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

Saying yes to the right things

Biltmore caktusA few years ago I got a call from an organization that wanted me to volunteer as a member of their board of directors. They were rushing to get their nominations in before an upcoming meeting and the person assigned to ask me to join had fallen a bit behind on the process. The caller described the board's work - overall purpose, meetings, and responsibilities - and said that my name had come up as someone who could be good to serve.

Nice! Right?

I had little to no history with or context about the organization's leadership, and this call was the first time I was really aware of its board. So I asked a question:

"What particular projects or efforts is the board working on that you think I can specifically contribute to?"

In other words, "tell me why you think I'm a good fit for you and you're a good fit for me."

The caller was a bit thrown off by this, saying that's a good question that they had not been asked before, and one that they didn't really have an answer for. (It turns out this particular board is a fiduciary oversight kind of body, mostly expected to rubber stamp what the organization's staff proposes.) I tried to give the caller a few chances to fill in some detail, but they didn't seem interested in trying that hard.

I thanked the organization for thinking of me and said no.

Continue reading Saying yes to the right things

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

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

Charitable giving, receiving FAIL

It's science!I recently had this experience trying to make a charitable donation to a not-for-profit organization I want(ed) to support:

I Googled their name to find their website. The "Donate Now" button was located prominently on the front page of the site, so I followed it to the donation form where I filled out my contact information, my credit card number, etc. and hit "Donate".

I got the form back with an error message in red saying "An error occurred during processing. Please try again." There were no other messages indicating whether the error was with something I'd put in one of the form fields, or if it was an error on their side (perhaps talking to their credit card processor, etc.). I fiddled with some of my form data (maybe the phone number field needs dashes? Maybe the postal code field doesn't actually accept 5+4 format?) but still got the red error message.

So then I sent email to the generic contact address on the site saying "I'm trying to donate to you online, here's what happened." I sent them all the details they'd need to troubleshoot the issue, including a screenshot of what I saw on the form.

Several weeks went by with no response to the email message. So then I saw that they had a fairly active presence on Twitter, and I sent them a message there saying something to the effect of "I'm trying to donate to you online, are you still taking donations?"

No response.

Continue reading Charitable giving, receiving FAIL