Inspired by Doug Glanville’s Triple Threat: Baseball, Journalism, and Social Justice

A modern-day baseball anthropologist, Doug Glanville is a former Major Leaguer whose activism and advocacy for social justice is as inspiring to me as his incredible talent as a writer and journalist.

For years I’ve enjoyed his essays and reporting on sports, society, and life from The New York Times to ESPN to The Atlantic to speaking at TEDx. Check it out — now he’s debuting as a college professor.

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Whether you love baseball metaphors or not, Doug’s a triple-threat.

(Hat tip, Tom Willett — aka my Dad.)

Head of HR Lori McCleese on Automattic’s Learning and Development

 

I’m excited to see that Culture Amp’s blog features Automattic’s Global Head of Human Resources Lori McCleese sharing our latest efforts for learning and development: Three tested approaches to driving learning and development.

As an Automattic employee and team lead I’ve benefitted directly from these perks and benefits — from private leadership coaching in a 1-1 setting to in-person training course led by Reboot to diversity & inclusion speakers and courses. We’ve upped our game and it’s already born fruit in my own teams and relationships, as well as given me new resources and ideas.

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Footnote: I highly recommend following Lori’s personal blog, too — her photos, stories, and thoughtful essays on life and travel and friendship bring joy to my life. For example, see this fun inside look at her recent move across the US from San Francisco to Asheville, NC. 🌰

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.

 

Get Involved: Engineering Managers Community

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If you manage technical teams, are looking to grow and learn and broaden your network — you might enjoy connecting with this community of peers from all around the world: Engineering Manager Slack.

I’ve enjoyed participating in the discussions around books, conferences, remote companies, and more. Useful to both get a new perspective once in a while as I’m exposed to fresh ideas outside my own company’s culture and norms. And also to get a zeitgeist feel of my industry, my “people.”

Co-organizer Cate’s put up a brief recap of the first year or so in New-ish Eng-Manager Slack, >1 Year On.

I believe in community, and the value of peer-mentoring, and it’s been great to create a space for that and have others value it too.

Join us!

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.

Synthesis: Navigating Levels Effectively

One of my favorite takeaways from Principles by Ray Dalio is the notion of above-the-line and below-the-line (hat tip: Matt). Dalio describes how to navigate both levels effectively in both work and life.

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To synthesize well, you must 1) synthesize the situation at hand, 2) synthesize the situation through time, and 3) navigate levels effectively.

Synthesis, in my own words, means the ability to identify, understand, and combine bits and pieces into a whole. A coherent end point. As my colleague Ian Stewart says, “Keep your eye on the prize. Or, on the next step.”

You could apply this principle in many areas of work and life:

  • Keeping meetings on topic with clear decisions at the end.
  • Converging on a minimum viable product launch.
  • Coaching and feedback conversations with peers, mentors, employees.
  • Business strategy and decision-making.
  • Presenting important information to a group: telling a story that sticks.

In addition to navigating the levels effectively, there’s an added benefit of shared language:

Use the terms “above the line” and “below the line” to establish which level a conversation is on.

This makes clear when a divergent or convergent conversation is needed.

Navigating the levels well means you are an effective communicator and decision maker. Able to balance inputs such as thinking, planning, and research with a clear and purposeful decision to move things forward.

Sensible Ideas

To engage you need sensible ideas.

It’s not enough to be the squeaky wheel. Barack Obama said that politicians and governments respond to people making noise and demands. But the biggest mistake made by activists “is once you’ve gotten the attention of people in power then you have to engage them and have sensible ideas.” Obama added that you have to do you homework, have your facts straight, and be willing to compromise. He is addressing this issue head on with the Obama Presidential Center, which is designed to help the next generation of activist leadership.

Via Fortune: Barack Obama: Lessons on Leadership, Power, and Effecting Change (May 2017).

Rare and Valuable Skills

The goal of my career philosophy is to craft a remarkable working life. The definition of “remarkable,” however, differs for different people.

On one extreme, it might capture a life of power and respect, where you’re at the center of important matters. While on another, it might capture a life of exotic travel with a minimum of work and a maximum of adventure.

Something most such visions have in common is that they contain traits that are rare and valuable. If you want them, therefore, you need rare and valuable skills to offer in return. This requires that you stop daydreaming about a perfect job that will make you instantly happy, and instead focus on becoming so good they can’t ignore you.

Cal Newport in 2012

What are your rare and valuable skills? (Emphasis mine.)

Extract Your Own Insights

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Don’t ask for advice. Ask for experiences. Then extract the insights yourself.

Via the “Top Performer” class notes from Cal Newport and Scott Young.

And Then Grace

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The work you do when you are graceful is what we need, now more than ever.
—Seth Godin, in Graceful

This path is before me, whether chosen by the universe or because I’ve listened and cared deeply. Craft first, then connection, and then grace.