Cassandra Wilcox

Startup CTO | Follow me for tweets about software engineering, technical strategy, and early stage startup leadership.

[Cassandra Wilcox @CassandraWilcox]

@KaraokeBats oh dang
thatswaycooler

[Cassandra Wilcox @CassandraWilcox]

ok i did it. turned off auto caps so i look more like a genz

[Cassandra Wilcox @CassandraWilcox]

I just added ‘Fractional CTO’ to my list of experiences on LinkedIn and I feel like I’m winning a silly but lucrative game.

[Cassandra Wilcox @CassandraWilcox]

Just because you haven’t experienced successful Remote Work doesn’t mean it doesn’t work. Every interaction doesn’t have to be scheduled. You can create team agreements that allow for anything. This is a disappointing perspective from “tech leadership”.

[David Sacks @DavidSacks]

It’s time to admit that Remote Work doesn’t work. WFH Friday is a 4 day work week. Full WFH is a 2 day work week. Every interaction has to be scheduled, which means a lot of information-sharing doesn’t happen. Remote is a great lifestyle, not a way to build a great company.

[Cassandra Wilcox @CassandraWilcox]

All it really takes is an OUTCOME FOCUSED CULTURE.

Stop worrying about how many hours people are putting in if they are hitting or exceeding metrics.

As a founder, why would you spend so much of you capital on a building just to watch people do their work???

[Cassandra Wilcox @CassandraWilcox]

Just got off the phone w a CEO who's convinced that being colocated is essential for leaders and managers.

I was so curious & excited to ask why. I was open to understanding the value of it!

Unfortunately I got a defensive, micromanagy, fear-based answer... 😳 (a thread🧵)

[Cassandra Wilcox @CassandraWilcox]

But he was dismissive and questioned the success of these companies (hint: they're super successful) 😬

Sure, it takes a particular competency to succeed at managing a remote company. So fine, run your company according to your strengths.

But dang what an expensive limitation!

[Cassandra Wilcox @CassandraWilcox]

@philosohacker @join_atlas_ai Congrats! This looks so cool!

[Cassandra Wilcox @CassandraWilcox]

I guess it’s about time for my new haircut. I’ve been thinking about a tattoo as well…

[Cassandra Wilcox @CassandraWilcox]

spoke w/ a CTO yesterday & he shared an interview question he asks Engineering Manager candidates:

"after being at this company for 3-5 years, what do you want to be known for?" 😍

gives insight into what their passionate about & what they aspire to! 🙌

what's your answer??

[Cassandra Wilcox @CassandraWilcox]

Sitting on a blanket in a park with my laptop, using my phone as a hotspot, wondering how I can replicate this level of serenity in a more functional workspace.

Currently nomadding and having trouble finding relaxing places to work. Cafes are noisy and libraries are cold!

[Cassandra Wilcox @CassandraWilcox]

What I've seen actually works better to foster an enjoyable work environment is to meet people where they're at and to get comfortable with low energy, as long as meetings are effective.

This let's people know its ok to be human. No need to act like something you're not!

[Cassandra Wilcox @CassandraWilcox]

I observed a new engineering manager trying to raise the energy level of engineers in a sprint planning meeting today.

Well intentioned, but to much radio silence...

Does this sort of thing rub anyone else the wrong way?

[Cassandra Wilcox @CassandraWilcox]

I get wanting to foster a fun work environment, but I think pushing for excitement can come across as patronizing.

People will get excited when it makes to. It doesn't need to be forced.

[Cassandra Wilcox @CassandraWilcox]

It it normal for cafes to blare loud music? A friend of mine was just complaining about this, wondering if its a passive-aggressive way to prevent laptop campers. If so, its not very effective. Nearly everyone in here has a laptop and headphones. WHY SO LOUD???

[Cassandra Wilcox @CassandraWilcox]

I love this Main Quest / Side Quest analogy!

I'm def on the Main Quest now, "winning" as CTO at a VC-backed startup. And I've often considered what's next..

TBH a Side Quest seems pretty fitting! I used to see it as a step down, but this perspective is much more validating!

[Karthik Hariharan @hkarthik]

The lucky few tech folks who weren't laid off are starting to poke around for new jobs.

Some advice that I've shared with a few of them is to think about their careers like a Role Playing video game.
🧵

[Cassandra Wilcox @CassandraWilcox]

@maiab hahaha its true! everything I heard you say in person I saw you tweet as well! 🤣 I wasn't sure which came first, but I'm not on Twitter as much so it was news to me when you said it lol

[Cassandra Wilcox @CassandraWilcox]

@maiab do social security cards even exist?