About a decade ago I migrated into community work [1] from a non-community background. This is the guide I wish I had read back then.

[1] When I say community work, I am talking about stuff like Wikipedia: large distributed groups of people doing something together, usually online, often unpaid. Usually international, often nerdy, often (but not always) FLOSS or FLOSS-adjacent.

You are going to be doing a lot of writing. Do it well. Phone calls and Hangouts don’t scale. Face-to-face is expensive for distributed groups and therefore rare. Real-time tools like IRC and Slack disadvantage people in minority timezones. And so, in an online community, your main way to communicate is likely going to be email. Which means you need to be good at it. Take the time to write carefully, fully and precisely. And since text is going to do so much of your communicative heavy lifting, consider being a little more explicit about emotional signal-sending than you might be otherwise. (“I am happy…”, “it is sad…”, “I am grateful.”)

In all your communications, be conscious of your group’s diversity. The group you’re speaking with is likely more diverse than what you’re used to. There may be children and teenagers as well as adults. For many or most, English won’t be their first language. They probably live in multiple countries, have had a broad diversity of experiences, and and hold a wide array of beliefs. This creates a bunch of potential pitfalls. Your jokes may fall flat or offend people. Cultural references (sports, movies, history) may be meaningless. Even for those of us who aren’t American, it’s easy to come across as U.S.-centric. Metaphors, allusions and convoluted sentence structures may not be worth the time they’d take readers to untangle, and make translations much more difficult. High diversity argues for a style that’s literal, straightforward, and well-structured.

Be cautious about creating an insider culture. This is a tough one, because inside jokes and shared history and assumptions foster a sense of belonging. But every in-group requires an out-group, and having a lot of shared lore is unavoidably exclusionary: it makes it harder for new people to join. A strong culture will also inevitably move you towards demographic/attitudinal narrowing, rather than the reverse.

Publish early, publish often. If you are building a plan or a proposal, don’t wait until it’s flawless and polished to publish: release it while it’s still raw and half-baked. For folks from a non-community background this will feel dangerous, like you’re leaving yourself vulnerable to criticism. But in a community context it builds trust and empathy, and will be understood as an invitation to collaborate. Do tons of signposting. Explain what you’re trying to do, and why. Sketch out how you imagine it may work.

Be aware that volunteer time is different from paid time. Staff need to begin their public work as soon as they possibly can (sooner!), and to build in lots of elapsed time for community discussion. Community members have other priorities: school, jobs, families. You can’t expect them to make your work their top priority, so you need to give them the biggest-possible window in which to contribute.

Write (and publish) a greater volume of stuff than you think you should. This feels counter-intuitive for people who’ve been execs in traditional contexts, because in an ordinary executive context the scarcest resource is time, and so we get used to providing summaries, bullet points, upshots, and key takeaways. Succinct=good. In a community context though, comprehensive beats succinct. This is only logical: if you’re writing for a wide diversity of stakeholders, they’re going to want to know a wide variety of stuff. Manually asking and answering questions is slow and laborious and splinters the information so you can’t get it all in one place: it’s faster and better, as much as possible, to anticipate questions and answer them in your original communication.

Assume good faith. This is so easier said than done ;/ But for real, assume good faith. When someone asks a question and you think they are trolling, it’s entirely possible they are not. (Maybe they are 15 years old, or their English is imperfect, or they have an impairment of some kind.) Even if they are trolling: there will always be onlookers who don’t know it, and who, whatever the provocation, will recoil if you are curt or unkind. Trolling also gives you an opportunity to equip onlookers with reasonable arguments that they can go on to use themselves.

Bias towards transparency. Way, way, way more than you think you should. I remember being taught change management back in the early 2000s. Our instructor beat into us that wherever there is a communications vacuum, it will be filled by gossip and fear. That is a million percent true, and even more so in online communities. Gossip and fear grow out of power imbalances and information asymmetry which are to some degree unavoidable in distributed and voluntary groups, and you need to compensate for that. Publishing everything also scales well, because it equips everybody, not just you and your inner circle, to help explain what’s going on.

Note that if you’re the boss it’s insufficient to ask your staff to be transparent, because as long as there is any risk of penalty for over-publishing, they will do the opposite. You need to make it clear that nobody will ever be punished or shamed for being transparent, then you need somebody to publish something they shouldn’t have, and then you need to not punish them. Only then will people begin to take you seriously about transparency.

When you change your mind, say it publicly, and explain why. This is another one that’s tough for execs from a non-community context, where we got trained to express more confidence than we felt. But for real: in a community context, changing your mind and explaining why will not erode your credibility; it will earn you more.

Pay attention to people you disagree with. In an ordinary work environment executives get insulated and protected from honest disagreement. This is bad for them and for their company. Community work is different: there is no shortage of people who will disagree with you, loudly and repeatedly, in public. It’s natural to avoid or ignore those people, but if you do, you’re wasting an opportunity. Consider instead that they may, occasionally, be right.

So. A year ago I left my position running the Wikimedia Foundation and began the process of figuring out what to do next. (Spoiler: not yet complete.)

I had eaten, slept and breathed nothing but Wikimedia for seven years — in effect, I had embodied it. That may sound unhealthy but it really wasn’t: there was lots of overlap between me and Wikimedia, and I didn’t mind parking the stuff the job didn’t need. But it did mean that afterwards, it made sense for me to do some self-scrutiny and a kind of reset. What had been actually me versus what was just the job, and therefore what did I want to keep doing, to discard, or maybe revive.

The first thing I did was spend a month in Iceland looking at volcanoes and lounging in hot springs. That was glorious and I recommend it to anyone.

I’d guessed by the time I got back I’d be ready to dive into something, but I was wrong. And so I spent many months in a kind of lazy exploratory mode. Making risotto. Playing board games. Collecting together and synthesizing everything that is known about the gender gap in tech. (Yes, for real. It’s here.) Travelling. Reading. Giving talks. Advising friends.

And simultaneously, trying on possible futures like they were hats. Did I want to run an important cultural institution whose influence was starting to wane? No. How about a campus speaking tour? No. A start-up with a difficult business model and some tough marketing challenges? Ha. No.

My goal has always been the same. I want to work on stuff i) that’s aiming to make the world better for ordinary people; ii) that is actually making the world better, not just trying and failing. And iii) where I can personally be most useful. I care about impact and scope and scale and effectiveness. And so the question for me was pretty simple: where were the biggest and most important problems, that need help from someone like me.

Gradually that answer started to come, at least provisionally, into focus. By now we know that the internet shakeout is well underway, with power and money increasingly consolidated among a tiny number of players. As Bruce Schneier has famously said, the internet’s business model is surveillance: most of the industry makes its money by tracking and stockpiling and monetizing information about its users. (Of those who don’t, many have no obvious business model at all, which is .. not reassuring.) That mountain of user data has turned out to be irresistible to state actors and other authorities, who now find themselves able to know vastly more about the habits and activities of ordinary people than was ever previously imaginable.

This all sucks. Initially it looked like the internet would rebalance the scales and empower ordinary people, but what’s actually happening is the opposite.

So here’s what I’m going to do.

Starting now, and supported by the First Look organisation, I’m beginning two projects related to anonymity, privacy, and free speech.

The first is narrowly focused on Tor, where I’ll be developing a strategic plan for and with the Tor Project.

I’m doing that because Tor is important — it’s the most secure and widely-used anonymity-supporting software that we’ve got. Tor is controversial because (like phones and cars and banks) its users include criminals. But what matters more to me is its use by people like Chelsea Manning and Edward Snowden. I want the organisation behind Tor be as strong and effective as possible, and so I am going to put some energy towards helping make that happen.

My second project will be to research the broader state of “freedom tech” — all the tools and technologies that enable free speech, free assembly, and freedom of the press. I want to figure out, from a user-centric perspective, what kinds of freedom-enabling technology products and services people have access to today, what impediments they’re running up against in trying to use them, what functionality is needed that’s entirely missing from the current landscape, and what kinds of interventions would need to be made in order to start getting it built. Do we need easier, faster funding, and/or other forms of support, for individuals and tiny teams? Or bigger, better-funded organisations, with expertise the space currently doesn’t have? What would move the needle? That’ll be my focus.

I’m extremely grateful to Pierre Omidyar and First Look for funding this, and to the Tor Project for being so fabulously welcoming to me. This is important work, and I’m super-pleased to embark upon it.

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.