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Why I Let New Hires Ask Me Anything

woman in a town hall meeting raising her hand
Embracing open dialogue—and sharing failures rather than achievements—allowed this CEO to create a unique bond with employees.

If you were to compile a list of topics you felt were important to share with new hires, what would you include? You’d probably put your company mission, vision and values on the list. If you are a little more pragmatic, you might also address work hours, dress code and the process for requesting time off.

However, would you include your biggest failure as a professional, or the most embarrassing moments in your personal life? I recommend you put those things on your list because I’ve discovered through embracing an open dialogue with my company’s new hires that those are two things people joining your company want to know, and I believe there are good reasons for sharing them.

What open dialogue can accomplish

We allow our new hires to ask me—their new CEO—anything. It’s a no-holds-barred Q&A session that can delve into my personal or professional life. Yes, it can get a little awkward at times, but I think it is a valuable tradition that I wouldn’t think of doing away with.

We do this for several reasons, beginning with our desire to lead with humanity. It is important to me to come across as someone who is approachable. To achieve that, I strive to find ways to show my team I am a person just like any of them.

Our Q&A tradition humanizes my position. By sharing stories of my failures and regrets, which are two questions I am regularly asked, I can connect more authentically. In the end, the culture and connection it fosters allow me to provide more authentic leadership.

Open dialogue also breaks down unhelpful barriers that can exist between employees and management. Traditional business hierarchies created divisions in many companies, like the first-class and economy sections on planes where mingling between classes is discouraged. We communicate that all voices have value when we encourage open dialogue and communicate that employees should feel free to ask whatever questions they have.

If you want to build trust with your new hires, allowing for open dialogue is an excellent way to do this because it shows your commitment to transparency, reassuring employees that you support a culture in which they can expect to get an honest answer to their questions. I never want an employee to feel uncomfortable about sharing a thought or a concern.

Finally, I find that encouraging open dialogue in this way also helps to cultivate a healthy connection for remote teams. My company is a global leader in virtual assistance and administrative support services and leverages the power of virtual assistants widely in our own operations. We know how challenging it can be to provide effective remote leadership that keeps employees feeling connected and results in high-performing remote teams. My commitment to answering any question contributes to a sense of closeness and camaraderie.

What open dialogue looks like in action

I’ve learned through bringing this practice to life that there are a few practical steps you can take to make it more effective, such as allowing for anonymity. People will want to ask questions that might cause a little discomfort, but they don’t necessarily want you to know they are the ones asking them. To address this, we invite everyone to write their questions down on a piece of paper, and then have it read to me by someone else in the room.

I’ve also learned it is better to keep it light and have fun with the questions. People will want to laugh when they hear about your most embarrassing moment, so make sure they know it is perfectly okay to do so.

If you embrace this practice, you’ll find that you’ll get many of the same questions from each new wave of new hires. “What are your hardest moments?” is one of the questions that comes up repeatedly. As new hires, they may be anxious about encountering challenges that will highlight their weaknesses. Knowing you struggle with specific issues—maybe even the same issues they struggle with—can be reassuring.

I also get asked regularly if there are decisions I’ve made in the past that I would go back and change if I could, which is a great question to answer because it shows you have made mistakes in your past just like everyone else. Providing an honest answer to this question also shows you are willing to admit that you don’t always know the best way to proceed.

These questions, along with those focused on your greatest failures and embarrassments, reveal something very important about the people who make up your organization. They care less about your accomplishments, which is what the typical CEO speech focuses on, and more about your shortcomings. They want to know how you overcame your struggles, how you failed, and how you got back up afterward.

When you are willing to be vulnerable and share on that level, you create a valuable bond. You become a leader who is more relatable, more likable, and easier to trust.


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