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

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.

A Conversation Shines the Light

When you need to find common ground, a conversation shines the light.

Talking with Group A:

“Oh, they’ll [the “others” in Group B] never go for that.”
“Have you asked them yet?”
“Well, no. We tried to get a meeting and they declined.”
“What about just quickly posting your questions?”
“Oh, OK.”

Later, talking to Group B:

“What do you think about the proposal?”
“Well, we had some alternate ideas but they [the “others” in Group A] would never want that.”
“Oh? What did they say when you brought it up?”
“We haven’t talked to them about it yet.”

Facepalm moment for me as the facilitator. It turned out the two groups hadn’t ever connected on this topic. Once a conversation shined a light on it, we saw the shared goal in plain sight. Assumptions dissolved.

Alignment is knowing versus thinking we know.

Continue reading “A Conversation Shines the Light”

Leadership Gap: Scaling Presence With Distributed Teams

In my practice as a team lead at Automattic I keep coming back to the challenge of scale. Scaling up both in scope and in size, taking on larger projects and bigger teams with more overhead and management. Going from a small team paying attention to one product all the way to a group of teams across a many channels.

One reason it’s a been a difficult challenge for me is that with the increase in scope and size, my time to give individual attention to people and projects decreases. I find myself asking, “How can I best scale up my presence to keep in touch with everyone on everything they’re doing?”

The second part of the challenge is our particular work style: Automattic is fully distributed, biased toward text communication, and most interactions are asynchronous because of time zones. Our culture is optimized for personal flexibility as we set our own work hours and schedules — and office locations change daily.

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I’ve started writing down the principles that lead to my mindset for being present — plus the techniques that have worked well so far. I’m sharing them here publicly to keep myself accountable for the practice.

To scale my presence on distributed teams, I will:

  1. Build connections to build trust.
  2. Conduct pulse checks on a regular basis, including skip-level chats¹.
  3. Share regular updates to the group to expose my thinking, highlight important messages, and provide insight into what I’m tracking both internally and externally.
  4. Ask everyone to share their observations with me.
  5. Make coaching a priority, so others can learn to help themselves.
  6. Delegate more. Can someone else do it?
  7. Be true to my word.
  8. Be visible.

Your ability to have influence at a larger scale within your organization starts with knowing how to connect and influence people in your immediate team. Alyssa Burkus in How to Be More Present With your Team (Actionable.co)

But wait… these are all practices for any leader, even when located in the same building, same city. The last one — being visible — is the key to solving the difficulty of a distributed, async workforce.

Ideas that I’ve tried for improving visibility include connecting more over video, to “share a tea” virtually as we chat. Posting short personal updates on what I’m up to outside work. Jumping into short, high-fidelity check-ins over voice and video to unblock a communication gap, which is a boost to the human bond. The view into someone’s office can lead to questions like, “What’s that book on your shelf?”

Teams and individuals at Automattic socialize together via chat or photoblogs or videos or GIFs. Whether that’s around hobbies and shared interests, building cultural awareness, and following each others’ lives via social media. As my coworker Cate says, “Make it feel like a team.” Ultimately it’s about humanizing the distance.

Making it feel more human means involving myself in the connection over the distance. It’s not just a transaction — we’ve bridged the gap to interaction.

I’d love to hear from you, too. What’s worked best for you to be more present for your team?


  1. Footnote: the vocabulary of scaling teams is fun. Learning to scale my leadership also means picking up industry lingo around scaling teams and companies. Everything from skip-levels, business units (BU), direct reports (DR), individual contributors (IC), org chart, directly responsible individual (DRI), “manage up,” and more. Not all the buzz words are new to me, but I typically avoid using corporate-sounding vocabulary. As I seek to understand everything at scale, I find myself using these phrases and acronyms more often now with certain audiences. I’m picking it up as I go! Something new each day.

 

No Job Is Beneath You

No job is beneath you. In a similar vein as killing your ego, be eager to jump in and get dirty with your team. Garrett St. John

Read the full article: Humility in leadership.

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I’ve been enjoying Garrett’s Technical Leadership email newsletter — they arrive with perfect timing for certain issues I’m dealing with at work and at home. If you lead technical teams — or work in any group setting — I highly recommend it as a resource. You can sign up for Garrett’s newsletter here.

Flow Fallacy

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Because the goal of commercial software development isn’t to create code you love—it’s to create products your customers will love.

Recent efforts with my team at Automattic to improve the WordPress.com experience — and understand our customers better through “exposure hours” — reminded me of this classic software development essay from 2013 (via Andrew).