Tag: leadership

End Every One on One the Same Way

I think about communication a lot!

It’s such a huge, and hard, and important topic for anyone trying to become a better leader. Especially in 2016, as the ideas of “management” and “leadership” become murkier and more difficult to nail down, and the tools we use to communicate with one another are exploding in number (if not quality) – it’s always on my mind.

Continue reading “End Every One on One the Same Way”

Exposure Therapy and Building Expertise

Do you follow me on Instagram?

It’s not professionally very interesting (I try to save that for Twitter, and, of course, this blog).

In the description of my Instagram profile, I mention:

I live with The Doctor (a doctor), Mango (a baby) and Elmira (a cat).

The Doc is, more specifically, a clinical psychologist. We met in college – I was in graduate school for philosophy, and she was finishing her PhD. Our relationship is rich: we’ve moved across states, have a second kiddo on the way, and have successfully kept a Maine Coon alive (and very sassy) for almost a decade.

I count myself lucky because I learn things from the Doc all the time – she’s the closest thing to a genius that I’ve found, and has a gift of being able to share complex ideas in a way that overlaps with and takes on the character of the experience of the person she’s sharing with.

One idea that she and I have discussed at great length is an approach to treating anxiety disorder, called exposure therapy. Broadly, the big idea behind exposure therapy is that exposing a person to small amounts of something that makes them anxious (or stressed, or afraid), starts a process that can eventually help that person overcome the anxiety or fear at a larger level.

(I’m very likely butchering this concept by working in broad strokes – read the Wikipedia page, it’s good, and short.)

If, like me, you have an unhealthy obsession with Nassim Nicholas Taleb’s work Antifragile, you may have already identified that there’s a parallel here between exposure therapy (exposing someone to a small amount of what makes them anxious in order to help them become less anxious) and hormesis, the concept in medicine and (since Antifragile) economics, that shows us that benefits do not always follow a linear or even exponential path – but rather many inputs have a hyperbolic curve, where limited benefits can be found in one particular application, but then the downside becomes infinitely worse as the input is continued to be applied.

One example is water – in too-small amounts, lack of water will kill you. A somewhat narrow band of water application is ideal, enough so you’re not thirsty and are able to operate in a healthy biologically appropriate way. Once you exceed that healthy space though, any additional water will have more and increasingly horrible effects – pretty quickly leading to death and only death on down the line.

The mental model of hormetics is controversial: it’s not universally accepted nor is it universally applicable. In this case, it’s a helpful way to think about a bigger model for our otherwise more specific cognitive behavioral exposure therapy.

The reason all of this is meaningful is because it ties into a bigger question that I have about my life, and I figure some of you all do, too – how do we build expertise? How do we get better at a skill or practice?

The answer is, like in exposure therapy and in hormesis: with a little bit at a time. You don’t go from being horrified of public speaking to a keynote lecturer overnight: you have to create a plan, exposure yourself to the stressor in small amounts, building over time, and move toward your goal.

One point that I want to make very clear here is that executing this idea necessarily means pushing yourself out of your comfort zone – pushing a little into that uncomfortable place, and sitting there, working there, allowing yourself to survive and thrive though that low level discomfort. That’s how we get better. That’s possibly the only way we get better.

Recognize that both exposure therapy and the hormesis model agree: large jumps are not productive. Too much water will kill you. Start small, and recognize that you have to climb a ladder from the bottom – small steps, building on one another, is where change comes from and what makes things stick.

Once I started to think about exposure and hormetics in this way, as a mental model, it’s the type of idea that is very sticky, and has started to map onto my work in many other interesting ways. You can see how exposure therapy has clear parallels to things like delegation, helping your team build expertise, and even in customer relationships.

The next time you want to build your skills or hone your practice, ask yourself: what part is the scariest for me? What looks like it’s the hardest, most out of reach bit? Then, break off the smallest chunk you can, and attack that, and only that, until you’re comfortable. Then, get started on the next chunk.


Risk and Support in Leadership

Not long ago I had the pleasure of hosting an old friend in Saratoga (where I live).

Rob and I became colleagues first, by working together in high end coffee in New England, and then eventually friends.

Rob had worked in coffee longer than I had when I joined that industry, and is still a big part of the community in Providence. He was in my neck of the woods visiting clients of his – he’s a coffee trader these days, and sells green unroasted coffee to folks who turn that coffee brown and sell it to the general public.

Over wine and Hatties’ fried chicken, we talked. We talked a lot! We talked about family and career and what it means to live a good life. It was an excellent visit with a great friend.

One of the things that he introduced me to was the idea of thinking about leadership in terms of risk and support. You can imagine these two ideas as different dimensions on a field, like so:

Screen Shot 2016-07-12 at 7.53.10 PM.png

In a leadership position, the decisions you make will tend to fall into one quadrant most of the time – the way that we can think about these dimensions are in terms of how we work with our team.

Support here means, how well do you as a leader back up the members of your team?

When someone falls down, when something doesn’t work as planned, do you step in, do you take responsibility for the team? Or do you allow the individuals to face scrutiny and take the blame themselves?

If a member of your team tells you that they have a bold career plan, as their lead do you find ways to help move them along that journey, finding or manufacturing opportunities for them? Or do you nod, ask about their day, and let them try to find their own way with neither help nor hindrance from you?

These are both different ways that we can compare high support and low support.

Risk here means, how much risk do you allow or encourage your team to take on? Do you fully insulate them from the winds of your organization’s politics, content with their low amplitude day to day work? Or do you allow them to wander outside your team’s safest places and experience both the opportunity for great work and the chance of failure?

Risk and Support are not always absolutely good or absolutely bad – you can imagine a lead who exposes their team to great risk could create a terrible environment to work in. You can also easily imagine a leader who fully supports her team in all they do, but never offers up any Risk, which means the support isn’t ever really needed.

This is why truly great teams balance the two, and achieve a state of both High Support and High Risk – offering opportunity (and the accordant risk) when appropriate, and doing all they can to also provide support for the decisions made in pursuit of that opportunity.

As far as a guideline for leadership and leadership decisions go – I like this one a lot. I’ve been asking myself, “Am I allowing for some risk? Am I supporting bold choices?” 

This is pretty half baked on my end – there’s a lot here to consider (how much risk is appropriate? Can one over-support? What does high-risk low-support look like? What about low-risk high-support?

Have you heard of this kind of structure before? How does this gel with your own experiences, as a team lead or as a team member?



Sheryl Sandberg, Iran, and Leading Well

I can acknowledge that I am late to the party, but I’m reading Lean InIt’s fantastic.

There is a ton to think about in this book, and I have a few pieces brewing on the topics within, but there was one passage that has really struck a chord – it fits into something that I’ve been wrestling with myself, the kind of idea that has a few pieces, and they don’t quite come into focus until suddenly, they do.

Let’s start with that passage, it’s on page 132 in my copy:

After the married women spoke about how hard it was to balance their lives, the single woman interjected that she was tired of people not taking her need to have a life seriously. She felt that her colleagues were always rushing off to be with their families, leaving her to pick up the slack. She argued, “My coworkers should understand that I need to go to a party tonight – and this is just as legitimate as their kids’ soccer game – because going to a party is the only way I might actually meet someone and start a family so I can have a soccer game to go to one day!”

(Just a sidebar here, I thought about cutting the last part, from ‘because going to a party…’ because I think it subsumes the agency of the single woman and sort of reduces her desires into an early-game version of the married womens’ desires, but I’m leaving it since that’s how it was in the book.)

One of the other pieces of this suddenly-in-focus idea comes straight from the headlines of January of this year. Remember when the French President Hollande turned down a State Lunch with Iran because they demanded that the meal be served without wine?

Here’s a New Yorker piece on the event. It’s a good piece, and approaches this event from the perspective of hospitality – to what do we owe our guests? It is, after all, that the Iranian delegation placed their request out of religious observance – not merely to inconvenience or to bully the French.

As I do, around this time I grilled my friends about the topic – have you heard about the French Lunch? What do you think about the Iranian argument? They were mostly avoidant, being very polite and generally pretty proper. The impression I got was that in a general way, it’s assumed that religious beliefs tend to trump social norms in cases like this.

One voice that really resonated with me with David Plotz, speaking on a podcast (the part I’m referring to starts at 1:00:08) – Plotz sees this debate not as one of religious freedom, but rather in terms of what it means to lead a Good Life; “…the things that you claim as fundamental to you.”

I don’t always agree with Plotz, but here I think he is on the right side.

This idea of a Good Life is a highly personal one, and not something that we can quantify or really lend objective judgment to. A person’s life, and the goals that they have for that life, and the things that they hold dear, are deeply personal and generally not subject to debate – especially not at work, and especially not by someone who thinks seriously and deeply about leadership.

Like most of what I write here, this is geared toward folks leading teams remotely, working with people who they rarely see in person, how to make that work in a way that works. This piece is applicable to folks in traditional workspaces as well, but is especially important for remote teams.

What Iran, Sandberg and Plotz have helped to show me is that I’ve been making big assumptions about what a Good Life is, and in bringing my own sensibilities into my work, I think I’ve probably failed to serve some of my peers as well as I could have.

I think that many of us unintentionally give preference to certain ideas of the Good Life in a way that unreasonably ranks other ideas of the Good Life lower on the totem pole. Imagine at your workplace a colleague says that they cannot make an off-hours meeting because their little boy has a recital. Now imagine the same colleague says that they cannot make an early meeting because they have a brewery tour to go to.

We give preference to a particular vision of what a Good Life is – it’s kids, it’s a mortgage, it’s the picket fence and a rescue dog. This is not everyone’s Good Life.

There are arguments to be made to prefer or reject any vision of the Good Life over another – maybe having children and raising them well is good citizenship. Maybe having children contributes to the global overpopulation problem.

As a leader it is not your place to give preference to anyone’s conception of the Good Life.

Unfortunately, you probably are, though. I know I have. How many times have I assumed that a single member of my team will work on a holiday because other folks have kids out of day care? In simple terms, I was bringing in my own idea of a Good Life and using it to give preference to folks on my team.

On one level, giving up my own idea of the Good Life is in part setting aside my own ego. After all, I chose my own idea of the Good Life, I want to believe it has value; to accommodate other ideas of success means acknowledging that at the worst I might be wrong or, (gasp) there may be multiple ways to be right.

In addition to ego, there has to be a rejection of judgment – and this is probably the hardest part of all. In making space for and allowing for folks on your team to conceive of and pursue their own idea of the Good Life, it means defending that pursuit in ways that, at least at first, may seem very strange to other folks who are coming to work with their own ideas around the Good Life.

You can see more clearly now why that last part of the Sandberg quote does not really advance my argument – if the single woman had simply said,  “My coworkers should understand that I need to go to a party tonight – and this is just as legitimate as their kids’ soccer game,” she and I would be more simpatico.

Using the party as a route to marriage, etc, simply acquiesces to the existing status quo Good Life.

If a member of your team is productive, and efficient, and creating the results that the team needs to find success, as their leader it is not only your job to allow them to pursue their own vision of the Good Life, but to defend that vision against other members of the team, and even other people within your organization.

The reason this is more important for remote teams than for geographically co-located teams lies in the trust remote teams need in order to be performant. Working without daily schedules or shared office space means that, as a leader, you have to trust your team explicitly, and believe that they’re making the best choices for themselves and for the organization.

The pursuit of the Good Life has to be included in that trust. In a remote environment especially, knowing that you respect their choices and will stand up for them is a big piece of serving your team well.

I don’t have a great call to action on this one. It’s hard to step outside of my own idea of the Good Life. I’m starting to see things more clearly now, and I hope that you’ll think on this too, and try to recognize when you’re unintentionally bringing in your own idea of the Good Life in a way that’s reducing the Good Life of others.

Iterating on One on Ones

I know, I know – I’ve written about one on ones before.

If you’re not familiar, a one on one is a short sit down between a team lead and a member of the team. Folks much smarter than me have written some really insightful stuff about them, why they’re important, what they’re for. Here’s a great one, from Rands.

I do them once a week, for about thirty minutes, with every member of my team. I’ve been thinking about one on ones quite a lot recently – some feel really productive, some feel like I’m really getting to know the team member, and some feel functional, perfunctory, useful not maybe not productive.

This coming week, we’re starting a new structure of weekly updates. Since Athens’ inception we’ve done roughly weekly updates with our sister team (Sparta, obviously) on Wednesdays.

These updates weren’t really structured at all – folks would write about their home being remodeled, or their recent projects, or their ticket or chat count, or maybe an upcoming vacation. They were nice, but not especially helpful, as someone trying to understand how folks were doing, what they were working on, etc.

We didn’t even have a great reason to be doing them on Wednesdays – at one time, all of the teams at Automattic did updates on Thursdays, so it made sense to schedule internal team updates on Wednesdays.

Our company wide updates are still called Thursday Updates, but they are usually posted on Fridays, sometimes the following Monday, depending on what time zones the team’s members tend to work from.

The time we scheduled the updates didn’t make sense anymore. Our internal stats for chats and tickets run Sunday > Saturday, so to do any kind of regular volume updates meant folks had to do some math by hand, which was a point of friction.

Wednesday was also suboptimal because it was right about the point in the week where folk started to catch their groove – breaking it up with unstructured reflection (or being ignored, or populated with throwaway content), wasn’t the best we could do.

Short story long – starting this coming week we’ll be doing our updates on Monday morning, with a consistent structure for each person on the team, including me. There are expectations for clear and transparent reporting of individual volume, as well as how it compares to our team baseline, which is a sort of cooperative understanding of what a day’s work looks like for us at this time.

This brings us around to the obvious question; what does this have to do with one on ones?

In considering the one on ones that I really enjoy, that I feel are Working, they’re consistent in that they are not simply status updates – they’re not “I did X. This week I’m doing Y.”

Instead, they’re about experiences and approaches, friction and family. They’re about building a relationship rather than communicating things I can easily find elsewhere, especially with our commitment to communication and transparency.

As our weekly personal updates become more focused, I think it’s entirely possible that they could take the place of the more status-update-like one on one conversations. This isn’t to say that I’ll stop doing them (I love one on ones), but rather I’ll have a chance to start doing them correctly – using them to get to know my team, rather than getting to know the stuff around them.

I think it is probably also a good move for me to start being more clear to my team how I think about one on ones – if they are meant for talking about bigger career thinking, about navigating the waters within Automattic, about finding the right way to be impactful, there is likely a better way to structure that.

I’m not sure what that structure will look like – I have been reading about OKRs quite a lot, and it seems like they could fill that not-daily-work-but-still-important-work structure.

I am also trying to be more aware that my natural inclination toward more structure is not always the right move – although, I think I’m probably right about this one!