In a reaction to my answer about “Investor Relations” one of our fellow Heretics asked me how you best keep your investors, advisors, mentors, board members and partners in the loop. You will find yourself in situations where you either want or actually have to keep these people informed and communicate with them on a regular basis.
Here’s what worked for me (both from the perspective of the sender as well as the receiver):
First of all — establish rhythm. Make it a habit to send updates on a regular basis. A good frequency is probably once a month or so. More frequent might be overkill, less frequent feels too long and makes your communication disjunct.
Secondly make sure that you write your updates in your very own personal style. See these updates as a wonderful way to engage with the people who surround your startup — not only as a way to convey information.
Focus on the big things; the accomplishments you want to celebrate and the topics where you have questions and need help. Don’t go into details, instead encourage your recipients to follow up with you if they need/want more information.
And always ask. Ask for help. Ask for introductions. Ask for brutally honest intellectual feedback. All those people — your board, your advisors, your mentors, your investors are there to help you (and have a vested interest in you doing well).
Lastly: Don’t over-think it. Don’t spend hours designing a wonderful email template and setting up a newsletter system. Instead write what feels right and send a plain email.