Stressful customers

In support we often write to confused and frustrated people. After all, they likely got in touch with us because they’re confused and frustrated with our products. That’s okay, we’re expert communicators. We can help them get set up.

One thing we can do as part of that is not presume a customer is “abusive” or “rude” or “unreasonable” at the first mention of profanity and frustration. We want to resist our first impulse, which can often be to admonish the customer on their tone. This will more often than not aggravate their frustration.

Instead, when confronted with a profanity-laden message, our first instinct should be to give the customer the benefit of the doubt.

We must treat their frustration as a signal that we should invest more in our understanding of their situation. We need to pause, step back, and focus on the issue at hand. That means fully understanding the history of their interactions with us and their issues with our product.

It also means keeping the conversation focused on resolving their issue. We can recognize their emotion without condemning it nor playing into it. Every person we interact with is, well, a person. We all have moments when our frustration gets the better of us and we’re harsher than we mean to be with a company.

I believe our role in support is to help people be successful. And to see every conversation as an opportunity to change someone’s impression about our business and our product. Even the angry, profane, and ALL CAPS people deserve our help. After all, it’s typically our product or our missteps which have pushed them to frustration. That’s alright, our world-class communication can turn things around.

Replacing Instapaper with Pinboard

After Instapaper’s odd GDPR-related decision to (temporarily) block EU access I decided to re-evaluate what tool I use for my reading list. I’ve used Instapaper every day for the better part of a decade but something about their recent decision didn’t sit right with me.

I’ve had a Pinboard account since 2009 and decided to try it as a read-later tool. So far so good. If you’re interested you can see what I’ve recently read here.

The import process to Pinboard was a bit of a pain. It’s supposed to be automatic but for some reason my export files weren’t importing. I didn’t have that many articles in my backlog, so I ended up migrating these manually.

On the settings side Pinboard has a bookmarklet you can add to your browser for one-click article saving. I also set it up to mark everything as private by default. That gives me a private to-read list and a public already-read list.

iOS is where Pinboard is the least competitive with Instapaper. What’s worked well enough for me is the Pinner app (on both iPhone and iPad). That makes it easy to read articles through Safari’s reader mode. Plus it’s then much easier to turn articles into bookmarks. The main downside is that there’s no offline storage, though I rarely used that with Instapaper.

The bonus feature is that Pinboard has, for a fee, built-in archiving. For $25/year it will crawl every bookmark you add and save a cached version for as long as you have an active, paid account. It’s a nice protection against link rot.


Allerton Garden.

Leah and I just got back from 9 days in Kauai. This was our second trip to the island and we enjoyed it just as much as the first. On the activities side of things we went for a hike along the south shore, did two intro SCUBA dives, and more. Plus, this was our view for the week. No complaints.

I also read my way through 5 books: Leonardo da Vinci by Walter Isaacson, Museums: A Visual Anthropology by Mary Bouquet, The End of Average by Todd Rose, A Guide to the Good Life by William B. Irvine, and Anathem by Neal Stephenson.

Three rules of maintenance

The condo building I live in has a property management company. This makes sense. The building is 120+ units across 12 floors with retail and office space. What doesn’t make sense is this same company’s poor communication. They are consistently unclear and underwhelming, particularly when it comes to maintenance.

Today they were servicing the fire safety system. This also makes sense. Fire is an existential threat to a 12-floor building and maintaining that safety system is key. But during this maintenance the alarm system speaker in our unit continually blipped on and off. Imagine the sound of plugging headphones in-and-out, in-and-out. Just a little blip. But that blip emanates from a unit typically used to signal a fire alarm or emergency. So let’s call this a disconcerting blip.

You’d imagine that ahead of maintenance like this a property management company would notify homeowners, right? Wrong. You’d also imagine that after being alerted to this disconcerting blip that company would acknowledge the impact, right? Nope. And you’d imagine that, even though a vendor was performing the maintenance, the property management company would take ownership of the mishap, right? Not really.

In thinking about this snafu it solidified some ideas in my mind around support and maintenance. I think they apply to software systems and physical infrastructure alike.

Provide awareness
It’s vital that you provide awareness for customers ahead of maintenance. Either passive awareness (like a status page they can check) or active awareness (like an email notification) can be successful. What counts is that you communicate somewhere, someway to your customers.

My property management company didn’t do this. At all. There was no email, letter in our mail, or notice on a bulletin board that this was happening. So when that disconcerting blip started I was just confused. That sucks. To resolve that confusion I went downstairs and talked to the on-site building manager (who is fantastic). He cleared things up instantly. But that’s not really his job.

When you don’t provide awareness for your customers you’re rolling the dice. Maybe everything goes well. If so, that’s great. But a single success does not signal a resilient process. Because when things don’t go well your failure to provide awareness amplifies your customers’ frustration. Now they’re angry at the impact of this maintenance and they’re angry at you. Best to avoid that.

Acknowledge impact
I know the maintenance plan calls for your customers to be fine. The maintenance won’t impact them. But, well, it might. And when it does you have to acknowledge that impact. That doesn’t necessarily mean you have to apologize. Things change. They don’t go according to plan. That’s life. Your customers will understand. Your first step has to be acknowledging that your work impacted their time.

My property management company didn’t do this. After talking to the on-site manager I sent the management team a short email explaining what happened and asking for a heads up next time there’s maintenance. A reasonable request, I think. Instead of any real acknowledgement, though, I got back this:

I spoke to Name (copied) and he said the speakers should not have sounded in your unit. There may be a problem in the system. He needs more information and will contact you to get this resolved.

That’s…factual? Nowhere in that do I hear an acknowledgement of impact. No, “Thank you for letting us know. This maintenance work wasn’t intended to impact homeowners and I’m sorry it did. We’ll improve our notification process going forward.” It’s nice to at least know the impact wasn’t intended. But when writing to your customers try and be a little less…cold. Acknowledge that, despite your best intentions, your work may have adversely impacted their day.

Accept ownership
Maintenance can be tricky. Maybe you’re dealing with third-party vendors. Maybe your data center’s backup generator ran out of fuel. Maybe you just didn’t account for weird edge cases. But here’s the thing: it’s your maintenance and they are your customers. Own that.

My property management company, again, didn’t do this. After getting that coldly factual email I replied to say, essentially, “That’s nice but my point about proactive communication stands.” Had they followed the previous rule and acknowledged their impact then we wouldn’t have gotten to this step. Instead they said:

Sorry Andrew. We were assured by the testing vendors that no units would be affected and therefor did not send out a notice.

Well that’s nice. Didn’t end up meaning much, did it? Passing off the impact you have on customers to a third-party doesn’t divorce you of responsibility. When you avoid taking ownership you convey to customers that you’re not really invested in their success. You know you had an impact on their work. But you’re choosing to just sort of go, “Eh, but it wasn’t really our fault.” When you do this you offer no reassurance that this maintenance problem won’t happen again. And again.

When it comes to maintenance, communication is key. You need to keep your customers aware. You need to acknowledge when you have an unintended impact on their day. And you need to own your role in causing that. When you don’t do these things your customers are just pissed off. And worse, they’re doubting you. Because if you can’t communicate well around routine maintenance then why should they trust you to communicate well around more important matters? They shouldn’t.

Asia-Pacific Hiring

One of our big goals at Automattic is to cover support 24/7. Our customers span the globe and we want to always be there for them. Since we’re distributed that means we also seek to hire great people from around the world.

Hiring like that helps us be around 24/7 without necessitating graveyard hours. And right now we’re keen to hire more team members throughout Asia-Pacific.

As part of that Deborah and Pam from our hiring team will be in Australia and New Zealand next week. If you’re interested in Automattic or if you just want to chat about how we handle support you can find them in a few places.

They’ll be in Sydney March 8th and 9th, including at the local WordPress meetup. Then they’ll be in Auckland, NZ from March 10th through 12th, including at the local WordCamp. And finally they’ll be in Melbourne March 13th and 14th where they’re hosting a local event.

And if you’re in Asia-Pacific and reading this, we’re hiring.

Resume advice

In helping a friend with their resume this morning I shared some of the advice I wrote up with the Support Driven community. Folks seemed to appreciate it enough that I wanted to log it here for future reference.

These aren’t necessarily deep insights. They are things, though, that I’ve often seen job applicants forget or skip over.

  • The more succinct your resume is the better. You don’t want to cut important experience. At the same time, though, 4+ pages is too long. If you can fit your relevant past experience into one page that’s ideal.
  • Your resume’s brevity matters because a hiring team will only ⁠⁠⁠maybe⁠⁠⁠ look at the resume and ⁠⁠⁠if⁠⁠⁠ they do then ⁠⁠⁠maybe⁠⁠⁠ they’ll go past Page 1. The more complete Page 1 is the better chance you have of an accurate first impression.
  • Visually it helps to make the content scan-able. If a hiring team has just 90 seconds to glance at your resume then how can you use font weights, color, and text size to draw their eye to the right things?
  • For each job application read through your job summaries and focus on whether the descriptions are clear to your audience. Are there things you want to emphasize for one job but maybe not another? Are you including the right project samples and client names?
  • For how you describe a job, cater to your audience. Your descriptions should be different depending on whether a hiring manager, an engineer, or the HR team is reviewing applications. Who reviews your resume may influence what they’re looking for. It helps to think that through.

If you follow that advice you’ll likely also realize that it requires writing a different resume for each job application. That’s intentional. When your resume is generic and not tailored to the company or role you are applying for it shows.

I think the main goal of a resume is to be interesting ⁠⁠⁠enough⁠⁠⁠ to get you a conversation with the company. If you don’t cover every project, client, or skill that’s okay. What counts is covering the sampling of things which will be ⁠⁠⁠most⁠⁠⁠ relevant toward getting you on to the next step of the process.


One of the things I’m most proud of from this year was helping to organize the first ever SUPCONF in San Francisco. I spoke about how to build a career in support and helped plan pieces of the event. It was amazing to see a Slack community come together in-person and connect.

Later this month we’re holding the next SUPCONF in New York City. Over two days we’ll host speakers from Medium, SmugMug, Wistia, Help Scout, Automattic, and more. Beyond that we’ll have dedicated time and space to talk with other attendees.

That time and space for connecting with attendees was one of the things I was happiest with from SUPCONF SF. I think attendees walked out of the two days having gotten to know far more people than a traditional conference would have allowed for. A hallway track can be great for outgoing folks. Being intentional with how it’s organized, though, can give even those who aren’t outgoing the confidence to engage.

We also have many other events happening around the conference. From a pre-event cupcake social to a GIF battle to a hosted dinner and conversation there’s a lot going on.

If you find that interesting I’d recommend registering soon while there are still a few tickets left.

Building a career in support

The following is the text of a talk I gave at the inaugural SupConf last month in San Francisco. The talk itself varied a bit from my notes, but the core ideas are below. The video will be available later and in the meantime I wanted to share the talk and slides.

I want to talk today about the next steps you can take for your career in support. As part of that I’m going to share things I’ve learned over the last 10 years as I’ve built my own career.


To get started, I want to briefly share my own career path. I started working in support while in college. There I worked in an on-campus video production lab. Going into college I knew that I needed a job to cover expenses. It wasn’t an interest in support that drew me to that job, it was necessity combined with the appeal of getting paid to tinker with and learn technology.

It was there that I started using WordPress, which led me to working with the student newspaper. That connected me with a group of students across the country who were all fundmentally dissatisfied with the software available their campus newspapers. Most schools relied upon a limited, proprietary CMS. The group of us banded together and ran a company called CoPress that did WordPress hosting and support for student newspapers. I was the Hosting Director there and it was my real introduction to support. I worked with clients to get their sites set up and help train their newsrooms in how to use WordPress.

All that work with WordPress led me to apply at Automattic, where I started as a Happiness Engineer in 2010. When I joined the support team was around 8 people and we covered email support for Since 2010 I’ve worked as a team lead, led our support hiring process, and now lead our 150-person support organization. And we’ve expanded to cover support for a half dozen different products across live chat, email, forums, and social media.


But that’s just my career. I also want to talk about what your career in support means at a high level. Because a career in support is a wonderful thing. Support at its heart is about helping people. A career in support means a lifetime of service. It means helping people use your product. Because if you’re not helping people use your product, why are you building it in the first place?


The opportunity exists for your career in support to mean many things. Do you want to build and manage a team? That can be your career in support. Do you want to genuinely teach people every day for many years? That can be your career in support. Do you want to perfect your writing skills and convey technical information in a way people can relate to? That can be your career in support. Do you want to understand how hospitality improves the financial health of a business? That can be your career in support.


And I think that’s why you’re here today. You know that support is more than answering questions all day. Support is a craft that takes time to master. Support as a career means concerning yourself with all aspects of the customer’s experience. You have to look at all aspects of the experience because support doesn’t stop when you hit reply.


In support you are the human connection to a company and its product. For many customers the support team is the company. You may be the only employee a customer really knows. And you may be the only employees who really know your customers. Your relationships with customers provide an opportunity to influence your company at a very foundational level.

So if support has all this opportunity why do we need a conference about how to build a career? If your career can be all of those things, then why are we here? Why don’t we see a burgeoning trend of people clamoring to land support jobs? And why is support still seen as something that’s just entry-level and a dead-end?


The answer to all of those questions starts with recognizing that SupConf, and this community, are special.


Let me ask you something. When you tell people you work in customer support do you think they picture SupConf? When you tell family and friends that you’re headed to a customer support conference do you think they imagine the environment of the last two days?


Because I’ll bet they don’t. I’ll bet what they picture looks a lot more like that room than the atmosphere in here.


When I first started working at Automattic I’d meet people who asked what I did. I’d say that I worked at Automattic where we make and see their eyes light up with interest. “Oh, what do you do there?” they’d ask. When I said I worked on the customer support team more often than not I’d be met with an…


“Oh…” which sapped all questions from their brain.

After a couple times of that happening, though, I realized that it’s not their fault. Their reaction was understandable because much of the world is not like us; we’re not the predominant norm. Much of the short-sighted thinking characteristic of big business doesn’t share our view of support. That doesn’t mean those companies and those people are wrong. It means we have work to do.


We have work to do because that world sees support as nothing but a cost center. That world sees support as a dead-end job. That world compensates support as if anyone can do it. And that world puts nothing into career opportunities because, let’s be honest, who in their right mind wants to make support a career?


We do. But there’s no guarantee that the work we love becomes a viable career path. What we’re talking about here is whether the career we all want becomes the industry norm. The more that happens the healthier and deeper our career paths are.


So if we want to improve this, what’s the work we have to do? We have to first acknowledge that building support as a viable and thriving career path won’t be easy. It’s going to require taking initiative and demonstrating our value to other teams in our companies. More often than not there won’t be existing career systems in place for us to build upon. We need to lay that foundation and share what we learn with others.

There are a couple pieces that I think can help us lay this foundation.


We first need to be comfortable measuring ourselves. And we need to be comfortable tying metrics to company goals and priorities. If we can do that we can start adding value across the company. And we can actively combat the notion that support’s just a cost center.

We need to understand that many aspects of our work can, and more importantly should, be measured.


This doesn’t mean we have to become dogmatic, though. And it doesn’t mean we have to become Comcast. Please don’t build your company to be Comcast, one of them is enough for the world. What we need to do is seek out healthy metrics for ourselves and our teams and then hold ourselves accountable.


When it comes to healthy metrics having a strong perspective helps. On our core focus right now is 24/5 live chat coverage. That’s a highly measurable goal that we need to inform with metrics. We need to look at how many Happiness Engineers we have online, when customers need to chat, how many customers we’re missing in chat, and what our overall coverage is like. Those are all directly measurable things.

But that metric is right for our goal for our customers. You should find what works for your team. Set goals that are relevant to your customers and your business. Your perspective on what works for your team is vital, maintain that. If your team does live chat don’t measure yourself against our 24/5 goal, instead hold yourself accountable to what’s reasonable for your team and your company. When you lose that perspective you risk demoralizing your team and creating misaligned incentives for your customers.


We need to build our support teams to add value across the company. We’re all expert communicators. We know not just the ins-and-outs of our product but how to convey our expertise in a way that’s relatable to our customers. That’s an immensely valuable skill. Our next step must be communicating back to the company what we learn from customers and from each other.

It’s that next step where we all too often come up short in support. We’re great at communicating with customers but, at times, terrible communicating internally to other teams at our companies. How many times do you hear about a development team not being on the same page with support? Or a sales team that makes promises to customers which support knows they can’t do? Those are real problems. And while they’re hard problems they’re solved with clear, consistent communication across teams. That’s our specialty!


Measurable goals, a healthy perspective, and building value across our company are all great things. In most cases, though, you’re not going to find a pre-existing company structure here that builds a path for support to follow. The initiative for defining that path is on you. When it comes down to it you have to own your career. Be proactive, because no one is going to build this for you.


Those are all some things we can do to improve our careers. You can get to a successful career in support. It’s out there. I want to share some stories, more failures than successes, from my own experience to help explain some of this.


One of the things I’ve learned in my career relates to the importance of measurable results that I mentioned earlier. When I started leading a team I was blind to the role goals and measurable results played for a growing team. I say a growing team in particular as when you have 4 people joining every few weeks that means you have 4 people asking questions like: How do I know if I’ve had a successful day at work? What’s the kind of impact our team looks to have with customers? What’s the type of impact our team looks to have in our company? When there are no key measures in place you’ll end up with those new people asking 5 people that question and hearing 5 different answers.

For me, I’d written goals off as too formal and corporate. They’re not. Measurable results are a key piece for communicating the value of our work. It’s important to start this work early, too, as if you’re like me you’ll likely do it terribly at first. When I first started setting goals for the team I looked more at what other companies were doing than where we were as a company. I lost the perspective of what was relevant for our company and our customers. That set us back as a team because our effectiveness is not always about getting more done; many times it’s simply about getting the right things done.

At one point we had a backlog of 5,000 tickets and response times of over a week. And I’d talk about how our goal was to get below 5 hours. 5 hours?! Ha! When you’re 5,000 tickets deep a 5-hour response time goal is about as helpful as wishing you had a magic wand. It sounds great, but just isn’t going to happen.


Another core piece to a successful career is pride. Remember earlier when I told people I worked in support only to be met by their blank stares and raised eyebrows? Well, I have an admission. After a couple times of doing that I started saying I was a Happiness Engineer. That’s the title much of our support team uses at Automattic. The word “engineer” would pique their curiosity in a way that support just didn’t. It let me fake it by talking about how the role also involved new feature testing, bug reports, documentation, and more. It’s not that the role didn’t include those things; it did and still does. It’s that I didn’t feel a sense of pride in owning the fact that I worked directly with customers.

It wasn’t until I realized there were people like Chase, Jeff, Scott, Christa, and others out there that I felt comfortable owning support as my thing. I’d hear Chase talking about his deli job on SupportOps and realize that customer support was a legitimate lens for your work and expertise. He’d relate lessons from the deli to how he helped customers at Basecamp. Food service was also my first job and I’d relate easily to those deli anecdotes. Once I found those commonalities it became much easier to seek out help, advice, and build resources to accelerate my career.


I realized that a strong community was there to support my career. The more I contributed the more I felt comfortable asking others for help and advice. By proactively taking part in discussions, writing blog posts, and sharing how our team does things I was able to build connections that I now draw upon to help me solve problems our team confronts. Being active in a community like Support Driven is the best way we can all support each other.


So what should you do next? Let me recap today by highlighting the three qualities I’d like you to take away from this. I think these form the foundation for a career mindset.


First, you need to be proactive. Your career is like a well-tended garden. If you’re not proactively given it attention and care then it’ll just be a bunch of weeds. On the work side this means taking your career into your hands. Is there a skill you’ve always wanted to learn? Then start; don’t wait for your company to tell you it’s ok. Is there a part of your product that customers hate? Then improve it; talk with customers and communicate with other teams in a language they understand. On the social side: the relationships you build will form the network that propels your career forward. Build and maintain those in a way that’s comfortable for you. At the end of the day it’s your career.


Second, you need to maintain a healthy perspective. Doing this will accelerate your own career progress. Measure yourself by how far you’ve come, not by how you fall short against others. Basecamp didn’t get to 5-minute response times overnight; they put in the work over many years. Your team can do the same. When you’re just starting out the gap between you and others doesn’t mean you’re behind or worse than another. And if you’re 6 years deep that experience doesn’t mean you’re ahead or better than another.


Third, take pride in what you do. Your career is something to shine a light on and show people. Own the fact that you work in support. Don’t sell yourself and your talents short. If you’re not confident in the value of what you do then why should someone else be? Pride in your work is the foundation for your career; and that’s true whether you want to build and manage a team, help people everyday, perfect your technical writing skills, or any other career path support provides.

So be proactive. Maintain a healthy perspective, especially around measurable results. And have a sense of pride in your craft. Those are the steps I’d like you to take toward your career in support.

If that sounds interesting to you, we’re always hiring for people passionate about support. And if you have questions, feel free to get in touch.

Management and Leadership

The following is the text of a talk I gave internally at Automattic last week. It was part of Simon’s Developing Leadership workshops series. The idea was not to assert static truths. Instead my goal was to sketch out an idea that’s been kicking around in my mind about how management and leadership are, at their core, different mindsets. It’s been a useful framework for me in thinking about things.

What I’m going to talk about today is an idea that’s been kicking around in my head for a few months. I’ve been thinking more about the role of a manager and that of a leader; and I’ve been asking myself whether they’re really the same role at all.

Broadly speaking we tend to use these words interchangeably. Your boss is your manager and that person leads your team. That might work in some companies. For Automattic, though, I think there’s value in distinguishing between the roles. What makes someone a great leader? And how do the mindsets, tools, and habits they employ differ from that of a manager?

I find those interesting questions to dive into given Automattic’s growth and evolution. As we’ve become a larger and more complex organization the distinction between manager and leader is one that has become trickier to navigate. There is both more clarity and more questions around a team lead’s role. Our lead role is also different from many companies; this makes it trickier to grok as we don’t fit into the more traditional mental model. Our leads tackle things that many companies place in other departments.

I’ve talked with leads who ask themselves whether their role is to be a manager, a boss, a leader, a coach, or some combination of all that. My hypothesis is that the success of our distributed nature hinges upon strong leaders, not strong managers.

Let’s first take a half step back. What do I really mean when I say that a manager and a leader are different roles? Let me explain a bit via contrasting examples.

The manager focuses heavily on what tasks need to be done. That focus on tasks ensures that the work is going to get done. The leader sets the vision for Why the work needs to be done. That focus on meaning ensures that the right work is going to get done.

The manager is deferential in waiting for direction. Before acting they expect deference from their team members; you’ll find their team asking, “What should I do next?” The leader takes initiative to seek out the right direction. Before acting they do their homework and investigate different paths; you’ll find the leader asking their team, “For these reasons I think this is the right thing to do next. What are your thoughts?”

The manager is rooted in a mindset of distrust. They are the helicopter parents of a company and constantly worry that if they miss a correction the whole house will fall down. The leader is rooted in a mindset of trust. They understand that success comes not through constant monitoring but through creating the right environment for progress to happen within.

These distinctions will surface again so keep them loosely in mind.

So why is the manager not a great fit for a distributed company? Am I saying that success cannot happen under a manager?

As a distributed company it’s important to remember that, well, we’re distributed. There’s no 9-5 office schedule to keep. A team lead may overlap only a few hours at most with their individual team members. When you work with a manager’s mindset you miss an opportunity for empowerment and you limit the growth of your team members. If, instead, you work with a leader’s mindset you seek to build the right environment for success to happen, and then you get out of the way.

Here’s the danger in a manager’s mindset: it may very well outperform the leader’s in the short run. Their heavy focus on tasks may appear, at first, to be the best decision. The team starts fixing bugs, answering tickets, and incrementally getting things done. All the while, though, they lay the seeds for future pain.

Our distributed nature works best when we also distribute trust, ownership, and the capacity for acting on our best judgement. When every team member understands Why the work needs to be done the team itself will successfully get all the right work done. They’ll minimize false starts, sunk costs, and eventually leave the manager’s team in the dust. A leader outperforms a manager in the long-term; and we’re a long-term focused company.

With all that in mind, here are a few ideas for how you can work as the very best leader you can be. If you, and your team, execute on these things then you don’t need a manager. You can leave that helicopter parent behind.

The core building block to successful leadership is to really own your work. A successful leader takes responsibility not just for their own job but for anything that will impact their team’s work. A leader acknowledges that there are no bad teams, only poor leaders. This means that when things go awry it’s your fault, not your team’s.

Second, think of goals as hinging upon setting the right expectations. It’s not about telling folks what to do next. Successful projects have a rationale for the work that is clearly stated upfront. That rationale is built upon to set realistic milestones for work. And those milestones are clearly communicated so that everyone on the team can sense when things stray off course.

And, finally, when things do stray off course be clear in your correction and gentle in its directional change. Corrections are bound to happen, that’s ok. Remember that mistakes in direction are your fault, not your teams. And the greater the deviation from that direction the more unclear your plans were upfront.

These three principles are important because what we do is knowledge work. There frequently isn’t just one right answer to a question.

Those three pieces above may help you get started. They’re really just starting points, though.

If you’re wondering what habits form the basis of the best leader, I have a couple ideas. These come with the upfront caveat that they’re easier to state than do well. They’re the milestones I personally aim toward but frequently come up short against.

The best leader is one who’s responsible for the team’s performance as a collective unit. They ensure that every team member is aware of the team’s overall performance and what the team’s primary and secondary foci are. The best leader ensures that any Automattician can find clearly communicated updates that reflect on that team’s performance. The goal for the best leader is one of mentorship and development; it’s to build a team into a collection of people that you trust deeply.

The best leader is one who’s responsible for the team’s performance as a collection of individuals. They ensure that every individual is improving in both a measurable and a qualitative sense. The best leader ensures that a significant regression in performance is addressed quickly and that each individual knows how they are performing in their role.

The best leader encourages meaningful communication. They seek to create an environment in which people feel compelled to communicate publicly with the team rather than sit on their answers.

The best leader aims to create the healthiest team environment for successful work. They understand that it’s about providing resources, information, and measurable accountability. The best leader also understands that it’s not on the them to improve a team member’s work, it’s on the team member.

Finally the best leader is also one who asks, “Why?” They ask this of their team, of themselves, and of their lead as well. The best leader doesn’t just accept a course correction they don’t understand. They ask, “Why?” to make sure that they understand the intent. Only by understanding intent can they best relay the direction to their team.

If these ideas sound interesting but you just don’t know where to start here are three questions to ask yourself:

  1. When things go off track, do you say, “My fault.” or do you think it’s the team’s fault? Remember that leadership starts with ownership.
  2. If a team member’s performance regressed, how long would it take you to notice that? To be a strong leader you need a strong and repeatable process for yourself.
  3. Have you asked your team members what, in their words, the expectations you have for them are? What you say and what they hear are not the same things, that’s ok.

If you want to I’d recommend reading this book about the Navy SEALs and this book about company leadership.

A note on feedback

I had an epiphany recently about performance feedback that seems so obvious in hindsight. One of those things you realize and then think, “This took me 6 years to figure out?”

At Automattic a lot of our feedback conversations take the form of a 3-2-1-Oh chat. It’s a mix of a team member writing a self-assessment and a team lead writing a review. The conversation centers around answers to these bullet points:

  • What are 3 things you’ve done well?
  • What are 2 areas or skills you’d like to develop?
  • What’s 1 way your team lead or Automattic itself can support you?
  • And, oh, can you write a sentence or two about how you see your career developing?

I’ve done these conversations with team members for over 3 years. In every instance I approached the 3-2-1 as an exhaustive review of each and every aspect of someone’s work. I tried to solve all the problems in one go. I’d review hundreds of ticket replies, P2 posts, and try to cover an evaluation of everything. It took me until this week to realize that’s an untenable position.

That exhaustive approach was time-intensive and, likely, did each team member a disservice. On my side it took at least 10 hours for each person. On their side it resulted in a deluge of ideas on what they should improve.

If timely and meaningful feedback is your goal then spending 10 hours to put it together is near-impossible. If regular and incremental growth in a person’s work is your goal then an avalanche of ideas for improvement inhibits that.

I now realize that spending a little less time, more regularly, to generate fewer ideas will better serve my team members. It’s better to keep someone on course through a series of small adjustments than through a U-turn. My goal is to have these conversations on a quarterly basis. Trying to improve a host of things about your work in that limited amount of time isn’t realistic. It’s better to narrow your focus and then regularly revisit and adjust goals.

If you’re a team lead tasked with helping people grow and improve, try distilling your feedback down to just 2 ideas. It will add clarity to your own thinking and definition to your team member’s plans.