Dream in Years, Plan in Months, Ship in Days

This guideline pops up often inside Automattic via folks like Matt, or me, on internal memos when discussing how best to balance product planning, strategy, and execution. With a bias toward action, we aim to learn more quickly by launching directly to users and customers.

Source: I first saw this message in 2015 via a tweet by Luke Wroblewski.

Luke later shared a poster version on Twitter in 2016, which I purchased for my office Zoom background (buy on Startup Vitamins).

DJ Patil, US Chief Data Scientist during the Obama administration tweeted an expanded version in 2017:

Here’s the full text from DJ’s hand-written note on White House stationery.

Dream in years
Plan in months
Evaluate in weeks
Ship daily

Prototype for 1x
Build for 10x
Engineer for 100x

What’s required to cut the timeline in half?
What needs to be done to double the impact?

DJ Patil

I love this philosophy for product strategy and execution because it puts the right balance on each activity.

Dreams take time and effort to accomplish, and a clear product vision means looking ahead enough to inspire and motivate people to join the mission.

When we don’t know an accurate launch date at the beginning, monthly plans split the work into smaller projects and tasks that’ll bring improvements out to the public quicker. This means we learn faster, measure the immediate impact of a launch, and track usage as close as possible to real-time.

Speed matters in marketing, business, and product development. Sometimes we aren’t confident the current change is the right one, yet shipping before we’re fully confident leads to a smarter set of next changes — informed by the people using the product.

Ship daily, measure weekly, and plan in months to find out what works sooner than later.

🚀

Manage During a Crisis: Deliberate Calm + Bounded Optimism

Enjoyed this timely and practical organizational leadership guide from McKinsey.

Key elements include priorities, roles, time, and energy.

Deliberate calm: How to steer into the storm.
Bounded optimism: How to mix confidence and hope with realism

As human beings, we can practice integrative awareness before, in, and after the moment.

Screenshot from the McKinsey study on personal operating models.

Six steps:

  1. Adapt your personal operating model.
  2. Set your intention.
  3. Regulate your reactions.
  4. Practice reflection.
  5. Reframe your perspective.
  6. Manage your energy.

Leadership in a crisis like this is an enormous responsibility, yet it can also be seen as a great privilege. Integrative awareness keeps leaders centered in the storm, giving them the focus they need to take care of themselves and the people and organizations they lead.

Lead with purpose!

Deal With Unresolved Grief By Looking Outward

Grief is inevitable. Unresolved grief doesn’t have to be. To overcome grief, leaders must become consciously aware of the problem; accept the pain of the loss; and take actions to first let go of the past, and then to find new meaning from the experience.

Via The hidden perils of unresolved grief (McKinsey)

The outward shift described here resonates with me as an action I can take every day. Under my control to break the inner gaze — the running loop of emotions in my mind — with frequent pauses to stop the cycle. Like an athlete would: train, play, rest, and recuperate to replace depleted energy. Same thing, but mentally.

Opening up emotionally allows those who have suffered from unresolved grief to restart the process of bonding with other people. As their focus shifts outward, their internal dialogue shifts from defensive to positive. This brings calm, clarity, gratitude, and even playfulness.

Thought-provoking prompt from McKinsey for anyone feeling overwhelmed, grief-sick, and exhausted: Hidden perils of unresolved grief. Food for thought for leaders and our teammates alike. “Grief can be a creative force that turns loss into inspiration.”

The OG Team Lead Whisperer Peter Drucker on Responsibility, Automattic Style

Originally posted on an internal Automattic leadership blog, part of our asynchronous communication system called P2.

This is my loose interpretation of Peter Drucker’s words in his famous book The Effective Executive — where I replace “executive” with “team lead” and edit he/him pronouns to be more inclusive. Adding a few Automattic specific references such as “P2s.”

Effective leaders focus on outward contributions.

The question “What should I contribute?” gives freedom because it gives responsibility.

The great majority of team leads tend to focus in and down. They are occupied with efforts rather than with results. They worry over what Automattic, Matt, and other senior leaders “owe” them and should do for them. And they are conscious above all of the authority they “should have.”

As a result, they render themselves ineffectual. The effective team lead focuses on contribution. She looks up from her work and outward toward goals. She asks: “What can I contribute that will significantly affect the performance and the results of Automattic?” Her stress is on responsibility.

The focus on contribution is the key to effectiveness for a team lead:

  • In their own work — its content, its level, its standards, and its impacts. Setting a good example in what’s produced personally.
  • In their relations with others — superiors, peers, subordinates.
  • In their use of the tools of the team lead — such as meetings, P2 posts, and performance reviews.
  • In setting clear expectations that everyone is aware of — nudge those who aren’t aware, and manage out those who can’t get it.

The focus on contribution turns the team lead’s attention away from her own specialty, her own narrow skills, her own department, and toward the performance of the whole. It turns her attention to the outside, the only place where there are results.


Takeaway: The most effective team leads maintain a constant focus on the contributions everyone at Automattic can make: user experience, customer happiness, building the company, and healthy revenue growth.

If you haven’t read Peter Drucker’s work— he’s known as the “godfather of modern management” — and “the one to read” even if you are a skeptic. He defined the standards for both the intellectual and real output for knowledge workers in the modern workplace.

Notable leaders in our industry that we still read today built on his work, from Andy Grove to Ben Horowitz to Camille Fournier — and, naturally — many team leads at Automattic. Drucker (Austrian-American, 1909–2005) was a true polymath known for his depth and teaching across many subjects: art, history, literature, music, and religion.

Kathleen Eisenhardt on Simple Rules To Unblock and Make Faster Decisions

When analyzing my work with teams, projects, and my own contributions I often try to find the bottleneck in the system. What’s blocked? How could we move faster? What’s are the important decisions?

Kathleen Eisenhardt is a professor at Stanford University who dives deep into these questions, and more. Below are two examples that share insights from her work around complex systems, decision making, and how simple rules can make all the difference.


Kathleen Eisenhardt: What Are Simple Rules? — We’re more likely to remember and act on 2-5 simple rules.


Kathleen Eisenhardt: Effective People Think Simply — You can make decisions faster when the rules are simple.

Start from both ends — open versus closed, and structured/complex versus chaotic.

What are the likely scenarios?

  • Product development teams that are highly complex might launch the wrong product very efficiently.
  • Product development teams that are highly chaotic — and anything goes — have a great time launching nothing.

Questions to ask:

  1. What are we trying to achieve?
  2. What’s the bottleneck in the process? What keeps us from achieving our goals?
  3. What are the rules? For example, understand your own data while also bringing in outside experts.

You can make decisions faster when the rules are simple.

“Stopping” rules are the hardest to learn. People are good at starting! Bad at stopping.

One of the biggest mistakes business people make is staying in something too long. A stopping rule helps you get out of that.

Kathleen Eisenhardt

Involve people around you to determine the rules — they shouldn’t just be from the top.

I hope you learn as much as I did from Kathleen Eisenhardt’s work.

One Foot Higher Each Year

Phil Knight: “We have so much opportunity, but we’re having a terrible time getting managers who can seize the opportunities. We try people from the outside, but they fail, because our culture is so different.”
Mr. Hayami: “See those bamboo trees up there?”
“Yes.”
“Next year they will be one foot higher.”

I understood. When I returned… I tried hard to cultivate and grow the management team we had, slowly, with more patience, with an eye toward more training and more long-term planning. I took the wider, longer view. It worked.

Nike founder Phil Knight describing a learning moment in his memoir Shoe Dog.

Love this view of better results from growing leaders up from the people already around you, slowly and surely building a strong bench. Not simply expecting new faces to show up and solve everything.

Read my Goodreads review of Shoe Dog by Phil Knight of Nike (4 stars).

SOUL-mate Decision Framework

I love this “SOUL-mate decision-making framework” shared by Aman Bhutani, CEO of GoDaddy. How do you know if a current, or new, role fits well?

Something you want to do.
Opportunity to help people more than yourself.
YoU should bring something special and unique to the role.
Learning is key, there has to be something you’re learning in the role.

Hat tip: Matt.


The S is for Something you are hungry for (not just interested or passionate about – truly hungry for). This will make sure you wake up every morning ready to succeed in the new role.

The O reminds you that there should be opportunity for everyone and not just you. Successful people do a lot of things right, and luck plays its part, but they also ride waves.

The U means that YOU must bring something special to the table. There must be a reason you are a match – you should have a competitive advantage over others.

Finally, L is for learning. If you are not going to learn anything, don’t take it. Remember that this often comes from the people just as much as the role itself.

Aman Bhutani on Twitter

Joining Tumblr

Thrilled to announce I’ve joined Tumblr as head of product and technology. This new role means I get to work alongside industry veterans on a brand and a platform that I’ve admired for years — all while engaging with and creating new experiences for an amazing and diverse community of fans, creators, and brands.

With Automattic and Tumblr joining forces in September 2019, we’re keeping momentum going as we build products and experiences together. Tumblr is alive and kickin’! Especially recommend checking out the mobile apps (available in App Store and Google Play Store) as strong evidence of a thriving product development culture that deeply understands its user base.

What most excites me is the fit of my skills and experience with this new challenge. New learnings. Combines years of experience as a hands-on product developer with cross-functional operations at the executive level. My full range! Success means nurturing and developing an outstanding technical organization, purpose-driven to support a thriving online community and grow a healthy, sustainable business.

For product news and updates follow the Tumblr blog to keep up with the latest and greatest. Y también hablamos español, síganos en Tumblr: El blog del equipo.


For a brief taste of Tumblr:

Explore the archives on this isn’t happiness — an art scrapbook that’s curiously addicting…

Find the warm fuzzies on cozy.tumblr.com, as an alternative to news-obsessed social media…

Hear stories of discovering a community around shared interests at explore what you love;

And, enjoy Garfield Minus Garfield. (I love this one).

Follow me on Tumblr, too.

Two blogs going so far, with a few more in the works: nanobar.tumblr.com (main) and blackedoutrims.tumblr.com (side obsession número uno).

So many fun features to discover including this never-ending TV show and — for pros — lesser-known features like the dogear, fast reblog (use a long press on mobile), and fancy archive pages.

Leaders Shorten the Distance

Our job as leaders is to close the gap between the inconceivable to some but inevitable to us.

Paraphrased from Nancy Pelosi’s 2020 commencement address as Smith College (emphasis mine).

During this crisis and in the days, years, and weeks that will follow, the world needs your leadership too,” Pelosi said to the graduates. “Our goal as leaders is to shorten the distance between the inconceivable to some, but inevitable to us … Because Smithies are relentless and persistent, I’m confident in your ability to do so,” she continued.

Boston.com

Free Tutorial: Optimize Your Business Website

For any business owner, freelancer, entrepreneur, or anyone interesting in building an online business or side gig. This free webinar from WordPress.com web design pros (YouTube) will teach you tips on site design, SEO, monetization, and mobile optimization.

Kathryn Presner

Two weeks ago, my colleague Marjorie asked if I’d be interested in helping run a webinar for small businesses, with tips on getting the most out of their website. She knew I’d done a lot of public speaking and thought I might be interested. Even though we wouldn’t have a lot of time to prepare, it took me all of three seconds to accept.

Fast forward to yesterday, when my colleague Steve Dixon and I presented a one-hour online workshop called Optimize Your Business Website: Secrets from Web Design Pros. Topics included essential pages for business sites, layout templates, the WordPress block editor, and what it takes to optimize a site so it’s both easy to find in search engines – and easy for visitors to use. We also looked at how to make sure your site is both accessible and mobile-friendly, along with a few different ways to…

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