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

Zero to One

I thoroughly enjoyed Peter Thiel's Zero to One: Notes on Startups, or How to Build the Future.

It's one of the few "business books" I've read recently that incorporates anything resembling a coherent global ethic into thinking about what it means to create and grow a business. Beyond that, he gets into some great reflections on human creativity, optimism and pessimism about the future, and investing.

I didn't always agree with Thiel's views or counsel, but I found his thinking to be clear and his insights helpful, especially on what it takes to build something that makes a substantial and/or lasting difference in the world. Read through the lens of my past experience creating a startup tech business and my current thinking about what I can do for the world in the future, there were some lovely and/or cringe-worthy "ah-ha" moments.

I highlighted many passages as I read, here are a few that stand out:

Continue reading Zero to One

Distributed vs. In-Person Teams

TreehouseOne of the questions I get most since joining Automattic is about what it's like to go from working with a company where we were mostly collaborating in one office space in Indiana, to working with a fully distributed company, where everyone works from home, coffee shops, co-working spaces or similar spots around the world.

(The other main question I get is about what it's like to go from being "the boss" to working for someone else - a post for another time.)

The short answer: I'm appreciating and enjoying it, and I think it is the future of many kinds of work.

The longer answer follows.

The question of a distributed versus in-person setup for a team or company is discussed often in tech circles, perhaps even more so right now as tech companies face hiring challenges and consider related immigration policy issues. I feel like I've experienced both sides in some form now, having built and managed a web development firm for close to 17 years with a strong focus on working together in the same physical space (experimenting with remote workers along the way) and now having worked almost 8 months in a fully distributed configuration.

Going in to my new job, I was initially skeptical that I would find a distributed setup to be better than what I'd experienced working with my team in an office together. I thought it would be exciting, interesting and different, and despite all of the enthusiasm I'd built up for it (especially after reading The Year Without Pants: WordPress.com and the Future of Work) at some gut level I still suspected it would be a kind of nominally acceptable, second-best alternative to working with people in person. Continue reading Distributed vs. In-Person Teams