A Few Things to Consider Before Becoming A Remote-Friendly Company

A few years ago when I was at Clubhouse I blogged about our process of becoming a geographically distributed team. In that case, the first stumblings towards global domination were not made to acquire talent but rather in an attempt to retain talent vital to our team (talent = people we really loved working with and didn’t wanna lose!). In that article, I outlined some of the ways we tried to bridge the gap and some of the things that were still just tough.

I’ve also written about some of the reservations I have about working from home, especially as it pertains to underrepresented people in the workplace.

Since moving to Nylas and serving on the top-notch leadership team here, I’ve been even more privy to some of the business-side challenges of having a team where people are working from all over the place. SO I thought I’d pull together a quick blogpost of my learnings.

Things to Consider Before Opening Up Satellite Offices or Having Remote Teammates

People In Other Places Are Often In Other Timezones Too

I know it sounds obvious, but it needs to be stated. If you employ someone somewhere else, their day may overlap with yours a lot, a little, or not at all. You need to think about how that’s going to affect everyone’s ability to get things done. If your SF-based team is making most of your decisions synchronously in meetings or Slack, how will that affect your support folks in Berlin, your UX designer in Medellin, or your developer in New Zealand? Will they have to work odd hours just to keep up with HQ or can you start relying more on async tools?

When working across large distances across the globe, it is important to establish a baseline in every area for when they should be online and working and when they should stop and go live their lives. While you might sometimes need a teammate to work before or after their formal working hours, it is useful to know, clearly define in the calendar, and respect those agreed-upon working hours.

If you’re going to be working across significant time differences, I recommend trying to move meetings to times that work better for people and leaning more heavily on tools like Clubhouse and email that allow people to communicate on a more humane timeline.

Flights and Hotels Are Expensive

Cohesion across teams does require some amount of time spent together in fleshspace. Getting people together often means flights, hotels, and expensed meals. Just make sure you have the money for this — and that you earmark it especially for those purposes.

A/V Is An Investment…Good A/V Even More So

I am of the opinion that videochat software is painfully immature and being relied on too heavily for important communication. I use videochat every single working day and it is very much in the “can you hear me now?” phase. This is unfortunate because around the world in so many contexts people rely on it to make crucial decisions (read how Skype Trial has tragically become the norm for US immigration court).

Despite videoconferencing’s weakness as a replacement for “the real thing”, it is what we got. So doubling down to make it work is important. Headphones, good mics, fast wifi, and good webcams can cut down the distance between co-workers and enable you to have vital conversations with less muffle, crackle, and static.

When these all fail you — as they inevitably will — try to keep your teammate’s phone number nearby and just call them on the phone. I’ve had so many hours wasted fighting with videochat. Don’t let that be you and your team.

Employing People In Other States and Countries Can Be Costly and Time-Consuming

Different states and countries have different employment regimes. If you intend to employ people there, you will need to be in compliance with those requirements. HR companies like Gusto can likely help you with red tape, but it will still require some time and money to make sure you are following the rules of (and engaging the insurance market of!) the state or country where your fantastic new potential teammate lives.

Benefits Can Be Lopsided

If your company offers special perks to people in the office, you’ll need to carefully consider which of those you can/want to extend to people working from home or a satellite office. Things like free lunches and free office massages or whatever are often there to entice people to come in to the office and stay there. They tend not to be as feasible to make available to people who are working from home.

It is important to think about offering a benefits regime that doesn’t cause lopsidedness or ill-will when your HQ folks and your remote folks compare their cards.

None of this is intended to discourage you from doing what you need to do to attract and retain great people for your company. The last 10 years of my career have been spent working in organizations and teams that span state and national borders, and I’ve rarely had to rule someone out because of their location.

Remote workers do work; geographically-distributed teams can and do work—even on a small scale. They just work best when you go in with your eyes open to the challenges.

Fund What You Love

I’ll be honest: I don’t love my job and I don’t think I’ve ever truly loved any job I’ve ever had since I began my working life in earnest. Don’t get me wrong. I’ve had several lovely work environments in beautiful offices with truly fantastic co-workers — many of whom I still count as my closest friends — but I’d still not call that loving my job.

No, I’ve had jobs from unbearable to perfectly survivable, and the older I get, the more I realize that here in late-stage capitalism, a job I love is not the goal, –being able to put time and money and resources into things I want to see flourish is. I don’t do what I love, I fund what I love.

By this I mean, I am a donor of my money and time and skills. I currently do unpaid work for at least five different groups and give money and/or advice to dozens more. I don’t work on the front lines of any efforts to cure the sick or free the encaged or smash the empire, but I do my best to give to groups that do. And I’m finally coming around to realizing that funds and funders matter.

I recently facilitated a dinner event attended by people from both the commercial and nonprofit spaces, and I noted a distinct snootiness towards people who hadn’t committed their lives to radical struggle defined as working in a cooperative or a foundation-funded NGO. I’ve encountered this sensibility throughout my journey as an independent activist/organizer and it’s lame and wrong. The “revolution” will no more be funded by large non-profit donors than it will by Silicon Valley venture capitalists.

The truth is that the struggle has and will always require a diversity of tactics, as well as a diversity of funding and energy sources. The more we radicals understand and accept that, the easier it will be to start building cultures and structures of support that help us better share responsibilities and promote self/mutual care.

Activist guilt, that feeling that you constantly should be doing more for the movement, is real. Survivor/thriver guilt is real, but so is activist/organizer burnout and illness. If we embrace a model of funding what we love rather than doing what we love to death, we just might move our lives and efforts into balance, and begin modelling that new world we seek.

A Few Mistakes to Avoid if You Want to Get Hired

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As a manager in the technology space, I have the great responsibility and privilege of hiring people into my company. As part of this work, I have to: help write job descriptions, spread the word, parse through resumes, meet referrals, conduct interviews, conduct/attend hiring meetings, write offer letters, write rejection letters, and onboard people.

While I’m done with “diversity in tech”, I do try to lift up people in my networks. Unfortunately,  too often I am disappointed by people’s inability to conduct a successful job search.  I am not even going to blame those people per se; it is ultimately one of the many ways our educational systems have failed us. That said, I am tired of seeing people (especially my people — specifically white women and people of color and especially black women!)  make the same frustrating mistakes over and over.

So I’ve pulled together a quick list of some of these common missteps in the hope that you can avoid them.

1) Not connecting with a referrer or potential referrer before sending along your resume.

If I tell you about the job or tell our mutual friend about the job, reach out to me! I am happy to make connections if I have them. If I work at the place, it is worth your while to use me as your “in”.

So many times I’ve had friends say that they don’t want to have an “unfair advantage”. Fairness in hiring is not the responsibility of the applicant; it is the duty of the hiring organization. Your only job is to be honest and put your best foot forward; so if you have a leg up, use it.

Which brings me to my next point….

2) Not mentioning you were referred by someone who works there

Related to the previous point. If you met me and I encouraged you to apply to my place of employment, you should mention that in your cover letter. Even if I dropped the link in a Slack or other community that we are mutually involved in, you can say “Per the job ad shared by Camille in the Smash The State Slack” or whatever in your cover letter.

Use your in!

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Credit: WOCinTech

3) Not writing a good resume or sending an overly long resume.

Your resume needs to be brief and tell a coherent story. It is not your autobiography, and your work history is not your total worth. You have a lot to offer the world, but it doesn’t need to all be represented in your resume. My pal Andrew Spittle wrote good, short guidance on how to write a resume here.

4) Not highlighting how you meet the job requirements. 

Make sure you read the full job description and tailor your resume to fit most (if not all) of what they are looking for. Add bullet points that explain the work you actually did and any notable accomplishments.

I would discourage you from highlighting the qualifications you are missing unless you want to explain how your other skills and talents make up for it.  Job descriptions are never really an exact description of everything the job entails and the exact skills you need to accomplish it.

You can paint a fuller picture of yourself and your capabilities once you get in for that interview.

5) Not mentioning the company name and the reason you are interested in the company in your cover letter. 

Look, I’ve been there, fam. I remember a period many years ago in which I must have applied to 70 -80 different positions. (Seriously, I had a huge spreadsheet to keep track of it all). But there is never any excuse to use the same generic cover letter over and over again.

I’ve seriously had people send cover letters with another hiring manager or company’s name there. Really, folks?

If you are genuinely interested in the job, it needs to show. Visit the companies’ websites, find out what they do, and then figure out why the company AND the position interest you.
We all need money, but (for some perverse reason) people at these hiring organizations want to feel wanted too.

Even if the place and the position seem dryer than a bone, there has to be something there that appeals to you. If there isn’t, you probably should not apply. If there is, make sure you mention it clearly (and briefly) in the cover letter.

6) Not asking a referrer to pass along your resume

If we meet and chat about the position, don’t hesitate to ask me if I can pass your resume along. The worst I — or any potential referrer — can say is no, and even then I think many of us will admire you for your tenacity!

7) Not actually being familiar with what the product or service is before you apply/interview. 

You need to understand what the company does and how you will fit in. If it is software, sign up / download ( if you can) and try it out. If it is a shop, maybe go by and visit and see what they have to offer. Just do your best to understand the company, their offerings, and their possible challenges so you can come in and be the answer they are looking for.

8) Not taking an interest in the people/person interviewing you. 

You’ve probably heard it said before, but job-hunting can be a lot like dating. Everyone shows up kinda awkward and nervous and unsure of what the outcome will be. While the interviewer will be asking the majority of the questions, you should come prepped with questions of your own about the company and the interviewer(s).

If possible, take the time ahead of the interview to learn a bit about who you will be talking to and what they do. How would your role and their role interact? I always like to end with the question, “So what brought you here and what keeps you here? Interviewers usually aren’t expecting it and often have to search for an answer. The answers are often pretty raw, honest, and telling of their feelings about the company.

Also, science has shown that people LOVE talking about themselves. So get them doing something they love and they just may associate that good feeling with you!


This is of course not an exhaustive list, beloveds. It’s just a few observations borne from my years of hiring and trying to get hired. For more tips, I highly recommend Catt Small’s fantastic post “Impress for success: Strategic ways to seem more hireable”.

Look, I know capitalism is a soul sucking system full of mind-numbing contradictions, and I strongly believe that we’d be better off without work as it is modernly construed. However, we are where we are at the moment, and in this time, I want to see my folks getting whatever paper and esteem we can amass while we work behind the scenes towards a better world.

Go on and get them legs up, my peoples! 

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Disagree and Commit

From Jeff Bezos’s 2016 Letter to Amazon Shareholders

“Third, use the phrase ‘disagree and commit.’ This phrase will save a lot of time. If you have conviction on a particular direction even though there’s no consensus, it’s helpful to say, ‘Look, I know we disagree on this but will you gamble with me on it? Disagree and commit?’ By the time you’re at this point, no one can know the answer for sure, and you’ll probably get a quick yes.

This isn’t one way. If you’re the boss, you should do this too. I disagree and commit all the time. We recently greenlit a particular Amazon Studios original. I told the team my view: debatable whether it would be interesting enough, complicated to produce, the business terms aren’t that good, and we have lots of other opportunities. They had a completely different opinion and wanted to go ahead. I wrote back right away with ‘I disagree and commit and hope it becomes the most watched thing we’ve ever made.’ Consider how much slower this decision cycle would have been if the team had actually had to convince me rather than simply get my commitment.

Note what this example is not: it’s not me thinking to myself ‘well, these guys are wrong and missing the point, but this isn’t worth me chasing.’ It’s a genuine disagreement of opinion, a candid expression of my view, a chance for the team to weigh my view, and a quick, sincere commitment to go their way. And given that this team has already brought home 11 Emmys, 6 Golden Globes, and 3 Oscars, I’m just glad they let me in the room at all!”

Some More Hands on Support

I am speaking about engineering – support collaboration this week at The Lead Developer conference. If the topic interests you and you wanna dig in further, here are a few handy links. US_Navy_030521-N-9109V-003_Sailors_and_embarked_Marines_flood_the_flight_deck_with_salt-water_solution,_scrub_brooms,_and_plenty_of_elbow_grease_in_a_mandatory_wash_down.jpg

(at Clubhouse) Eyes Wide Widened: My ‘Evolving View’ of Developers on Support

(at FullStory) How to avoid empathy fatigue on your support team

(at Big Cartel) Why All Hands Support Didn’t Work for Our Company

(at Statuspage.io) All-Hands Support: Why, No Exceptions, Everyone At Our Company Talks To Customers 

(at Wistia) All Hands Support

(at Automattic)