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.
I took part in the 20th altMBA group, April–May 2018. A wonderful experience! I highly recommend it for folks looking to challenge themselves, grow into leadership, and meet motivated folks with a similar mindset.
The altMBA is an intensive, 4-week online workshop designed by Seth Godin for high-performing individuals who want to level up and lead.
AltMBA website
I found the course a larger time commitment than expected, much more than 2-3 nights a week and all day Sunday. Ended up being every day for me, at least a few hours of homework, if not more. The main task of the smaller group you’re assigned is to review each others’ work—three to four homework assignments a week. My altMBA experience, like many things in life, gave me back much more when I put in more.
What I didn’t expect was that shipping my homework wasn’t all; I also reviewed and commented on my group members’ work, then had two more steps for each assignment: rewrite mine again based on the feedback, and then publish it publicly.
The small group cohort style and tools are familiar to those working remotely at a company like Automattic: Zoom, Slack, WordPress. There are coaches that help out at various times, but most of it is self-study or a small group effort. The altMBA team sends you a box of books ahead, and if I had to do it over, I’d read them more carefully. I referenced them a ton during the coursework and group sessions—and have continued to use many of the books as a reference.
Overall, the course was worth the investment in my case. I still keep in touch with my small group, including on the alumni website, and made a few great friends there. People still connect with me on LinkedIn to share stories, ask for advice, and check in on the work I shared—much of which related to taking bigger steps in my career. Indeed, the “forced” growth via the exercises and homework became essential to taking a bigger leap at work last year. I’m grateful.
My shipped projects are on Medium: medium.com/@lancewillett — the platform and format were required; otherwise I’d prefer publishing on WordPress. Here’s an article that made it back to this blog: A Napkin Sketch is Enough.
In a brainstorming exercise with my group at the altMBA, I expected to dive deep into the work, tuning our understanding of business models while working under pressure to create as many ideas as possible in a short time. We did just that, relishing our creativity and ingenuity.
Yet the most satisfying outcome wasn’t how deep or wide we ranged as much as the practice of creating the right space for it to happen. Allowing discovery, allowing the best work to shine through. The moment created by the creative space was the true prize.
In our session there grew a playfulness and a natural building up of ideas as serendipitous intersections occurred where a concept, channel, or stream could be cloned to adapt to a new business idea. Growing, it created momentum and provided a sense of space — room to roam.
The diversity of the team made for richer output as we kept exploring. Ideas born from one member cloned rapidly into new ones by tapping into our backgrounds, affinities, and environments. Though we started together pitching and editing out loud, it was slow going. The pace accelerated only after a 45-minute switch to brainwriting, writing solo to bring more life to the list. We successfully avoided the problem of “one loud voice” by taking turns narrating and typing.
Creating the space to run together started with finding a format that built enough structure without slowing us down. We later dubbed this the napkin sketch for its simplicity.
The napkin sketch technique produces a great number of ideas without too much detail. Just enough to explain a business idea or “micro” business model to a friend in plain English.
Here’s how it works:
If you freeze an idea too quickly, you fall in love with it. If you refine it too quickly, you become attached to it and it becomes very hard to keep exploring, to keep looking for better. The crudeness of the early models in particular is very deliberate.
— Jim Glymph, architect
Jim Glymph (Gehry Partners, architects 1990–2007) explains the value of crude early models—what my altMBA group called “Napkin sketches.
Originally posted on Medium—and if Matt’s reading this, it’s required for the course. 🙃
Read my altMBA roundup for notes on the overall experience.
Why a Flat Organizational Structure will Fail as You Grow is an insightful and thought-provoking study from Lighthouse, a software tool for managers. Keeping in mind when considering any decision that someone else — somewhere before — solved the same issue. From my personal workflow, to team processes and habits, all the up to key decisions on company structure.
There are a few advantages and many disadvantages to a flat organizational structure as you grow. We share how growth breaks a flat organizational structure
…if you think it’s a good use of your time to try to innovate in employee on-boarding, performance feedback, quarterly reviews, promotions or weekly all hands meetings, you are mistaken at best and destroying your company at worst.
Call ten friends who work at great companies and crowd source the best practices. These best practices are widely understood and broadly implemented, and the differences are minimal or arguably irrelevant.
What makes a company or product unique? What makes it exceptional? Even though we should continually seek to improve, a strong legacy most likely won’t come from rethinking the 1-1 check-in chat, how we process payroll, or even our technical toolkit.
By modeling organizational excellence on what is already known to work everywhere else we can focus our creativity and innovation on improving the product experiences that help our customers succeed.
Note: My colleague Cate points out that the origins of most technology company practices are outlined in Andy Grove’s classic book High Output Management (1983), describing how to build and run a company.
This is day 14 of 15 in a short series on inclusive design. If you missed any of the earlier posts, see day 1 here or view the full list.
Inclusive and diverse teams make better, stronger teams — and these teams make better decisions. Because our work and thought patterns are influenced by our background and biases, working with a diverse group means not only fresh, new ideas, but we also counterbalance the tendency to design for people just like ourselves. A higher standard.
And that is why representation matters, not just to those who are represented, but to all of us. Because it expands our sense of what’s possible, and what we have reason to expect. —Cate Huston
For maximum learning and a broader perspective, not limiting yourself to your immediate team or company; seeking out a wide variety of inputs from mentors, coaches, and other advisors.
If your team is limited and you don’t have the ability to expand, actively seek out people with other perspectives to consult or act as project advisors, and give special consideration to their feedback.
I learned from Sara VanSlyke and Trace Byrd at Atlassian that it also matters how a diverse team is represented, in their article “Illustrating Balanced and Inclusive Teams.”
As a company that wants to unleash the potential in every team, depicting people is especially important. How we represent the people who make up teams should be just as important. We’ve always known that the best teams are balanced; made of a diverse group of people with different backgrounds and perspectives, but our illustrations haven’t always reflected that.
The authors found that even though their team aspired to be more inclusive, how they represented themselves visually wasn’t keeping pace with the true diversity of the team.
Promoting diversity and inclusion within our brand is a persistent and multi-faceted effort. And it’s a challenge to depict diversity without it feeling merely perfunctory or symbolic until the reality of our industry truly represents the customers we serve and the world at large. More needs to be done outside of the brand to promote an inclusive workplace, but we’ve found that the results of constant vigilance and open conversation are worth the time and energy.
To truly represent our customers is something Automattic is improving — we still have a long way to go. If you missed the story about updating the WordPress.com brand illustrations to be more diverse, see Inclusive Design, Day 5/15: To See Yourself in Imagery — with illustrator Alice Lee and my designer colleague Joan Rho.
See also this YouTube series introducing Automattic employees from all walks of life. A diverse group! I’m proud to work with them every day.
For a thorough treatment of this topic, I highly recommend reading and bookmarking “On Improving Diversity in Hiring” from my Automattic colleague Cate Huston. In this in-depth article, she shares her hiring expertise to build diverse teams, everything from onboarding and recruiting to specific tips and tricks during interviews.
This rule of thumb about stopping the behavior before someone is hired hit home with me as this is something I need to improve on personally. An off-color joke here, a comment there; I’m learning to speak up more when I notice these things.
A good rule for inclusion pre-work to diversity is to stop doing things you would have to change if the demographics of your team better reflected the demographics of the world. —Cate Huston
One practical tip shared by Cate that I’ve put to good use is Textio, a service to help make job descriptions more inclusive. I used it in 2016 to update the Excellence Wrangler job posting, replacing phrases like triage ruthlessly with triage efficiently.
Cate’s influence in the last year or so has helped me improve my hiring to be more inclusive, both in mindset and in practice. She’s inspired me to read more broadly, and think more openly.
In closing, a word from Scott Page via his Aeon article titled “Why hiring the ‘best’ people produces the least creative results:”
When building a forest, you do not select the best trees as they tend to make similar classifications. You want diversity.
(Scott has a new book out on this topic: The Diversity Bonus, How Great Teams Pay Off in the Knowledge Economy. I haven’t read it yet.)
For day 15 of 15 of inclusive design, the last day, I’ll share a recap of all the inclusive design learnings I’ve shared in this series so far.
About this Inclusive Design series — Tomorrow I’ll give a talk on inclusive design at WordCamp Phoenix 2018. Leading up to the conference I’ve been publishing notes on voices, stories, products, and other resources: everything I’m learning about this emerging practice. This is day 14 of 15. Read more about the series.
An oldie but goodie from Paul Graham: Maker’s Schedule, Manager’s Schedule.
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 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.
A gem from Mary Meeker I found when reading the 2017 Internet Trends report published by Kleiner Perkins Caufield Byers (KPCB). Via John.
A mental model that keeps coming up for me is “the unscripted dance.” This captures the idea of going into a situation knowing you can rely on your skills to adapt to the other party. Even without knowing ahead. Even without preparing for each move, each step, or each word you’ll use.
In a work setting, this could be a 1-1 chat with a direct report or a quarterly check-in with your boss.
When you’re dancing with an accomplished partner, you may allow the moment to unfold because you trust that a script is not necessary. If you’re dancing with an unaccomplished partner, you may use a script to start with because it helps guide the dance until once again, it becomes unnecessary.
Conversations at work can be like a dance when you are there “in the moment” — so attentive that you are aware of yourself and your partner at the same time — moving in and out of sync. My mind says, “When I don’t have to mold the conversation, it leads to nice possibilities.”
My leadership coach, Akshay Kapur, calls this “Listening” with a capital L. It can be quite fun, but also scary, especially if you’re used to always having things planned out ahead of time. The “Listening” also means not allowing other thoughts to take over my mind; those next questions or points that need to come up in the conversation. When that happens, I’m no longer listening — I’m just following my original plan. That’s when I miss out on insights and understanding.
The unscripted dance helps to improve my communication. To be more open and aware. Especially in established relationships with long-time colleagues where we can naturally move across topics.
I used to try to move the conversation in a certain direction, or get something out of it — my agenda for the conversation. Now I try my best to let the other person drive it. If they don’t have anything to share or ask about, I’m ready with a short list of topics or questions, just in case.
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.
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.
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.
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.
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.
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
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?
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.
The Sensible Leader 