Interviewing senior engineering leaders.

February 18, 2020. Filed under management 99hiring 8

A friend recently reached out for advice on interviewing and hiring senior engineering leaders. I’ve spent a good deal of time on this topic over the last couple years, starting with partnering with Laura Hilton to design Stripe’s interview loops for engineering leadership, and more recently going through a search for my own role. Leadership hiring is particularly interesting as a window into an organization’s psychology: for the highest stake decisions, do they turn to structure or to intuition?

Mailbag: Evolving your engineer career beyond the career level.

February 13, 2020. Filed under career 11mailbag 2staff-eng 1

Recently I got an email asking about evolving your engineering career after you’ve hit the career level, but before you feel like you’ve accomplished what’s important to you. I wrote up my response here in case others are interested.

Crowdsourcing CTO/VPE learning circles.

February 11, 2020. Filed under management 99

As part of moving into a CTO role, I wanted to take a stab at putting together learning circles for folks in CTO, VP Engineering and Staff+ Engineering roles. This is the sort of thing I've done interally within a company before, but most companies only have one CTO or function-leading VP Engineering, so this sort of learning circle needed to happen beyond the scope of a single company.

Do you work at a tech company?

February 10, 2020. Filed under hiring 8culture 1

The most unnatural stage of hiring someone is when you’ve extended an offer, know they have other offers, and you are trying to give them advice on which offer to take. The obvious answer is that they should _your_ offer, but you end up in some interesting discussions toeing the line between objectivity and outcome. Typically the offer numbers are already out in the open, so the topics tend to get more abstract. I recently had one of these discussions that hinged on an unexpected question, "What denotes a technology company?"

Share stories, not advice.

February 4, 2020. Filed under management 99

A few years ago I was trying to figure out how to incorporate product management techniques into infrastructure engineering, and I had the very good fortune of having Astrid Atkinson answer a few of my questions. I explained a challenge I was having and asked for her advice, and was surprised when instead of answering Astrid asked, "May I share a story?"