Should CEOs spend "a day in our shoes"?

At my first company Mention we had everyone spend 1 day per year doing customer service ride alongs. This was such an instrumental experience. CEO, developers, sales, marketing, etc. all did this. I loved the exercise not only as a CS leader but as a team member. It gave the entire team exposure and learning to new things.

I've been a strong advocate for recording all our calls, stressing the importance of sharing snippets across departments. This initiative has significantly improved our organization's understanding and empathy towards customers.

It's also great to see this practice gaining traction within our Sales team. Everyone now sees the value in "hearing directly from the customer." Plus, having recordings means our CEO doesn't need to be present during every conversation; they can be reviewed at any time.

These recordings are also invaluable for onboarding new team members and revisiting old feature requests as they're incorporated into our roadmap.

At my previous job, our CEO did participate in a listening tour. One limitation, however, was that it was specifically focused on our largest, highest revenue customers while a lot of the pain points our teams experienced were from our smaller, SMB customers. However, I think anytime you're getting people in front of customers and talking to them directly it makes a huge difference in the empathy and understanding across the business. No matter how many times you share quotes, case studies, etc. in-person conversations will always have a greater impact.

I don't think it created as much empathy for Customer Success teammates, I think if that's the goal of the exercise then a day in the life of is more impactful where the CEO is a silent observer on calls, etc. Many customers will behave differently if they know an executive is on the line. Just as you would talk directly to a customer to understand them, talk directly to your teammates if you want to understand their experiences.

The risks we saw were promises being made to customers that were perhaps less than realistic. At least for our CEO, his initial reaction was to try to offer solutions when problems were raised (great in theory!), but often was not in touch with complexities of the problem or time/effort to deliver a solution. In several instances, it resulted in our team having to back track after the fact and reset expectations with the customer.