Bucketing and Synthesis


When we’re synthesizing, a lot of what we’re doing is putting things into buckets. The hope is that the buckets help us make sense of things. For this to hold true, we need to make sure we’re using the right buckets for the right reasons… and the right people. Figuring this out is hard and takes lots of tries. For this reason, good synthesis usually includes lots of iterations where different bucketing schemes are validated with the people who will use them. Bad synthesis usually stops at one or a few iterations, with little to no testing.

One important thing to remember about bucketing is that there doesn’t have to be just one scheme for everything. Different bucketing schemes might work better in different circumstances. Be conscious of the different levels and intentions.


“Knowing how to do this” + Open Space

Wanted to share some followup thoughts from our solid kickoff last Thursday.

First, when it comes to understanding how to have and support a group of any kind or size in working through long-term strategy and culture, I want to ban, “We don’t know how to do this,” from Miles River’s vocabulary and eventually from Wye’s as well. At a high-level, we definitely know how to do it. The devil is in the details, but we can (and will) figure those out.

The main obstacle is commitment. It’s like training for a marathon. We know how to do it at a high-level, but the details will vary. The main thing is recognizing that it’s going to be hard and painful and hopefully enjoyable too. If folks are committed to doing the strategic equivalent of running every day, then they can do it, and they’ll have a high probability of success. Until we all recognize and acknowledge that commitment, we are not going to succeed.

Second, how are we going to pull off this April meeting? First, kudos to Eden for quickly landing on the later date, which buys us two weeks. It’s not a whole lot, but it makes a big difference.

In order to figure out the support time needed to design and facilitate a meeting, I take the number of meeting days (in our case, three) and multiply it by a number between one and three, depending on the complexity of the meeting. So a minimally complex meeting would require six days total (1 x 3 for design time + 3 for the meeting itself, not including followup). A very complex meeting would require 12 days total (3 x 3 for design time + 3 for the meeting itself, again not including followup). This is all per support team member, so the numbers pile up quickly.

There are several assumptions that go into these numbers. First, the meeting itself will be participatory (and awesome). Second, in order for that to happen, the design process should also be participatory. Third, at least half of the design time is spent aligning around goals and success. The more complex the meeting, the harder that is, hence the need for more time. Aligning around clear goals and success requires participant time. Once you have that, the support team has more agency in designing the meeting itself.

Our April meeting will not be minimally complex. You could make a strong argument that it’s actually maximally complex, since it’s meant to be the start of a larger process with lots of unanswered questions and a currently flawed container. I would typically want at least four months to design for such a meeting. We will have about two months… and that’s on top of a whole lot of other work we’ll be doing over the next few months.

So how on earth can we make this work?

If the goals were clearer, we could make the design process less participatory. That’s not our situation, so that’s out.

There’s a fine balance between design and facilitation. A well-designed meeting is less reliant on the skill of the facilitator. If you eliminate design time, you are more reliant on the skill of the facilitator for success. That was our situation for our November meeting. It wasn’t optimal, but you can make it work. We can do this for April, but I’m reluctant to do so, because it’s riskier, it repeats a reactive, rushed pattern we’re trying to break, and it won’t build the capacity of Miles River.

So what’s left?

Open Space. Open Space is optimized for self-organization and emergence. It provides just enough structure to support the participants, but ultimately, they’re responsible for their own success. If they’re good (and we know our participants are), they’ll be successful. The basic design is more or less a template, so it doesn’t require a lot of time to design the days themselves. Facilitation is very light touch as well.

The best Open Space meetings have a strong invitation and at least three days. (Most people make the mistake of constraining their Open Space to one day or even less, which doesn’t leave enough time for shared understanding to develop.) We have three days, and we can use the design time we have to develop a strong invitation.

Because it’s light touch, the participants recognize that they are fully in charge of this ship. Not only does it force them to take responsibility, but when they see that it’s successful, they will be more motivated and empowered to replicate it on their own. Ultimately, we want to break them of this notion that highly skilled facilitators are required for them to be successful. (It always helps, but it shouldn’t be required in every situation.) Open Space will help us do that.

That won’t mean that they won’t be supported. There is an art to facilitating Open Space meetings effectively, and on top of that, we’ll be providing knowledge support. We’ll use artifacts to help facilitate sessions, and we’ll make meaning of those artifacts together at the end of each day. Those artifacts will help the conversations themselves be more productive (see the Tic-Tac-Toe exercise from Thursday), and they will also serve as the basis for sharing what happens with those who couldn’t make it. It will also be great practice opportunities for all of us.

We’ll also create some real-time dashboards to help them see themselves and prioritize. For example, we might put up an Eisenhower Matrix, and at the end of each day, cluster the sessions that happened in the corresponding quadrant. That will help the participants themselves see where they’re spending their time and whether or not they need to make an adjustment.

There’s still some stuff to think through, and enrollment will likely be a challenge, but I think this is the right direction overall. Feedback and pushback encouraged!


Shifting Quadrants in the Eisenhower Matrix

Jodie likes to frame the work that we’re doing as shifting quadrants in the Eisenhower matrix (popularized by Stephen Covey) from Urgent-Important — where most of our leaders tend to live — to Not Urgent-Important.
It’s a great frame, not least because our leaders (having been introduced to it at Rockwood) are familiar with it. The goal, ultimately, is not to help shift these individuals, but to also shift their organizations and supporting structures. Without the latter, people are likely to stay stuck in their old habits.

The concerns raised at the last Wye meeting about security and surveillance offer both a great case study and a potential set of experiments. The fear and uncertainty that people feel fall squarely in the Urgent-Important category. Unfortunately, the solution lies in the Not Urgent-Important category. There is no universal checklist that solves people’s concerns about security. You have to look at the problem systemically, and you have to implement solutions collectively.

Here’s what I mean. Several people insisted that all Wye web properties use SSL before we start using them. I actually think that’s a fair thing to ask for, and we’re in the process of implementing it. The more important question, however, is why? Why should we use SSL on our website?

The stock response is, “Security experts told us we should do that.” That’s not a good answer. Perhaps it’s okay for EDs to have that answer, since security policy might fall under someone else’s purview, but at minimum, EDs should be able to concretely name what they’re afraid of and to quantify their concerns.

For example, they might be afraid of the information in the website falling into the “wrong” hands. Whose hands are these? The government? Corporations? Members of conservative organizations? Members of other progressive organizations not participating in Wye?

If that’s the fear, what are the biggest threats? Is it the lack of an encrypted transportation channel? Is it the fact that we have one password for the entire site? (Again, that’s by design.) Is it the fact that anyone can easily copy and email the information to anyone else? Is it the fact that people have the password (and many others) saved unencrypted on their phones, and that they leave their phones lying around all the time for anyone to peek at or steal?

What are the costs of those threats? How much time and resources should people be investing to mitigate them?

Your security policy needs to be part of a larger strategy, and every ED should understand what that strategy is. I’ve been doing some research and talking to some trusted colleagues to find orgs that are doing this well, and good examples are few and far between. Which makes total sense. If the overarching culture is not to spend time in the Not Urgent-Important quadrant, then these strategies never get formed, and people resort to busy-work tactics that might not actually address your problems.

So what can we do about this? First, we need to model. STP needs to do some threat and risk modeling, build an organizational strategy around that, and implement it. Miles River needs to do the same.

Second, we can support experiments around helping other orgs do this.

Finally, I just want to acknowledge that this stuff is really hard. One of those “universal” recipes that every individual should be doing is using a password manager. If you’re not already using a password manager, starting to use one is a pain-in-the-ass, and learning how to use one and integrating it into your workflow takes time. Furthermore, simply using a password manager is only a first step. You have to start randomizing your existing passwords as well, which is additional work, and creates new problems. Even this “simplest” of steps results in a not-insignificant change management challenge.

It’s hard work, but we’ve got to start doing it. The muscles for doing it well are the same muscles required to build shared systemic understanding, to do long-term visioning and strategy, and to constantly learn and adapt.


Managing the Panic Moment

I’ve been reflecting on the design process we’ve all been in together and on the unique complexity of this upcoming meeting. I’ve been thinking about how I’ve been handling the complexity, and I’m wondering how you all have been handling it too.

On the one hand, I was heartened by the checkouts from all of you on the Design Team call today, and how a number of you expressed confidence. On the other hand, I know that it’s been a rocky, intense journey and that the stakes feel very high, especially post-election. These leaders are trusting us to help them manage the complexity of what they’re trying to achieve. That trust is a large burden, and I am so impressed and appreciative of how well you all have been handling it.

As I think I’ve told all of you many times before, there is always a panic moment before these kinds of participatory, emergent meetings. Everyone has them, and it’s totally understandable, because in the absence of certainty, you are reliant on faith. That’s a hard sell, especially when you have limited experience with these types of gatherings — or worse, bad experiences.

Part of the role of a good consultant / facilitator is to guide the participants through that pre-meeting panic moment. But another role is to manage that panic moment yourself, because if you’re being honest with yourself, you should be freaking out also! In fact, if you weren’t freaking out, I would question whether or not you were thinking things through rigorously enough.

I get nervous before every meeting, and I have at least one panic moment as part of every design process. I’ve already had a few for this one. I was talking about this with my sister over dinner tonight, and I said, “Do you know how I manage it?”

She responded, “Yeah, you do that Jack Donaghy thing, right?”

For those of you who are not 30 Rock fans, this is what she is referring to:

I do in fact have a Jack Donaghy-style psych up routine, which is a crucial part of my pre-meeting ritual. But that’s not how I handle the panic moment in the design process. I handle the panic moment in the design process by remembering what I learned from one of my mentors, Gail Taylor:

The success and failure of the meeting does not depend on you. You are simply part of the system, and the whole system is holding the space, not just you.

I want you all to remember this. We are lucky to have a strong team, from Miles River to the Design Team, and that alone gives me comfort about our meeting. But even this group of 11 people is not responsible for the success and failure of the meeting. Everybody in the room is part of the system. Everybody in the room is bringing their own special wisdom and will be helping hold the space.

We design with this assumption in mind. We trust the intelligence of the participants. Most importantly, we trust in the strength of our relationships, which creates resiliency. Failure is simply part of good process, not something to avoid at all costs.

When I remember this, my panic subsides, and my faith is restored. I hope you all remember this and believe this in your bones, and I hope it helps you too.


What the Heck is a “Container”?!

On our call with @jodie, @idelisse, and @alison yesterday, I raised a design challenge that I was pondering about the makeup of the folks who will be in the room in November (2:1 ratio of Wye members to invited guests). I figured we’d all quickly acknowledge it, say a few words about it, then move on. To my surprise and frustration, we ended up spending the rest of the call on it. Afterward, Alison and I debriefed, which helped me get clearer about what I was trying to say and perhaps why the conversation went the way it did.

Even before the election, we knew that two things would be hard about the upcoming meeting:

  1. Shifting focus and attention away from the short-term and toward the long-term
  2. Having enough of a “process” conversation to ensure success after this meeting

The election results make both of these things harder. Two of our Design Team members have shown leadership with the full Wye group about maintaining focus on the long-term at our meeting. This is not a new stance among Wye, and their alignment around this following the March meeting is the reason why we’ve been doing what we’ve been doing this past year. I feel pretty good about getting the Wye folks somewhat aligned around this before the meeting.

I don’t feel as good about this with the invited guests. They haven’t been part of this group in the past, they don’t have that history, and they are likely coming to the meeting to be with a group of their peers at a time of distress and need, not to help Wye in particular figure out what it wants to be and do in the next year and beyond.

We need to do our best to make sure the guests are clear about what will be happening at the November meeting. Even with that, their tolerance for talking about process more granularly will be lower than everyone else’s for the reasons stated above. That’s the point I was trying to make yesterday.

I think part of the reason our conversation yesterday was so difficult was that we are not on the same page about what a “process” conversation needs to be and why, and what “two-feet in” looks like.

There are two components of a “process” conversation:

  • Roadmap — the mechanics of what will happen, when, and how
  • Container — the “space” and agreed-upon norms in which we’ll have this conversation

Creating a “container” for a face-to-face meeting or for a process that is meeting-oriented is relatively straightforward, because most people have a clear, visceral understanding about the different aspects of the container. The most obvious component is the actual physical space, which people can see and touch.

The harder aspect of container-building has to do with agreements for how the group will behave. These tend to be hard regardless of whether the group is in a face-to-face meeting or not, although in a face-to-face context, it’s more easily understandable and enforceable, because the behavior is transparent to the entire group and there is usually facilitation, which means that the feedback cycles are more or less immediate.

For example, we ran into this challenge with the Future Forward process we did with Ev last year when we discussed the working agreement for transparency at the kickoff meeting for the meeting itself. In theory, that should have been straightforward — the proposed agreement fulfilled the need the participants described — but it was an emotional issue, and we needed to slow down to work it out. Discussing it for the six-month process as a whole was even harder, but because we took the time to work it out when we were all together, we were able to come to agreement fairly quickly are do our work successfully.

These kinds of conversations are laborious, and they suck, but they are necessary, especially for asynchronous processes and especially when they constitute a significant shift in culture for the group. Because of the trust in the room, we could propose something at a high-level and possibly skate by, but as soon as people start experiencing the ramifications, they will start questioning the container.

This exact scenario happened with STP a few months into the experiments process, when Alison and I announced that we were going to make our Facebook group published. We had agreed on this months earlier, but the reality of it triggered a much different response in the moment, and we had to work through it.

If we want our container to be resilient, we need folks in Wye River not only to go along with our suggestions, but to be advocating themselves for them. That means they have to understand them deeply and sit with them.

The specific challenges we’ll have will be around questions of transparency, roles, and permeability. The complexity and abstractness of these challenges was what was making our November design challenging pre-election, but they will be even more challenging now, especially with the high ratio of guests (who won’t have the same context and motivation to be in this more “process-y” conversation) to Wye members. That’s all that I was trying to say yesterday.

Idelisse brought up a good point yesterday that I want to address. Decision-making / governance is another one of those “container” issues that are very challenging to work out. The network principle I abide by to help with this is, “Avoid group decision-making.” You can generally avoid most governance issues when the group is small and trust is high. But the questions we’re wanting to work through around transparency, roles, and permeability are necessary, and we need this core group to be on the same page from the beginning.


North Stars and Stretching the Visioning Rubber Band

Wanted to share a few thoughts about visioning, offer some resources, and make some suggestions.

@idelisse and I talked a few weeks ago about “terminology trauma.” We all have it. Someone uses a word, we have bad experiences with how that word is practiced, and so we flag it and sometimes are even triggered by it. In this case, the word I’m referring to is “visioning.” As always, if Miles River is experiencing terminology trauma about something, it’s a good test case for us, because Wye River will likely have it even worse.

Just to repeat what I said on our November 3 call, I don’t think we should do a visioning exercise at our November meeting. But I want us to build on the exercise we did last March. And if folks approve the POP, then we’ll be doing even more visioning next year. So we need to get very clear about what we’re talking about when we talk about “visioning.”

First and foremost, I’d highly encourage all of you to read (or re-read) my blog post about rubber bands and visioning. We may want to consider sending it as part of our pre-reads.

It’s relevant, because it speaks to why designing our November meeting has been so hard. It’s not simply a matter of tackling topics one-by-one. It’s doing it in a way that folks are experiencing the effect of the rubber band.

(As a sidenote, we may also want to consider bringing rubber bands this year to reinforce the metaphor.)

This morning, Susannah Fox shared a really great example of what a clear vision + North Star looks like.


It reminded me of something Susannah posted a few years ago that also was a great example of a clear vision. Check out the cartoon in this post.


When you have an artifact that represents a clear vision and north star that the group itself arrived at together and own, then it is tremendously powerful and catalyzing. That, ultimately, is where we want to get to with this group next year. As a path to that, I want to take their work from March and start offering possible artifacts that might help them get there.

One way possibly to do this (and Ide, I would love it if you played with this idea) would be to create a physical visioning space in our room in November. What would it look like to physically transform a corner of that space to represent some of the vision that folks put out last March? How might we do it? Would love to hear people’s ideas!


Where Are We Going (This Year)? Why? How?

The organizations we’re working with are in it to win it. While they have gotten stronger in their leadership, while their organizations have gotten stronger, and while we’re seeing more collaboration, they’re currently not winning.

Business as usual will not get us there. We need to be thinking and working together smarter, not just more. If we do that, we think we can start to win… and keep on winning.

If business as usual will not get us there, then how we try to create that time to think and work together smarter cannot look like business as usual. In particular, we know that — for most of us — operating in the Important, But Not Urgent of the Stephen Covey quadrant is very challenging. (In many ways, we can frame the How of what we’re trying to do as finding ways to spend more time in this quadrant.)

So how do we create that time and space? Start small. This is why we’re starting with one-on-ones. It’s the easiest thing to make time for, and it’s high-value. Because of who are leaders are, it’s highly unlikely that they will make time to talk to each other and not get value out of it.

How are we supporting this process?

First, by creating a feedback mechanism. Remember the angsty email we got from one of our leaders about not holding up her weight? That’s a very common feeling among all of us. Part of what the engagement tracker + visualization does is show us how much time we’re actually spending, so that we’re not beating ourselves up based on perception.

Second, by synthesizing and reflecting back what is heard, so that we’re constantly building, not repeating, and so that the conversation becomes collective, not just one-on-one. (Synthesis + reflection is the essence of good facilitation.)

Third, we’re trying to co-create a container with the leaders. We can push them on what a good container looks like, but they have to do the work in the end, or this process fails.

One of our main challenges is reminding folks how what we’re doing now is connected to the big picture. A visualization might help, but it won’t solve the problem for us.

In Built To Last (the classic book by Jim Collins and Jerry Pollas), one of the leadership practices they cite from extraordinary organizations is constantly communicating the big picture. CEOs from these positively deviant companies spend up to 50% of their time doing this.

We need to be doing this with the design team, and the design team needs to be doing this with their peers. This isn’t happening right now, at least not at the level it needs to be.

So how do we address this? Time. We need to be spending more time on this with our design team leaders, and we need to be on message when we’re talking to them. The prerequisite for this is for us to have that message deeply engraved inside all of us, so that we are all regurgitating it with ease.

What’s made this extremely challenging is circumstances. Trying to do this in July and August of an election year is the worst possible time to do it, because people are on vacation and they’re also ramping up for the elections. On top of that, over half of our design team either spent a significant portion of the summer on leave or are missing key members of their senior staff.

This is not an excuse, it’s the reality. And, we have still done remarkable work together. The rich content on the Wye website as well as the data and infrastructure on this one don’t lie. Think back to where both we and Wye were one year ago. Think about what’s different now. Think about all the work we’ve done that’s made things different.

Our minimum goal for July-August is 10 leaders engaged. We’re at 7 with less than two weeks to go. We may not hit that goal, but we’re already close. We need to acknowledge what we’ve accomplished, but also make the adjustments we need to have success.


Mediated Mirrors


Our participants are smart. They’re already talking with each other and doing the work. When they’re in the room together, they experience that viscerally. When they’re disperse, they don’t sense it directly, so it becomes a matter of faith.

Our job is to reinforce that faith by creating mechanisms that enable them to see each other, especially (but not limited to) when they’re not in the room together. Once they see themselves, they’ll know what to do, and they’ll act accordingly.

We’re essentially putting a mirror in front of all of them, except we can do a lot more than show a physical reflection. I hope yesterday’s visualization brainstorm is helping you all see the possibilities.

To truly design this well, we want to take advantage of a beautiful little side effect. Mirrors are great, but mediated reflections are better. When a reflection is mediated, people not only see themselves, they see themselves through another person’s eyes. In other words, they know that they are being seen.

Listening and reflecting back is critical for the work, but it’s also a relational experience. It tells people that they matter. It’s one of the reasons I’m so excited about @idelisse’s sketching experiment, where she’s not just capturing people’s words, she’s showing their spirit.

Reflection is our role, but we shouldn’t be the only ones doing it. The more we can help our participants build that muscle and habit, the more powerful this network will become. It’s another reason I’m emphasizing the sharing muscle itself and am de-emphasizing the content of what they share. Sure, it’s valuable for everyone else to get to see what folks talk about, but it’s even more valuable for people to see themselves reflected in each other’s eyes, even in small ways.

Part of the fun and challenge of our work is experimenting with mediated mirrors. But right now, we’re faced with a much more fundamental challenge: Getting the participants to look!