Kerry Liu on Team Leadership: Three Important Things

Insight on team leadership and management from my colleague and technical team lead extraordinaire Kerry Liu.

Remember these three things: don’t fall into the safety of your old job, listen, and provide useful feedback.

These are the three most important insights I gained from working as an Engineering Team Lead at Automattic. 

Read the full article: Three Important Things.

Check Your Fuel Gauges

Via McKinsey Quarterly Q1 2018, The four questions to ask when serving on a nonprofit board. Question 4 hit home for me as I ramp up my leadership IQ, “Do we have the right ‘fuel’ to drive our organization?”

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Screenshot from McKinsey Quarterly Q1 2018.

If you want to be an effective strategic leader, you can’t settle for a regimen of reading board books and showing up for quarterly meetings. You must engage fully on your organization’s mission; seize opportunities to observe frontline work; and, at each board meeting, take every chance to confront the big, long-term issues by asking tough questions.

After checking the gauges, you’ll know what to do next: keep effective performers, remove laggards, and ask the tough questions and demand answers.

This advice for board members applies equally to an executive team member in a business setting, leading teams at Automattic. In short—do the work, be open to the burden of responsibility, and seek out direct connections.

Agile Thinkers Know When a Best Practice Isn’t Best

I have a hiring heuristic called ABCDEF, which stands for: agility, brains, communication, drive, empathy and fit. For gatekeepers, I’ve found agility is the most important attribute. To test it, I ask them: ‘Tell me a best practice from your way of working.’ Then I ask: ‘Tell me a situation where that best practice would be inappropriate.’ Only agile thinkers can demonstrate that a best practice isn’t always best,” says Ries. “For an attorney, that might be probing for a situation where you shouldn’t run everything by a lawyer. Hopefully they don’t say ‘criminal conspiracy,’ but you want someone to say something like: ‘You know what? If you’re a two person team, and you’re just doing an MVP, and six people are involved, you don’t need a lawyer.’ It requires some common sense and mental flexibility.

Via First Round Review: Lean Startup’s Eric Ries on How to Make ‘Gatekeepers’ a Source of Power and Speed.

Your Judgement Differentiates You

Keep learning. You’ve only touched the edge of the issue. Develop your judgement, which is essentially decision making under uncertainty. Pattern matching: keep growing your pattern matching database, and be very conscious about it.

Heard on the a16z podcast for March 26, 2018 with Andy Rachleff, Wealthfront founder and CEO.

A Higher Standard

Last week I shared Amazon’s Leadership Principles, which includes “insist on the highest standards.” Modeling the higher standard myself, and expecting it in others I work with. The concept of leaders training new leaders is on my mind a lot lately, because it’s central to my role at Automattic and in the WordPress community.

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When looking for new models to refresh my inputs and broaden my understanding, one logical source of inspiring leader is the military.

My introduction to military leadership started with One Mission by Chris Fussell, which led to Team of Teams by General (Ret.) Stanley McChrystal — see my notes here.

Now I’m pleased to discover A Higher Standard by General (Ret.) Ann Dunwoody (Goodreads), the life story and lessons from the first woman promoted to four-star general in US military history. Hat tip: Matt.

The book follows Gen. Dunwoody’s wonderful and amazing life journey through career, family, and life. She grounds the narrative with lessons and principles. Guideposts.

Here are a few guideposts that resonated with me.

Whatever you believe about the nature of leadership, true leaders never stop learning, refining, growing, and adapting—and that’s the primary focus of this book.

On setting a high standard:

Meeting the standard is the expectation, but those who strive to exceed the standard send a signal about their character and their competence.

After managing nearly sixty-nine thousand employees, one thing is clear to me: there is a higher standard that provides the foundation upon which every effective leadership journey is built. It’s the difference between the leaders who excel and the leaders who fail. It’s their thought process, attention to detail, and execution that enables them to inspire and motivate their workforce to create and sustain high-performing, successful organizations.

If you take nothing else from this book—never walk by a mistake, or you just set a new lower standard!

Putting this high standard into practice means not walking by a mistake without correcting it — at Automattic we call this “trash pickup.”

He taught me to never walk by a mistake. Far too often we let little things slide. But just turn on the news and listen as the anchors lament an auto-part defect leading to deaths and multibillion-dollar recalls or a small leak in a gas pipeline causing an explosion that endangers wildlife. Recognizing when something is wrong, big or small, and holding people accountable can save industries billions and citizens their lives. Sergeant Bowen instilled in me instantly that if you do walk by a mistake, then you just set a new, lower standard.

In my world I also think this task falls to people acting as “chief quality officers” for products and services — see my recent post on the topic of product leadership.

On energy and balance; see also my recent thoughts, On Self-Management and Energy:

…working longer hours doesn’t necessarily equal better performance. Working harder doesn’t mean working smarter. Longer hours mean less sleep, fatigue, ulcers, compromised decisions, and a lack of balance in one’s life.

On developing other leaders — what I would call “training the trainer” — finding your successor is another essential aspect of leadership.

The job of senior leaders is to develop other leaders. It requires senior leaders to weigh in on key decisions. Leaders who don’t weigh in lose their vote.

One of most important jobs a senior leader has is to develop leaders or to “build the bench.”

When leaders help subordinates overcome weaknesses or mistakes, they help the subordinate, they help the organization, and they help themselves become better leaders.

…as a lifelong skill, I have worked on developing the skill of giving people chances to improve their performance after a failure.

On diversity and inclusion:

Although the power of diversity is sometimes hard to quantify, Childs definitely got my attention. His success revealed a few points: (1) diversity wasn’t about numbers or quotas—having one of these and one of those—it was about diversity of thought, and not just anyone’s thought but the best-of-the-best thoughts; and (2) these folks had to have a platform from which their ideas could be heard and implemented.

I believe the strength in diversity comes from being able to leverage diversity of thought.

View the A Higher Standard: Leadership Strategies from America’s First Female Four-Star General book on Amazon and Goodreads.

Leader as Gardener, Not Chess Master, to Create the Space for Great Work

A frequent topic I talk to other leaders and managers about is how to influence change. This goes for anyone working in a team, of course — not just managers. I’d like to share how my ideas have evolved in the last year or so as I’ve scaled up my own role at Automattic across bigger teams and projects.

Starting from control

Early in my career, my mental model centered around influencing others to change. Whether by having bright ideas myself and communicating a clear vision, selling and pushing others’ best ideas, or simply wearing the other parties down by being persistent.

Through experience and mistakes I can now see that pressing my mind against others’ isn’t the most effective way to work together. I could try to convince someone to see my way by force or pressure, but it won’t last long. Nor is it a healthy environment for collaboration.

Environment is more important than control

My mental model for leadership now removes influence from the equation. Instead of convincing or controlling, I start instead by creating the right environment for change. A space for sharing insights and lessons together to build momentum. A space where change comes naturally from individuals and teams themselves. “Your job as a leader is to edit more than you write,” to paraphrase Jack Dorsey.

Creating this space is a major component of a healthy company — you could even say it’s the key to a productive and effective team culture. I’ve certainly seen it in the last year on my team at Automattic.

Finding a mental model: gardener

Last year a new way of seeing this new leadership model came to light for me when I came across Stanley McChrystal’s TED talk “Listen, learn… lead”:

I’d read McChrystal’s book Team of Teams just before seeing the video, and both carry the same message. How over his military career he evolved his leadership style, going from command-and-control to empowering. A leader as more of a gardener than chess master.

The connectivity of trust and purpose imbues teams with an ability to solve problems that could never be foreseen by a single manager—their solutions often emerge as the bottom-up result of interactions, rather than from top-down orders.

The role of the senior leader was no longer that of controlling puppet master, but rather that of an empathetic crafter of culture.

Gardener is a perfect fit for me

McChrystal calls this a “gardener” role, and it fits my mindset perfectly.

The temptation to lead as a chess master, controlling each move of the organization, must give way to an approach as a gardener, enabling rather than directing.

The gardener cannot actually “grow” tomatoes, squash, or beans—she can only foster an environment in which the plants do so.

First I needed to shift my focus from moving pieces on the board to shaping the ecosystem.

Creating and maintaining the teamwork conditions we needed—tending the garden—became my primary responsibility.

This is now exactly how I view my own leadership model: Create the space for great work.

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A note to my readers — if you’re new here, hello! Old time simpledream readers, drop me a line if you’re still with me in this journey. I’ve evolved the blog a bit to focus on my journey as a leader, though still connected to WordPress and front-end engineering and web standards.

Readers, I welcome your thoughts in the comments or via social media. Better yet, post to your blog and link it back here. I’d love to continue a conversation about what you’re learning and seeing as well.

Cheers,
– Lance Willett, The Sensible Leader

Decision Journals and Framing Your Bets

Decision journals are designed to create a log of the decisions you’ve made and why you made them. To both capture a snapshot of your thinking at the start, then use the notes to improve your decision making process when you review it later.

I first heard about decision journaling when Ian Stewart pointed to a Farnham Street post a few years back. Then it came up again in late 2017 via Matt on the OFF RCRD podcast. I decided to take another look.

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Screenshot of the Farnham Street post about decision journals, highlighting the need for quality control of our decisions.

“You can think of a decision journal as quality control” for your decisions — yes, that fits my mindset. A quality check in six months or a year to prevent hindsight bias.

Here’s the Farnham Street template as a downloadable PDF: Decision Journal Template.

I haven’t made this a standard practice yet, probably because it feels like too much overhead. These days when reviewing success and failure I find myself reflecting back without a full picture of where my mind was at the start. What have a I learned in between? Will I repeat the same mistakes? How can I repeat the top bets that paid off?

For example, for a given decision, what do I expect to change? What am I betting on, and how will I know if I’m right or wrong?

In 2018 I hope to be better at stating my intentions ahead — taking the time to create the snapshot of my thinking at the start. Blogging this publicly to keep myself accountable for journaling the decisions at the start.


Bonus: Two recent mental models for framing your decisions as “bets” that I’ve come across, in case you find them helpful.

  1. Mind the Product’s bet matrix, via Brie Demkiw. “I bet that [this decision] will create [this outcome]. I’ll know I’m right when I see [this evidence].

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    Screenshot of the Bet Matrix by Mind the Product.
  2. Ray Dalio’s expected value calculation in Principles (see my book review):

    Make your decisions as expected value calculations. Think of every decision as a bet with a probability and a reward for being right and a probability and a penalty for being wrong. Suppose something that has only a one-in-five chance (20%) of succeeding will return ten times (e.g., $1,000) the amount that it will cost you if it fails ($100). Its expected value is positive ($120), so it’s probably a smart decision, even though the odds are against you, as long as you can also cover the loss.

 

The Real Reason People Won’t Change

I first heard the concept of uncovering competing commitments in a talk by Rich Sheridan of Menlo Innovations. On the topic of embracing change he pointed to the act of uncovering as a key activity when teams are blocked. And when addressing low performance.

In the Q & A of this session I asked:

When someone isn’t performing well, how do you motivate them to change in the positive direction — without using fear-based tactics around losing their job, if they don’t turn things around?

Rich answered:

For general performance issues, always check in with them as a person first. What are their other commitments? [He then referenced the HBR article about reasons for people’s resistance to change]. If it’s truly a performance issue that needs addressing, and the fear is no longer artificial, communicate that clearly as you kick it off.

Curious to dig in more, I thought: what are other possible causes of low performance, and how am I doing in my assessment of those cases to separate the perception from the truth?

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Screenshot of the Harvard Business Review article, “The Real Reason People Won’t Change” (2001).

Competing commitments are detailed in the article Rich shared: The Real Reason People Won’t Change. The authors describe concealed commitments that block change where people hold on to and hide their assumptions. To get to the truth, they suggest an exercise is to turn the questions or complaints around — rephrasing them — to find out what they are worried about and how it’s preventing their success. And more important, which part they play in resolving it.

At the team level this exercise often takes a deeper dive over a long period of time. Something I haven’t found on my teams that we take time to do, especially with large groups of people, many moving parts, and urgent deadlines. Partly because taking the time derails progress; the abstraction of examining complaints and gathering enough data to find the source of low performance. That takes precious time away from shipping continuous product iterations for customers, which is our primary mission.

One pattern I’ve seen with projects that go on too long, the responsible parties in the end often admit they didn’t know quite how to solve the problem. Or, they ran into a blocker that needed help outside the team. But they didn’t feel comfortable openly admitting it.

Based on this research, I can now say that disagreements passively held are often indistinguishable from poor performance.

A lack of passion or drive — which in turn blocks progress to follow up or complete something — could indicate someone isn’t connecting personally to the goal, or to our company culture, or their team.

Which helps answer the questions: 1) Why does someone “go dark?” and 2) Why does a team underperform?

A key point from my experience is that when you uncover the assumptions behind the low performance, you might find out that the underlying fear or disagreement is real. By pointing to something real — together — you can discover the missing alignment. The commitments made after that discovery shine the light on the truth and guide the next steps. Steps toward clarity and alignment.

Amazon’s Leadership Principles

Still haven’t found a better list than Amazon’s Leadership Principles. Concise, clear, ambitious. A benchmark.

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Bookmarked this in 2017, now printed it (on paper!) for a weekly read and review.

Here are my favorites.

Bias for Action
Speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk taking.

Insist on the Highest Standards
Leaders have relentlessly high standards – many people may think these standards are unreasonably high. Leaders are continually raising the bar and driving their teams to deliver high quality products, services and processes. Leaders ensure that defects do not get sent down the line and that problems are fixed so they stay fixed.

Customer Obsession
Leaders start with the customer and work backwards. They work vigorously to earn and keep customer trust. Although leaders pay attention to competitors, they obsess over customers.

Ownership
Leaders are owners. They think long term and don’t sacrifice long-term value for short-term results. They act on behalf of the entire company, beyond just their own team. They never say “that’s not my job.”

A Product Lead is a Quality Driver

As my product lead role evolves I’ve started to see patterns emerge in my work across WordPress.com teams at Automattic. Two that keep coming up for me are focus on people, not technology and be a quality driver. I’d like to dig into the Quality Driver aspect in this post.

A Quality Driver navigates all the levels, end-to-end

Here’s a recipe for success as a product lead that I’ve now written down on a paper card near, and placed on my desk. I’m working on internalizing it as I put it into practice.

+ Obsess over customers.
+ Know how we want to communicate our message.
+ Understand our business goals and core mission.
+ Keep in touch with where the technology is headed.

Driving quality as a product lead takes place at many levels, from strategy to operations to tactics. At the highest level we write stories — sometimes framed as bets — to set the vision. Then working with teams on projects, schedules, organization — all the way through to the details of design, engineering, marketing, and support.

The key for me as I grow into this role is to synthesize everything as I navigate through the various levels. (For more, see my previous post on Synthesis: Navigating Levels Effectively.)

Another way I’ve to frame this Quality Driver  is in the form of a job description. A bit aspirational and ambitious to motivate me to grow and scale my product leadership. It’s my new mindset.

Quality Driver as a job description

Strategic — Raise awareness for the top issues facing our customers, and coordinate with teams to make the needed product changes. Pay attention to the end-to-end experience of our products, acting as the chief quality officer. Hold a holistic view across the business and own every aspect of the customer journey.

Operational — Act as an effective facilitator between developers, team leads, and company leadership. Align team resources to company goals and product initiatives. Engage with product teams for effectiveness, motivation, and project management. Build a culture of trust, quality, and high performance.

Strategic — Communicate a strategic vision and turn it into action. As a compassionate and effective product steward, use the ability to succinctly communicate our CEO’s vision to teams, as well as communicate everyone’s aspirations to the CEO. Find the gems, bring them to light, and move the needle. Work on the right things, avoid crashes, and be a few steps ahead of everything — knowing how every change fits in with our plans. Help everyone understand the context of their work and the broader vision for our products.

Knowing my success

Following the recipe I started with above, I can measure my impact as a product leader by watching for:

  1. Business growth for a sustainable and profitable future.
  2. Better customer engagement and satisfaction.
  3. A natural and healthy flow of communication.
  4. The happiness and effectiveness of teams.