I once had a team leader who I found to be charming as soon as I met her. She was charismatic, confident, articulate, and clearly came from a well-to-do family in India. She was self-deprecating at times, particularly about being Indian from India with her Indian-accented English, while at other times, she was extremely confident and would have staring contests with individuals she disagreed with. She was certainly a force to be reckoned with, and in many ways, I definitely did reckon with her. She was charming… and manipulative and controlling, and absolutely loved to instill fear in everyone around her.

One thing she loved to do was, well, telling people what to do. She prided herself on never, ever spending the company’s money on anything that did not absolutely have to be spent. So, when it came to things like taking teammates out to lunch, the rare times this did happen, she would spend this money out of pocket instead of expensing it. Her philosophy? “If you are offering to take someone out, you should be true to your word and take them out. Don’t say you will take them out to their face and then expense it. In that case, isn’t it [X company] taking your colleague out and not you?!”

When we had the occasional team outing (our team, depending on the time, ranged from 7-10 people), she or her manager (let’s call him X VP) would spend their own money for bowling or for food and drinks for us. Before and after the event, she would meet with us as a group and give us the same lecture. “You should be grateful that X VP is being so generous to take you all out. I hope you appreciate this gesture. Make sure to remember to thank him and be kind. And don’t do anything ridiculous at the event to embarrass me.” The day after the event, she would send a one-line email: “Please remember to send X VP a thank-you email acknowledging his generosity for taking you out, and let him know you had a good time.”

Well, thanks, Mom, for all the much-needed reminders on good manners and etiquette. We all really needed that, especially since we’re all babies, just between the ages of 22-35!

A former colleague of mine sent me a quick email asking to catch up over the phone sometime soon. He had left the company over a year ago, and he had developed quite the reputation for himself. He rarely came into the office. When we had to travel to San Francisco and Napa for team events or the annual company kick-off, he would make every excuse from “my mom is having a tumor removed” to “my basement flooded during the storm last week, and I need to take care of it.” He frequently stole office supplies when he’d be in the neighborhood on the weekends (our office manager told me this, as she saw the footage on our office cameras installed by both entrances). And when we finally caught up over the phone, he admitted to fake expensing on average about $3K/month for his last nine months at the company. “I milked them for every last cent that I could,” he said, gleefully. He made up business trips to see friends who lived in other states who happened to be located in the same cities where he had customers in his book of business. He wrote in work notes that he was doing “quarterly business reviews” with customers, when in reality, he never went onsite to see the customer for more than a “hi, how are you?” Instead, he took them to expensive, plush restaurants and wined and dined them. Well, those were his “business reviews.”

In the end, he got fired, but in a “nice way”: he was given a few days to say his goodbyes, tell his customers he was leaving. Management wanted to frame it as though it was voluntary to make him feel better. They gave him one month’s severance and even paid health insurance for him and his family for two additional months.

I’ve seen a lot of shady and unethical activity working as a “white-collar” professional, but I truly believe that this guy really took the cake.

A few weeks ago, I had a 1:1 Zoom meeting with our company’s CEO. It was a little strange. The request came out of the blue, as he normally asks my opinion about topics ranging from company morale, New York City office morale, how I think the customer success organization is performing and what could be improved, to where I think he should travel next for vacation. He wanted to ask my opinion on what he could be doing as the company’s leader to create a more diverse and inclusive environment that is ultimately anti-racist.

Our conversation was supposed to be only 30 minutes long, but it ended up going for about 45. We discussed what I’ve read in the How to be an Anti-Racist book, as well as the White Fragility book. He made a verbal commitment to me that he would at least download the White Fragility audio book and listen during his daily exercise. But the part that he seemed to miss the most is that he did not understand the inherent fact that I’ve mentioned a number of times on this blog: that it’s impossible to have a conversation about racism and have everyone in the room be comfortable or feel included. The whole idea of discussing “third rail” topics as he likes to call them is to be confronting, unsettling, to spur one into action. He disagreed. “The whole idea of diversity and inclusion is to be inclusive,” he insisted to me. “If we are not being inclusive, then this is not what we want.”

I paused. He still didn’t get it. How could I make him, a wealthy, privileged white man living in one of the most expensive suburbs of Northern California in a $12 million+ mansion, understand the crux of this issue? I elaborated on the background of Robin DiAngelo, the anti-racism educator and author of White Fragility. I told him that she has specialized in researching and educating on this area for nearly three decades. She has workshops every single day with people who seek to be more anti-racist, but fail miserably because they want to speak in generalizations as opposed to zeroing in on their own actions and what they can personally change in their day to day life. To ask someone to change their daily behavior, daily thoughts, is EXTREMELY challenging, if not impossible. And if she, as a 25+ year educator on this topic, still manages to “upset” and “exclude” people due to their white fragility and self implosion when confronting these issues, is the problem really her, the educator, the one prompting these questions, OR, is the issue the people who she’s attempting to reach who refuse to be reached due to their white fragility? When I said this, our CEO’s face suddenly changed. He appeared more contemplative, a bit more empathetic, a little closer to realizing that maybe, just maybe, it’s not the educator’s fault, the one posing the question’s fault, that maybe, the audience who is crying their white tears is actually at fault.

I’m not sure if I really reached him. It may all have been an act on his part. It may have been his way of weaseling himself out of the conversation to seem like he could be bendable, amenable to tangible change. Or maybe, just maybe he actually wanted to see some real change, something really move within our predominantly White company. I will never know for sure. But what I do know for sure is that most CXO teams across organizations around the world now are facing the same issue: they all want to participate in this:

“We at [Brand] are committed to fighting injustice by posting images to Twitter that express our commitment to fighting injustice.

To that end, we offer this solemn white-on-black .jpeg that expresses vague solidarity with the Black community, but will quietly elide the specifics of what is wrong, what needs to change, or in what ways we will do anything about it. This is doubly true if [Brand] is particularly guilty of exacerbating these issues.

We hope this action encourages you to view [Brand] positively without, you know, expecting anything from us.

-[Brand] (credit to Chris Franklin via Twitter)

For us, specifically, our CEO added a blog post to the company website noting that “Black Lives Matter,” that the leadership team would be encouraging employees to donate to these organizations as well. No monetary donation on behalf of the company would be given. No real changes made internally would be communicated via the blog post. It was an empty blog post that, around the same time, was also launched with BLM messaging added as a banner (which links to donating to Color of Change) when customers login to their accounts). At the same time, this organization is also happily taking money from organizations that support the Trump administration (many people in our sector of tech were happy and quick to point out this hypocrisy on LinkedIn posts that went viral). How does this organization reconcile this hypocrisy, if at all? Or do we just continue the BLM messaging on our blog and user platform while at the same time oppressing the lives of people of color?

For the last 12-plus years I’ve been working full time, I’ve worked both in SaaS as well as at digital marketing agencies. Although I’ve had many ups and downs during the course of my full-time working career, I’ve never stopped feeling grateful for all the good fortunes I’ve been privileged to have. I know that I have it better than probably 80-90 percent of the full-time working population given the opportunities I’ve been given, the perks and flexibility I’ve enjoyed, and the travel I’ve been lucky to have done to various parts of this country, not to mention how I’ve been paid. But even within our moments of gratitude, we also need to acknowledge what is right and wrong within our bubbles and identify what needs progress and why. I think that’s something that a lot of people fail to do for various reasons: they are scared to deviate from the status quo and “stir up trouble,” as that may put their own jobs and positions in jeopardy, they don’t want to create controversy, particularly because that disturbs their own comforts they get to enjoy, and well, they’re just lazy and don’t want to do anything that will require any proactivity on their part. It could also be a combination of all the above.

During my time working in the agency world, I realized how easy it was to get too comfortable with everything from the status quo, mediocrity, substituting activity for achievement (oh, this one is a HUGE theme across work in general and is not just about the agency world, though given that agencies make their money based on a percentage of spend from brands, this plays quite prominently here), and just doing your day to day, literally paper pushing.

But what has also happened is that a friend of mine who has remained in the agency world (and is still at the same agency I left) has repeatedly told me how toxic and awful the tech industry is once I rejoined it in 2013 because of the rampant politics, sexism, and racism that has gotten the spotlight due to reports from major tech companies like Google, Facebook, Amazon, and the like. He’s insinuated to me that he doesn’t think I should work in tech anymore and that my desire and decision to leave was misguided. My general feeling about this is that it is true that the tech industry is not perfect; it is part of the working world, isn’t it, just a specific sector, so it will never be immune from the issues that our society or world faces. Yes, the tech industry wears a mask of being more progressive, promoting diversity and inclusion efforts internally, and taking care of its employees more than the average (read: crappy, cut-throat, bare-bones) American company through its offerings of attractive perks that range from “unlimited PTO” (I will deconstruct this myth/recruiter selling tactic in a later post), free snacks, daily lunches, reimbursement of all commuter costs, 100% employer-covered medical/dental/vision premiums, fitness/gym/massage reimbursements, to even fertility and egg freezing benefits, but because they do actually go above and beyond with these types of perks on average vs. other industries, that is enough to make someone want to jump over from another industry into tech. Why? Because the relationship you have with your employer is transactional, as I learned pretty much the very first time I got laid off in 2009. You offer your expertise and services to your employer in exchange for a salary and whatever benefits they are willing to offer. There is nothing more to this relationship, so you should not think anything more of it… because we know, for sure, they certainly will not. They will not hesitate to cut you when they no longer think they need you (whether that’s because you actually are under performing or, in most cases, because certain key people may not like you. Hello, politics). Because of this cold, blunt fact, why should we, as potential employees, not want to take advantage of every potential benefit and perk an employer is willing to give us and milk it for as much and as long as possible? We’re only maximizing our own gains, and if we do not think of ourselves first, it is guaranteed that no one else ever will — and certainly not your employer – past, current, or future. Therefore, with that said, this is why I strongly believe that unless you are working for yourself and can call all the shots, the best industry to be working in to maximize the “you” benefit is in tech. Just don’t work at one of those loser, backwards tech companies that offers zero of the attractive benefits noted above — otherwise, why are you even working in tech?! Do you think you are going to change the world? Don’t be that naive and take care of yourself — knowing that no one else will.

I had a call scheduled this morning to chat with Chris’s friend who works at a company that I’m interested in. He’s been friends with her for a few years, but I’d never met her before since he likes to keep separate parts of his life separate, and there was really no reason for me to meet this person, so I never really cared to ask. So I called her to get a sense of what the company was like and how she liked it, and it was clear from the beginning of the call that she really loved working there. She talked about the company leadership, the culture, the nature of her work, and she gushed endlessly about how great it was. It got to a point where the entire conversation just seemed like the type of conversation I’d have with the company’s HR or recruiting team; she said glowing, nearly-canned positive things about the company like “great work-life balance,” “everyone is so amazing here,” and “senior leadership is really accessible, their ‘door’ is always open for you; the only blocker to developing a relationship with them is yourself.” I nearly vomited in my mouth a little when she said that last part. How often have I heard that from recruiting teams in the past, or people who truly drink the kool-aid.

While I appreciated the time she spent to chat with me, I didn’t really appreciate the PR-spin on her perspective; it came off as too enthusiastic, a bit disingenuous, and well, not authentic. Luckily for me, I have other contacts I can speak with at the company through personal connections, so I can get a more well rounded perspective, but it just struck me as odd that she was technically supposed to be a personal connection through Chris, but she gave me a not-very-personal perspective of the company.

My mom always says that the older you get, the wiser you get. I actually don’t really agree with this. The older I have gotten, the more confused I have gotten about why and how people are so twisted and weird.