Security Strategy, Plan, Budget

Just because people don’t speak up doesn’t mean they understand security

“Not getting it right” and being labeled as “the one who doesn’t understand” leads to a fear spike, says leadership columnist Michael Santarcangelo. (Nazan Akpolat/iStock via Getty Images)
"Not getting it right" and being labeled as "the one who doesn't understand" leads to a fear spike, says leadership columnist Michael Santarcangelo. (Nazan Akpolat/iStock via Getty Images)

Security is complex and often hard to explain, which leads us to mistake a lack of pushbacks or challenges as a sign of understanding and agreement. The appearance of agreement in confusion creates friction and frustration that slows us down. Instead, learn to probe for understanding to get better results.

Cyber spider

I’ve often joked that when people hear “cyber” they think “spider,” complete with the natural reaction to kill it, preferably with fire. Of course, these days most folks recognize that both spiders and cyber are useful — but that doesn’t mean they understand or want to be around, either.

We face a weird situation when trying to explain complex cyber concepts to others, especially when we need their agreement and support. We end up with the misguided expectation that when we communicate, we’ve done a good job.

Confirming understanding: the responsibility and challenge

As the communicator, it’s your responsibility to check for understanding.

Confirming understanding is a challenge. Everyone brings different framing, experience and perspective to the situation. While this is good, it sometimes complicates how we navigate to mutual understanding. Especially when we rely on words with multiple meanings and connotations — even when we think we’re precise with our language.

Our perception of communication gets in the way, too. I used to sample people in my communicating value workshops ahead of time to assess their communication effectiveness relative to their colleagues. In most situations, roughly 90% of participants assessed themselves as effective communicators while also determining that roughly 90% of their colleagues needed help.

Most of us are or want to appear confident and competent in our communication. This affects how we assess understanding.

Fear drives both sides of the equation

The person communicating often invested time to get it right. Asking for feedback and exposing themselves to the potential they didn’t land the message — that they didn’t “get it right” — creates a fear spike. Same with getting asked a question they don’t know the answer to.

On the other hand, the reason most people avoid pushing back to challenge or asking for clarification is also due to fear. We don’t want to get labeled as the person who didn’t understand. We probably got laughed at in life for asking a question. As a result, most people don’t admit they don’t know.

Better ways to check for understanding

The key is to set the fear aside. If you’re the communicator, let go of the fear and ask if your message landed. If you’re the listener and didn’t get it, speak up.

How you ask is what matters.

“Do you understand?,” “does that make sense?” and similar questions provoke a predictable and entirely useless response: “Yup, I’m good.”

Instead, ask in a way that allows someone to come at it safely. I like to ask for variations in thinking, hearing and feeling. Consider asking:

  • Does that feel right to you?
  • Does that match your experience?
  • How does that sound?

Sometimes I just acknowledge the complexity and suggest my effort might have created more confusion, then ask them how it landed. Whatever the approach, take on the responsibility of getting it right to take the pressure off them, allowing them freedom to respond entirely from their perspective.

Better understanding with less friction

You might experience some “story-swapping,” when the other person asks, “is it like…” and then offers a story or scenario. Often you’ll counter with a changed version of their story or a slightly different one. Eventually, you’ll reach a point where one of you blurts out, “that’s right!” Usually, that happens with a slight uptick in pace and energy, too.

I don’t know if this is how we get more people to like spiders — or cyber. But this is how you set the stage for whatever comes next — with less friction and more trust.

Michael Santarcangelo

Michael Santacangelo is the founder of, author of Into the Breach, and creator of the leadership-driven Straight Talk Framework – with our favorite question, “What problem are you trying to solve?”

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