I know a lot of people who’re starting up new nonprofits, and most don’t have any prior experience with fundraising. That was me!, back in 2007 when I took over the Wikimedia Foundation. And so, the purpose of this post is to share some of what I learned over the past eight years, both from my own experience and from talking with other EDs and with grantmakers. I’m focusing on restricted grants here because they’re the most obvious and common funding source for nonprofits, especially in their early stages of development.

Restricted grants can be great. Grantmaking institutions fund work that’s socially important, that’s coming out of organizations that may have no other access to funding, and that is often risky or experimental. They take chances on people and organizations with good ideas, who may not yet have a track record. That’s necessary and important.

But restricted grants also pose some specific problems for the organizations seeking them. This is well understood inside nonprofitland, but isn’t immediately obvious to people who’re new to it.

Here are the five main problems with restricted grants.

Restricted grants can be administratively burdensome. At the WMF, we actively sought out restricted grants for about two years, and afterwards accepted them only rarely. We had two rules of thumb: 1) We would only seek restricted grants from organizations we knew well and trusted to be good partners with us, and 2) We would only seek restricted grants from organizations that were roughly our size (by staff headcount) or smaller. Why? Because restricted grants can be a lot of work, particularly if the two organizations aren’t well aligned.

Big institutions have a big capacity to generate process: forms to fill out, procedures to follow, hoops to jump through. They have lots of staff time for meetings and calls and email exchanges. They operate at a slower pace than smaller orgs, and their processes are often inflexible. People who work at grantmaking institutions have a responsibility to be careful with their organization’s money, and want to feel like they’re adding value to the work the nonprofit is doing. Too often, this results in nonprofits feeling burdened by expensive process as they procure and report on grants: time that you want to spend achieving your mission, instead risks getting eaten up by grantmakers’ administrative requirements.

Restricted grants risk overwriting the nonprofit’s priorities with the grantmakers’ priorities. At the WMF, we didn’t accept grants for things we weren’t planning to do anyway. Every year we developed our plan, and then we would (sometimes, with funders we trusted) seek funding for specific components of it. With funders we trusted, we were happy to get their input on our priorities and our plans for executing them. But we weren’t interested in advancing grantmakers’ goals, except insofar as they overlapped with ours.

Too often, especially with young or small non-profits, I see the opposite.

If an organization is cash-strapped, all money looks good. But it’s not. Here’s a crude example. Let’s say the WMF knows it needs to focus its energy on mobile, and a funder is interested in creating physical spaces for Wikipedians to get together F2F for editing parties. In that context, agreeing with a funder to take money for the set-up of editing cafes would pose a distraction from the mobile work the WMF would need to be doing. An organization’s capacity and energies are always limited, and even grants that fully fund a new activity are necessarily drawing on executive and managerial attention, as well as the organization’s support functions (human resources, accounting, admin, legal, PR). If what a restricted grant funds isn’t a near-perfect fit with what the organization hopes to accomplish regardless of the funding, you risk your organization getting pulled off-track.

Restricted grants pull focus from core work. Most grantmakers want their money to accomplish something new. They’re inclined to see their grants as seed money, funding experiments and new activity. Most successful nonprofits though, have important core work that needs to get done. At the WMF for example that core work was the maintenance and continued availability of Wikipedia, the website, which meant stuff like hosting costs, costs of the Ops team, site security work and performance optimization, and lawyers to defend against censorship.

Because restricted grants are often aimed at funding new activity, nonprofits that depend on them are incentivized to continually launch new activities, and to abandon or only weakly support the ones that already exist. They develop a bias towards fragmentation, churn and divergence, at the expense of focus and excellence. An organization that funds itself solely or mainly through restricted grants risks starving its core.

Restricted grants pull the attention of the executive director. I am constantly recommending this excellent article by the nonprofit strategy consultancy Bridgespan, published in the Stanford Social Innovation Review. Its point is that the most effective and fastest-growing nonprofits focus their fundraising efforts on a single type of funder (e.g., crowdfunding, or foundations, or major donors). That’s counter-intuitive because most people reflexively assume that diversification=good: stable, low-risk, prudent. Those people, though, are wrong. What works for e.g. retirement savings, is not the same as what works for nonprofit revenue strategy.

Why? Because organizations need to focus: they can’t be good at everything, and that’s as true when it comes to fundraising as it is with everything else. It’s also true for the executive director. An executive director whose organization is dependent on restricted grants will find him or herself focused on grantmaking institutions, which generally means attending conferences, serving on juries and publicly positioning him or herself as a thought leader in the space in which they work. That’s not necessarily the best use of the ED’s time.

Restricted grants are typically more waterfall than agile. Here’s how grants typically work. The nonprofit writes up a proposal that presumes it understands what it wants to do and how it will do it. It includes a goal statement, a scope statement, usually some kind of theory of change, a set of deliverables, a budget, timeline, and measures of success. There is some back-and-forth with the funder, which may take a few weeks or many months, and once the proposal is approved, funding is released. By the time the project starts, it may be as much as an entire year since it was first conceived. As the plan is executed the organization will learn new things, and it’s often not clear how what’s been learned can or should affect the plan, or who has the ability to make or approve changes to it.

This is how we used to do software development and in a worst-case scenario it led to death march projects building products that nobody ended up wanting. That’s why we shifted from waterfall to agile: because you get a better, more-wanted product, faster and cheaper. It probably makes sense for grantmaking institutions to adapt their processes similarly, but I’m not aware of any who have yet done that. I don’t think it would be easy, or obvious, how to do it.

Upshot: If you’re a new nonprofit considering funding yourself via restricted grants, here’s my advice. Pick your funders carefully. Focus on ones whose goals have a large overlap with your own, and whose processes seem lightweight and smart. Aim to work with people who are willing to trust you, and who are careful with your time. Don’t look to foundations to set your priorities: figure out what you want to do, and then try to find a grantmaker who wants to support it.

I do a lot of talks, and I’ve worked with event organizers ranging from awesome to, uh, not so great. I’ve found that how the organizer handles me, both before and during the event, has a definite effect on my performance. And so the purpose of this post is really simple — it’s to help you, the organizer, make it possible for your speaker to do a great job at your event.

The invitation

In your invitation, say why you’re inviting the person and what you hope they’ll talk about. Tell them how they’d fit into the event — e.g., would they be keynoting, in plenary, a workshop, opening or closing. Are you flexible on the format. How long would the talk be. What’s the expected audience size. What’s the date and location. Do you pay, and if so how much. How do you handle travel.

(If you’re inviting me, you send all this to the Lavin Agency.)

The planning stage

Once your speaker’s accepted, have a call or exchange some mails. Tell your speaker how many people will be at the event and what they’re like demographically, what kind of work they do, what they know or don’t know about the speaker’s topic. Are they at the event to work/learn, or is it more of a junket or social experience. Why will they be in the room and how will they feel about it.

The most useful things organizers have ever told me: “everybody is very angry about [x recent thing], and it will be an undercurrent to all the questions”; “really this is their holiday: they will just want to enjoy themselves” and “we are very interested in this topic but we are Finnish so nobody will ask questions.” The better your speaker understands the audience, the better a job they will do.

Then, send one email with all the logistical information. It needs to include the date and time and location of the talk including the full street address; the talk duration including split between presentation and Q and A; formatting practicalities (e.g., aspect ratio, acceptable formats), and contact information including cell numbers for anyone the speaker might need to reach during the event. Ideally it’ll also describe the room and AV setup (e.g., what kind of microphone, will there be a confidence monitor, size of screen, how the seating will be configured). It’s awesome if you can attach a photo of the room. Personally I’m always really interested in screen size and room brightness, because a big screen in a dark room lets me emphasize visuals, but the opposite does not.

The mail should tell your speaker what time to arrive, where to go and who to ask for. If you’re arranging travel, it should include those details too, even if the speaker already has them.

Essentially, you want this mail to contain all the practical information that the speaker might need, then or later. The more structured the better, so it can be parsed by applications like TripIt and Google Now.

Then, in the weeks leading up to the talk, send your speaker a couple of reminder mails. It’s easy for talks to slide off people’s radar, and more than once I’ve appreciated prompts that the day is getting closer :/

Day of the talk 

Empathize with your speaker! He or she has spent dozens or maybe hundreds of hours getting ready for your event. They may have travelled a long distance. They may be jet-lagged or not-yet-caffeinated or distracted by something happening at home. They may be nervous. Your job on the day of the event is to help them get into the right performative headspace.

To that end, make sure there’s somebody assigned to greet your speaker and get them settled. That person should be present, knowledgeable and friendly. If they don’t know the speaker’s work, it’s polite to vaguely pretend otherwise. I once watched a speaker’s confidence visibly degrade when a stressed-out stage manager asked him, for the fifth time in five minutes, how to spell his name.

Ideally you want to let the speaker do a quick rehearsal onstage, at least an hour beforehand. This is the opportunity to sort out any glitches such as missing adaptors, dead batteries or broken deck formatting. It also gives your speaker a chance to get used to the stage, which can be helpful because stages are often squeaky or creaky or bouncy or otherwise weird. Once I spoke from one where the audience and I were separated by 27 feet of yawning open orchestra pit, and I spent the entire talk reminding myself not to fall in. Better to discover and adapt to that stuff beforehand.

This is also a point at which your speaker might ask for some adjustments. I do this a lot. I’ll ask for chairs to be moved around, tables to be switched from classroom to tiered style, or changes to the lighting. If you can adapt to the speaker’s preferences, try to — they’re not trying to hassle you, they’re trying to make the audience experience as good as possible.

Give the speaker a green room or other quiet place for at least an hour before the talk. Make sure they have water and have eaten. A live feed of the event is great.

Some organizers seem to feel like it’s part of their job to entertain the speaker, but it really isn’t. Most speakers I know don’t want to chitchat: they want to rehearse mentally, or warm up, or just work quietly. It’s totally fine to use this time to run the introduction past them if you haven’t already, and to tell them if anything important has changed about the set-up or timing. Otherwise, try to ensure they’re left alone.

Make sure there’s water onstage. A glass or open bottle is good; hard-to-open bottles are bad, and the worst are those super-flimsy ones that crackle when you touch them and then spill all over the place :/ If there’s no lectern it’s a good practice to have a small table at the side of the stage for water and miscellanea like the speaker’s phone or notes.

Afterwards

It’s nice to send a quick mail thanking your speaker and telling them about how the talk was received — basically, whatever you heard in the halls afterwards. Most organizers do a good job with this.

And finally

None of this is intended to increase organizer stress! Most speakers are super-flexible, and will be fine in imperfect conditions. I did not fall into the orchestra pit! Everything will be okay :)

A while back I was startled while researching someone in a work context, to come across a bunch of NSFW self-portraits she’d posted online under her real name. She was mid-career in compliance-related roles at big, traditional companies, and the photos raised questions for me about her judgement and honestly her competency. Didn’t she realise the images were public? Hadn’t she ever thought about what could happen when somebody –a colleague, a boss– randomly googled her? Was she making a considered decision, or just being clueless?

I was surprised because nowadays, that lack of caution is so rare. That’s partly because people have gotten a little more sophisticated about privacy controls, but mostly I think we’ve just given up. We can’t be confident our stuff is private today or will stay private tomorrow — if we didn’t know that already, we know it now from The Fappening and the Guardian’s uncovering that Whisper tracks its users.

And so I think that most people, most of the time, have decided to just assume everything we do online is public, and to conduct ourselves accordingly. It’s a rational decision that’s resulted in a tone and style we all recognize: we’re cheerful about work, supportive of friends, proud of family; we’ve got unobjectionable hobbies and we like stuff like vacations and pie. Promotions and babies and parties yes, layoffs and illnesses and setbacks not so much.

Secret, the app that was super-hot last winter, was briefly an exception. People talked on Secret about bad sex, imposter syndrome, depression and ADD, their ageing parents, embarrassments at work. You may remember the engineer who posted that he felt like a loser because he, seemingly alone in Silicon Valley, was barely scraping by financially. It was vulnerable and raw and awesome.

But I ended up uninstalling it pretty fast, after one too many humble-brags showed up in my feed. (The final straw was a guy boasting about how he’d bought a new iPad for a kid at the airport, after watching her mom get mad at her for dropping and breaking theirs. Blah.) I couldn’t bear seeing people diligently polishing up their self-presentation as confident and fun and generous and successful, on a service whose whole point was to enable risk-free vulnerability.

Reverse-engineering user behaviour on Secret, it read to me like people were hedging their bets. Secret users seemed to be operating (maybe without even thinking much about it) on the assumption that one day, due to a data breach or change in privacy policy or sale of the company, their activity on Secret might be available, linked to them, to their friends or insurance provider or boss or mom or bank. They didn’t trust their activity was permanently private, and so they acted as though it wasn’t.

That feeling of always being potentially in a spotlight leads us to relentlessly curate how we self-present online. And that is bad for us.

It’s bad for individuals because we run the risk of comparing our own insides to other people’s outsides, which makes us feel crappy and sets us up to make decisions based on flawed assumptions. Brene Brown: “If you trade your authenticity for safety, you may experience the following: anxiety, depression, eating disorders, addiction, rage, blame, resentment, and inexplicable grief.” Erving Goffman: “To the degree that the individual maintains a show before others that he himself does not believe, he can come to experience a special kind of alienation from self and a special kind of wariness of others.”

It’s bad for society because it makes people feel alienated and disconnected from each other, and also because it has the effect of encouraging normativity. If we all self-monitor to hide our rough edges, our unpopular opinions, our anxieties and ugly truths, we’re participating in the narrowing of what’s socially acceptable. We make it less okay to be weird, flawed, different, wrong. Which sucks for young people, who deserve to get to freely make the stupid mistakes of youth. It sucks for people who’ve been abused or poor or sick, and who shouldn’t have to hide or minimize those experiences. And it sucks for anybody with an opinion or characteristic or interest that is in any way unconventional. (Yes that is all of us.)

Anonymity was one of the great things about the early internet, and although we benefit enormously from the ability today to quickly find and research and understand each other, as individuals we also need private spaces. We need, when we want to, for our own reasons, to get to be predictably, safely, unbreakably anonymous/pseudonymous, online. That’s why I use Tor and other FLOSS services that support anonymity, and it’s why I avoid the closed-source, commercially-motivated ones. I trust Tor, like a lot of people do, because it has a track record of successful privacy protection, and because it’s radically transparent in the same way, and presumably for the same reasons, that Wikipedia is.

I’ve got nothing to hide (and oh how I hate that I feel like I need to type out that sentence), but I value my privacy, and I want to support anonymity being understood as normal rather than perverse or suspect. So I’m increasingly using tools like Tor, ChatSecure, TextSecure, RiseUp, and DuckDuckGo. I’ve been talking about this with friends for a while and some have been asking me how to get started with Tor, and especially how to use it to access the deep web. I’m working on a post about that — with luck I’ll get it done & published within the next few weeks.

For the past 15 years I’ve been a client for leadership development work both on my own behalf and on behalf of organizations I’ve led. I’ve used the industry a lot, and gotten tons of value out of it. That said, the world of work has been changing pretty dramatically, and I can’t honestly say I feel like leadership development is keeping pace.

When I first started getting leadership training, way back years ago, here are some of the messages I was given:

The boss should talk less and listen more. Bosses should practice empathy, and learn how to give calm, clear, actionable feedback rather than yelling or being punitive.

Not everything can be reduced to numbers and deliverables and milestones and targets: the human side matters too.

Bosses should practice some degree of self-disclosure and let themselves be vulnerable: that builds trust and healthy working relationships.

People should be encouraged to admit mistakes, to change their minds, and to constantly iterate towards better.

Bosses shouldn’t pretend to have all the answers: they should be receptive and open to the ideas of others regardless of their position in the formal hierarchy.

Transparency is generally good. If people don’t know what you’re thinking, they make up stuff that’s way worse than reality.

Those are good messages. They helped me think in a more explicit way about the practice of leadership, and gave me permission to be the kind of boss I’d like to think I’d have been anyway. But once you poke at them a little, it’s clear they’re built on weird assumptions.

I was a journalist in broadcast media, a totally non-command-and-control industry. I’d never even had a command-and-control boss. Roughly 50% of the people in senior roles in my organization were women, and women bosses are widely understood to be more inclusive and communicative than male ones. My then-organization was 85% unionized and the unions were pretty strong: when management wanted to exert its will, our most useful tools were influence and persuasion.

So why were our coaches and trainers putting so much energy into guiding us away from being autocratic jerks?

Eventually I concluded that the leadership development industry, built as it is on decades of studies and analysis and practice, probably generally has a bias to lag behind reality — meaning, it’s shaped not so much by what’s actually happening now, or might happen tomorrow, but by past experience. And therefore it implicitly, reflexively, assumes an old-school boss: a guy, maybe in his fifties, who’s smoking a cigar and barking out orders.

The trouble is that while that may have been the typical boss 50 years ago, with each passing day it’s less and less our reality. We just don’t work in command-and-control environments as much as we used to. And to the extent that leadership development is designed to fix the problems of autocratic jerks, it is limiting its ability to be useful for everybody else.

I live and work in the Bay Area, in media and tech. Everybody I know is experimenting with organizational design and leadership style, whether they’d say it explicitly or not. People are trying to figure out how flat their orgs can reasonably be, how to devolve power, how to maximize cohesion and buy-in and organizational agility. Gruff Shouty Boss is just not our failure mode.

Here’s the kind of thing people I know talk about.

  • How to, in decision-making, balance inclusivity against efficiency and speed.
  • How to balance an individual contributor’s sense of personal agency against the organization’s need for everyone to row (or bail) the boat together.
  • How to maintain leadership accountability while fostering broad ownership and responsibility throughout the organization.
  • How to have leadership be accessible to all levels of the organization, without drowning the execs or undermining middle management.
  • How to create a strong, shared work culture without accidentally turning into a monoculture that doesn’t tolerate people who don’t fit.
  • How to, in organizations that over-value harmony, ensure disagreements are openly expressed and worked through.
  • How to create an environment that enables the effectiveness of creative, talented people who have depression, ADD/ADHD and/or Asperger’s.
  • How to equip leaders from underrepresented groups to manage their imposter syndrome and to successfully handle subtle biases among their co-workers.
  • How to lead in a period of experimentation, when the boss can’t pretend to have all the answers.

These are the kinds of questions that leaders in the tech sector are facing today and, as software eats the world, they’ll increasingly be faced by leaders in every sector.

There are people working on figuring out this stuff — for example, I like Michael Lopp and Venkatesh Rao and Joel Spolsky, and I think boot camps and foo-type camps are useful too. But I feel like, in focusing on fixing the mistakes of the past, the LD/OD industry itself is erasing, rather than helping shape and define, new and emergent forms of leadership. That’s a huge missed opportunity.

I travel a lot and I’m kind of .. obsessive. Herewith therefore, my very favourite travel products, time-tested and iterated-upon over the past decade. Note: Yeah, I am shaking my head as I press publish here. I comfort myself with the knowledge that I am not alone: lots of people are just as weirdly fussy about this stuff as I am. Nonetheless, I reserve the right to come back and caveat stuff here if I end up being publicly shamed ;)

scottevest

Scottevest travel vest with many pockets. OMG I love my Scottevest. It has 17 internal zippered pockets including ones perfectly sized for passports and ID cards, plus built-in channels for holding earbud cabling. I carry in it anything and everthing that I might need for flying: travel documents, pens, disinfecting wipes, nasal sanitizer swabs, Purell, eye drops, a tiny flashlight, lip balm, various adapters and cables, Sudafed, Benadryl, painkillers, zinc lozenges, tiny toothbrush and toothpaste, a notebook, mini-kit for repairing things, kleenex, stain removal pen, and immigration/residency documents. I wear it to and from the airport, and leave it in my suitcase otherwise.

Drawbacks. None. Zero!

Variants. There are other versions of this vest out there (like this Tilley one or this from Magellan’s) but I’ve never tried them. The built-in cabling solution is unique to Scottevest AFAIK, and that alone would keep me with that company. Annoyingly, women seem to be underserved in this category by everyone, with nowhere near the amount of product variety that men get.

clear

Clear vinyl zippered bags from MMF Industries. I use these to collect together small things in my luggage (e.g. power cables, toiletries) so they don’t get lost. These are great — transparent, washable including in a dishwasher, and completely indestructible.

Drawbacks. None, except I wish they came in additional sizes.

Variants. A lot of people recommend just using ziplocs but I find even the thicker ‘freezer’ ones rip too easily. Mesh bags and translucent bags don’t offer enough visibility into their contents, and many offer zero protection against leakage. This bag from the Container Store doesn’t pack neatly and over time the brittle plastic creases and cracks. This Tom Binh bag has fabric sides so isn’t easily washable/wipeable. This translucent bag and this canvas bag from Arsenal are super-durable but neither is transparent and I found them a little bulky. If I need something waterproof I use these clear bags from Alosak, but they’re not as durable as the MMF one: after a few trips, they often tear under the seal.

muji

Tiny clear plastic flip-top bottles from Muji. I have used a thousand variants of travel bottles/jars/tubes/whatever and these are the best — they’re great for carrying small amounts of stuff like cleanser, moisturizer and hair product. They don’t leak or drip. Squeezeable so you can get out all the contents. Translucent which means you can see when it’s time to refill.

Drawbacks. Mouth is slightly too narrow which means you need to use a pipette for non-liquids, or be extremely patient.

Variants. For smaller amounts or thicker products, these wee containers from Muji hold only 10g and are pretty much indestructible. For larger capacity, these Nalgene bottles from the Container Store are durable and reasonably leak-proof. These tiny ziploc bags are great for collecting together and mildly protecting small quantities of dry items like Sudafed, adaptors, USB sticks, change, buttons, stickers or jewelery, and this vitamins/medication case is rugged and compact. GoToobs are really popular but I found they leaked, and they were an awkward shape for packing. This set of stacking pill containers is also awkward for packing and breaks if you drop it, this Muji pill box is cheap-feeling and flimsy, these small Nalgene jars annoy me by having lids larger than the part you fill with product, and although these small round pill boxes from the Container Store are pretty good, they’re a hard plastic and do sometimes crack if dropped.

ebags

Packing cubes from eBags. Frequent travellers are split on packing cubes — some find them useful, while others think they waste space and weight. I like that they offer mild protection and keep my stuff organized, and a couple of times I’ve been grateful that they made repacking super-easy after my luggage got rummaged through by airport security. (Airport security people never actually open the cubes: I don’t know why.) I use them for clothes and non-fragile equipment/gear, particularly if it’s awkwardly-shaped. I pack clothes by outfit, which is great especially for red-eyes because I can pull out a single cube to change quickly at the hotel or airport.

Drawbacks. None.

Variants. I’ve tried a number of variants but they all had drawbacks. I colour-code by type-of-content, which means Rick Steves cubes and Tumi cubes, which only come in black, won’t work for me. You can’t colour-code with Ziplocs either, plus they rip too easily. I find the Eagle Creek cubes too heavy and the prominent branding bugs me. Travel folders cause wrinkles and are fiddly for repacking, and they’re best for people who are carrying multiples of things like button-downs, which I am not. Compression bags cause wrinkles and can be a hassle to repack: they’re not worth it unless you’re super space-constrained. Travel shoe bags really only fit flat shoes not heels or boots, and are usually too bulky/rigid to be useful: I try to avoid carrying extra shoes but when I need to, I just wrap them in soft bulky clothing and bury them in the centre of the suitcase.

anker

Portable battery pack from Anker. At 20000mAh, this is the highest-capacity general-use portable battery pack I know of, and when I did the math in July 2013 it had the best charge:weight ratio on Amazon. It charges my phone and tablets multiple times before needing to be plugged in — I’ve never yet fully drained it. It lives in my suitcase: I bring it with me on day trips and long flights when I won’t have access to power, and use it sometimes in hotels or public spaces when I can’t easily access an outlet. It’s beautifully designed and built.

Drawbacks. Too big and heavy to drag around every day. Supports many laptops, but not mine.

Variants. This 13000mAh charger from Powergen is pretty good, although I like Anker’s build quality, form factor and aesthetics better. I find the Anker fits better in my bags than this boxier 12000mAh charger from New Trent, plus I’ve had multiple New Trent products stop working for me after only a year or so. This 4500mAh charger from Anker is light and small: it’s good as a backup for giving my phone a single charge and I carry it with me everywhere, but I’m not thrilled with the hideaway cable which seems fragile.

tripshell

Travel adapter from Tripshell. These are well-built and durable, with no attachments to lose. I carry two or three in my suitcase and various charging kits.

Drawbacks. Because they disappear against dark backdrops, I’ve left a few behind in hotel rooms and meeting rooms. (There’s a dark red and a white version but they’re not much better.) I would love if somebody made these in a fluorescent.

Variants. There’s a Kensington adapter that’s practically identical to the Tripshell. The square all-in-one adapters always feel flimsy to me, plus they are slightly bulkier. Adapters with multiple components are too fiddly, and I lose the components.

monster

Four-outlet power strip from Monster. I love this power strip. It’s super-useful in hotels with limited or not-very-accessible outlets, and I’ve used it frequently on planes and in airports and event venues as well. It’s compact and durable, has widely spaced outlets that let you plug in multiple adapters, the plug is flat which means it fits into tight spaces, and when you plug it in it lights up to show it’s drawing charge.

Drawbacks. Would be great if it had a swivel feature.

Variants. I’ve used a bunch of variants but this is the best. This Belkin power strip works great at home, but is too bulky for travel. This USB wall charger from ARCTIC offers similar functionality to the Monster one, but has multiple parts that can get lost and is an awkward fit in tight spaces. This Belkin travel charger offers three outlets plus USB plus surge protection but again, the form factor limits its usefulness in tight spaces. The same is true for this wall charger from Anker, which only supports USB.

This post requires a number of caveats and acknowledgements. They’re at the bottom.

In 2008 I was interviewing a candidate for an engineering position at the Wikimedia Foundation and as we talked I found myself imagining what a terrific impression he would make on donors. He’s so shiny and cheerful and mission-oriented, I found myself thinking — donors will love him!

As soon as I thought it, I had the grace to be embarrassed. And although we ended up hiring the guy, we did it because he seemed like a talented engineer, not because he was charming. I was horrified at myself for a while afterwards anyway, and the whole thing ended up being a bit of a turning point for me, as well as a cautionary story I sometimes tell. Because that was the moment that crystalized for me what’s *actually* wrong with nonprofits.

Preface! I’ve always been irritated by people who assume nonprofitland is self-evidently suckier than forprofitland. I’m particularly irritated by people who say that nonprofits “should be more businesslike,” with businesslike as a kind of confused stand-in for “better.” That just seems dumb to me — I feel like it’s obvious that nonprofits function in a specific context including challenges unique to the sector, and that solutions aimed at increasing our effectiveness needed to be designed to respond specifically to those actual, real circumstances. That’s what this post is about: my goal is to describe a serious problem, and point to where I believe we’re beginning to see solutions emerge.

Here it is.

Every nonprofit has two main jobs: you need to do your core work, and you need to make the money to pay for it. In the for-profit sector when you make better products, you make more money — if you make awesome socks, you sell lots of socks. Paying attention to revenue makes sense in part because revenue functions as a signal for the overall effectiveness of the org: if sales drop, that’s a signal your product may be starting to suck, or that something else is wrong.

Nonprofits also prioritize revenue. But for most it doesn’t actually serve as much of an indicator of overall effectiveness. That’s because donors rarely experience the core mission work first-hand — most people who donate to Médecins Sans Frontières, for example, have never lived in a war zone. That means that most, or often all, the actual experiences a donor has with a nonprofit are related to fundraising, which means that over time many nonprofits have learned that the donating process needs –in and of itself– to provide a satisfying experience for the donor. All sorts of energy is therefore dedicated towards making it exactly that: donors get glossy newsletters of thanks, there are gala dinners, they are elaborately consulted on a variety of issues, and so forth.

By contrast, when I buy socks I do not get a gala dinner. In fact it’s the opposite: the more that sockmakers focus relentlessly and obsessively on sock-making awesomeness, the likelier I am to buy their socks in future. This means that inside most of nonprofitland –and unique to nonprofitland– there’s a structural problem of needing to provide positive experiences for donors that is disconnected from the core work of the organization. This has a variety of unintended effects, all of which undermine effectiveness.

It starts with the ED.

EDs prioritize revenue because a fundamental job of any CEO is to ensure their organization has the money it needs to achieve its goals. That means fundraising is necessarily the top priority for a nonprofit ED. That’s why the head of fundraising normally reports to the ED, and it’s why, I’d say from my observation and reading, the average ED probably dedicates about 70% of his or her energy to fundraising.

Optimizing for fundraising distorts how the ED behaves. To the extent EDs optimize themselves for fundraising, they tend to spend time outside their organization — being interviewed, attending conferences, publicly demonstrating wisdom and thought leadership. An ED must hone his or her self-presentation and diplomatic abilities, even at the expense of other attributes such decisiveness or single-mindedness, because that’s what donors see and respond to. There’s an obvious opportunity cost as well: spending 70% of your time on fundraising leaves only 30% for everything else. (That’s why, in a different context, Paul Graham argues that start-ups should have only one person designated to handle fundraising: to preserve the bulk of organizational resources for other stuff.)

The second effect: Optimizing for donor experience promotes a general emphasis on appearances rather than realities. Appearing effective rises in importance relative to being effective.

Here’s how the mature nonprofits I know self-present. Everyone is very polite and the offices are quiet. Their reception areas display racks of carefully-designed marketing materials. One I know has gorgeous brushed stainless steel signs attached to its conference room doors, engraved with an exhortation to be silent in the hallways. Typically the staff dress like academics — the women wear interesting jewelry, with the men in shabby suit jackets and corduroys.

By contrast I noticed in my early days running the WMF, we were quite different. Our staff were young and messy and wore hoodies. They were smart and blunt, sometimes obnoxiously so. The office was often half-deserted because everybody worked all the time, often while travelling or from bed. I’m pretty sure at one point we had a foosball table in the middle of the room, and later there was a karaoke set-up and a Galaga game. What if donors think we’re erratic, undisciplined slobs, I found myself worrying. What if they’ve never met programmers before?

Most nonprofits, it seemed to me, optimized to self-present as competent, sober, and diligent. I think if they optimized to get stuff done, they might look different.

The third effect. Nonprofits are generally conservative in their approach to regulatory compliance, administration, finance and governance practices. (Why? Partly it’s because the core work is complicated: hard to do and hard to measure, so people drift towards stuff that’s simpler. Also, the nonprofit sector is too small to support a diverse array of service providers, and so the services provided by consultants tend to be extremely generic. Boilerplate recommendations on term limits and that kind of thing.) Optimizing for donor experience makes that worse.

Why? It’s easy to describe for donors the core problem a nonprofit is trying to solve, but explaining the work of solving it –and how impact can best be measured– is hard. Far easier to show that the 990 was filed on time, that the org got a clean audit letter, and that the ED’s compensation was determined according to a highly responsible process. And donors seem relatively willing to accept the proposition that administrative effectiveness is a good proxy for overall organizational impact, even though such a proposition is actually pretty weak. A whole industry has developed around this: supporting good compliance and measuring it, as a service for potential donors.

This effect is amplified by the presence of major donors, who are typically wealthy retired business executives.

That’s because major donors like to feel their advice is as useful as their money, and they have decades of experience of people taking their opinions seriously. But they can’t necessarily say much that’s useful about the specifics of helping victims of domestic violence or rehabilitating criminals or protecting endangered gorillas in the Congo. So many nonprofits create opportunities where they can help. They are put on the investment committee, they are asked to help with the audit firm selection process, their advice is sought about when to launch an endowment campaign. This has the effect of focusing the ED’s attention in those areas — because the ED, of course, wants to make sure the major donor’s experience with the org is a positive one. More unintended consequences: “providing a good donor experience” becomes an unstated job requirement for the head of finance. A great head of nonprofit finance needs to not just be a person who’s financially and administratively competent: he or she also needs to be credible, composed, tactful and likable.

So. A major structural flaw of many nonprofits is that their revenue is decoupled from mission work, which pushes them to focus on providing a positive donor experience often at the expense of doing their core work. That’s bad.

What can we do about it?

I believe the problem is to some degree newly now solvable. I know that, because we solved it at the Wikimedia Foundation.

Here’s what we did.

From 2008 until late 2009, the WMF played around with various fundraising models. We applied for and got restricted grants, we cultivated major donors, we made business deals that brought in what’s called in nonprofitland “earned income,” and we fundraised online using what we grew to call the many-small-donors model. After two years we determined we’d be able to be successful using any of those methods, and an important study from Bridgespan had persuaded us to pick one. And so we picked many-small-donors, because we felt like it was the revenue model that best aligned with our core mission work.

Today, the WMF makes about 95% of its money from the many-small-donors model — ordinary people from all over the world, giving an average of $25 each.

It’s awesome.

We don’t give board seats in exchange for cash. Foundations’ priorities don’t override our own. We don’t stage fancy donor parties (well, we do stage one a year, but it’s not very fancy), and people who donated lots of money have no more influence than people who donate small amounts — and, importantly, no more influence than Wikipedia editors. Donors very rarely visit the office, and when they do, they don’t get a special dog-and-pony show. I spend practically zero time fundraising. We at the WMF get to focus on our core work of supporting and developing Wikipedia, and when donors talk with us we want to hear what they say, because they are Wikipedia readers. (That matters. I remember in the early days spending time with major donor prospects who didn’t actually use Wikipedia, and their opinions were, unsurprisingly, not very helpful.)

The many-small-donors models wouldn’t work for everyone, mainly because for it to succeed your core work needs to be a product or service that large numbers of people are aware of, understand, and want to support. About a half-a-billion people read Wikipedia, and we get on average 11 cents a year from each one, which is not much. I know a couple of nonprofits that’ve backed away from the many-small-donors model after doing that math. But I think the usefulness of the many-small-donors model, ultimately, will extend far beyond the small number of nonprofits currently funded by it.

Why? People are slowly getting used to the idea of voluntarily giving smallish amounts of money online to support stuff they like — look at Kickstarter and Donors Choose and Indiegogo. These are not self-interested transactions made after a careful evaluation of ‘what’s in it for me': they’re people funding stuff because they think it’s great. Meanwhile, the online payment processing market is maturing, with an increasing number of providers supporting an increasing number of currencies and countries, and fees are starting to drop. And, note that donations to the WMF have risen steadily every single year (we’ve been named the nonprofit with the fastest growing revenues in the United States, which probably actually means in the world) — even though the WMF’s fundraising is deliberately restrained. Eleven cents per user per year is nowhere near a ceiling, for Wikipedia or for anyone.

The advent of the internet has given ordinary people access to the means of production, and now they (we) can easily share information with each other on sites like Wikipedia. That’s been playing out for more than a decade, and its effects have included the disintermediation of gatekeepers and middlemen of all types. I think we’re now seeing the same thing happen, more slowly, with the funding of mission-driven work. I think that among other things, we’re going to see the role of foundations and major donors change in surprising ways. And I think the implications of these changes go beyond fundraising itself. For organizations that can cover their costs with the many-small-donors model I believe there’s the potential to heal the disconnect between fundraising and core mission work, in a way that supports nonprofits being, overall, much more effective.

Notes: This post is written from the vantage point of somebody who thinks many nonprofits do good work in difficult circumstances: please read it from that perspective. Lots of people think nonprofits are lazy and inefficient and woolly-minded. That’s sometimes true, but no more so in my experience than at for-profit orgs. The world has no shortage of suck.

I also want to thank some of the people who’ve influenced my thoughts in this area. Although the views expressed here are my own, Erik Moeller and I have talked a ton about this stuff over the past half-dozen years. He was the first person to point out to me the absurdity of overheard ratios, and has written about them extensively and publicly, starting back in 2009. Afterwards, he and I discovered the good work of Dan Pallotta and also the Urban Institute, investigating overhead ratios and explaining why they’re bunk. I’ve also benefited from reading Jim Collins’s monograph Good to Great and the Social Sectors, as well as two books from Michael Edwards: Just Another Emperor? The Myths and Realities of Philanthrocapitalism, and Small Change: Why Business Won’t Save the World. I was helped by a conversation about difficulties facing new nonprofits a few years back at the Aspen Institute, as well as by dozens of less structured conversations with fundraisers including particularly Zack Exley, as well as with my fellow EDs, including ones on whose boards I serve. David Schoonover has done some analysis of U.S. non-profit funding models that has influenced me, and he and I have talked extensively about challenges facing the nonprofit sector, including this one. The folks at Omidyar have also been helpful, including pointing me towards the very useful Bridgespan study linked above.

Because I’ve been working lately on issues related to grantmaking and Wikimedia movement entities, it might be tempting to assume my arguments here are somehow aimed at informing or influencing those conversations. They’re not. To the extent anything here is useful to those conversations that’s great, but that’s not why I wrote this.

On August 22, the soldier formerly known as Bradley Manning announced she wanted to be called Chelsea, and recognized as female. Within an hour, the English-language Wikipedia had renamed the article and changed its pronouns. That kicked off a week-long often-acrimonious debate among Wikipedia editors, which resulted, over the weekend, in the article title being reverted back to Bradley Manning. (For further context, here’s a news story and some detailed analysis.)

This disappointed me. I think Wikipedia did the right thing in promptly responding to Manning’s announcement, and I feel like reverting the change was, for many reasons, a bad call. And, I’m dismayed by subsequent on-wiki discussions that look like they may result in revisions to editorial policy that would support, in the future, similar bad decisions on trans issues.

The purpose of this blog post though, isn’t to argue why Wikipedia should respect that Chelsea Manning is a woman. (I’ve already done that extensively this past weekend on-wiki, as have others.) The purpose is to talk about the underlying factors that I think led Wikipedia to make a bad decision, and point to where I think solutions might lie.

First, I want to question some of the frames people are currently using to understand what happened here. Some editors have been characterizing the debate as political in a narrow sense — with left-leaning Wikipedians favouring use of Chelsea and right-wing Wikipedians favouring Bradley. Others are framing it as accuracy versus kindness — saying that editors who support using Chelsea are motivated by a desire to not hurt her feelings, and are prioritizing that goal over truth. I think both those frames are wrong. I think what the debate is actually revealing is a blind spot that Wikipedia has about gender.

Last summer I drafted a blog post about Wikipedia’s coverage of rape. I haven’t published it yet, and at this point I think I probably never will: its moment may have passed. But the similarities between what I observed in our discussions about rape, and what I’ve observed over the past few days as we talked about trans issues, are I think instructive. In both cases a non-negligible chunk of our editing community, all of whom ordinarily value accuracy and knowledge and expertise, seem instead to be going on gut feeling and knee-jerk assumptions. We aren’t applying our normal judgement and standards.

On rape and trans issues, the typical editor probably doesn’t have much expertise. That’s not at all unusual — people edit on topics they don’t know much about, all the time. We fix typos, we smooth out writing styles, we dig up and add citations. What’s unusual here is that rather than deferring to people who had read and thought a lot about the article topic, as we normally do, instead a substantial chunk of the community seemed to let itself be swayed by prejudice and unexamined assumptions. (To be clear: I do not mean that a large chunk of Wikipedians are themselves prejudiced. I mean that they let prejudiced ill-informed people establish a tone, an overton window if you will, of what was acceptable to think and say.)

Here’s what’s normal: When Pluto was declared to not be a planet, Wikipedia deferred to the experts, and reflected what they said in the article.

Here’s what’s not normal: When Dominique Strauss Kahn was accused of having raped a hotel cleaner, and when Todd Akin made pseudo-scientific claims about rape and pregnancy, many Wikipedians’ discussions were (I thought) remarkably ill-informed. Some editors seemed to believe that false accusations of rape were common. Some didn’t seem to realize that rape is seriously underreported. They didn’t recognize that there’s a body of knowledge on rape that’s well-sourced and reliable.

It took me a while to connect this to systemic bias — to realize that rather than Wikipedians being unusually lacking in knowledge about what rape is and how it works, I might better understand it as me being more-knowledgeable-than-the-average-Wikipedian on the topic. Because I’m a woman, and also a journalist, I’ve followed rape issues pretty closely in the media, I’ve talked about it a fair bit with my female friends, and I’ve read a couple of dozen books and studies on it and related topics. It took me a while to realize that that level of interest, and therefore expertise, is unusual on Wikipedia, presumably at least partly because our editor community skews so heavily male.

The same is true for transgender issues. A number of editors have made truly ignorant comments over the past week or so, comparing Chelsea Manning to someone who woke up one morning believing herself to be a dog, a cat, a Vulcan, Jesus Christ, a golden retriever, a genius, a black person, a Martian, a dolphin, Minnie Mouse, a broomstick or a banana. In saying those things, they revealed themselves to be people who’ve never thought seriously about trans issues — who have never read a single first-person account of growing up transgendered, or a scholarly study or medical text, or maybe even the Wikipedia article itself. That in itself is perfectly okay: different things are interesting to different people, and I for one know nothing about trigonometry or antisemitism in the 19th century or how a planet is determined to actually be a planet. But I don’t deny that there is stuff on those topics worth knowing, nor do I mock the knowledge of others, nor accuse them of bias and POV-pushing.

Wikipedians normally don’t either. Wikipedians won’t ordinarily defer to someone just because of their credentials, but we do normally attach extra credibility to people who’ve demonstrated they know more about a topic than we do. In this instance though, Wikipedians are considering sanctioning the two thoughtful and well-informed editors who originally made the change from Bradley to Chelsea. Which to me suggests systemic bias fuelled by groupthink.

So what needs to happen now?

The entire controversy has been referred to Wikipedia’s Arbitration Committee, the body of experienced editors who’ve been elected by the community to adjudicate difficult issues.

My hope is that ArbCom will clarify Wikipedia policy, and affirm that we have a responsibility to respect the basic human dignity of article subjects, to not mock or disparage them, and to attempt to avoid doing them harm. That we must not participate in or prolong their victimization.

I also hope ArbCom will weigh in on how Wikipedia handles trans issues in general. I’d be particularly interested in an examination of the role that subject-matter expertise is playing in our current discussions, and an exploration of how editors might choose to conduct themselves in disputes in which they have little expertise, and in which systemic bias risks skewing outcomes. In the Manning situation, for a variety of reasons that almost certainly include systemic bias, discussion didn’t achieve a result consistent with our desire to protect the dignity of an article subject.

So. Here’s the question. Given that Wikipedia makes decisions by consensus, how can majority-culture (male, young, Western, heterosexual, cisgendered) editors best participate in discussions in ways that work towards good decision-making, rather than groupthink?

For anybody reading this who doesn’t know: I’m the ED of the Wikimedia Foundation, and I’m also a Wikipedia editor. It’s in my latter, volunteer capacity that I wrote this blog post. What I say here is mostly informed by my experiences editing, but of course my experiences as ED have also shaped my opinions. Also: everything I say here, I say with lots of respect for the Wikipedia community. This is a rare misstep: an unusual and unfortunate blind spot.

Thank you to the people who vetted and gave feedback me on the draft version of this post — I appreciate it :-)

Edited to add, as per Aoife’s request in the comments. Here are some of my arguments in favour of titling the article Chelsea Manning. Here are some pages where you can read all the discussions we’ve been having.

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