I think that it would be important to answer the following questions.

* Who comes up with the "thoughtful questions"? And are they new every week?
* Who is responsible for the answering of these questions?
* What is the pace of the start-up?
* Will every team's concerns / progress / roadblocks / setbacks be relevant to management?
* How much time should each team spend on developing its response (related to point 2)?
* "...help employees feel heard, ..." - How do you plan to measure this?
* Is a weekly cadence the right pace?
** Can teams align their "wrap-up" with their natural development cycles (this is more relevant if the company is a technology company)?
* Will these wrap-ups be relevant to other teams?

Answering these questions can help develop how relevant these emails are both to employees and to management.

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?

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!

I believe this "send to management" idea will create hierarchy issues within your team and will limit your employees providing honest feedback to the "management"

Try this;
Each Friday afternoon work stops for 2 hrs. Everybody gets together, office turned to a social venue. Sandwich, Pizzas, Drinks (arrange as you wish) afternoon tea or even lunch
-First two weeks nobody will speak but its your job to open the conversation, talk and ask questions. They must be comfortable. Answer questions in front of them so they are comfortable approaching you, avoid confrontation reply later in private
-Talk about the past week, figures and plans next week, talk to top performing employees, share their story, tell a funny story from last week, talk about markets, share your opinions
-You can ask to prepare questions submit before the meeting or they can ask you during the meeting
-After a month this becomes a ritual, people will need to brings cakes etc,... team spirit.. ideas will flow and have a great impact on your business
-Be careful, if people asking questions about how to do their job, there is a training problem.
-if you are looking for a online survey, just buy one of from internet..if you are looking for a real-time chat platform buy one of from internet, if you are looking for a mail distribution use your email client
-Your employees is everything to you, make sure you interact with them

I would keep it as simple as possible. The more complex it is, the more likely employees will give up.

My advice; 4 categories;
Positive: what is going well this week/month...?
Negative: what is not going well?
Comments: neither positive or negative but worth mentioning
Actions: what do they want to do or want the management to do?

That's it...

Steven

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

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.