Openness, Supportiveness, and Leadership

In the Fall of 2015 I took the Emerging Leaders Program at the University of Denver. I really enjoyed the class. Gave me a great framework and space for thinking about how to improve my ability to lead a team. Below is my final essay for the class. The goal of the essay was to review yourself and create a plan for how you want to become the leader you want to be. Since openness is a key part of what I want to do better, what better way to practice than by publishing it to the 100+ people that visit my blog each day. 

What Leadership Aspects I Value

A number of the values of great leadership resonated really strongly with me. I especially get convinced by evidence, so the When Teams Work Best readings felt very compelling (still on my list to read the whole book). The most effective teams practice being open, supportive, action oriented, and having positive personal styles (the venerated “no jerks” policy). Of these four aspects, openness and supportiveness are the characteristic most prevalent in the most successful teams.

I work at a completely distributed company where most folks work from home all over the globe. Openness and supportiveness are values that are very strongly encouraged (intentionally) at Automattic, and I believe are an important part of our culture. When you are distributed and growing you need ways to communicate asynchronously, both across time zones, but also to new employees who will join you next year. Email is terrible at this, so we rarely use it. Our primary form of communication, p2s, are all open by default; our financials are open within the company; all of the metrics we track are open.

And of all the places I have worked I have never seen a similar level of support for for giving folks autonomy and trying to enable each other. Basics like our systems team defaulting to yes when someone has an idea are a stark difference to many other places. That doesn’t mean debate doesn’t occur, but unlike many places the default never seems like a ‘no’.

I have been working in this open, supportive environment every day for over four years now, and yet I feel like I am terrible at being open and supportive. Some of this is certainly the general self doubt we all carry around with us. I’m ok at it, but for working at an open source company it’s striking how little I’ve contributed to open source projects. My blog is the best example of my contributions to Elasticsearch in the open, and the openness I’ve expressed there has been incredibly rewarding when I make time for it. But wow do I find it hard. When I look around at other Automatticians and how fluidly they seem to practice openness, I don’t come anywhere close.

Looking back at the 10-12 managers I have had in my life, I also realize that the best of them were both really open and really supportive. Those two or three jump out immediately to me, and the rest fade into the background noise of a 15 year career. And yes, one of the top three managers I have worked with is my current team lead. That’s what makes now such a great opportunity to learn.

Reviewing Where I Am At

About 6 months ago I expanded my role on the Data Team to try and help fill some of the gaps that have been developing as the team has expanded to 20 people and our team lead has expanded his role within the company. In some areas I feel like I’ve been fairly successful, others have been less so. The role was announced under the title “parity bit”, as a witty reference to the simplest form of error checking data. In some respects the role has also been about being a co-lead, or more accurately, a backup lead for the team. Like most things at Automattic, the role is continuing to evolve. I think it is becoming more of a mixture between a product/project manager where I try and facilitate organizing specific projects and initiatives rather than being a catch-all for everything. Not a dramatic shift, but it feels like it has more focus than a generic “backup” lead.

From these short six months I feel like openness and supportiveness are the things I most need to work on. They are probably aspects that always need to be worked on, but they don’t come naturally to me, and that is probably because I haven’t practiced them enough. Both of them seem tightly bound to a leader’s Emotional Intelligence (self awareness, self management, social awareness, and relationship management) which has been found to be up to 90% of effectively leading a team. Taking an emotional intelligence test during the class I ranked average to moderately high for self awareness and self management. For both social awareness and relationship management I was average. So I have some things to work on across the Emotional Intelligence (EQ) spectrum.

You Can Only Control Yourself

There is not a perfect mapping or path for which EQ aspects to work on to cultivate an open and supportive environment, but for the short term (six months) I have decided to focus on a few specific behaviors. My own behaviors are the only thing I can control, so that’s what I need to work on:

1. More regular journaling. I think best when I put words on paper and need to form a coherent thought. I’ve re-picked up my intermittent journal that I started back in March of 2004. Let’s see if I can make it a habit. I should probably practice more openness here, and post some of these on my blog too.
2. Practice Reframing Problems (at least partly through journaling). This was the first item brought up in class, and it jives with a number of other things I have read. In the book Your Brain at Work (discussing brain biology and understanding how you and others react) reappraisal was one of the key methods for controlling your emotions and reframing feels like a similar methodology. Run into a problem or an emotional response, and reconsider it from a different perspective. Find a different benefit or a different way to interpret the event. Or just recognize and treat it as a normal emotion to have. I also want to practice reframing problems so that they are inspiring and sensible for others.
3. Practice Openness and Supportiveness. This is really broad, but a few ideas really resonated:
   • Post more often. Automattic has embraced chatting through Slack at the expense of p2s. It has mostly been good, but our per capita p2 posting and commenting rate have dropped significantly. So has mine. I think it makes it harder for future Automatticians (and current ones) to stay up to date. Posting takes time, I should volunteer to do so more often, and through that help to clarify project and role clarity.
   • Ask questions rather than providing solutions. I’m terrible at this, I always want to be the one to provide solutions when really helping others to find solutions, enabling them, is far more effective in the long term. It is also more supportive. And yet despite knowing this I catch myself failing at this almost every day.
   • Bring up the uncomfortable issues. We are all smart, we all know there are lingering issues. Be the one to ask about them rather than letting them fester.
4. Improve my listening. I had a fairly low score on the listening survey I did. 11 points out of a possible 25. So I’m picking a few specific things that I rated myself low on to work on:
   • Don’t think about what I am going to say while someone is speaking.
   • Intentionally learn something from every person I meet.
   • Don’t assume I know what the speaker is going to say before they say it.
   • Be comfortable with allowing silence, allow people to think and react.
5. Manage my own energy. Again this was a topic that also came from the Your Brain at Work book, and is something I’ve tried working on in the past. Despite not being a muscle, the brain burns 15-20% of your calories every day. Certain times of day my brain is at its most effective. I should intentionally choose to do things that take more mental energy at those times. Control distractions and interruptions, and recognize at any one moment what i can mentally handle working on. Running… meditation… journaling… these are all tools that I know work for me and I should use them more judiciously.

This feels a bit like too many things to really focus on. Choosing is hard and I should consider paring it down, but feels helpful to write them out. I would also really like to have some metrics to track how well I am doing at these, but I don’t think I can come up with them for everything. Ultimately I think everything is about changing habits (The Power of Habit – another great book), so here is how I am approaching these:

1. For journaling I have already added that into my regular habits three times a week (I use a great little app called Balanced to remind me of habits I am trying to form).
2. Reframing is tied to my journaling where I am trying to regularly pick an event from the day before to reframe. I added an automatic prompt every time I open my journal that is: “Event from yesterday to reframe: “.
3. I can easily track posting more. We have good metrics of how many posts and comments I make internally. On average since I started I have been posting 20 times a month and commenting 100 times a month. But while I am commenting at a faster rate in 2015 than prior years, I think my posting rate has fallen to 12 or 13 per month.
4. Listening seems hard to have a metric or habit for. The best I have come up with is going off of Julian Treasure’s five methods for listening better. I think of them, practicing silence as a part of meditation is the one habit that would be worth trying first.
5. Which brings us to managing energy where I am positive that meditation is something that I need to build a stronger habit around. My current goal in Balanced is to meditate twice a week, and it’s great when I really make it happen. One related habit that I have been pretty good at building over the past few months is to have a minimum morning exercise routine based off of the Royal Canadian Air Forces’ 5BX 12 minute exercise program. Having something that is short and minimal every day is a much easier habit to maintain.

Looking back at the five major areas of improvements I’ve suggested for myself feels fairly daunting and maybe too large of a thing to focus on. Maybe even unrealistic. At the same time, the individual habits that I think get me there don’t feel that onerous. Like everything, it will require some more iterations and more experimentation.