Lowlights
Report 1-2 real misses without softening them into non-problems. This is the section that builds long-term credibility with investors.
Fred Wilson (AVC) has written that the updates he trusts most are the ones that include real bad news, not just good news.
- 1-2 real misses, stated plainly
- What caused it and what's being done about it
- Fake lowlights that are actually humblebrags ('we're growing so fast we can't hire quickly enough')
- More than 2 lowlights, which reads as panic rather than candor
- A section titled 'challenges' that contains no actual challenge
- Disguising a real problem as a minor operational note
- Omitting lowlights entirely for several months in a row
- · Would a board member reading this be surprised later to learn what actually happened?
- · Is this a real miss, or a win wearing a modest disguise?
The miss this month: [what went wrong], caused by [reason], and we're addressing it by [action].
"Only real challenge is that we're growing so fast the team can barely keep up, a good problem to have."
"Churn ticked up to 4.2% this month, driven by two mid-market accounts that cited missing SSO. SSO ships in 3 weeks; we've already re-engaged both accounts with a timeline."
Nimbus Payroll names the number, the cause, and the fix in three sentences.
Quick quiz
1. What makes a lowlight fake?
- ○ It has a number attached
- ✓ It's secretly a win in disguise
- ○ It mentions a fix
- ○ It's short
Statements like 'we're growing too fast to hire' read as bragging, not as honest difficulty.
2. Why does Fred Wilson value real lowlights in updates?
- ○ They make the email longer
- ✓ They build trust that the good news is also real
- ○ Investors are legally required to see them
- ○ They replace the metrics table
An update that only ever contains good news becomes one the reader stops believing.