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
We've been now running Weekdone.com weekly team status updates and reporting service for over 3 years. Here is my experience.
First decide if the information you want to get is task-oriented or more about open-ended feedback questions. First is more item oriented (our standard template is PPP as used in Ebay, Skype et al meaning Plans, Progress, Problems). The second is based on questions to have employees open up. Here is one blog post I did on 10 questions I've seen that work well among our users: https://blog.weekdone.com/10-questions-to-ask-your-employees-today/
The key to get the process working well is by the way feedback and replies from you to employees, based on what they report. If you make it a one-way black hole from employees to managers it rarely works. It has to be 2-way communication. That's where many leaders fail. Without that employees take the attitude that nobody reads the updates and no changes are made by you and other managers.
