StaffPlus New York Agenda - March 16, 2023

As we get more senior, more and more tasks compete for our time. With the many different responsibilities, it becomes harder and harder to find time to actually code. In this talk, I will discuss some of the pros and cons to continuing to code, along with how some of my peers and I have thought through and continue to think through this decision.

Technical leadership is a difficult proposition even when there is an agreed and welcome mandate for it. The moving pieces are complex and relate in difficult ways. The challenge is significantly bigger if that leadership needs to happen from the sidelines or from a support position - for example, Security Engineering - and the person providing it is not a formal member of the team. In this talk we use the experience of a Security Engineer tasked with helping a development team raise their security posture, without being part of it. We will look at what works and what failed, propose tactic and techniques to best position the outsider in, and what observed results were achieved.

The Data Group at Squarespace has been on a transformational journey to migrate our systems to the cloud. At the beginning of 2022, we were running entirely on our own hardware; but by the end of 2023 we expect to be 100% cloud native. 

Picking where to start, and how to prioritize our efforts took considerable planning. Dozens of compute resources and data sets have come along for the ride up till now, and more are to come. 

Ultimately, some key steps we took have enabled us to succeed thus far. 

Our talk will cover the strategy, tactics and execution that went into effect to make the migration to being cloud native over possible. 

In the talk we’ll cover how we chose a variety of tactics and accepted trade offs to enable the effort required in order to migrate. Themes in the talk will include:

• Strategic Direction and its influence on the architecture.
• Alignment and guiding policies, and how the lack there of slowed our first steps.
• We had to carefully consider which components to keep and which to re-evaluate. 
• Quite often we found we couldn’t simply “lift and shift”. In fact, we found that the cloud turned our conventions into anti-patterns.
• Being a first adopter amongst our peers posed challenges. 
• We had to learn our chosen Cloud platform and while establishing guiding policies. In effect, we were paving the way for the rest of the company. 

It is common for Staff Plus Individual Contributors (ICs) to be “parachuted” into teams that are struggling (e.g. delivering, reacting to incidents, etc.). These problems are compounded when the teams are involved in high priority deliverables. At Recursion, with our “We Learn” value, the right thing to do for these teams and the business is to help them figure out how to get back on track. Temporarily embedding Staff Plus ICs on these teams provides this extra help and improves success around the company priorities.

In the last 18 months, I have embedded on two different teams across business units with a diverse group of people (engineers, data scientists, operations, and product managers) to successfully deliver on company priorities by improving the health and productivity of the teams. Working together, we improved our delivery on quarterly goals from 30% to 90% in a span of two quarters. 

In this talk, I will share my learnings with the process of embedding broken down into stages. For each stage, I will describe the focus areas, key relationships to build and nurture, outcomes to anticipate and finally how to unembed, making the team self-sufficient and self-confident in their ability to deliver. Leading with empathy is the central theme of my talk; how you can mold yourself to get the best out of each individual, and grow the team to deliver. As the team grows in confidence, I will go over how you can step back but also weave a safety net to ensure you are there to catch them if they fall. Finally, how you can be unembedded from the team as they transition to a healthy state. This talk will build on the basis of an article that is scheduled to be published with LeadDev.

Working as a staff+ engineer can be a lonely or confusing experience. In a leadership role, it’s often impossible to directly emulate the behaviour of other coworkers and unclear whom to go to to get feedback and provide or receive mentorship and coaching. As a result, many staff+ engineers can end up relatively siloed while the business requires them to have a broad outlook and provide feedback on areas they are not directly working on.

In this talk, I’ll discuss the following: 
- the three types of relationships critical to cultivate: mentor, mentee and peer
- how to decide which relationships to invest in vs move on from
- how to use these relationships to improve your career, your success and work and build up everyone surrounding you
- how to still do this when remote or timezone separated from your coworkers

Aggravations! Annoyances! Failures! Flaws! *UGH*! 
Frustrations are inevitable at work — doubly so when you’re given the increased visibility of a manager or staff+ developer. Calling out imperfections around you is an important step in making them better. But with increased visibility comes increased scrutiny and personal influence with other developers. A single poorly-placed snide side remark can wreck your reputation.

I, a serial complainer with a catchy smile, will walk you through the steps I take to make sure my complaining is heard and felt without causing pain:

• Portraying a positive persona: smiling, and taking the ‘meat’ out of some of your feedback sandwiches
• Knowing when to take conversations private - or just give up
• Re-reading “How to Win Friends and Influence People” (the 21st century edition) once a year
• Seeing your messaging through the eyes of your teammates
• Taking time to stop complaining and feel good about the situation (or quit)

These tips and strategies will help you keep complaining in a positive, action-oriented manner — without alienating the rest of your company.

A lot of us love to be the engineer who does the most. Sometimes we feel we have to do it all. However, I like to think that we all got here because we figured how to prioritize what's best for the company. Sometimes we forget we also have to prioritize ourselves. This talk is a reminder of how to keep yourself in focus while still delivering value. I'll also include examples of how you can bring yourself back to a place of focus when you feel your organization is trying it's best to have you do-all-the-things.

Some projects are paint-by-number endeavors with solid management support. Other times, what’s needed are radical transformations, a different architecture, or decommissioning a legacy system. Riddled with risk, communication challenges, and cross-team dependencies, these messy Staff+ projects are all around us.

This talk is about lessons learned over my career about executing challenging projects. The types of projects with politics, drama, tech debt, or past failed attempts. How do we know if the project is worth doing? Why has it failed before? Who’s blocking it? How do we know when to cut our losses and pause or cancel the project?

Staff+ engineers are often the only hope for an organization to overcome and deliver on these types of projects. Don't panic. I believe progress is possible and I'm here with tips.

During the summer of 2020, Slack's performance infrastructure team was tasked with building a load testing solution that could simulate hundreds of thousands of users in a single team ahead of a big customer launch. What followed was two months of prototyping: figuring out the right balance between simulating high-fidelity usage, efficient usage computing resources, and speed of execution. After a momentous, successful ramp up to 500k simulated users, we kept going. We continued to build momentum, enabling the ability to test specific user flows, and ramping up to just under 2 million simulated users to see how far we could take Slack's infrastructure. Join me for a roller coaster ride of a story and a thrilling live demo of what our load testing systems can do!

Have you ever had thoughts like "I should know how to do this" or "I shouldn't share that with my team; it will make me look like I don't deserve to be here"?

The idea of asking questions, admitting when you don't know something, or sharing when you're struggling might make you uncomfortable, it certainly has for me. But the vulnerability you demonstrate by doing these things is precisely what makes a great leader.

There is a fear that vulnerability will be seen as weakness, when it’s actually the root of building authentic and meaningful connections. Once you can push past the discomfort, being vulnerable at work opens the door to creativity, innovation, and trust with your team.

In this talk, I will share my personal journey with vulnerability, as I learned to reframe my discomfort as opportunities for growth and eventually find the courage to be vulnerable. Together we’ll explore some questions and answers that came up during this journey, such as:
• Why should I be vulnerable?
• What does vulnerability look like in practice?
• And how can I be vulnerable while respecting my personal boundaries?

By the end of this talk, you will leave with the tools to become a better leader and start practicing vulnerability in your life.