In my dream job, I learn the customer and business needs and focus the team on delivering them in a sustainable manner. Simultaneously, I help team members grow, develop our culture, and build valuable tech. When talking to others I prefer a couch to a table, and when I need a break, you might see me juggling, practicing magic, or riding my folding bike—often in the office.
My Dream job via various lenses
Engineering Manager or Tech Lead: Engineering Manager
I’m passionate about tech, but I’m even more passionate about aspiring to be the best boss my team will ever have. Part of being the best is having a deep understanding of the tech, so I always have some small projects on the side, and every few years I’ll do a rotation as a tech lead.
Product Domain? Well-being, Productivity, and Natural Language Processing
As a human, I’m incredibly passionate about well-being. I’m excited about the whole field, from nurturing mindfulness and increasing satisfaction to solving loneliness and enabling self-reflection.
Such jobs are rare, so if that’s something you need help delivering on, please reach out immediately.
I’m also very excited by Natural Language Processing and Productivity, so if you need help delivering them, reach out immediately!
Startup, Turnaround, Accelerated Growth, Realignment, Sustaining Success: Startup and Turnaround
If you don’t know those words, read about STARS
At this point in my career, my favorite situation is a startup (e.g. Smile, Amazon Video Shopping, Employee #50 at Azure) because it allows me to build a high-performing team that can use ingenuity to get a solution out the door as quickly as possible.
Turnaround situations (e.g. Cache) can be much like startups, except instead of going from “0 to 1000,” you need to go from “-100 to 100” with the existing team. Because the start of a turnaround includes lots of demoralized players, it is both incredibly difficult and also intensely satisfying for me once progress is made.
Accelerated Growth, Realignment, and Sustaining Success aren’t things I’ve tried yet. I’m looking forward to trying them to both round out my skills and learn how much I enjoy them.
B2C, B2B, Infrastructure? B2C
At this point in my career, I’m interested in making the lives of others better. Right now, I’d like to do this via consumer software.
Technologist or Entrepreneur: Entrepreneur
As I get older, I’m finding more satisfaction in solving a customer’s problem than extending the limits of technology. That said, I’ve built badass complex technical systems for the first 20 years of my career, so I make sure we build and use the right architecture and technology to effectively meet the customer’s needs.
Product/Market Risk or Technical Risk: Product/Market Risk
Incubations need to prove a risk can be overcome, either product/market or technical. Product/market risk is “Do customers want your product,” while technical risk is “Can we build the tech to deliver it.”
I’m most interested in proving product/market fit. That said, with over 20 years of experience as a software engineer, I’m well-versed in resolving technical risk, an expert at system design, code, and mentoring developers.
Signals, Inferences, Experiences? Experiences
A lot of modern software can be decomposed into three layers: signals, inferences, and experiences. Signals are the raw input in the system, both static and dynamic. Inferences are the computations performed over the signal to determine something meaningful, often involving big data and ML. Experiences are the way inferences and signals are presented to the user—this is often an app and the services which power the app. Inferences and experiences often become new signals to drive the system.
I’m most interested in building the experiences, but that requires me to deeply understand and drive signals and inferences. Steve Jobs says it well:
One of the things I’ve always found is that you’ve got to start with the customer experience and work backward to the technology. You can’t start with the technology and try to figure out where you’re going to try to sell it. And I’ve made this mistake probably more than anybody else in this room. And I got the scar tissue to prove it.
Business, Experience, Technology: Business and Experience
Technology leaders need to divide their time among the business, experiences, and technology. While each of these is interesting, at this point in my career, my technology skill is well-developed, and now I want to focus on building my business and experiences muscles.
Regardless of my job, I will be successful when
My manager skills are continuously improving
I am the best boss my team has ever had
Everyone gets value from personalized coaching
Work is filled with peak moments
- (In very special places …) I run Feelings meetings
The team is high-performing (even if they start off in trouble)
Going to work is like hanging out with friends.
My dream job via a motivation lens
Intrinsic vs Extrinsic Motivation
TL;DR: The best “extrinsic reward” you can give me is more time to spend of my own choosing.
At this point in my career, I’m financially confident and content with my career stage. The closest I have to extrinsic motivation is bonus time off (which ironically I spend a significant chunk of on career development—see mastery).
Autonomy
- Getting to work with amazing people
- Getting to set a sustainable pace
- Picking side projects to invest in
- Having room to explore
NOTE: Things that a boss can do that do not feel like a lack of autonomy for me:
- It’s OK to piss on my shoes, just don’t tell me it’s raining.
- Reminding me what is most important
- Aligning and understanding priorities
- Input from another perspective (as long as you expect it to be input, for me to evaluate, not an order)
- Telling me things you worry about and want to review together
Mastery
- Dedicated time to retool/think
- Growth as EM (From team to organization):
- Hiring
- People Growth
- New manager mentoring
- Grow technical:
- Play with new AI models/paradigms
- Play with new tools (now all AI-assist, Python/data libraries)
- Contribute to open source
- Growth as presenter
- I need to give talks, make vertical short form videos!
- I love mixing magic and tech presentations
- Complex people/collaboration issues
- I really value when my boss brings me opportunities for the above.
Purpose
- People Axis: Grow team + Help org
- Product Impact: Well-being, reduce loneliness, build relationships