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
This seems like a good idea initially, but I think you'll find it's incomplete.
Here's the problem: for the employee, sticking their neck out and telling the truth is a potentially career-limiting move.
So they will never tell you the full open truth.
From experience, the best format is to use an impartial intermediary the employees do not report to, and whose stake is not in management's way of doing things.
Then employees can open up.
Why do you think Suggestion Boxes are anonymous?