. E’ sostenitrice del coraggio e della costanza, delle ri-partenze  e attraverso simboli marcati e tratti blandi ritrae la quotidianità, gli stati d’animo, la sua vita attuale e i suoi trascorsi. Ritratti di vita comune, di evoluzioni, di realismo. Una pittura segnica prevalentemente black e white – a parte qualche rara eccezione – dove ogni simbolo è un racconto, una confidenza, una riflessione, una nuova consapevolezza nei confronti di se stessa e dell’umanità.

Il suo è un linguaggio profondo che mira al raggiungimento di una stabilità fisica e intellettuale; crede nella condivisione di un equilibrio e di un’armonia che mirano al miglioramento comune dello spirito e del nostro inconscio, che fanno coesistere bianco e nero, caos e quiete, il dare e il ricevere ma che portano sempre ad allargare le ali, a rimettersi sulla strada giusta.

Sfumature, tratteggi, abbinamenti e assemblaggi di oggetti da riciclo e materiali di ogni tipo e forma. MC si dedica alla pittura, alla scultura, alle stampe, alla grafica e alla moda e li mette assieme combinando tinte a minerali naturali, oggetti, resine, acrilico, metalli e legno stagionato. Che sia una tela oversize in canvas, una felpa, un cucchiaio di legno, una borsa in pelle rossa, una giacca in denim o dei tatuaggi temporanei, tutto quello su cui Mika dipinge lascia addosso un senso di rinascita e “lots of positive sun energy”.

“Energy can neither be created nor destroyed; rather, it transforms from one form to another. That’s a scientific fact and also how I choose to respond to all the political nonsense. 
I choose to take the hate energy and not hate back or declaring those with opposing opinions to unfollow me, instead lead by example and transfer it into something positive. 
So I beg you creatives, create harder than ever. Don’t get sucked down into the drama of the news; instead please write, paint, sing, dance your heart out. That’s what this life is about – finding what we love and to channel it everywhere we go. 
It’s up to us to take the hate and turn it into love.”

-MC-

Un vero onore per me averle potuto rivolgere alcune domande.

1. The chromatic choice of painted symbols is mainly black and white. Is there a reason? 

One of the most recurring concepts for me in my work and what I strive for in life is balance. The idea that things are not really black and white, rather finding the grey in between.
White symbolizes purity, new beginnings (manifestation), safety. Black being a color of death, the unknown. For me, death is the opportunity for renewal, like the winter turning into Spring…when things are taken away, it creates space for new so I think they feed each other, like yin and yang.
I also play a lot with the concept of taking the negative and turning it into a positive. Because everything is energy, if we can harness the negative energy and use that energy to create good, then all energy brought to us can be used however we decide to use it.

2. In your opinion how important is meditation for an artist?  

I would recommend mediation to anyone, not just for artists as it has been a transformative tool for me to maintain that balance. Everyone tends to mediate slightly differently but I focus a lot on the breath to get me centered. Sometimes it is simply breathing mindfully when faced with a new or stressful situation I am trying to process or it can be a full 10-20 minute ritual. I meditate before and during the creative process with all my work so personally it’s a major part of my method.

3. How are your typical working days?

As a creative and mom of two, I wouldn’t say I ever have a typical day, haha! Two days a week, I co-curate and manage a production space, Witness Apt (@witnessapt) that is also my office in NYC.
I am also a creative consultant and arts + culture editor for @vanish.today – a new media platform focused on outside lifestyle that also helps brands navigate emerging and converging lifestyle markets.
The rest of my week is ideally spent in either my resin studio or my painting studio. I have a bunch of new work I am preparing for for my next show so trying to get into my studios as much as possible these days.

4. You have an enviable body. How is food and fitness important in your life?

Food and fitness are very important to me and also part of my methodology in order to maintain ‘the balance’. Food is fuel so I am mindful about fueling my body with good, fresh nutrients because I need a lot of energy to keep up with my girls and to work out. I like to switch up my fitness routine with a mix of pilates, yoga and cardio circuits. I used to do a lot of trail running and swimming but haven’t had as much time for that recently. As a mom of two girls, I do my best to be a model for them in every way possible so being fit and strong has been something I have always made time for. 

Per scoprire tutto quello che realizza Mika date un’occhiata ai suoi profili e stay positive guys!

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 Francesca Maria

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