john.smith@startup.com <– The founding team is all from Microsoft and can’t shake it if they tried.
For the longest time, Microsoft email addresses were limited to 8 characters for backwards compatibility with older email systems. They were always of the form "First Name + Last Name initial" with adjustments for duplicates. e.g
billg - Bill Gates
billgr - Bill Gross (made up)
billgi - Bill Gibbons (also made up)
And then as they grew bigger, the system sort of fell apart for common names - I know one of at least 14 Jeff Johnsons that had email names that were impossible to guess correctly!
Of course, 'jeff.johnson@' doesn't work for the 14 identical name case either!
"john.smith@startup.com <– The founding team is all from Microsoft and can’t shake it if they tried."
Alternatively, one or more members of the founding team has a name that doesn't map easily to a name + initial for English speakers. I know that jsmith@foo.com has a first name starting with J and a surname of Smith, but who is balaswaminathan@startup.com? Is that a first name and a last name, a first initial and last name, or just a last name? And where is the demarcation between first and last names?
You can argue that it doesn't matter, but then why have a systematic email address at all?
Something I was wondering a few days ago is which is better to avoid duplicate names, [first initial][surname] or [forename][surname initial]eg: pgraham@ycombinator.com vs paulg@ycombinator.com.
Depends on the ethnic composition of your employees. Some cultures have only a small number of first or last names.
40% of Vietnamese people have the surname Nguyễn, if you use the first initial + last name system then by the birthday paradox, there is a 50% chance of a first initial collision with 6.5 Nguyễns in your organisation. That means that if you have more than about 16 Vietnamese employees, you have a 50% chance of an email id collision. It's actually higher than that because Vietnamese-American first names are often English, so the distribution of first initials is not evenly distributed.
That you're systematic, coherent and understand that there is often more than one way to solve a problem. It tells us you welcome communication and want to ensure that even if someone doesn't have your email address that they are given different common options which will get a message to someone, given a name. I presume you also have suitable group aliases. You're the type of people who don't rush things and make mistakes, preferring to analyse and do things properly with consideration for the future and the unknown.
Of course, 'jeff.johnson@' doesn't work for the 14 identical name case either!