Hi, I'm Darren, and you're awesome! I'm currently GitLab's Head of Remote 🌎.
I've spent my entire career across the spectrum of remote — over 14 years leading remote teams and charting remote transformations in colocated spaces, hybrid-remote environments, and all-remote. I hold a Guinness World Record in publishing.
This page is intended to help others understand what it might be like to work with me, especially people who haven’t worked with me before. It's also a well-intentioned effort at building some trust by being intentionally vulnerable, and to share my ideas of a good working relationship to reduce the anxiety of people who might be on my team.
Please feel free to contribute to this page by opening a merge request. (Also, a hearty thank you to Jeremy for building an excellent README framework for others to use.)
What is a Head of Remote?
I work at the intersection of culture, operations, people, talent branding, marketing, and communication.
I collaborate with all functions of the business to support GitLab clients and partners seeking guidance on mastering remote workflows and building culture.
I collaborate with our People Group to improve onboarding and manager training.
I champion and evangelize GitLab's all-remote culture and initiatives through content creation, interviews, webinars, case studies, podcasts, and partnerships with organizations and universities.
I work across the company to ensure that GitLab team members acclimate well to remote, give themselves permission to embrace our values and operate with remote-first workflows, and share our learnings with those outside of the GitLab organization.
Deeper conversations on this topic can be found in the below articles, podcasts, and video interviews.
I've found that watching a video of someone can be helpful in establishing a relationship. The above shows me in an interview on remote work at GitLab Commit SF 2020.
I love writing. I am passionate about informing and entertaining through the written word — so much so that I earned a Guinness World Record doing it.
I've flown over 1.2 million miles (equivalent to flying to the moon 5 times) and have tracked every single flight. You can peruse my destination history at FlightMemory. I've been blessed to travel to all 50 states in the USA, over 40 countries, and over 60 national parks around the globe. I was born and raised in North Carolina, USA, and am proud to call it home today.
Things I love outside of work: aviation, playing music, photographing beautiful landscapes, hiking in national parks, collector cars (driving and ogling), exploring locales foreign and familiar, connecting people with opportunity, making someone's day better.
The highest honor of my life is being chosen to be a dad. I'm an adoptive father, and I am a steadfast advocate for open adoption. It has transformed every part of my life, and expanded my family in a beautiful way. I will answer any and all questions about adoption. Nothing is taboo. Please, ask if you're interested!
I am upbeat and enthusiastic about life. I view every moment as a gift, even the stressful and trying ones.
I love meeting people and making connections. I appreciate when someone answers the question "So, what do you do?" with a story about their life and what moves them, rather than defaulting to their job title.
Remote work is deeply personal to me. I value geographic flexibility and workplace autonomy over the usual suspects of salary, title, and fame. Working remotely has fundamentally shaped the fabric of my family. Our adoption would not have happened without the flexibility that remote work affords.
It is my goal to enable ever more people to free themselves from a daily commute and work where their soul is most fulfilled. I believe remote work can reverse rural depopulation, make communities less transitory, and spread opportunity to underserved areas. I believe all-remote is the purest form of remote work, where every individual is treated as a first-class team member.
Provide GitLab with thoughtful, good work. Tell me if there's something preventing you from this, and we'll work together on fixing it.
Be public by default. Default to GitLab issues and merge requests, as this creates searchable order in a discussion.
Have a bias for action. Instead of waiting, move problems forward with a merge request or issue by default.
Document relentlessly. If you have a tip, suggestion, or are moving a conversation forward, either document in real-time or immediately after so the information isn't weakened by time.
Connect the dots. Relate issues and merge requests to each other where applicable. Communicate using low-context, and add the most detail possible. Write things down as if the audience has never heard of a given project before, and has no historical background to pull from. If you feel like you don't have time for this, you likely have too many commitments. Do fewer things with higher quality.
Communicate. If there's a problem or you're blocked on something, please bring it up. I'll generally interpret silence as "everything's fine".
Don’t save urgent matters for a 1-on-1. Please bring them to my attention on Slack.
Please try to avoid email. Most takeaways in email need to be translated into a GitLab issue or merge request, so start there if at all possible.
Please avoid fragmenting conversations. Keep discussions going in a GitLab issue or merge request. Resist the urge to break off into email, Slack, or other mediums such as carrier pigeons.
I like explicit asks. I’m better at helping when I have a good idea of what you need. “Take a look” is less helpful than “I’m looking for feedback on X and Y, by end of month”.
I like knowing what you've already tried. Explain what you've already searched for on your own, and what assumptions have been challenged.
I am a Hub in the Strength Deployment Inventory (SDI). This essentially means that my motivator is to be flexible to the needs of everyone else. If I sense that a group needs leadership, I lean red (assertive). If I sense that a teammate is struggling or being overlooked, I lean blue (nurturing). If I sense that a group is rushing to conclusions, I lean green (analytical).
I tend to place the needs of the individual above all. My initial consideration when analyzing any new work is: "How will this impact a person's life — their time, their mental health, their stress levels, their pride, their planned PTO, etc.?"
The above sheds light on a growth area for me: understanding what to say "no" to, and how to prioritize an ever-shifting array of demands.
I believe in the power of white space. I prefer time after a meeting to process and document takeaways. I prefer time before a meeting to properly prepare and devote my full attention to the person or people who are being gracious with their time.
Being booked at 100% is a risk, so I work to avoid this (see Kingman's Formula for the mathematics behind this). The ebbs and flows of life cannot be predicted — after all, it's impossible to know everything. If your standing commitments have you at 100%, you have no room to react thoughtfully to life, or to plan for improvements. I aim to allow space in my life for spontaneous projects and serendipitous partnerships.
I've worked in all stages of remote companies, from no remote to all-remote. I've managed teams, projects, and process in small startups and large multinationals.
I have many strong opinions, but they’re weakly held. I love finding a new perspective that makes me change my opinion, because it means that I’ve gotten a chance to learn something substantive and new. This also means that I expect my working style will evolve over time.
I embrace asynchronous workflows. I prefer variety in my workday as opposed to routine. I work best when leveraging a non-linear workday, maximizing daylight hours for exercising and being outdoors with my family. Some of my biggest breakthroughs came to me while scaling a mountainside, far from the reaches of an internet connection. None of my biggest breakthroughs came while sitting in an office, tethered to a string of pings and notifications.
You’re the DRI. You’re better at your job than I am! You know best, and you’ll tell me if there’s something preventing you from doing your best work possible.
If I ask you to own a project, even if it's funded entirely by my budget, it's because I trust your expertise. It's not a trap. I truly want you to control the destiny, as I believe you will do superior work in that area. I'm grateful for your genius and capabilities!
If I disagree with you, I may try to steer you down a different path. But me disagreeing with you doesn’t mean that you’re doing something wrong as long as you’re collaborating effectively with me and our teammates.
You’ll ask for my input and help if it’s needed.
You have more going on than the one thing we're discussing.
Work is absolutely not the most important thing in your life. I assume that there are cherished relationships and personal interests that are more important to your happiness, and it’s hard to be happy with your job when work detracts from those things.
Everyone is likely fighting a battle I know nothing about. 💛
What I want to earn
Your trust.
Your psychological safety. I want to allow you the space to take risks, be vulnerable with me, and tell me when I could be doing something better.
Your partnership. Life is more fun with community, working together to achieve common goals.
Communicating with me
I tend to make suggestions and asks, rather than commands.
This can make my input unclear. If I’m not communicating expectations effectively, please say so and I’ll do my best to adjust my style. If I have a strong opinion about something, I will say so.
I try to express gratitude frequently. This is genuine.
I try to be a structured communicator and thinker, but sometimes start to speak in an unstructured way when I get excited about something, when I'm on the go, or when I'm crunched for time.
Please interject if you’re not getting what you want out of me.
Brevity does not equate to being rude, short, or perturbed.
Please do not take offense to periods of silence. I prefer long, uninterrupted windows of time for deep work. I disable all notifications on my Mac and everything but iMessage on my phone. This allows me to focus deeply on one task at a time, which is a more efficient way of working than attempting to multitask. In return, I will devote my full attention to your request and respond thoughtfully, with context and passion.
Unless specifically mentioned, I don’t expect immediate responses from anyone. I respect others’ time and want you to have the space for a thoughtful response.
