How to Encourage Asking Difficult Questions in the Workplace

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In a past organization, we had the question asked about why don't we have more people of color or women in our organization? And to their credit, this was a valid question. 

If someone asked that question all hands, how do you think the leadership would answer it? Would they want to answer it on the spot? Maybe something generic, “We are working on it but it is a challenge to find candidates….etc” First do you think it's getting asked? No way. Because they're not going to put the leader on the spot. There is really no upside to dealing with that question, in the moment, with the entire company. Now, maybe if they have been totally prepared for that and given a presentation on the company's Diversity & Inclusion initiative then maybe it gets asked. 

However, if we had LoopingBack at our previous company, people would have felt more comfortable asking those important questions. As a CEO if I was asked an employee that question via loops, in the next loop I sent out, I would actually share the employee's question with the company. As an example 

“hey everybody, I don't have a great answer for this right now. We're working on this and I want to ask each of you to challenge us in this way. Thank you to the employee, for asking this difficult question, which is a meaningful, important question. We're working to try and create more diversity in our workforce. I will come back to you guys with some updates, and if you know of some things that we can do or if you have ideas, please let me know. The one thing that I really want everyone to know, is that this type of feedback is what we need.”

From our perspective, asking difficult questions in the workplace should be celebrated rather than discouraged, making for a better company culture.