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
I have served as advisor to some HR managers and growing startups on these issues, and we have found that the first principle is guaranteed anonymity for any software-initiated polls. While open ended answers give more data, they also open the employee up to identification and pollutes our information.
Best approach is a mix of in person approach and online polling, the personal touch allows for people to share attitudes they didn't even know they had. That of course requires a specifically trained staff, so online methods are preferred by industry.
This polling would be better aligned with events and important dates rather than periodic weekly intervals to prevent a "punch a button" feeling.
I'd be happy to elaborate more on best practices for polling in a call and show how even the in person methods can be introduced to complement them!
