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Don’t be the last to know: How to overcome your leadership blindspots

As a CEO, business executive or manager, you can be caught in a bubble. Here’s how to break through and get the employee feedback you need.

“Have you ever been the last to know something in your company?”

As the CEO of Know Your Team, an employee communication software tool, I’ve asked this question to dozens of business owners, founders, and CEOs. The response is almost always the same…

“Yes, I’ve definitely been the last to know something in my company.”

Perhaps you were surprised to learn that some new hires felt a bit disconnected from the rest of the office? Or you had no clue one of your employees was under-performing when you thought things were going well? Or worse, were you blindsided when a senior employee you’ve leaned on for years put in her two week’s notice?

If you’d only known about these issues earlier, then you could’ve done something about them, right?

You could’ve avoided a small setback from snowballing into a bigger problem. You could’ve implemented a company change that would’ve been well-received. You could’ve kept a few key employees longer…If only you weren’t the last to know.

That’s the real cost to being the last to know — you lose time, energy, money and people. It’s dangerous to run a company and not know it as well as you’d like. It means you’re flying blind.

So why does being the last to know happen in the first place? And, as a business owner, founder, or CEO, what can you do about it?

Why you’re always the last to know

Being the last to know is a natural part of being the boss. When you’re the boss, there’s an inherent power dynamic underpinning every interaction you have with your employees.

Fear comes into play. Employees worry about you treating them differently if they speak up. In an employee’s head, you might take a comment personally and become defensive. You might choose to delay a promotion. You might even fire her or him.

But this feeling of fear is not the biggest reason why employees choose not to share what’s on their minds.

The number one reason employees don’t speak up at work is because of a sense of futility — they believe even if they were to say something, nothing would change. They don’t think their opinion or idea will have an effect on the outcome. In fact, studies have shown futility to be 1.8 times more powerful than fear as an obstacle to giving feedback.

This means as a manager, founder, or CEO, you need to overcome these sentiments of fear and futility if you don’t want to be the last to know…

How to avoid being the last to know

Here are four strategies you can employ to foster employee communications and convince staff their opinions will be acted on.


If you want an employee to share their honest opinion with you, you have to be willing to share your honest opinion with them first. You can’t expect someone to be open with you, if you’re not open with them.

One way to “go first” is to ask for advice, instead of for feedback. When you frame the conversation this way, it takes pressure off the situation. People are always willing to give advice, or to lend a hand… versus giving feedback, which can feel like giving a critique.

Try saying this: “I could use your advice on this…”

Another way to “go first” is by admitting a vulnerability. This might be in the form of you sharing a problem you’re struggling with. This sets the expectation that you want to hear honest, non-sugar-coated information.

Try saying this: “I’m struggling with…” or “Can you help me understand something?” or “Hey, I don’t have all the answers…”

Your job is to make your employees feel as safe as possible to speak up. You’d be surprised how simply leveling with an employee can influence how much she or he opens up to you.


To get the information you want about your company, you have to ask your employees what you want to know. You can’t expect the answers to come to you. Answers only come when you ask questions.

But the questions you ask can’t be just any ol’ questions. If you ask a general, half-hearted question, you’ll get a general half-hearted response.

For example, ask someone “How’s it going?” and I’ll bet that nine times out of ten, the response will be, “It’s fine. Things are going fine.”

Instead, ask “What’s one thing about the last project we completed that could’ve gone better?” I guarantee that you’ll unlock a lot more valuable honest feedback because you’re asking for something specific (“one thing”). This question is also anchored around a specific event (“the last project we completed”). The more specific the question, the better.

Try saying this: “What’s one thing… ?” or “How did that last meeting go… ?” or “What could have we done about the client project we just finished… ?” or “What should we talk about during our next all-company get-together… ?”

Another way to ask specific questions is to time box the question to a specific period of time.

For instance, instead of asking, “What do you think we could improve on?” you should ask, “What one thing in the last two weeks could we have improved on?” By asking someone to reflect on the last two weeks, all of a sudden it’s easier for that person to recall and think through what feedback they have for you.

Remember, specific questions yield specific answers. General questions yield general answers.


As a leader people look to your actions as an example. This is especially true when it comes to communicating openly and honestly.

When someone brings up a tough topic, do you get testy and a bit defensive? Or do you calmly listen and ask thoughtful questions? Your reaction will be their benchmark of whether they’ll feel comfortable bringing up these hard conversations with you in the future.

Use this to your advantage. Set an example with your reaction and create the tone you want in your company. You want your reaction to exemplify, “Here’s how we treat bad news… We welcome it. We want to hear it.”

One way to do this is to show gratitude to an employee who brings up a dissenting opinion. Thank that person, and do it publicly.

Try saying this: “I appreciate that viewpoint…” or “It means a lot to hear…”

Another way you can set an example is to emphasize what you have in common with the other person you’re talking to. Despite you disagreeing with an employee, you want to remind them that you have shared intent and mutual goals. You’re all playing on the same team.

Try saying this: “I know we don’t agree on everything, but here’s what I think we do agree on…”


Take action. That’s the most important thing you can do to make sure you’re not the last to know. After all, that’s the point of getting this information from your employees — to dosomething with it.

It might sound obvious, but knocking out a quick win (no matter how small) can make a real difference.

Is there a low-hanging fruit you just haven’t gotten around to yet? Delegate it to someone you trust and take care of it right away.

Is there a decision that you’ve made that isn’t a big deal to you, but is a big deal to someone else? Pick your battles, be open to changing your mind, and let someone else “have” that one.

Try saying this: “Because of this suggestion, we’re going to do this…”

Employees value responsiveness. They’ll feel encouraged that their words led to action. That momentum will have a positive effect on morale.

Discover more about your company

I get how hard this is to do. Especially as a CEO myself, it’s something I still personally struggle to prioritize. It’s anxiety-inducing to open ourselves up to something we don’t want to hear. And sometimes it feels like a distraction, when we’re just trying to execute on the day-to-day of running a business.

But if we want our business to be the best it can be — to serve our customers well, to be great place for our employees to work — we have to dig deep and be willing to learn what we don’t yet know.

We have to commit to discovering more about our company.

We don’t have to be the last to know.

This piece was originally written on our friends’ Intercom Blog

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Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.