leadership | Shedding Light

The Four Os of Meeting Preparedness*

There are quite a few resources from WordPress contributors over the years about how to identify and resolve conflicts in open source projects. There are posts that cover why conflict occurs, the structure of conflicts over time, and what to keep in mind while in the middle of conflicts.

I’d like to share some additional explanation of my Four Os checklist, a tool that I use to make sure I know the facts of a situation as well as the feelings. This was first shared on Andrea Middleton’s primer on Conflict De-escalation in Open Source which I also highly recommend.

Why Prepare for a Meeting

If you’ve never mediated a discussion or helped to de-escalate a disagreement before, you will be surprised just how much the emotional state of the participants in the room can affect you. To make sure you are a well-grounded, calm-headed guide, there are two things you have to know going in: Know the facts, and Know the fights

In the heat of the moment, your short term memory can fail you, so having done the work ahead of time to assess the situation is important. Also, if you have asked all participants in a mediated discussion to answer these questions as well, then it’s easy to see where there are agreements, so folks can focus on working through the disagreements.

This is my primary checklist before heading into any conflict resolution work:

The Four Os

Origin: Before you can help anyone through a conflict, it’s important to know what caused the conflict. Getting an understanding of the context, the catalysts, and the primary concerns gives you the lay of the land and the beginnings of a map to see what is real. Questions that you can ask yourself:
- What made this meeting necessary?
- What are the circumstances around it?
- What made this unsolvable on its own?
- What are the perceived risks? What are the actual risks?
- Are there imbalances of power, knowledge, or access that you can see?
Objective: Knowing the purpose of a meeting is a differentiator between good leaders and great leaders. Awareness of what needs to happen during this valuable shared time together will help keep the discussion focused and increase your chances of a workable solution.
- What do you want to happen in this meeting?
- Is this a “see the other side” conversation or a “debate the solutions” discussion?
- How do you expect the other participants to engage?
Obstacles: If you’re new to strategic planning or communications, it can feel counter productive to think of all the ways that your plan can fail. However, I believe strongly that the only way we can keep ourselves from falling along a journey is to look for the rocks and sticks in our path.
- What do you think might interfere with this objective?
- What’s your plan if that comes up?
Outcome: Give some thought to what you want to have happen as a result of this meeting. The best way to look at it as on a spectrum from the minimum hope is for next steps all the way through to the best long-term changes that come from resolving this conflict.
- What do you want to walk out of the meeting with?
- What’s your desired outcome?
- What are the best next steps?
- What compromises are available (where everyone has to let go of something)?
- If this is resolved perfectly, a year from now what is different?

Bon Courage!

These might not all apply to every situation you encounter. Not all conflicts have deep and meaningful context (and that’s a good thing), sometimes it comes down to miscommunication. When we’re working across cultures, sometimes the role of an impartial guide through some facts and feelings is the thing we need most.

* I know this is a terrible name, but honestly, it’s all I can come up with. 🙂

Is documentation really a DEI* initiative?

Posted on June 21 by Josepha

Have you ever stopped to ask why documentation gets created? Those little bits of paper that arrive with your latest online purchase or crammed into that IKEA box, those make sense. They are there to tell you how to use the thing in the box. Their primary function is explanatory, but you could argue that “documentation” as we know it can broadly include these functions:

To describe the use, care, purpose, or design of something
To train or inform someone
To introduce you to features in a product

If you’ve never considered how documentation could be seen as a *diversity, equity, and inclusion effort, I’ve got a few things that will probably help open up that area of thought for you.

Documentation makes learning available – When you write down how to use something, then that information is available at any time for anyone. It removes potential barriers to entry of having to know the right people or having time to set aside for classroom learning. It also enables translation of your words so that learning isn’t limited to those who speak the same languages you do.
Documentation lets you account for many audiences – Documentation also creates the opportunity to account for different ways of learning. Some people are able to learn and retain information simply through reading it, but if you have a video or audio component to your docs, then you can also provide that learning opportunity to visual and auditory learners. And of course, kinesthetic learners will solidify what they’ve learned as they practice.
Documentation clarifies entry points – This one is probably specific to open source or communities, but any time that you document “the way things work” in a community you are making it easier for other people to get involved. And the more we can help people get involved in our communities without making them know specific movers and shakers the more resilient and effective our organizations become.

Had you ever looked at documentation from that point of view? What are other ways that “writing the docs” could bring more diversity into your communities?

Dungeons and Dragons for Team Trainings

Posted on May 20, 2022 by Josepha

If you’re not familiar with Dungeons and Dragons (or table top games in general), the best way to describe it is “collaborative story crafting where a group of characters try to solve problems, save folks in trouble, and survive quests that they uncover along the way”. A colleague of mine, Andrea Middleton, once used a Dungeons and Dragons style session to introduce contributors to some basic issues that arise during the course of organizing an event, and ever since that session folks have asked for more trainings in the same style. I had the opportunity to do this recently myself, so I thought I would share some tips for hosting a training adventure of your own.

Getting Prepared

When you’re hosting these sessions, it’s important to do some documentation before you meet. You will be playing the role of everyone except the people who are in the room so there is a lot to think through. But also, don’t worry about getting too granular since your team will be a little unpredictable—just know the general shape, the main players, and the key elements.

Make a list of what to learn – Spend some time thinking about any skills gaps or knowledge gaps within the team. Is this a basic training on everyday tasks or more complex? Are they already familiar with working as a team or are they just starting to form?
Find a scenario where you can practice – Brainstorm some scenarios that will provide opportunities to learn one or more things from that list. For instance, if you want them to learn where the company directory is, then maybe your scenario takes place at a registration desk.
What do they need to know already – Determine any pre knowledge that will be required. If it’s a lot, consider sending it ahead of time. If it’s mostly “know where to ask questions” you’re probably their best resource. 🙂
Outline your story – start at the end with your learning outcomes and work your way forward. Make particular note of any decisions that would cause the outcome to branch. Try to think through what the best way through the problem is, but also the most common first steps, missteps, and failures.
- In my session, Missteps triggered a random encounter or external input and Failures triggered “It’s a trap” moments where the problem became worse.
Know the required parts of the story – Note any important facts or people they should seek out while they are collectively working through solutions. What information will they try to find? What information must they find? Are there specific people who they have to find or they will get stuck?

Getting Adventursome

Before you host your session, determine how familiar your group is with this type of game. Not everyone plays games let alone adventuring table top games. If people have never played before, make sure you give them an overview of the process (or send them your favorite one shot). Also, if you are going to use this to track goals and progress over time, consider some sort of “character sheet” to document progress. Don’t get too rigid with the mechanics, though. You want them to come out having succeeded at the learning objective!

Welcome everyone! Explain how each turn will work and have them roll initiative (so you know what order they will go in). Since there’s no Dex to break ties, I just had my players roll to break their own ties. 🙂
Read the scenario and ask the highest roller what they want to do. Table talk and discussion is encouraged, so it’s important to confirm with your player that they have decided on an action. Once they have completed their action, read out the results of the action and move on to the next highest roller.
Make notes of the table talk and progress. You don’t want to move them through anything too quickly. They should have a chance to discuss, ask questions, and ponder possible outcomes. This is a time for them not only research and explore the problem, but also to learn how to work together toward their common goal.
Don’t let them flounder! If they get too stuck, you do have some options:
- Remind them that you are a resource (“I’m playing all parts except you all, so feel free to ask me anything.”).
- Roll in a random encounter (“a friendly community member DMs you to ask…”).
- Roll in a skills check (if they asked almost the right question, roll a Charisma to see if they get some extra info. Do they need information that they aren’t aware of or can’t find? Roll a Knowledge/History.)
Rinse and repeat until the problem is solved! As far as one shots go, these might be pretty much on rails, with a few clear alternative endings/solutions.

Getting Closure

Once you’re finished, I recommend doing a little debrief if you have time. If you take good notes during their session, you’ll be able to go back and look at the various branches and see what could have been done differently.

This is a loose concept based on my recent experience. If you end up trying this, let me know in the comments!

Leading at Any Level

Posted on March 5, 2021 by Josepha

The concept of leading at any level comes up frequently and focuses on the idea that leadership isn’t the sole responsibility of those at the top of an organization. This idea happens to fit well with my definition of leadership in general, which is that you are a leader if you have anyone who looks to you for support, guidance, or trusts you with collaboration.

You might notice that I didn’t include anything about reporting structures, employment, or hierarchy and that’s intentional. I think that you can lead from where ever you are in your organization, because I don’t believe that “telling people what to do” is the ultimate expression of what it is to lead.

There are leadership tasks that will always be the sole responsibility of top-down leaders, such as vision setting or responding to crises, but the day-to-day work of keeping momentum and upholding values belongs to everyone. And in WordPress—where we have top-down coordination, but prefer to rely on leading by coalition—our most successful* leaders are those who understand how to lead from where ever they are.

The Pillars of Leading at Any Level

All parts of leadership can be taught, so if this concept is new to you I’ve got a quick list to get you started.

Supporting the Culture (or how we engage, motivate, guide)
- Set an example – Guidance doesn’t start and stop with active advice that you’re providing. If people ask for your guidance, they will also watch what you do (or don’t do) to know what is acceptable in the community.
- Set the tone – You are responsible for the tone you bring to the space. Meeting attendees, community members, and team mates will take their cues from leading voices, and it’s up to us to make our spaces welcoming and ethical.
- Communicate clearly – Share what you know and don’t know clearly. When possible, be transparent about decision making so it’s clear that disagreements are safe and give people insight into the full journey.
Supporting the People (or how we train, enable, nurture)
- Acknowledgement – Open source acknowledges good experimentation and honors past work. As leaders in open source we should also acknowledge our contributors by setting up in a space where they can fail safely (like new contributor meetings), and thanking them for their contributions.
- Redirection – I think that solving the software’s biggest problems according to users is always the primary agenda. Early redirection of passionate contributors can offset future resentments when their passions lie with non-priority things. Letting someone know that they can work on it, but we can’t guarantee it will ship is the right and ethical thing to do.
- “Yes, and…” or “No, but…” – Respond to questions in a way that makes people feel comfortable asking. Encouraging exploration is part of how we commit to the open source idea of good ideas coming from anywhere. Respond to questions in a way that encourages future exploration for the asker (which can be hard when you’ve done it for the 100th time) and tells them that it’s good to ask.
Supporting the Changes (or how we respond to crisis)
- Caveat: Many crisis responses require named leadership, but for those responses that don’t this list will help.
- Be Balanced – Differentiating between urgent issues and emergent issues is hard, especially if you don’t have the full context. But putting some thought into what the impact might be can be a good start.
- Be Present – Leading in a crisis requires a lot of time and attention. Staying visible in public spaces (and not resorting to private spaces by default) is uncomfortable but necessary. When you have to have closed sessions, and you will, report back on what was said.
- Be Judicious – Discern how best to combat the most urgent issue amongst many emerging issues. Knowing whether to fight a fire with fire/water/vacuum takes some practice, but at the very least have a sense of what will make a crisis worse.

* What do I consider a successful leader? Successful leaders aren’t defined by how many decisions they have to make or how many people report to them. They are defined by how many leaders they send out into the world. They are defined by their consistent engagement with their community, that results in sustainable practices and proactive avoidance of burnout. They are defined by the resilience of an organization that can survive long after they have left by ensuring they aren’t a single point of failure, by encouraging people to participate, and by committing to guarding their own resilience. And, in any organization where coalitions are key, successful leaders are those who when faced with making really uncomfortable choices, can help people find the reasons to commit despite their disagreement.

Making Hard Decisions Easier

Posted on May 27, 2020 by Josepha

Over the course of my career, especially as I was learning to lead, I made a lot of mistakes. Most turned out fine in the end, but basically all of them required me to go and find an adult. And as I became more proficient as a leader, there were two truths that used to shock me a lot:

I am the adult now. If I need help, I have to find adultier adults.
At some point my mentors were also shocked to find that they were the adults.

I am here to debunk this myth for you: leaders don’t always know the answers and they aren’t always fearless. My mentors—the people who have taught me how to do this—what they had that I now also have is a network of advisors, and a few excellent tactics to work through inaction.

A Few Excellent Tactics

I use these tactics routinely, not as a way to hack my productivity, but as a way to ground myself in where my autonomy lies. As an added bonus, they can also help you address specific, short-term fears in a way that I have found to be truly empowering.

For When You’re Afraid
Use the 10-10-10 Rule. This can help you to identify if the thing you’re afraid of is a short-term problem. You pretend you made the decision right now, and ask yourself how you would feel 10 minutes from now, 10 weeks/months from now, and 10 months/years from now. If you’re afraid to contradict someone (10 minutes), and you know that the change will be complex (10 weeks), but you’re certain that the long-term benefits balance it all out (10 months), then you know that you can stand the discomfort of the decision.

Next Level: Check for the area of effect – are you using single use potions or spells that help all surrounding allies. If challenging a path forward will inconvenience two people, but save multiple hours of work for seven, that might be a fair trade.

For When You’re Overwhelmed
Use the Eisenhower Matrix. This can help you identify where your time is best spent. For every task that is on your plate you determine if it’s urgent or not, and whether it’s important or not. Where each tasks lands in those quadrants will tell you how you should handle them. If it’s Urgent + Important, then you should focus on completing the tasks. It’s it’s Not Urgent + Important, then you can plan for a time to do that. So on and so forth.

Next Level: The practice of identifying the differences between urgent/emergent/routine tasks can help us to find more autonomy in the decisions we make. This decision matrix can help define what you can affect change on, so you can have a more proactive pattern of approaching your work (also known as circles of concern and influence).

For When There Are No Good Options
Use the Maximin Strategy. This can help you identify how to minimize the potential negative impact. When faced with nothing but bad choices, you think through who is impacted and how. Thinking through how big the negative impacts can be, can give you some way of ranking options that originally all felt less than optimal. At the very least, it will quickly clarify which options are not possible.

Next Level: If you can state clearly why you decided against any option, then it can help identify why you would say yes. It’s so often the case that there are many possible “yes”es and far fewer “no”s. Discovering one will help reveal the others.

Still stuck?

It happens. Your advisors might have some insights, but they aren’t perfect either. If you don’t know how to proceed, but you must choose something, then remember these things.

Limit information gathering to what’s immediately relevant.
A mistake is only as dire as the outcome that follows it.
And when you do make a mistake, think of it as a lesson learned.

You can do it! Good luck!

Building a Culture of Safety

Posted on March 2, 2019 by Josepha

When I think back over the many communities I’ve been part of over the years — whether at work, as a volunteer, or in a church — those that were most vibrant had many things in common. They had leadership that was engaging, they had regular gatherings, and they were clear about who they served. As I’ve grown into my own concepts of leadership, I have come to recognize that one of the largest (and most hidden) things they had in common was a dedication to cultural safety. Letting people come as they are, and honoring that, was foundational to how they operated.

Safety can mean different things to different people, though, so here’s a quick overview of how I see it.

Types of Safety

Physical Safety – The ability to remain free from bodily harm. For my current work in the WordPress project, this mostly comes up in relation to in-person events.
Psychological Safety – The ability to express yourself freely. This comes up in all of the community’s communication channels, from Slack and team blogs to twitter and events.
Social Safety – The ability be your whole self among others. This, naturally, comes up in all of our spaces both in-person and on-line.
Moral Safety – The ability to reconcile your work with your morals. This comes up mostly with volunteers in WordPress.

Though I’m sure this isn’t a comprehensive list, I do feel that these four kinds of safety line right up with some basic needs of healthy modern communities: personal safety, open communication, inclusivity, and aligned values.

The Panel Predicament

Posted on October 25, 2018 by Josepha

For anyone who has worked with me organizing content-driven events, you will have heard me say regularly how much I hate panels. I am quick to declare my dislike of them, but generally only in the safety of a group of organizers. I’ll try to provide some clarity in the need for panels, why I dislike most panels I see, and what we can change to make them better.

The Value of Panels

In theory, I understand the appeal of panels. There is a lot of information available in the world, and it’s increasingly difficult to assess how trustworthy to consider the opinion of any self-proclaimed expert. There are many ways to achieve expert level opinions: by education, by research, by practice. Probably other ways, too. To solve the problem, we host panels. We gather industry thought leaders or experts and have them discuss things openly, in the accountability-forging context of “filming in front of a live audience”. We then leave it up to the audience to decide — what is your version of this truth that we’ve presented to you, almost without editorial aid?

The Failing of Panels

In practice, panels are far from that. They are either overpowered by a single voice or are overpowered by apparent fighting among the panelists. Moderators double as panelists and leave the group with no discernible direction. Panelists answer in a round robin style, often leaving no time for interesting or informed viewpoints to shine through. Panels are overstaffed and used as a way to prevent the discomfort of having to turn down speakers. Most people don’t apply to be on a panel, and many who get assigned to participate on a panel think that it means no preparation is required.

The Best Panels

It’s not that we’ve never seen a good panel. We see them from time to time, on TV or at large-scale niche events. There is a lot of writing available about how to be a better speaker, but not a lot about how to be a better panelist. Or even how to craft an excellent panel as an organizer. So I’ll tell you what’s proven to work for me over the years, as a long-time event organizer.

Crafting an Excellent Panel

In my experience, the best panels require a thoughtful moderator and panelists with a decent level of rapport (but not best friends). It’s great if you already have a group that fits that description. If you don’t there is a short, simple process that you can follow to foster one from the expert panel you have assembled.

Dedicated Moderator – Find your moderator first, because you’ll need them throughout this process. The best moderators keep the discussion moving by helping with time management, directing questions toward particular panelists, and resisting the urge to join the discussion.
Limited Number – If the time allowed for your panel is one hour, you should select no more than three panelists not including the moderator. That gives each speaker about 15-20 accumulated minutes assuming everything else is perfect.
Prepare Panelists – Your moderator and panelists should have two meetings. Each meeting should take about an hour and be via voice (or a video call if you feel fancy). In the first one, do some general introductions and learn about everyone’s expertise as it relates to your broad topic. The moderator should take notes* and the panelists should explore what they are all excited about so that a topic can be defined.
Clarify Your Topic – After the first meeting, the moderator will know what the most interesting areas of expertise each panelist has. That will help them guide questions (whether prepared or from the audience) to the right people. It will also help create a panel title that is clear, concise, and marketable.
Written Questions – In the second meeting, the moderator should have some questions that have already generated interesting discussions among the panelists. Ask the panelists if, since their last meeting, they’ve been wondering about something another panelist said. Write down 5-10 questions and be prepared to start the panel on the day with 2-3 of them.

Rinse and Repeat

That’s it! Five steps and most of them are talking. 🙂 The first time through it will feel strange and uncomfortable, but after that it’s like riding a bike. *A note on notes. If you’re the moderator the notes you’re taking are:

who has a tendency to talk the most
who needs encouragement to talk
what panelists do
what panelists wish they could do
why they do what they do (their philosophies)
why their future vision is what it is (their observations)
etc