Remote Leadership at Tumblr on PM for the Masses

I joined project management expert, friend, and coworker Cesar Abeid to talk about leadership, remote work, product/program management, and more on his “PM for the Masses” podcast, episode 137.

🎧 Listen here: Remote Leadership at Tumblr, with Lance Willett.

Enjoyed the discussion! Topics include:

  • Managing a remote team
  • Leadership philosophy
  • Product vs project vs program management
  • How to bring a sense of urgency

About PM for the Masses:

Besides sharing their own expertise with me and the audience, we try to understand the recipe for their success and do what us project managers do best: break their success down into manageable chunks and see how we can take similar steps.

— Podcast host Cesar Abeid

Follow the conversation on Twitter and LinkedIn.

A True Sense of Urgency

Inspired by John Kotter in A Sense of Urgency (2008), read from the local library in March 2021. 4 stars on Goodreads.


What URGENCY is not:

  • Frantic wheel spinning
  • Constantly questioning
  • Complacency
  • Ambiguous
  • Only about data (mind)
  • Slow
  • Busy
  • Status quo
  • Anxious or angry

Versus what is TRULY URGENT:

  • Patient daily progress
  • Not anxious
  • Aimed at winning
  • Alert
  • Whole-hearted
  • Speedy
  • Clear my calendar
  • Alert, proactive, fast
  • Ready to move and win


Tactics to make a sense of urgency into a daily habit:

  1. Purge and delegate
  2. Move with speed
  3. Speak with passion
  4. Match words to deeds
  5. Let everyone see it

A true sense of urgency is about starting today; grab opportunities and avoid hazards, and shed low-priority activities to move faster and smarter, now.

John Kotter in A Sense of Urgency

Stuck? Go back to the reasons you started. Try a different angle. Keep moving, even with small wins, to generate momentum. Be opportunistic.

My take? True urgency means to stay alert, bring outside oxygen in, address both heads and hearts, and prioritize movement towards what matters most. Ready to move faster and smarter.

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!

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.

(Video) Indistractable, Nir Eyal

Being indistractable is a super power. Nir Eyal started out his Mind the Product SF 2018 presentation by sharing that in the five years since his book Hooked came out he’s kept up with everything, gathered feedback, and learned even more about the neuroscience and behavior that drives our motivations and attention.

My main takeaway from his message is simple. You’ll know when you’re distracted by planning ahead. Using DND (do not disturb) mode to plan your time grants you freedom for what author Cal Newport calls “Deep Work” and Nir Eyal names “Traction.”

Working to your input each day rather than output to get important work done. Nir mentioned the “Forest” app to stay focused. In the few weeks after I attended Mind the Product my colleague Rachel McRoberts also mentioned this app to me. It’s a simple concept: each focus period grows a virtual green tree. If you interrupt the focus, the tree dies and you have to start over. Nir also uses the “Time Guard” app which allows you to set sensible limits to time spent on distractions.

I highly recommend watching this 28 minute video to hear and understand Nir’s latest work and pick up practical tips on decluttering and avoiding distraction.

Video courtesy of Mind the Product.

Maker Versus Manager

An oldie but goodie from Paul Graham: Maker’s Schedule, Manager’s Schedule.

maker-manager-screenshot.png

Posting this as a personal bookmark because it comes up often in conversations with new leads. When I talk to people new to management I highlight the mindset change from “just you” to “the team.” The context of an outward mindset is important — you don’t own your time when you manage more than your own time. Keeping track of everything changes drastically when you start paying attention to more that just your own time and tasks.

This explains the frustration of a work day gets cut short — which can happen if something comes up unexpectedly or you’re continually interrupted. The resulting “short period” of time for making or creating is essentially lost. The big project, like the essay or talk you need to start on, don’t get attention because you don’t have the time for deep work.

Another clue for discovering the maker-vs-manager mindset is how you view your calendar. By month — and not by week or day — means you could be in maker mode. If you care more about every hour or 15-minute interval, you’re likely in manager mode.

A visual note to illustrate this concept:

meetings-are-distracting.png
Screenshot from @phil_wade on Twitter illustrating how meetings appear to makers.

Meetings can be disruptive to makers, says @phil_wade on Twitter. This ties into the concept of “flow state” made famous by Mihaly Csikszentmihalyi and others. If you’re curious to learn more, search that name (hard to spell!) for his talks and books — and read my thoughts on the flow fallacy.

GTD: Sometimes You Just Need Simple Paper Tools

Some days my normal task list doesn’t cut it. To easy to be distracted, and not stick to the task at hand with 100% focus. At its worst, the more pressure I feel, the slower I seem to move. The end of the day looms with zero progress on important projects.

Wouldn’t I rather just get things done? GTD. Yes, ideally I’d move everything even a tiny bit ahead.

On the most productive and successful days I look back to see that I’ve advanced 8-10 tracks forward. This is positive for two reasons: 1) I want to spend time in more than one area, and 2) I’d like to start something in each track to unblock and gain momentum.

To systemize the day I often throw out my GTD software (closing the Things app) and go back to simple paper tools plus a timer.

  1. Index cards or a printed list. Write one task per card, or one task per line on the big paper. Start the timer. When it ends, flip to the next card or list item. Repeat.
  2. A timer. Could be the Clock app on the phone, or something like BreakTime.

system-of-the-day.png
Screenshot of how I format my task list before printing it on paper.

The use of time intervals to organize work is commonly known as the Pomodoro Technique (Wikipedia).

I alternate between 20 minutes on, 5 minutes off — or longer intervals of 50 minutes on, 10 minutes off. The length depends on criteria such as urgency, amount of items to get moving, and other obligations and distractions.

breaktime-app.png
Screenshot of the macOS BreakTime app, set to 25 minutes on and 5 minutes off.

In short: I turn to simple paper tools plus a timer to systemize the day when I need to focus. To get many tasks moving, I close my task manager and other apps to remove distractions. Maybe mute or turn off the phone. Bring out the paper tools, start the timer, and get to work.


See also my GTD Quadrant Flowchart, a simple flowchart designed to prioritize a task list.

Without Naming It

A short thought experiment to kick off Friday and the weekend. Can you work without technique? Without naming who, what, where?

Not everything we work on needs a label. Sometimes working without technique or a plan means we discover new things. Pathways emerge. Without naming it you can break free of limitations and boundaries.

On Self-Management and Energy

My word of the year for 2017 seems to be energy — some days I have, some days I have not. With clear results depending on the day and my energy level.

The following thought comes to my mind each day as I face the first decision of the morning: get out of bed and exercise, meditate, and read — or sleep in and feel more rested?

Use energy to get energy. George Leonard in Mastery

In the past my decision hinged on whether I thought one choice or the other would lead to a better Lance-at-work or Lance-at-home. Of course the right answer is both (chuckle).

Here’s the full quote.

The long road of always learning trumps a quick-fix mentality. To avoid burnout use energy to get energy, maintain physical fitness, tell the truth, set priorities, and stay on the daily path. Find joy in goalless practice itself. The plateau isn’t something to avoid; in fact, it’s one of the most important parts of the journey, and where you’ll be the happiest.

energyLike skipping meals, missing key rituals I’ve set up to start each day — habits that provide me with energy — means that I don’t perform at my highest level. High as measured by my presence and output at work. Not to mention the negative effect on my relationships and mood and self-esteem resulting from a lack of energy.

I’ve deepened my understanding of what this “energy” means. Leonard’s Mastery taught me about giving energy to get energy. How to Think About Exercise by Damon Young reminded me that fitness can bring much more than just bodily pride: it leads to intellectual and spiritual results: “We shouldn’t exercise only for health.”

This year another thoughtful deep-dive on energy came my way in The Making of a Corporate Athlete (2001) via Matt and Cate.

Extensive research in sports science has confirmed that the capacity to mobilize energy on demand is the foundation of IPS [ideal performance state].

Screen Shot 2017-12-27 at 11.34.28
Screenshot of an oldie-but-goodie HBR article. (And ,where would be without this treasure trove?).

The sports metaphor is appropriate. As knowledge workers we also train, exercise, and grow. Here are my takeaways from the research:

  • Energy is defined most simply as “the capacity to do work.” Training starts with the physical level because the body is the primary source of energy and “the foundation of the performance pyramid.”
  • The enemy is not stress but linearity: the failure to oscillate between energy expenditure and recovery. And stress can be a motivator and positive thing. I recommend looking up eustress if you want to learn more. “The problem is not so much that their lives are increasingly stressful as that they are so relentlessly linear.”
  • Physical stress can be a source of greater endurance as well as emotional and mental recovery: work fewer hours and get more done. In one case a manager saw success by increasing the good kind of stress in her life. “Because [Clark] no longer feels chronically overburdened, she believes that she has become a better boss.”

View the full article for the visual description of the “High Performance Pyramid” — for now, here’s how I understand it:

The performance pyramid is a mental model of energy, starting at physical and moving to cognitive, and finally to spiritual. Connecting everything with a higher purpose.