As I sit here typing this, Mark Zuckerberg is mea-culping live on CNN about Facebook’s privacy breaches. In parallel, our good friends (forgive the sarcasm) in Russia are endorsing their candidates for the 2018 U.S. elections. Not to mention, the credit reporting agency Equifax has—well, the kimono isn’t just open, it’s gone.

We get it: Security is important.

This is why companies hire “black hats,” or computer hackers who used to exploit security measures for personal gain. As outside consultants, the new goal is to point out security gaps overlooked by the in-house team.

There are talented security experts inside these companies, to be sure. Yet, subtle cultural factors—the rousing speech at the annual retreat, the valuable stock options, reassurances from like-minded teammates—can lead to insular thinking and blind spots. These blind spots could have, or perhaps should have, been fatal for some of these companies, like Equifax.

These black hats remind us that it takes an outsider to really get some perspective. But this outside scrutiny shouldn’t end with security. Because the brand is even more important to a company—in every sense, including to the balance sheet.

Let’s examine how critical thinking —or the absence of it—is impacting both mature and nascent brands. Years ago, an outside branding expert might have told Equifax: this is a commoditized space.

Why not double down on security (and be known for it) thereby providing a perceived difference, adding value and preference? Of course, as an ancillary benefit, the company’s actual security would have improved, which may have prevented the breach (and the 33% loss in value which accompanied it.)

Here are a few more examples of brands that could have benefited from critical thinking.

For years, Charles Schwab has been telling us to “Own Your Tomorrow.” It’s a good line, grounded in empowerment and self-sufficiency, but how are they actually delivering on that brand promise? Sure, they have a landing page with stories from individuals who have taken the road less traveled, but the content hasn’t been substantially updated in years. The bulk of the campaign is transactional, almost retail: a race to the bottom. If my decision to bank with Schwab saves me $2 on a stock trade, is that really going to empower me to “own my tomorrow”?

Compare their campaigns with Prudential, where almost every headline touches on the challenges and benefits of retirement savings: the race for retirement is one we can all win. Prudential’s campaign has finance professors out on the street teaching lessons on investing: it’s educational, but also heartening.

To put it another way, Schwab is talking a good game, but Prudential is following through. Enough about mature brands.

How are the tech start-ups faring? Not well, in short.

Without naming any names, here are snapshots of three start-ups—all impressive, possibly transformative, but making inadvertent, costly mistakes.

• One has a campaign that gives a nod to analog technology—which undermines its advanced AI capabilities (and thus, competitive advantage).

• Another uses an adverb repeatedly in headlines on the home page. This word also happens to be one of its largest competitors.

• A third has a site which doesn’t display well on mobile. This doesn’t inspire confidence in the offerings—hard for anyone, but particularly problematic for a Fintech company vying to handle large amounts of cash.

Again, there is no shortage of smart people at these start-ups. Inertia might be a factor, as we discovered with Facebook, but it’s hard to find a brand anywhere that could not benefit from some critical thinking.

Along that line: excuse me while I get going on some fixes to our website, because we’ve gotten some input that a couple of our pages aren’t exactly singing.

So time for a dose of our own medicine.