Risk and Failure on the Path to Staff Engineer

Even as inaction can be a risk, deciding which actions to take in one's career involves choosing between different bets. I've developed a rubric for judging specific risks that I've taken. Assessing these experiences together, we can identify useful commonalities for anyone navigating the path to Staff Engineer and beyond. 

I'll describe my career progression -- and regressions! -- as well the context that I've used to figure out what to work on and whom to work with. From this historical perspective, I'll distill a framework which you can utilize in your own work, as well as when mentoring others who are earlier on their paths. We will use this lens to ask what motivates us, what our goals are and where, as they say, "do you see yourself in five years?" By the end, we will have drafted an inventory of bets, their associated risks, how failure manifests in each case, and thus what we can do to avoid failure and hedge against risk, on the path to Staff Engineer.

Interview:

What's the focus of your work these days?

Site Reliability Engineering, internal Developer Experience, and Data Engineering.

What's the motivation for your talk at QCon San Francisco 2023?

I've made a lot of bets in my career. Many of them were failures. I want to share what I've learned along the way, and hear from others about similar risks taken, particularly failures, and what you've learned. Let's normalize taking risks!

How would you describe your main persona and target audience for this session?

Mid- or Senior-level engineers who want to take the next steps but either don't know how or are unsure of whether to do so. Staff Engineers and further on up, who want actionable examples of failures - so that they can preempt them and coach folks earlier in their careers.

Is there anything specific that you'd like people to walk away with after watching your session?

Specific examples of failures; clear ideas about how and whether to take specific risks; some notes towards a framework for taking bets and recovering from failures, as you're leveling up within an engineering organization.


Speaker

Caleb Hyde

Site Reliability Engineer @Expel

Caleb is a Systems Engineer by education, software developer by vocation, and hobby roboticist. Their work focuses on Site Reliability and Data Engineering.

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Date

Monday Oct 2 / 03:55PM PDT ( 50 minutes )

Location

Ballroom BC

Topics

Staff Plus Engineering Glue work Taking risks

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