Category: Remote Leadership

Fatigue: Emotional and Intellectual

I know not everyone follows my LinkedIn profile with rapt attention. That’s OK – I don’t follow your LinkedIn profile very closely, either.

So, you might not know; I’ve moved into a different-but-not-so-different role at Automattic (the folks behind WordPress.com, Woo Commerce, Jetpack, and a heap of other great stuff)

I was previously leading a support team, and have since moved into a role that we call a Data Analyst, on the Marketing team.

If you’re familiar at all with Automattic’s naming policies, both for jobs and teams, yes, this is an outlier in the direction of the mundane in both cases. I went from being a Happiness Engineer on Team Athens (and also technically on Team Redwood) to being a Data Analyst on Customer Activation.

100% consistent with Automattic standard, though, are the many and varied hats that come with this role: at other companies my day to day work could be described as Marketing, Growth Engineering, SEO, SEM, Pay Per Click, Customer Success, Data Science, even a little bit of database architecture. It’s a lot!

(As a sidebar, I think the job duties and title change may make it seem like I’m making a career change or otherwise sort of changing direction – let me assure you, my focus continues to be on building explosive value for our customers. I’m expanding my tool set – not changing my approach.)

Today, was a cognitively demanding day. Working remotely means taking on a lot of responsibility for structure and organization of one’s work – I’m still figuring out how to do that the best way I can, in this new role. It also means being disciplined to push back distractions which are constantly at the ready in any browser window.

Spending hours looking at databases, considering queries, performance, outputs, accuracy – this is work, it’s real work, and it builds fatigue. A day of work, focused, attentive work, can certainly leave me in need of a deep breath and a long walk.

(I personally find it especially hard to think critically and well about SQL, statistics, databases, and so forth, near the end of my work day. It’s like I’m running out of gas.)

What struck me today was how different this kind of fatigue feels, especially compared to the kind of fatigue I’d feel after a tough day leading a team of Happiness Engineers. I’ve reduced them into two distinct types for the title – Emotional and Intellectual – but I’m sure there is some overlap, maybe some days more than others.

Maybe the difference is, in the lead role, the fatigue comes from trying to serve others, trying to hold them and their full personhood in your mind, whereas in this analyst role the fatigue comes from the intensely individual and personal kind of focus it takes to do it well, to take it seriously.

It does feel different to say to my wife, “I had a hard day – I couldn’t get the data types to reconcile the way I wanted,” rather than “I had a hard day – I think I really let some people down.”

Maybe they’re not different. Maybe I’m different.

 

 

 

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?

 

 

If You’re Not Preparing for Your One on Ones You’re Wasting Everyone’s Time

I’m working on a massive opus of my thinking on one on ones, how important they are to remote teams, and a bunch of tall tales about the times I’ve messed them up, and how to avoid my mess ups in your own life.

(Note: This massive opus will not be a list of questions to ask during one on ones. We have enough of those 🙂 )

If I were writing for an actual publication and not my personal blog, it would have an SEO optimized, click-gravity headline: “The Ultimate Guide to Remote One on Ones” – “You Won’t Believe What This Dude Said in a Remote One on One!” – “56 Ways to WOW your Boss!” etc etc.

( You can see my first ever post about one on ones here: Communicating with a Remote Team: One on Ones)

One thing that doesn’t fit super well into that piece, but is still something I want to talk about, is that one on ones are important, and they are hard to get right.

Continue reading “If You’re Not Preparing for Your One on Ones You’re Wasting Everyone’s Time”

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.

Finding Your Own Structure

On the recommendation of my friend and colleague Andrew I recently picked up a leadership book called Extreme Ownership. Here’s his take on it.

There is a lot to talk about in this particular book, but the piece that really stands out to me is the idea that structure and discipline can help an individual to a life of greater freedom. This idea is especially germane to remote workers or folks otherwise enjoying highly flexible schedules and workplaces.

Having travelled in some pretty radical circles, I am familiar with the usual backlash against structure, process, and limitations on behavior – there is definitely a mindset that rejects these things in a wholesale way, and while I don’t agree with it (or find it to be particularly coherent as a political philosophy), there it is.

I can acknowledge that on its face, the idea of adding structure in order to increase personal liberty may sound counterintuitive. Stick with me. We’ll go on this journey together.

When I was studying philosophy one of the works that somehow found its way into all of my other classes was a paper called Two Concepts of Liberty.

If you’re so inclined, and have about sixty pages of time to dedicate, I totally recommend giving it a read in its entirety – it’s dense but brilliant, the kind of work you’ll get through and just nod, because it’s simply intuitively correct, something you understood before you even read it, but put into the very words you never could have.

The TL:DR of Two Concepts is that we can think of liberty as falling into two buckets: Positive Liberty and Negative Liberty. 

Negative liberty is essentially freedom of movement or freedom of choice. If I stop you from eating a donut, I’m infringing on your negative liberty. If I tell you to work on this project and only this project or you’re fired, I’m infringing on your negative liberty.

Positive liberty, Berlin says, is self mastery. Being able to make decisions for yourself in an informed and critical way means you have high levels of positive liberty.

When you answer Berlin’s question, “What, or who, is the source of control or interference that can determine someone to do, or be, this rather than that?” – if the answer is “I am the source of control,” then you’re enjoying positive liberty.

These two ideas are often at odds in ways that will help us to understand my above assertion, that through some structure and some discipline, we can ourselves become more free.

Consider driving. I live in the US, so I’ll be referring to US-based road rules – please substitute whatever is appropriate in your region of the world.

Driving in a car requires following certain rules – you stop at red lights, you drive at an appropriate speed, you stay to the right hand side of the road. These are necessarily restrictions on our behavior and as such, limiting factors of our negative liberty.

However, even as our negative liberty is constrained, we’re able to exercise greater positive liberty, as driving becomes a safe activity, it becomes reasonable to engage in, rather than some sort of Mad Max terror situation. We’re able to effectively self govern.

By creating a more structured environment, we’re all able to thrive more fully and accomplish our personal goals. What is the end goal of liberty if not to accomplish our personal goals?

In Extreme Ownership, they talk about a very serious level of discipline, but they’re also dealing with very serious personal goals; kill or be killed. For somewhat less severe goals (decrease churn, make our customers happier), less serious discipline is probably OK.

One of the things that remote workers gain is an open day. There are pros and cons, and the freedom at hand can be thrilling, to be sure.

When you consider your work, and the way that you approach your work, let me encourage you not to mistake negative liberty for positive liberty. Creating structure around your goals and around your day allows you more freedom, not less.

When you’re your own boss, or when you enjoy the freedom to essentially behave as though you’re your own boss, creating your own schedule, etc, one of the best things you can do is to create some boundaries for yourself, to intentionally limit your own negative liberty.

Maybe that means getting up at 5AM to go to the gym, taking away your own ability to stay in a warm bed. Maybe that means always shutting off the laptop at 5PM, because you know you’ll let work creep into your personal time otherwise.

Self mastery, positive liberty, is best accomplished when you impose your own restrictions on your negative liberty – but you do so intentionally, with an eye to your own broader goals and aspirations. A lack of organization will also surely fill your time, and surely will keep you occupied – but will it move you forward in the right ways?