Question
As our startup now grows FTEs, we want to initiate a wrap-up email they send to management (e.g. the cofounders) each Friday with a set of thoughtful questions that let us know how things are going for them, ideas they have, etc. Our hope is this will help employees feel heard, reflect on their week, and be platform for in person discussions.
I should note we are open to bringing on a consultant/advisor to help us ensure we are doing team development in a thoughtful way as we grow. But this seems like a no regret first step.
Answer
Some great comments and suggestions here. I am often involved with such things since I Coach Executives and their direct reports. Anonymity is King at the outset. How employees experience almost every aspect of how you set the stage and then conduct this will determine how well it works. Simple is better. Three samples might be...
What is most getting in your way this week?
Who deserves an Award for what they did this week?
What have you been measuring this week?
And by all means somehow publish all the responses you get from whatever method you use