Making Hard Decisions Easier

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:

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

All of my leadership skills were earned not learned, and 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 didn’t have was 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, 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.

  1. Limit information gathering to what’s immediately relevant.
  2. A mistake is only as dire as the outcome that follows it.
  3. 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

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.

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The Panel Predicament

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.
  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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