Often it has been around medical care. A few years ago we had a friend who spent more than a year in long-term respiratory rehab. Her daughter wasn’t able to visit much, and so we started to go most weekends just to see her. Not only did her emotional state improve but because we started to leave markers of loving family (a handmade afghan, photos, window clings, and other similar things) her medical care improved. That these things made a difference to how the staff treated her shouldn’t be true. When our own family members are in the hospital we try to ensure they get as much visitation as possible for the same reason.

Most recently it’s been while supporting children in foster care.

My wife and I serve as volunteer Guardian ad Litems in South Carolina (other states call the program CASA). It means we are court appointed advocates for children in foster care. We are the only people in their lives tasked with being openly biased in their favor. In practice it means we go to lots of meetings with professionals who should be better trained than us, better resourced than we are, and try to make sure they do their jobs the way the law requires. All children in foster care in South Carolina have a right to a volunteer advocate because the professionals who used to be paid to do this work didn’t do it as well as volunteers – nothing about that should be a true statement, but in 2010 the South Carolina Supreme Court ruled it was and from everything we’ve seen it is. So instead of a lawyer, they get us.

With just a few hours of training, that covered lots of information but barely scratched the surface, we were cut loose to help kids fight to make their lives whole again – ideally even better than before. We became part of a system run by underpaid, under-trained, and overloaded professionals. We go to all the meetings that happen in the lives of these children. We go to school and their home(s); we talk to everyone who passes through their lives during their time in the system; we visit the juvenile detention center to meet with our kids and prisons to meet with mom or dad; talk to doctors, lawyers (ours, their parent’s, and DSS’s but the kids rarely get their own in family court), case workers, detectives, probation officers, teachers and principals, parents, grand parents, foster parents, aunts and uncles, neighbors, and anyone else in their lives. Everyone else on that list worries about their own interests (like the parents do), other people in the family (like the case workers are federally obligately to do), are narrowly focused on one aspect of the child’s life (like their doctors are), or have worry about too many other people whose interests may conflict (like teachers must). My wife and I make sure we talk to more people than anyone else on the case, so that we can we represent the child’s interests and desires clearly and accurately.

We work with teenagers who have had all control of their lives taken away as they need to be learning to take more responsibility for their actions. The system is not designed well for the needs of teenagers, and so it falls to us to start helping these young people start to regain at least a little control of their destiny. The law requires us to meet with them once a month, but often it is more frequent (particularly with those prone to getting into trouble), and we become the only people they have who are both honest and unfailingly supportive. We are also too often the only people listening to their opinions about what’s happened and what they want to have happen next.

Our only real power, beyond being allowed into meetings, is that we are required to make recommendations to the court about what should happen. The court can ignore us, although they do so far less than people tell us to expect and the judges always listen with interest to to what we say. The vast majority of our impact happens outside of the court room, when professionals work harder just because they know we are watching.

Being a GAL is equal parts wonderful and infuriating, but at all times useful. We have discovered that just having a totally biased volunteer in the child’s life often makes the professionals more responsive to the child’s needs. Our schools are deeply under-resourced, and frequently seek to avoid providing legally mandated but expensive services so my wife is becoming an expert in education law to allow her to ensure the children’s rights are respected. But she has found that once she meets with the school administrators once or twice, and see that someone believes the kid is worth fighting for, they join us and help ensure the child is getting the support they need. Group homes, even terrible ones that openly allow their staff to beat children in ways that are banned for our prison guards (there is a true story behind that), are more careful when they know a volunteer is watching over a specific child and holding them legally accountable.

Sometimes just having a person around who cares, and thinks someone else is worth caring about, helps people who should do their jobs regardless of what’s happening, do their jobs better.

This isn’t the first time I’ve been part of a community that was changing how it organizes itself. In my religious life I am a Quaker, and for a long time I was a member of Philadelphia Yearly Meeting which is the regional organizing body for Quakers in the greater Philadelphia area. And I served for a time on several of their leadership committees. I’ve seen that 300+ year old group pass through at least three different governance structures, and while many of the fundamentals are the same, the details that matter to people also change a lot.

My great aunt put it into perspective during one of the long discussions about change. When my wife asked her for her opinion about a then pending proposal she responded that it didn’t matter much to her as long as it worked for those willing to take leadership roles at the moment.

So as the Drupal community grows through a process to change our leadership structure here are the things I think it is important for all of us to remember.

1. It will not be perfect.  We’re human, we will make mistakes, that’s okay.
2. It will change again. I don’t know when or why, but whatever we do will serve us for a time, and then we’ll replace it again.
3. Most of the community won’t care most of the time. Most of the time, most of us don’t notice what Dries, the Drupal Association, Community Working Group, and all the other groups that provide vision and leadership are doing.

I think we can all agree my first point is a given. I mention it mostly because some of us will find fault in anything done going forward. We should remember the people doing this work are doing the best they can and give them support to do it well.

On the plus side, whatever mistakes we make will be temporary because Drupal and its community will outlive whatever we create this time. We’ll outgrow it, get annoyed with the flaws, or just plain decide to change it again. Whatever we build needs to be designed to be changed, improved, and replaced in the future.  Think about it like the clauses in the U.S. constitution designed to allow amends to the constitution itself.

Finally, we should remember that community and project governance is insider baseball. Understanding how and why we have the leadership we do is like watching a pitching duel on a rainy day, most baseball fans don’t enjoy those kinds of games.  Most of our community wants to use Drupal and they don’t want to have to think about how DrupalCon, Drupal.org, and other other spaces and events are managed. That will not prevent them from complaining next time there are problems, but it is a fact of life those who do care should acknowledge.

Our community is stronger than we have been giving it credit for in the last few weeks. We need to be patient and kind with each other, and we’ll get through this and the divisions that will come in the future.

No one can promise you success, but I promise if you take a brand new tool and try to force it to be just like the tool you are replacing you are going to be disappointed (at best).  Salesforce is not CiviCRM, Drupal is not WordPress, Salsa is not Blackbaud. Remember you are replacing the tool for a reason, if everything about your current tool was perfect you wouldn’t be replacing it in the first place. So here are my steps for improving your chances of success:

1. List the main functions the tool needs to accomplish: This is the most obvious thing to do, but make sure your list only covers the things you need to do, not the ways you currently do it. Try to keep yourself at a relatively high level to avoid describing what you have now as the required system.
2. List the pros and cons of what you have: Every tool I’ve ever used had pluses and minuses. And most major internal systems have stakeholders who love and hate it – sometimes that’s the same person – make sure you capture both the good and bad to help you with your selection later. Develop a list of tools that are well known in the field: Not just tools you know at the start of the project. Make sure you hunt for a few that are new to you. You might think you’ve heard of them all cause you walked around the vendor hall at NTC last year, but I promise you there are more companies that picked a different conference to push their wares, and there are open source tools you might have missed too.
3. Make sure every tool has a salesperson: Open Source tools can be overlooked because no one sells them to you, and that may mean you miss the perfect tool for your organization. So for open source even the playing field by having a salesperson, or champion, for the tool. This can be an internal person who likes learning new things, or an outside expert (usually paid but sometimes volunteer).
4. Let the sales teams sell, but don’t trust them: Let sales people run through their presentations, because you will learn something along the way. But at some point you also need to ask them questions that force them off your script. Force a demo of a non-contrived example, or of a feature they don’t show you the first time. Make them improvise and see what happens.
5. Talk to other users, and make sure you find one who is not happy: Sure your organization is unique but lots of other organizations have similar needs for the basic tools – unless you have a software-based mission you probably do not want an email system that’s totally different from everyone else’s. A good salesperson will have no trouble giving you a list of references of organizations who love the tool, but if you want the complete picture find someone who hates it. They might hate it for totally unfair reasons, but they will shed light on the rough edges you may encounter. Also make sure you ask the people who love it what problems they run into, remember nothing is perfect so everyone should have a complaint of some kind.
6. Develop a change strategy: In addition to a data migration plan you need to have a plan that covers introducing the new tool to your colleagues, training the users, communicating to leadership the risks and rewards of the new setup, and setting expectations about any disruptions the change over may cause.  I’ve seen an organization spend nearly a half million dollars on customization of a complex toolset only to have the launch fail because they didn’t make sure the staff understood that the new tool would change their day-to-day tasks.
7. Develop a migration plan: Plan out the migration of all data, features, and functions as soon as you have your new tool selected. This is not the same thing as your change strategy, this is nuts and bolts of how things will work. Do not attempt to do this without an expert. You made yourself an expert in the field, but not of every in-and-out of the new system: hire someone who is.  That could be a setup team from the company that makes it, a 3rd party consultant, or a new internal staff person who has experience with different instances of the tool.
8. Get staff trained on using the new tool: don’t scrimp on staff training. Make sure they have a chance to learn how to do the things they will actually be doing on a day-to-day basis.  If you can afford to have customized training arranged I highly recommend it, if you cannot have an outside person do it, consider custom building a training for your low-level internal users yourself.
9. Develop a plan for ongoing improvement: you will not be 100% happy 100% of the time, and over time those problems will get worse as your needs shift. So make sure you are planning to consistently improve your setup. That can take many forms and what makes the most sense will vary from tool to tool and org to org, but it probably will mean a budget so ask for money from the start and build it into your ongoing budget for the project. Plan for constant improvement or you will find a growing list of pain points that push you to redo all this work sooner than expected.You’ll notice I never actually told you to make your choice. Once you’ve completed steps 1-6 you probably will see an obvious choice, of not: guess. You have a list, you listened to 20 boring sales presentations, you’ve read blogs posts, white papers, and ad materials. You now are an expert on the market and the tools. If you can’t make a good pick for your organization, no one else can either so push aside your imposter syndrome and go with your gut. Sure you could be wrong, but do the best you can and move forward. It’s usually better to make a choice than waffle indefinitely.

Then I started to work with large corporations. Turns out, all that money doesn’t necessarily bring you people who know how to spend it well.  Yes the margins are bigger, and there is less complaining about the basic costs of doing business, but when it comes right down to it they aren’t any more strategic than a small scrappy team of people in the communications department of any organization large enough to have a communications team.

This shouldn’t have been a surprise.  A great deal has been written about start-up culture and ways to help companies recreate the energy, passion, and creativity of their lean early days.  And there has been a great deal written about impostor syndrome which nonprofit communications staff tend to have in spades.

Of course I’m speaking here in sweeping generalities about two massive groups, but here is what I’ve seen working with both nonprofits and for-profits:

1. As a group nonprofit staff are there because they care about the cause(s) of the organization, and they are driven to help the organization succeed despite their lack of resources.
2. The lack of resources — both in terms of time and money — forces NPOs to find creative solutions to their problems. They moved aggressively into social media because it was a free way to spread their message: companies then used the lessons learned by nonprofits to craft their early engagements with social media.
3. Due to corporate donations, nonprofits actually have access to the best software tools money can buy. Salesforce, NetSuite, Google, Microsoft, Adobe, and others give nonprofits amazing discounts that allow them access to tools companies twice their size can barely afford. I used to (legally) get $20,000 server packages from Microsoft of $200. Google gives $10,000/month ad-word grants. SalesForce and NetSuite provide amazing tools at amazing prices.
4. Nonprofits are right to believe if they had access to better tools and more money they could do even better. Tools written for nonprofits tend to be second rate (look at the vast majority of fundraising toolkits), and they are held back in the places where they need specialized software. I have friends that write this stuff, they work hard, but with literally billions less in resources they have a big hill to climb.
5. Organizations like N-TEN have been helping nonprofits learn from each other and from the best of the for-profit world for nearly 15 years.  That community has benefited thought leaders like Beth Kanter, John Kenyon, Ryan Ozimek, and others who help NPOs focus on their goals instead of their tools.
6. For-profit marketing staff do not believe they have anything to learn from nonprofits, and are often making mistakes that the subject of basic talks at conferences like NTC 5 years ago.

Nonprofits often struggle to figure out the right way to leverage new tools because they try to leverage them first. When traditional companies start trying to market in new spaces they sometimes make it look easy because they have a path to follow.  A path broken by nonprofits.

What it did do was teach a small group of us that the online work was important, harder than we thought, and required skills we didn’t yet have.  I could list dozens of mistakes that we made in the course of the project, most of which were totally avoidable if any one of us had known then what we know now, but it was those mistakes that caused me to learn to constantly push to became better at what I do.

The biggest mistake we made was that we allowed ourselves to repeat mistakes. We were sloppy, and allowed the same errors to get posted over and over. Mark, my colleague and friend looked at me at one point and said: “Let’s always make new mistakes from here on.”  And we pretty much did – for the next 10 years (although he still makes fun of me for misspelling “signatures” over and over on the peace pledge site).

“Always make new mistakes” became mantra for us and the AFSC’s Web Team. We knew that we didn’t have the resources to bring in someone else teach us everything we needed to know, we were leading projects in a medium very few people had mastered, and we were human. So it was going to be impossible to avoid mistakes, but we could make sure that we learned from our mistakes, find ways to avoid making them again, and then push into fresh territory filled with new mistakes we didn’t know existed.

I still use the slogan for my own work, and encourage it with teams I am on. People laugh the first time they hear it. But they discover I’m very serious when they see me adjust my work process and products to deal with mistakes I failed to avoid during a previous project. And I invite them to set the same standards for themselves.

We all need to work hard to identify our mistakes and come up with ways to avoid them.  Some mistakes are easy to see and fix: if you have poor spelling, make sure you have someone editing everything you write (even web page headings).  Some mistakes are harder to see: if you use the wrong metrics you may appear to be succeeding while actually failing. And some mistakes are hard to admit: creating a web applications with very little experience meant I made just about every security blunder possible, and since I knew more about web development than anyone else around me, I resisted attempts by others to point out places the tools were at risk.

Think hard about your work, look for mistakes, own them as scars you earned doing something new, and figure out how to make sure you make a different mistake next time. You will be a better person and professional and better prepared to change the world.