The biggest mistake most bosses make when trying to be honest with workers, according to a former Google executive

If you've watched HBO's "Silicon Valley" or NBC's "The Office," you've seen several examples of obnoxious aggression and manipulative insecurity exhibited by leaders. 

It almost goes without saying that actual managers shouldn't look to mimic Michael Scott, or the command-and-control culture dramatized on television. Instead, leaders should strive for what former Apple and Google executive Kim Scott calls the radical candor approach, showing that you care personally while challenging directly.

While the concept is simple, Scott told CNBC Senior Media & Tech Reporter Julia Boorstin at the recent Disruptor 50 Connect event in San Francisco that she views it as radical because it can be difficult to show you care while challenging a peer at the same time.

"It's rare that we do both at the same time, especially with feedback at work, but really feedback in any part of your life," Scott said. "It's a matter of existential dread."

Avoiding the fear of providing honest feedback

That fear often keeps leaders from providing feedback that fits into the radical candor bucket, instead moving towards three types of negative feedback that Scott outlined in her "Radical Candor" book: Obnoxious aggression, or praise that doesn't feel sincere and feedback not delivered kindly; ruinous empathy, or feedback that tries to spare someone's short-term feelings but doesn't tell them what they need to know; or manipulative insincerity, actions like backstabbing or passive aggressiveness, which Scott said is the worst kind of feedback failure.

Scott said that the challenge for CEOs and leaders is balancing the desire to be "compassionately candid without being ruinously empathetic," something that can be solved by soliciting feedback.

"At the core of radical candor is a good relationship between manager and employee, between peers, and up, down and sideways," she said. "It's about a good relationship, and there are few things that are more destructive to a good relationship than a power imbalance, so if you have power, I recommend learning how to lay it down, learning how to solicit feedback from people, and prove to them that it's not only safe for them to tell you what they really think, but that they'll be rewarded."

Being tough but fair

Amid recent leadership scandals as well as the broader societal changes that have occurred, leaders will worry about upsetting workers when providing firmer feedback, but that is no excuse for being a poor communicator, Scott said.

"What's happening now is we suddenly became aware of a bunch of things that we should have been aware of before, but we were not, and people have retreated to manipulative insincerity, where they're neither caring nor challenging," Scott said. "They're so concerned about their reputation as leaders that they're saying nothing, and I get this question with some frequency from CEOs who tell me they're not going to give feedback to certain people on their team because 'I will get in trouble with HR.'"

Scott said it requires leaders who are willing to "challenge directly, even further than you may be comfortable going," while also being aware of how what you're saying is landing.

"Despite everything you might read on social media, most of us do actually care personally, but we're so worried about not upsetting someone or hurting their feelings or offending them, we fail to tell them something they'd be better off knowing," she said.