Tag Archives: work

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.

Work vs. Progress

On poorly managed teams conflicting and irrelevant work is allowed to go on because leaders don’t notice, care or take the time to guide people’s efforts in more useful directions. Capable people may work away in their private tasks, believing they’re making progress (and earning bonuses), when in reality they’re doing work that will be thrown away or even hurt the project. When someone puts their head down to work, how fast they’re going doesn’t matter if they’re heading in the wrong direction (or towards a cliff). How a talent is directed can be more important than the size of the talent itself.

Work vs. Progress – Scott Berkun.