What It’s Like To Work With Me As Your Manager

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One of my favorite introductions to a new boss happened in a follow-up email after meeting him on his first day. He sent me a blog post that explained what he’s like to work with. Documentation? On a manager? This was off to a good start.

Working with me shouldn’t be a mystery so I put my own together. The process helped refine my values and that’s a good thing. It’s broken out into four main sections: What I’m Like, What It’s Like To Work For Me, What Influenced Me As A Leader and What I Value.

What I’m Like

• I’m a dad, exercise a lot (mostly endurance sports), a music fanatic and relentless tinkerer. Outside work, I typically have 3–5 projects going at any time. Right now, the main theme is around adding customized electric motors to bicycles, writing fictitious joke letters to people with elaborate envelope art and playing guitar.
• I’m an experimentalist and not a theorist. My instinct is to research someone else’s design, start writing/building/tweaking immediately, crank out an MVP, ask someone for feedback, see what works vs what doesn’t, make a second version and keep going. Perfection is not my strong suit. Iteration is.
• I’m a notetaker by nature, process driven and planning makes me feel comfortable. Don’t confuse that with boring, though. That’s in pursuit of setting my sights on big big goals with a clear path to achieving them.
• I can code, but have never been a full-time software engineer. I’ve suffered through enough debugging and database schema refactors to be empathetic with your challenges, though.
• I like feedback and possibly in a radical way.
• I use LinkedIn every day and use to use Twitter every day, but am pausing that after Elon’s takeover. I can honestly say, though, my life is better with that noise.
• I’m big on mentorship, used to organize the Bay Area OWASP meetings and helped start the Day of Shecurity.

What It’s Like To Work For Me

• I wake up early, schedule tasks that require deep focus before noon, typically go for a walking meditation mid day, work out late afternoon, put some headphones on for crunching through emails/Slack and then call it a day. I try to spend quality time with my kids in the late afternoon and let my mind do some restful thinking about the day.
• I like daily standups in the morning (but not in the afternoon) because they make me feel like I know what’s going on.
• Annual Reviews are a quick copy/paste exercise with me. I’ve spent a few years developing a system of Quarterly Calibrations that are a better practice. These are supplemented by weekly 1:1s and, at the end of the year, your four Quarterly Calibrations are simply combined for the annual review. You can read about the process here. It’s something I came up on my own and felt some validation by when reading Bryan Cantrill’s piece mentioned below about motivating engineers where he talks about doing this bi-annually.
• I want you to take vacations and expect you to tune out. Vacation time is even discussed in your Quarterly Calibration. Don’t take advantage of unlimited PTO. I assume you’re here because you love our work.
• Remote work is 100% okay as long as the communication is strong. Work wherever you want and, for the most part, whenever you want as long as that doesn’t doesn’t disrupt the team.
• Error on the side of collaboration, always. Do more pair programming. Fire up a Zoom meeting instead of Slack messages. Show your ticket to someone else on the team. That hammer tests the end result and makes others feel like their opinion matters.
• I’ll do better the more I know about you. Let me know your quirks, your needs, your likes and your dislikes. Help me help you.
• I own my mistakes publicly, learn from them and try not to repeat the same one twice. They’ll turn into something of value with time.
• My team should expect a lot out of me and hold me accountable if it feels out of whack. Please do that. I don’t like trying to read someone’s mind.
• Finding you was hard, it took a long time and replacing you is expensive. I’m a big believer in Bryan Cantrell’s philosophy about what motivates an engineer: Mission (be motivated by the problem), Team and then Technical Challenges. Managers should construct an environment that allows engineers to be autonomous, master their skills, and find purpose in their work. Bring your passions to this job, all of them. Our team is an environment where you can learn what you want to learn and find a place to apply it. And please keep doing that year after year. If this isn’t fun or you aren’t having fun, let me know so we can do something about that.
• I like people who solve problems for me and that doesn’t just mean shipping code or closing Jira tickets.
• No task is too small or beneath me or anyone on our team. If you see me avoid work, it’s probably because I don’t want to create hero culture or set myself up to be in the path of a sustainable solution.
• Outcomes matter and that’s how I measure success. Don’t be scared of results and accountability. Understand them, scope expectations well and you’ll derive comfort from them. It’s perfectly fine to miss a desired outcome as long as it’s well understood by everyone.
• I’m not a micromanager, but I need a plan to feel comfortable. They also help me advocate and represent our team upwards. Create a good plan, demonstrate regular progress against it and that’s all I ask. Data is important because it almost always avoid arguments or disagreements about your proposal.

What Influenced Me As A Leader

• Fatherhood: Being a stay-at-home dad for three years taught me a lot about adults.
• Starting, Running and Closing a Business: I’ve made thousands of cold calls, learned far more about California payroll taxes than anyone should, written a business plan, lost money, made more, sold stock to pay for payroll, and shut the whole thing down. That last part takes far longer than most people appreciate. I’ve done every job at a company.
• Principles: A former client told me they’d been recruited to work at this ‘weird’ hedge fund. I went home, found Ray Dalio’s Principles as a PDF and have consulted it ever since. Radical openness isn’t for everyone. But it is for me.
• Zen and the Art of Motorcycle Maintenance: I tried reading this several times before finally persevering one winter break in college. Since then, I’ve read it probably another five times at different points in my life. It’s been relevant for different reasons each time and the concepts are something I think about daily in one form or another.
• Lila: An Inquiry Into Morals: The follow-up to ZATAMM, this takes the cold logic of defining Quality and sees the author apply that to a person. Does every single person intrinsically contain Quality? The distinction between Static and Dynamic Quality is one of my favorite concepts. TLDR: Neither is better than the other and a marriage of both typically produces the best outcome.
• Google SRE Handbook: I read this looking to ramp up my platform engineering understanding and, instead, took away a ton of value around the idea of building systems that allow people around me to fail fast with as little risk as possible. I talk to my son about that concept constantly and was surprised (not surprised) to find out the SRE Handbook has a second life as a parenting manual. Totally true.
• The Manual: One of the best books you’ve never heard of about product design, understanding your customer, motivating technical people, market fit and, yes, music.
• Burning Man Principles: I’ve run a big Burning Man camp for quite a while and the 10 principles are ones I apply to myself, being a parent, employee, manager and human out in the world.

What I Value

• Starters: Compassion. Diversity. Diverse opinions. Hard work. Creativity. Humility. Consensus decision making.
• Business Acumen: Customer experience. Where our money comes from. How we market our product. How our product works. Backend operations that keep a company operating. Understanding how it all works together helps me make better, compassionate decisions within our team and the company as a whole.
• Personal Development: I constantly have outside project going and basically crave knowledge. Moving from journalism > private investigator > liquor licenses > drones > coding > electric bicycles. Every one of those helped me get where I’m at today.
• Teams: I can distinctly remember the moment when I wanted to shut down my small PI agency. Working at a big company on a team of engineers would bring the opportunity to work on bigger datasets, larger problems and with smarter people than I had access to on my own.
• Mistakes: Mistakes are part of learning and growing. I make them all the time. You probably will too or you’re not reaching. My assumption is that people made the best decision possible with the information they had at the time. What they do after a mistake is a character-defining moment.
• Imposter Syndrome and Beginner’s Mind: Take a look at my blog post about why the term Beginner’s Mind is better than Imposter Syndrome. Related to Mistakes, if I’m not experiencing this feeling on a regular basis, I’ve probably lapsed into static patterns. I’m probably bored too. Stretching beyond my comfort zone involves self doubt. I try to accept it, be candid about the experience and use that as an opportunity to drive growth conversations. The most uninformed person in a conversation often drives the best conversations; their basic questions can test basic assumptions of experts. Imposter Syndrome never goes away. I still have it and hope I always will.
• Time Off: Breaks, days off and vacations are critical to well being. They also allow me to relax my mind and find space to think slowly about important matters. That can be work related or not. But without a doubt, the highest quality thinking I do every day is during my workout.

For more about me, here’s a Dark Reading post my background and the same material in podcast form at the Secure Developer.