Why I Love “Ask Me Anything” Sessions—Especially When the Questions Get Tough

As a CEO, how can I ever really know what our employees are thinking? This is a question that can keep any good leader awake at night. It’s just plain hard for most employees to be completely honest with executives about anything negative or critical.

As much as I try to be welcoming and open, I understand that it’s unrealistic to expect everyone to come to me directly with complaints—they may be afraid of disturbing me or don’t know me well enough to feel comfortable delivering bad news. And whenever I join in on a team meeting, I get the sense that not everyone is as candid as they’d normally be were I not around.

Of course the most powerful antidote to this is to cultivate a culture where open feedback and honest dialogue are welcomed and praised. To accomplish this, leaders must implement specific practices to support these values.

One of the best ways I’ve found of gathering honest feedback is by hosting “Ask Me Anything” (AMA) sessions. Employees submit their questions anonymously, and I respond to as many questions as I can at our monthly all-hands meetings.

I’ve found that holding AMAs is one of the most beneficial things I can do as a CEO.

Here are the reasons I think AMAs are such a useful tool for CEOs—especially when negative or challenging questions come up.

Giving complaints a forum actually helps mitigate them.

I realize that a lot of CEOs might be hesitant to hold this type of forum. You might fear that by giving complaints a voice, you’ll magnify them, and things could snowball from there. But I’d argue that it’s actually the opposite: If you don’t give complaints a forum, they’ll fester and become much worse. Giving people a regular opportunity to vent means that they don’t have to hold onto negative emotions for months at a time, and I believe that sometimes even just voicing a frustration helps to alleviate it.  

I don’t always have time to answer every question that’s been submitted for an AMA, but the regular cadence of AMAs also means that no one has to wait for too long to have their question addressed.

Negative feedback helps us improve.

Whenever I have the opportunity to talk to customers who tell me they love Greenhouse, my first reaction (after thanking them, of course!) is to ask them what they don’t love about our product.

This is not because I’m a glutton for punishment! It’s because I believe that negative feedback is one of the most powerful tools to help us improve. If something isn’t working, I want to hear about it, because that’s the only way that I’ll have the opportunity to address and correct it.

I feel the same way about the company: I want to know what’s making employees unhappy. I’d much rather learn about problems or frustrations from people while they’re still employees and I have the chance to do something about it. I certainly don’t want people leaving the company simply because they feel like their voices were never heard.

For example, we recently overhauled our employee perks package, providing a better set of offerings around employee health, financial wellness, and family/work-life balance. One of the first signals we had that this change was needed came via AMA questions, of employees asking us to improve the perks. The ability to ask anonymous questions this way was a powerful channel for employees to express concerns that otherwise they might have kept to themselves.

It’s an opportunity to address false premises.

In an organization of our size, some amount of miscommunication and misinformation is inevitable, and the AMAs give me the opportunity to address these misunderstandings.

For example, in a recent AMA, one of our employees expressed the frustration that it seemed as if career growth within his department had stagnated. But what he hadn’t realized was, three people in his department had been promoted within the past quarter alone! So, hearing that feedback taught me that not everyone knew what the career advancement opportunities were. This helped me identify opportunities to better communicate career growth and advancement within the company.

In this instance, I was able to share some information about the organization’s composition and remind everyone about our career ladders (we’ve defined the criteria for promotion to make this process as objective as possible).

I believe that in cases like this, the problem is not at all with the person asking the question, but with the way we as leaders have shared information. This is bound to happen occasionally in a company growing at our rate; so this is yet another way the AMA format is a uniquely helpful communication channel.

It means no one has to suffer in silence.

Just because you aren't hearing the negative stuff as a leader doesn't mean it's not out there. I can tell people that I welcome constructive criticism ‘til I’m blue in the face, but it doesn’t change the fact that it’s still really hard for most employees to share it with me directly. The anonymity of the AMA question submission process seems to remove some of that hesitation, and the fact that questions are submitted online through a form means that people can submit them at any time. Every time we hold the AMAs, I’m always impressed by the depth and quality of the questions, which further proves that employees really do respect this forum.

Each person who you enable to honestly express a fear or doubt is one fewer person who you are mistakenly thinking is just fine when in fact they’re not.

It reinforces our company value of authenticity.

Authenticity is one of Greenhouse’s core values, and I want employees to feel empowered to be authentic with me just as I strive to be authentic with them.

I rarely review questions before the all-hands meeting, so my answers are unscripted and off the cuff. This means that they might not always be “perfect”—for example, sometimes I don’t know an exact number that someone asks about but I can give the general range and follow up later with specifics. Sure, having those data points available might have made my answer “better” in some sense, but I believe that answering questions on the spot helps set an example of what authentic communication can look like. This is especially important with my responses to any challenging or critical questions.


Final thoughts

If you’re a CEO and you’re thinking about hosting an AMA session, my advice to you is simple: Don’t be afraid—do it!

This is such a valuable forum for company-wide communication and gives you insight that would be hard to gain through any other means. I understand that it can be scary to open yourself up to this type of scrutiny, but I hope that the points I’ve outlined above make the case for why the positives far outweigh the negatives.

Have any questions or thoughts about company-wide AMAs? Let’s continue the conversation! Leave a comment below or reach out to me on Twitter.

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Daniel Chait

Daniel Chait is CEO & co-founder of Greenhouse and has been a technology entrepreneur in New York City for nearly 20 years. Dan is a frequent speaker on the topics of recruiting and entrepreneurship and has presented at numerous venues including General Assembly, the University of Michigan Center for Entrepreneurship, Launch Scale, DEMO Traction, and the Wharton Entrepreneurship Conference. He graduated from the University of Michigan with a degree in Computer Engineering (#GoBlue!). Connect with Dan on Twitter.

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