Business Today Needs Deanna Troi

Nathan Shedroff
9 min readJun 17, 2017

When Paramount debuted Star Trek: The Next Generation in 1987, it included not only new characters but new roles for those who commanded Starfleet ships. Among the most original was the character of Deanna Troi, ship’s “counselor.” Many, including the writers for the show, weren’t quite sure what to make of this new role. It was part psychologist, part diplomat, part lie-detector, part-HR Director, and more than a little part eye-candy (she was originally supposed to have four breasts). This role was so misunderstood, that the character didn’t even appear in some of the first season’s episodes.

Over time, however, the writers started figuring-out what to do with her skills. Ships counselors even showed-up on other ships in the series, and not only filled by women. What confounded the writers then was two-fold: why would a ship need a therapist in a leadership position and how would you write interesting stories about why her skills would be important in the narrative. After all, most organizations (read: businesses, governments, etc.) don’t have such a role so there wasn’t much precedent.

Oh, if they had only foreseen business in the 21st Century instead of the 24th!

One of the most common complaints about businesses is that they don’t care about people and don’t “live” the values of the organization (if it even has any). Surely, this has been a problem for a very long time but it’s reached a critical boiling point in today’s work climate and no other company typifies this more than Uber. I’m not going to dump on Uber much since so much has already been written about it, recently. But, the “bro culture” prominent there (and so, so many other places) has grown to toxic, even weaponized levels. Unfortunately, it’s shifted tech culture in the SF Bay Area (both SF and Silicon Valley — oh, and the East Bay!) significantly but, hopefully, not irreversibly.

Before you send hate-mail talking about how egalitarian tech culture is, hold-up. Yes, it was more so pre-Internet boom 2.0 (that would be around 2005). In the early days of “multimedia,” “interactive media,” and Internet startups, people came to these fields, jobs, and technologies because they wanted to “change the world for the better” (so naïve-sounding but true) and build things differently. Companies and people talked about resetting disinetermediation, authoritative dynamics and changing culture. That all started to change after Netscape’s IPO and the kick-off of the gold-rush in the new media. It didn’t change overnight, but it did start then. Before, it was a funky-cool place for weirdos and idealists with skills and dreams. A.N. (After Netscape), no longer were people coming to change the world or even change the way a company could be run. Increasingly, they came to get rich — very, very rich. They came to make a “killing” but what got killed most was the culture. And, that attracted a different kind of person to the tech world.

I’m not saying that there weren’t cases of discrimination, sexual harassment, misconduct, and other cultural problems in companies back then. There were. But, companies made a point to try to define a new way of work. This was the industry that pioneered equality for women, gays and lesbians, those with disabilities, immigrants, and so many others — at least, in the business world. Apple didn’t just want everyone to “Think Different” but to work differently, too. And, they weren’t alone. People flocked to these firms, and this region. Silicon Valley, at the time, was a mecca for people who wanted to work under different conditions and many companies actively tried to foment a meritocracy — one of the most successful in human history. It wasn’t the only such place but it was a leader and bellweather, and still is—for better and worse. Perhaps, it was naïve, but it was also earnest.

That doesn’t feel like the tech world that exists, now. And, when I hear stories from colleagues, these days, the sum-total often confirms that there is a different dominant culture at work and that that ideal, likely unattainable, true meritocracy has lost a lot of ground and no longer seems possible. Most of my colleagues from then have actively fled the tech world, in one way or another, as a result.

Nowhere is this more true than in the tech finance world. Whether it’s venture capital, private equity, investment banks, angels, or any number of others chasing tech money, the “bro culture” that demeans merit over the familiarity of aggressive, unrestrained, and uncaring, quantitative-driven success and faux-loyalty is dominant — and rising in the companies that receive investments. Put plainly, there’s no evidence that any of Uber’s investors (key people or company) or anyone on the board cared one iota about the true culture at work inside the company until Susan Fowler Riggetti exposed all it’s raw ugliness this past February. Since then, many have written about “bro culture” and it’s pernicious spread throughout the tech industry but, keep in mind, it’s everywhere you want to be: in every industry. And, yes, this demeaning cultural extremism doesn’t just exist within male-dominated organizations (I remember a company in the 90s that declared “male free zones” and didn’t allow male employees to attend important meetings) but they are exceedingly rare.

Bro culture comes from the world of fraternities, where mono-culture is, well, cultured, focused, and strengthened. I don’t have a problem with fraternities, per se, but any organization that defines people so specifically, filters them so ruthlessly, and then modifies their behavior so strongly, is at risk of creating bad behavior. It’s as likely to occur in a company, a club house, a team, or the US Congress, as it is in a fraternity. It doesn’t have to exist, but it often does and it if it isn’t constrained by thoughtfulness, self-awareness, and care, it can destroy the very people who practice it, not merely those targeted by it.

My friend, Ken (not his real name), is right to reduce this all down to one word: ethics. And his answer is that all business schools should make an ethics course mandatory. But, if business schools need to require an ethics course for their students, that’s part of the problem: where are the ethical evaluations when they accept those students in the first place? You can’t relegate ethics to a side show and then ignore it in every other part of instruction. As Someone who helped build a pioneering, “new kind of business program,” I know about the ins and outs of this. Ethics has to be part of how every course is taught, implicitly and explicitly. We can no longer teach about law, accounting, finance, operations, supply chains, etc. without simultaneously illuminating for students their ethic issues and impacts. Indeed, we need to teach all of these subjects in completely new ways and, ultimately, create and deploy new tools that bake them right into the processes of doing business.

Ken told me about an investment company (one he describes as filled with some of the smartest people he’s ever worked with) who hires few men out of business school, not because they’re deemed inferior, but because the pool is so much smaller today since most of the “sociopaths” (their word, not his or mine) have moved to tech. They had to start hiring women and they’ve been pleased every since. So, for those companies who want to reignite that “new way of doing business,” what are they supposed to do?

One thing they can do is hire a Deanna Troi, a company counselor.

This role isn’t common but is commonly — even desperately — needed. And, it shouldn’t be stuffed under Human Resources as a service to employees in distressing times.

CEOs are supposed to be responsible for company culture but most aren’t skilled in how to recognize threats to it nor do most have time to focus on it. Having a Deanna Tori by their side would off-load the skill but without the responsibility. Deanna Troi was a trusted voice to her captain, not a box-checker intent on mitigating risks that standard HR processes and policies weren’t followed. She sat right next to him because her perspective was so important—so strategic—he wanted it at-hand, at a moment’s notice (and proactively, I might add).

What would this look like in practice?

Imagine an investment firm (of any kind, in any industry) that actually does due diligence of the people and cultural issues of a company and it’s leadership before they invest. Regularly, venture capital firms retain technical staff to analyze a potential investee’s technology. Likewise, they have analysts that comb-through a startup’s books to understand their true financial feasibility and check to make sure the stories their slide decks tell are real.

But, I’m not aware of (and have not been able to find) even one that does the same kind of analysis about the trustability and cultural maturity of a startup’s leaders. In fact, VC bro culture often looks for the opposite — those who mirror their own aggressive, mono-money-focused, win-at-any-cost dice-throwing they think necessary to succeed.

With all of the noise around “design thinking” and design-driven startups, not a single VC or angel even does a design-assessment as part of it’s due diligence (I’ve asked). And, that’s something they already identify as important. It’s time to put your money were your mouths are, leaders. If it’s important enough to espouse on at TED and SXSW and Techcrunch and BusinessWeek conferences, it’s important enough to make part of your strategic assessment and management process. Where are your Chief Design Officers? Likewise, where are your Chief Culture Officers?

Now, some will no doubt label this the “pussification of Silicon Valley” (a thesis introduced in Upside Magazine’s Dec 1999 cover article of the same name) and, indeed, it’s now a label plastered on every post-modern ill (the pussification of men, America, the left, the world, etc.). But, what does this really mean? I’m surprised it wasn’t leveled against Deanna Troi as the “pussification of Star Trek” back in 1987. Perhaps, it was?

But, think for a moment the enormous risks a company (and its investors) incurs when they get leadership, management, and culture wrong. If you can’t hire or keep the best people, if you incur sexual and other harassment suits regularly (or even occasionally), if you can’t keep leaders or board members and lose your investment in them when they leave because of their behavior, where does that leave you? Ask Uber’s investors right now.

Why don’t these firms assess these risks before they become an issue? Why invest in a company that is likely, from the beginning, to implode because of personality or cultural issues? Why build a team, a company, or staff a star ship with people and situations that undermine excellence, focus, and success? This isn’t about political correctness (and when did treating people nicely become political?), it’s about creating a culture where people perform, without having to deal with issues that divert them from their tasks. And, it’s an undeniably requirement in creative disciplines and for any kind of successful innovation.

What leader wouldn’t want someone trusted and skilled, on staff, to evaluate and advise, after a meeting, that this person “doesn’t seem trustworthy,” or “doesn’t seem to practice what they preach,” or “is a douchebag.”


Who wouldn’t want to go into a negotiation with someone skilled at calling bullshit or deflating hyperbole, or exposing potentially fatal practices? What investor wouldn’t want a report on conduct within a company, an equality-quotient, and a risk assessment on whether an investee wouldn’t “do the right thing”—by it’s company, it’s employees, or its investors?

I’ll tell ya who: those who are guilty of these very risks.

Erika Hall, a design researcher in San Francisco, made an impassioned plea this past week on Twitter to stop using the term “soft skills.” Indeed, the history of this term isn’t what you think it is. Social sciences are real sciences (sorry STEM folks). One glance at Uber over the past week (and, again, they aren’t the only ones suffering these problems), shows that these kind of “soft skills” sound pretty damned hard in their importance and influence. (Psst: they’re also scientifically verifiable.)

So, who is going to be the first VC or corporation to hire a C-level cultural analyst with strategic perspective? Which company is going to blaze the trail of hiring Deanna Troi to be a key part of their ongoing success strategy and risk mitigation?

The future is here. We’ve been in this century for 17 years already. It’s time to start acting like it. And, a good place to start is to take a clue from the 24th Century and hire someone skilled at seeing and, yes, feeling things you don’t in order to achieve that success you so want.



Nathan Shedroff

Nathan is a serial entrepreneur, including the new SEED digital currency: &