Another good trick: answer what looks like a bad-faith question in a straightforward way, as if it were a good-faith question. Thomas Maxwell responded to Esther’s tweet with a question about sleeping bags, as shown above.
It was probably a good-faith question, judging from Maxwell’s Twitter timeline, but put yourself in Esther Crawford’s shoes. She’s probably still processing her very public layoff and dealing with slings and arrows from critics. In her position — and even as an observer — Maxwell’s question could easily be seen as a bad-faith barb.
Crawford did the right thing: she answered it as if it were a legitimate, good-faith question. This has a double-advantage:
If it is indeed a good-faith question, she’s just answered it.
If it’s a bad-faith question, it shows grace. Or if you prefer a more Machiavellian, it highlights the attacker’s dickishness.
Rapid7 and High Tech Connect are teaming up to have a tech fest in Rapid7’s new office starting at 5:15 p.m.! If you’re looking for work, you’ll want to check this out, as there’ll be networking, an open resume review and Rapid7 hiring update and overview. Find out more and register here!
What’s High Tech Connect?
High Tech Connect is a meetup group whose goal is to facilitate connections in the Tampa Bay technology community. They do this by holding monthly “Tech Fests,” which include a number of companies, including a not-for-profit, a start-up, and 3 or 4 for-profit businesses.
It’s a great way to catch up with your friends in the tech community, make new friends, and find out what’s going on here in “The Other Bay Area.”
Here’s a true story about an opportunity that started at High Tech Connect: In the summer of 2019, I was looking for work and decided to attend the July High Tech Connect event. I ran into my friend Tracy Ingram at the gathering, and we got to talking. A little bit into the conversation, I asked Tracy “Hey, do you want to go on StartupBus this year?”
Long story short: it pays to go to events like High Tech Connect!
Rapid7 are a security company, and as a reader of this blog, you’ve probably heard of their pentesting tool, Metasploit, their digital forensics and incident response tool, Velociraptor, or their threat intelligence tool, Threat Command.
What’s happening at this event?
For starters, they’re showing off their new office space in Channelside, located between the Florida Aquarium and the Channelside Bay Plaza.
It’s also a recruiting party. Rapid7 is hiring! You can see the list of current jobs here, and here’s a list of future roles currently not on their site:
Technical Support Engineer
Salesforce Senior Solution Architect
(Senior) Business Systems Analysts
Product Manager, IT
Product Operations Manager
Senior Software Engineer
Lead Software Engineer
Software Engineer II
Principal Software Engineer
Finally, it’s a networking event. That’s why I’ll be there!
She was recently the subject of an article in the Financial Times on January 24th (barely over a month ago) titled The rise of Esther Crawford in Elon Musk’s ‘hardcore’ Twitter. It tells the story of how she managed to become one of the few pre-Musk employees to parley their way into becoming one of “Space Karen’s” trusted lieutenants and in charge of several initiatives to make the company profitable, including Twitter Blue.
Her “sleeping bag” tweet raised a lot of eyebrows, including this short, yet spot-on response from Grady Booch, one of the patron saints of software development (and object-oriented programming in particular):
Crawford followed up with a multiple-tweet response:
 Since some people are losing their minds I’ll explain: doing hard things requires sacrifice (time, energy, etc). I have teammates around the world who are putting in the effort to bring something new to life so it’s important to me to show up for them & keep the team unblocked.
 I work with amazingly talented & ambitious people here at Twitter and this is not a normal moment in time. We are less than 1wk into a massive business & cultural transition. People are giving it their all across all functions: product, design, eng, legal, finance, marketing, etc
 We are #OneTeam and we use the hashtag #LoveWhereYouWork to show it, which is why I retweeted with #SleepWhereYouWork — a cheeky nod to fellow Tweeps. We’ve been in the midst of a crazy public acquisition for months but we keep going & I’m so proud of our strength & resilience.
 I love my family and I’m grateful they understand that there are times where I need to go into overdrive to grind and push in order to deliver. Building new things at Twitter’s scale is very hard to do. I’m lucky to be doing this work alongside some of the best people in tech. 💙
And it was great to see this follow-up from her supportive husband. I’m a firm believer that a marriage is a team, and kudos to Bob Cowherd for this tweet:
I have nothing but respect for Crawford’s drive, determination, and willingness to put in “crunch time.” I have nothing but praise for Cowherd’s supportiveness. Having worked for similarly careless, callous, and capricious bosses — they just didn’t come up from apartheid emerald money — I believe that Crawford’s intense dedication was wasted on Elon Musk.
If you can afford not to, don’t go back. You’re being asked to go back to Hell.
Some people on Twitter were more blunt — and in hindsight, prescient:
Loyalty to a company
I’ve had more than a few conversations — often over drinks, so these are backed by in vino veritas — where someone says that loyalty to a company is a sucker’s game. I think the truth is a little more nuanced than that.
A certain degree of loyalty to an employer who has earned it is actually a good thing. You’re more likely to be happy at work, and that’s important, as you’re that’s how you’re going to spend half your waking life from Monday through Friday. With this kind of loyalty comes two-way trust, and as Steven Covey puts it: Without trust, we don’t truly collaborate; we merely coordinate or, at best, cooperate. It is trust that transforms a group of people into a team.
I like and trust the company I work for and the team I work on. In fact, looking at the teams I’ve worked with in the past decade, the current one is my favorite. I like my manager, my manager’s co-managers, my “skip-level” manager, and the various C-level people, most of whom I’ve had the chance to meet (and even play accordion for). They have my loyalty — within reason — because I know that I also have their reciprocal loyalty — also within reason.
It’s clear to me that the organization isn’t a family. It’s a publicly-owned corporation that operates in the present-day economy. My relationship with the company is pleasant, cordial, and thanks to its culture, convivial, but I know it’s also transactional. Implicit in the employment contract between me and the company is the understanding that the basis of our relationship is that I give them my time and effort and they give me money.
Even with co-workers, managers, and C-level execs who I feel conduct themselves with decency and honor, my loyalty — which is considerable; I have Auth0 stickers on my accordion — is given with reasonable limits.
I would not extend that same loyalty to less decent, less honorable people. And I would most certainly not extend that loyalty to a vaingloriously venal weasel like Elon Musk.
When Musk first came to the San Francisco headquarters just before the deal closed, Crawford introduced herself in the Perch, Twitter’s on-site coffee shop, and secured a one-on-one meeting to discuss her ideas around payments and creators, according to multiple people familiar with the encounter.
And that “sleeping bag” photo? In the well-lit conference room? That’s somehow pristine clean even though everyone was in crunch mode? That ain’t no candid shot.
Also consider that Crawford grew up in a cult. In that kind of environment, you probably learn a couple of tricks on how to handle leaders who think they are the spokespeople for a higher power, or worse still, think they are that higher power.
I have worked at places whose mission I believed in, but whose management I did not. I believe that Crawford’s was a similar situation. And I took a similar approach, all the while readying not just Plan B, but the additional Plans C through G.
Keep this in mind…
Many people are going to dunk on Crawford for the next couple of days. Some of them will be from the Elon Musk fan club, who will say that she simply failed to deliver. Others will be Musk detractors, who will say that it’s what you get for working an egomaniacal autocrat.
Many of them will be the sort whose tendencies are to punish women for the sin of being ambitious. Keep that in mind.
So what are the lessons here?
Even if the purpose of this post was to dunk on Esther Crawford — and it isn’t — I would still be “punching up.”
Crawford came to Twitter by way of acquisition. Twitter bought the video chat startup she founded, Squad, in late 2020. While the amount wasn’t disclosed, a look at Twitter acquisitions shows that they haven’t bought any company for less than double-digit millions. She has a great resume, she can always point to that profile in Financial Times,and she’ll likely be featured in a “What Next?” piece in some other tech or business publication very soon. She can even trade on the story that she worked with tech’s biggest jackass.
Simply put: Crawford will most likely be fine.
This article is not really about her, nor is it for her. It is, most likely, for you, especially if you don’t have a six- or seven-figure cushion to fall back on when the going gets brutal at work.
In my opinion, the lessons to take away are:
If you can help it, don’t work for assholes. If the option is available to you, try to work for and with people with at least some character. And try not to work for self-serving, whim-governed, spoiled emperors.
If it can’t be helped and you have to work for an asshole, learn to manage them. And while you’re at it, formulate a plan to minimize your exposure from said asshole, or get away from them altogether.
Favor high-trust environments over low-trust ones. Yes, there are a number of high-paying low-trust environments out there. In fact, the high pay is often used as a way of making up for the low trust. They might be great for your bank account in the short term, but they’re terrible in the long term.
There’s a fine line between singing your company’s praises and bootlicking. Each of us has a different idea of where that line is drawn. And some of us will talk pretty loudly about it.
Build a support network. A supportive spouse or partner can be a great help if you’re working at someplace like the current Twitter, and a network of peers can often be your key to escaping to a different organization.
The past couple of weeks have kept me pretty busy, but I didn’t want to let this one slip through the cracks: I recently appeared on Cyber Florida’sNo Password Required podcast! I talked with host Jack Clabby and guest host Tashya Denose (who hosts the Do We Belong Here? podcast) about how I got into my line of work, and a lot about how saying “yes” when opportunities arrives can pay off big time.
It was a fun interview that you can listen to using the player below…
…or if you’d like the video version, it’s here…
…or if you prefer more standard podcast sources, you can listen to it via these services:
It’s the short name for the Florida Center for Cybersecurity. In addition to being the people behind the No Password Required and Do We Belong Here? podcasts, they’re an organization with the missions of making Florida a national leader in cybersecurity education. They’re funded by the state of Florida and hosted at the University of South Florida, and among other things, they:
Work to build a robust pipeline of future professionals by introducing cyber safety and career awareness programs to K–12 schools.
Help Florida’s public colleges and universities offer degree and certificate programs that produce ready-to-hire graduates.
Create and champion pathways for women and minorities, veterans and first-responders, and career changers to enter the field to help address our nation’s critical cyber workforce shortage.
Invest in novel research that contributes to our nation’s competitive edge and conduct studies that yield new insights into cybercrime, privacy, user behavior, and organizational needs to help craft local, state, and national policy.
Engage millions of Floridians through awareness campaigns and host events and resources to help protect those populations and organizations that are most vulnerable to cybercrime.
What is No Password Required?
The No Password Required podcast brings in monthly guests who are at the very top of the cybersecurity field. I have no idea why they think I’m in that category, but I’m grateful!
The focus in this podcast is less on dry topics like cybersecurity measures, practices, techniques, and technologies, and more on their guests’ personalities and how they reached their current career status. This fits with Cyber Florida’s mission to create more Florida-based cybersecurity professionals! Each of their guests shares stories that made them laugh, think, and learn. It’s a fun listen.
What is Do We Belong Here?
Do We Belong Here? is a podcast dedicated to proving that everyone has a place in the world of cybersecurity. It’s hosted by…
Tashya Denose, the Cyber Whisperer
Pam Lindemoen, the Chief Information Security Officer Advisor at Cisco
…and it’s produced by Cyber Florida’s Sarina Gandy. It focuses on highlighting the industry leaders who are working to make cybersecurity a more inclusive and welcoming place, and having open conversations to show that we are never alone in our struggles.