Tag: business

Trust is key to successful distributed work

You can't successfully operate in a distributed/remote work model unless your organization is built on trust.

So many teams and companies are wrestling with questions around if and how to continue some version of distributed/remote work, now that public health concerns may not require it any longer.

Unfortunately, these conversations often focus on the mechanics of distributed work or in-person/distributed hybrid models: how many days per week, schedules, locations, finances, technology tools and more.

These are important considerations, but without a culture of trust to start, it's like choosing the color of a bicycle that has no wheels.

Managers and supervisors need to trust the people they manage and supervise. If you don’t trust that your people are there to do their best for the success of the organization, and to figure out a way of working that fits their needs and their role or team's needs, no amount of remote work tools or tips are going to help. If you don't empower and enable people to thrive in their work, and acknowledge them when they do, a distributed work model will lead to poor performance, isolation, resentment and worse. (Tip: this is also true in in-person work environments.)

Individual contributors who work together need to trust each other. If you don't trust that your co-worker is doing their best to balance the long-term interests of the organization and their role with their own health and wellness, no amount of communication tools or stand-up meetings is going to help. If you can't be gracious and generous with your co-workers around flexible scheduling, stepping away or taking time off when they need to, offering support and encouragement, and expecting all of that for yourself as well, then a distributed work model will bring out the worst in your professional interactions and relationships.

Is it okay to "trust but verify"? Is it okay to have systems of check-ins and measurement and reviews? Sure! But these should be built on the assumption that the people being verified, checked-in on, measured and reviewed are doing their best to fulfill the goals of their position in the context of everything else going on in the organization and in their personal lives. Instead of being about punishing or scolding, they should focus on offering guidance, direction, constructive feedback, support and encouragement — again, trusting that people are there to do their best work for the long run, and helping them get there.

What if you don't have that trust? What if the people in your organization assume the worst about each other's intentions? What if you can't possibly imagine letting a co-worker decide for themselves, in consultation with their team and stakeholders, what work environment, practices, schedule, tools and timelines make the most sense given everything you're trying to accomplish together? Then there's no way you're going to be able to thrive as a distributed team, or maybe at all, until that trust is repaired or rebuilt.

Can a team work effectively in a distributed model without trust? Sure, for a while. But it comes at the expense of mental health, job satisfaction, a sense of ownership, productivity and long-term engagement. The work will eventually suffer, the people will eventually suffer, things will break. This is not the way to build or grow an organization. (Tip: this is also true in in-person work environments.)

Successful distributed work requires trust. Without it, everything else may be a waste of time.

Disclaimers, notes and further reading:

  • No, I'm not saying that in-person organizations are inherently operating without trust. Nor am I saying that the proper alternative to distributed-without-trust is in-person-without-trust. So many in-person organizations have come to equate "at your desk looking busy" with "high performing hard worker" and we need to unlearn those unhealthy models about what trust in the workplace looks like.
  • If the people you've hired don't seem trustworthy, then you may have hired the wrong people, but it's more likely that you or someone else set a bad example that everyone else is just following. Figuring out what can be salvaged is hard work, but it's essential. Abbie Moore has a great article on how to get started rebuilding trust.
  • One way you can build trust is by frequently delegating reversible and/or inconsequential decisions.
  • I personally don't think hybrid models — some people colocated in an office, some people remote — work well or are sustainable.
  • Power works differently in a distributed organization. Lean in to those differences.
  • You can't have real trust without transparency. Default to having everything happen out in the open, including how you make decisions, handle conflicts, learn from mistakes, document progress. If it's not uncomfortable, you're probably not being open enough.

Photo by Belinda Fewings

A new venture, WP Lookout

A few months ago I had an idea for a new tool and service that I thought could be useful to WordPress developers and agencies who manage lots of WordPress sites, but who can't or don't want to go all in on automatic updates. After spending some time thinking through the details and researching what was already out there, I decided to go ahead and build it.

I started writing code and building features on July 1. A month later in early August I launched the first version to a production environment, and now I'm starting to tell people about it.

Please, allow me to introduce WP Lookout.

I've already written about why I think this service fills in some important gaps in the WordPress ecosystem so I won't say a lot more about that here. If you're someone who has worked with keeping multiple WordPress sites up to date and secure, hopefully you see the potential benefit. And there are a lot more features I'm excited to be working on.

Even if you don't travel in those circles, perhaps you'll identify with this sentiment: we have all of these things in our lives running software that someone else has written (routers, computers, apps on our phones, the navigation systems in our cars, the firmware on our TVs), and we're supposed to keep them up to date with the latest versions, usually in the name of speed and security. But often that turns into a part time job of logging in to those devices, finding the settings screen where updates are displayed, and trying to understand what's changed and how much it matters. Automatic background updates are helping in some cases. But wouldn't it be nice if these devices and tools could come to us and tell us when they're ready for an update, and what exactly has changed? So, WP Lookout is set to do that for at least one small corner of the Internet.

It's been a while since I've set out to launch and grow a new business from nothing. It's thrilling to again be thinking through architecture, strategy, business model, marketing, finances, legal paperwork, scaling, innovation and all the other pieces that go along with trying to make something thrive for the long term. It's also vulnerable to be putting something out into the world and wondering how it will be received, or if anyone will care.

I'm hopeful that good things are ahead. Regardless, I'm proud of what I've done so far. I've learned a lot along the way — about building a SaaS ("software as a service") business, about how awesome developing with Laravel is (I'll write more about that soon on my tech blog) and about what solutions people who manage multiple WordPress sites might or might not be looking for to make their lives easier.

After I'm a bit further along I'll share more details and updates. In the meantime, please check out WP Lookout.

Does your organization need help figuring out remote work?

If your business or organization has been struggling through the unexpected shift to emergency remote/distributed work, and now wants to step back and build a distributed work culture that actually thrives, I'd like to help.

How does accountability and management happen in a remote workplace? How do we avoid Zoom meeting burnout? What does a productive home office setup look like? What cultural shifts are needed? What collaboration tools and software might be most helpful? How do we make decisions quickly when we're not in the same place?

If your leadership is asking these or similar questions, I can help you find some answers.

There are now a ton of great articles, podcasts, interviews and other resources out there about the mechanics of remote work. For some organizational leaders, that might be enough to get you started. For others, you may benefit from a collaborative, customized process to look at your particular organizational culture and structure, and develop a plan for shifting into sustainable distributed/remote work.

So I'm beginning to offer just that as a paid consulting service. Through conversations, workshops, assessments and other forms of engagement, I'm helping organizations move past the emergency reaction phase and into a long-term distributed/remote work setup that works for everyone.

Visit Distributed.Coach To Learn More

I'm passionate about the benefits — to individuals, organizations and society as a whole — of the distributed work model. I also enjoy helping organizations think about and plan for change. I've built and led fully distributed teams, and I've also built and led organizations where everyone came in to the same office to work together. I’ve seen both models up close, and I know from experience what works and what doesn’t. Especially as the implications of COVID-19 have forced so many organizations to rethink their operations, but even prior to that, I have wanted to contribute to this global shift in how we work.

If you are a part of an organization that would benefit from my expertise, or know someone who is, learn more and get in touch at Distributed.Coach.

Create a story, join a story, tell a story?

As I have been thinking about and working on "what's next" for me professionally, a theme has emerged around storytelling. Despite the fairly technical nature of my work to date, storytelling is a concept and a practice that has consistently been woven into the challenges and projects I take on. And as I ponder the future, it's been useful to see how each possibility fits (or doesn't fit) with that theme too.

Here are some of the general possibilities I'm considering through that lens:

Create a new story. Found a company. Make something new. Write actual stories or books.

Tell other people's stories. Journalism. Publishing. Podcasting. Interviews. Investigations.

Be a part of someone else's story. For a while, anyway. Get another job at an organization I believe in. Help lead an organization or team through a time of transformation. Give my time and talents to a cause I am excited about.

Work on story-telling tools used by others. Launch a product or service. Build or contribute to software. Do consulting or freelance work.

Learn from the stories already out there. Read books and articles, listen to podcasts. Catch up with friends and colleagues. Browse the aisles of the library. Wander in the woods. Explore new places.

I'm early in my own process of discernment, but I'm settling on one point of clarity: I may be retiring from doing "just one thing." Recalling the different modes of living out my multipotentialite self, I think it's time to shift away from the Group Hug approach ("having one full-time job or business that fully supports you, while leaving you with enough time and energy to pursue your other passions on the side") and instead shift to the Group Hug ("having one multifaceted job or business that allows you to wear many hats and shift between several domains at work"). Embracing my multiple passions and a skillset that spans many different kinds of roles and industries will, I think, mean honoring the time and focus each one deserves, instead of largely relegating everything except a narrowly focused job or project to what I can get done in my spare time. Easier said than done.

I've also had a hard time describing this time of transition to others in any kind of concise or confident way. As one person said, I'm not conforming to normative standards for professional/life changes. It's great to acknowledge that, but still makes for awkward light conversation.

Helpfully, I recently encountered Scott Berkun's article, Changing your life is not a (mid-life) crisis, and it's full of good stuff, including:

I imagine for myself a lifetime of changes initiated by me. I know I’m too curious, and life is too short, to follow the conventional footsteps that everyone is quick to defend despite how miserable they seem in the following. We use the phrase “life long learner” but it’s corny and shallow, suggesting people who quietly take courses or read books after college as if the essence of life were merely a hobby. We need a term for life long growers, people who continue to examine and explore their own potentials and passions, making new and bigger bets as they change throughout life.

A hard thing about this time is resisting the temptation to make safe bets that I know I can win. I've been there and done that, and even when I've taken risks or tried new things that others were uncertain about, I've had an almost embarrassingly good run of professional success as a result. So now I'd like to take some risks make some bold moves and step further outside my comfort zone along the way. I want to create, or tell, or be a part of a story that has some good twists and turns.

Let's see where this dimly lit path (that may not be a path at all) goes, shall we?

Building momentum for your distributed work day

Imagine that you are about to go on stage to perform some amazing thing that you know how to do. You're waiting in the wings for your moment to shine, and you want to bring your very best to the experience.

But then also imagine that you spent the last several hours or even days in isolation. You haven't really talked to anyone or had much human interaction at all. No one has given you encouraging words or expressed excitement about what you're going to perform.

And then you find out that the time of your performance has not really been set or advertised. There will be an audience but they will be coming and going from the auditorium where you're performing, and they may or may not be paying attention to you. When you do the thing you're best at, someone may or may not notice. Oh and the stage is actually going to be a small, dark closet.

Now go out there and be awesome? Umm....

It's a silly scenario, but for some people who work in a distributed environment, especially one where a lot of collaboration happens asynchronously across individual schedules and time zones, this is what the beginning of our work day can feel like: quiet, slow, isolated.

In a traditional office setting where workers tend to arrive, collaborate and leave on roughly the same schedule, the energy and pace of work can come from the environment itself. But for distributed workers, even when there is actually a lot going on in the organization we're working with, it can be a challenge to build momentum at the start of our days. Sometimes the work itself is enough to generate that energy, but sometimes we need help getting into the right mental space for high productivity.

So how can you build that momentum if it's not coming from your physical work environment? Here are a couple of things that I've seen work well:

Continue reading "Building momentum for your distributed work day" →

On training people

As a follow-up to my post on what I've learned over the years about hiring people, this is a similar list of what I've learned about training and onboarding people as you welcome them into your organization.

Many organizations reduce training to a pretty simple process ("here's the training manual, here's your trainer, go"), but I find it to be one of the most complicated and fascinating periods in someone's life with an organization. The initial days, weeks of someone's employment (or, in a not-for-profit context, someone's time volunteering or serving on a board) are highly influential in shaping the experience they're going to have in the long run, and the work they're going to do.

It's a time when they start to reconcile their "outsider" impressions of what you do and how you do it with what they see as a new "insider" with fresh perspective. It's where any idealism and over-simplification that happens during the hiring process runs up against the nuances of internal processes and the texture of individual co-worker personalities. Training can prompt many moments of truth about the new person's image of themselves as a part of your organization: "do I belong here?" "are they going to like me?" "can I live up to hopes/expectations?"

From the perspective of the people doing the training, then, I think successful training is a careful balance between providing enough structure to properly educate and acclimate the new person to your organization while also allowing enough freedom and flexibility to accommodate their learning style, pace, interests and questions - especially the "why are you doing it this way when you could do it this other way?" ones.

Whatever you do, don't figure out training on the fly. Don't let it be a 100% self-directed experience in some hope that throwing someone fully into the deep end is the best way they'll learn. And don't underestimate the return on investment you'll get from an intentional, comprehensive approach to training.

As the process gets started, minimize assumptions. Communicate clearly and directly with the trainee (a word that feels a bit demeaning but is useful here) about every detail of their first moments as a part of your organization: where they should be at what time (and in what time zone, if you're a distributed team), in what medium the training will be conducted (in person, text chat, audio chat, video chat, in groups or one-to-one), how long the sessions will be, what they need to bring, and anything they need to do in advance. Give your trainee every opportunity to get past nervousness and make a great first impression by removing unnecessary vagueness in these critical first days.

Communicate expectations and set clear training goals. "Over the next X hours/days/weeks we're going to walk through everything from this to that. Your main trainer/mentor/buddy will be this person and they are your main point of contact for the process, ask them whatever you want. Here's the format we'll use, here are the materials we're going to cover, and here's a list of all the things we're going to touch on. Here's how we'll track your progress through this training, and here's what we expect from you at the end of the process." And then make sure all of this information is known to the wider team and company. Continue reading "On training people" →

On hiring people

After years of various roles in which I've been solely or jointly responsible for hiring people into businesses and organizations, I offer some thoughts on what I think works.

Hiring is ultimately about entering into a new relationship with someone. Actions and words that truly honor the joys, anxieties, vulnerabilities and interdependencies of that process will tend to make it more successful. Things that treat it as a cold, harsh, impersonal transaction will tend to make it (and your organization) less successful.

A successful process, by the way, could mean that someone is not hired just as much as it could mean they are. Clarity about the long-term fit is more important than short-term harmony and avoiding disappointment.

If you create an application, screening, interview and hiring process where people can check off a bunch of boxes that culminate in their employment, they will tend to optimize for that. It doesn't mean they are disingenuous or won't be good employees, but it may not be what you want as you build a team. Asking people to follow specific instructions is fine - it can be a good way to screen out bulk applications and clarify someone's interest. But lean more toward creating an interesting dance between equal partners, and then seeing how everyone feels when the music stops.

Keep candidates updated as much as possible at every step of the process. Let them know you've received their inquiry and when they should expect to hear a next response. If there are delays on your end in evaluating their application, say so. Try to respond to every candidate who follows your basic instructions about how to apply, no matter how far they make it in your process. Don't play mind games, you are not running Fight Club.

Résumés are useful as a summary of someone's professional identity, but should only be a starting point for understanding what they would bring to your organization. Putting together a flawless résumé (and possibly a cover letter) should be a baseline for understanding someone's attention to detail and ability to communicate clearly. A résumé with typos, lots of fluff or other problems can probably be discarded early on.

Continue reading "On hiring people" →

Power in a distributed org

It's striking to see the differences in where power gathers in a distributed organization, compared to where that happens in a more traditional office setting.

When people come together in a physical space there is a lot of time and energy spent on appearance. The work isn't just about "what are we doing" but also "how do we look and how do people perceive us while we're doing what we do."

When people come together to work in a virtual/online space, the focus shifts.

In an office setting, I see power and influence gather around...

  • The person with the newest, coolest and/or most expensive clothing
  • The person with the larger corner office
  • The person with the most assistants
  • The person with the most impressive sounding title
  • The person with the closest parking space
  • The oldest, richest, whitest males
  • The person who's allowed to create or interrupt meetings
  • The person with the most impressive social and public-speaking skills
  • The person who uses their power to get what they want

In a distributed organization, I see power and influence gather around...

Continue reading "Power in a distributed org" →

Working for someone else

This week marks two full years of my employment at Automattic. I was fortunate to celebrate in person with a number of my colleagues as we hosted a workshop for our clients and partners in beautiful Napa, California.

People who know that I co-founded and built my own tech business before joining Automattic often ask me what it's like to work for someone else. My short answer is usually:

  • I miss some of the joys and challenges that go with being ultimately responsible for the success of a business venture...
  • ...but Automattic is a place where I am trusted with a level of autonomy that I'd be hard pressed to find in many other employment situations, and
  • I am mostly just enjoying discovering new ways of doing things and being a part of a bigger team with greater resources available for innovation.

This post is my longer answer. While working at another company it has been useful and interesting to notice what it's like to have a change in my professional identity, not be "the boss," enthusiastically support something I didn't create, and try to balance the joys of "employment" with the inner itch to again be a "founder."

Continue reading "Working for someone else" →

Startup

startup-podcast-coverI've just finished raising $1.5 million in investor dollars, building an office and growing a staff to start a new media company focused on narrative podcasts.

Okay, not really.

But I HAVE just finished listening to the first season of Alex Blumberg's podcast Startup, which documents his process of envisioning and then creating exactly that new company, Gimlet Media, from the very beginning. The show is so well done that I felt in on some of the best and worst moments in starting the business, and I learned a lot along the way.

Continue reading "Startup" →