What Happens When You Let Your New Hires Ask Your CEO Anything

By Craig Goodliffe, CEO & Founder – Cyberbacker

Helping new hires integrate with their new team members is considered a critical component of onboarding. Conventional steps toward accomplishing that include introducing them to their new coworkers, connecting them with a mentor, and being transparent about company culture.

At my company, we take an unconventional step in our pursuit of integration by allowing new hires to ask me — the CEO – any questions they want, including questions about my personal life. It’s a no-holds-barred Q&A session the entire new hire group gets to experience together.

Is it awkward? Potentially, although not to the degree you might think, and from what we have seen it has proven extremely effective.

What does the Q&A accomplish?

We believe our new hire Q&A tradition is a powerful way to foster the sense of belonging that is critical to integration. One big way it accomplishes this is by breaking down the barriers that can exist between a leader and his or her teams.

In a traditional hierarchical structure, it’s rare to see CEOs initiate an open dialogue with employees. They might deliver a speech to new hires, although they are more likely to simply insert a written welcome in the new hire packet. Our onboarding practice communicates that we care deeply about new hires getting all the information they need to feel comfortable and empowered.

The Q&A also takes transparency to the next level. Experts have identified a long list of benefits that transparency brings to the workplace, including more engagement, stronger trust, and greater profitability.

Opening my personal and professional life to new hires makes a powerful statement about how committed my company is to transparency. Essentially, it shows them that there is nothing we won’t share with our people if it helps them to engage.

While integration is important in any workplace, it is especially important when remote workers are involved. A recent study showed that 72 percent of remote workers don’t feel connected to their company’s mission and purpose. As a company with workers on several continents, we know we need to go the extra mile to foster integration.

Allowing employees to connect outside of their teams has been found to be very helpful in supporting their integration. By allowing them to connect with the CEO on day one, we set the tone for ongoing cross-team connections.

How do we do it?

Allowing for anonymity is one step we have found to be helpful as we facilitate the Q&A. We don’t want shyness or the fear of embarrassment to prevent new hires from asking the questions that are important to them, so we have them write down their questions and have them read by another person in the meeting.

Making it fun is another important step. After all, the goal is to make people feel more comfortable as they come on board, and a little laughter can play a big role in alleviating any discomfort new hires may be feeling.

What questions do they ask?

If you are expecting the questions new hires may ask to be the type that pry deeply into your personal life, you’ll probably be disappointed. The questions typically do seek to hear some personal stories, but they rarely take a direction that could be considered awkward or inappropriate.

For example, new hires want to know if there are any decisions you’ve made that you would go back and change if you could. This is a question I love answering because it shows that I make mistakes just like everyone else.

New hires also typically ask about what you find to be most challenging in life. This is another question I love to answer because it shows that we all feel unqualified or incapable from time to time, which can be very reassuring for a person in the early days of a new job.

Questions about failures and embarrassing moments also come up regularly since these reveal that your teams are just as interested in your struggles as they are in your successes. Answering them allows you to show that your company has excelled not because its people are perfect, but because they are persistent and willing to learn from their mistakes.

Overall, a no-holds-barred Q&A allows you to show your humanity while also showing your commitment to authentic leadership. It allows your team to know from day one that you are a person just like them, who has failures, embarrassing moments, and things they wish they had done differently. It’s a powerful way to build trust, inspire engagement, and welcome them to join you as you pursue your company’s goals.

About the Author

Craig Goodliffe, CEO and founder of Cyberbacker, is an entrepreneur, leadership expert, and business coach, known for his expertise in cross-cultural business development. Under his visionary leadership, Cyberbacker has become a global leader in virtual assistance and administrative support services, transcending geographical boundaries to empower businesses worldwide. His insights have been featured in esteemed publications, including Inc., The Top 100 Magazine, and International Business Times, and he continues to share his insight as a contributor with Grit Daily and the Forbes Business Council. Craig’s global perspective is evident in the transformative impact he has on small business owners and remote workers, see more on CBS.