Startups 101: How not to lose mentors and irritate advisors

I’ve spent quite a lot of time “having coffee”, where “having coffee” involves discussions around social media strategies, product launches, presentation tips, CV polishing and so on.

Some of these are ongoing, quasi-mentor/mentee relationships; others are ad-hoc or one-off; not all of them actually involve coffee. Sometimes I leave these meetings exhilarated (which is saying something, given my introvert tendencies). And sometimes I leave these meetings irritated or frustrated, or with a strong sense of having had my time wasted.

Sometimes this disappointment stems from having been kept waiting (5 minutes – understandable; 15 minutes – piss take; 20 mins – I’m out) or from an obvious lack of preparedness by the other party (“so, what do you do again?”).

With that in mind (and inspired by Ty Ahmad-Taylor’s brilliant guidance to his mentees around email introductions), herewith the first version of the Galavant Guide to Not Pissing Off Your Mentors and Advisors:

Confirm the meeting and give at least 24-hours notice if you need to reschedule

Confirming the meeting the morning of the day before you’re due to get together isn’t just polite; it also acts as a reminder to your mentor/advisor and gives him/her an opportunity to reschedule or change the venue if needed. If you’re no longer able to make the meeting, give at least 24 hours (and ideally, 48 hours) notice if at all possible, and suggest specific dates/times for an alternative meeting (avoid open-ended statements like: ‘when is good for you?’). And above all, don’t be a chronic rescheduler.

Here’s a real example of how to make a less than positive impression (names and details changed):

– Send an email with the subject line, “Not sure what happened this morning”
– Get the date and location of the meeting wrong, suggest it was a mix-up on the other person’s behalf: “I’m sorry I think I must have had either a miscommunication or brainfart; I thought today at 9 we were meeting at the XXX offices. May I suggest we perhaps reschedule for another day this week at the same time?”
– When corrected as to the date/location of the meeting, manage to first be very late and then completely miss the actual meeting by getting lost in NYC
– Fail completely to email or call the other party after having missed the meeting

Don’t be late, but don’t be too early

Respect your mentor’s time. Plan your route well in advance and give yourself enough time that traffic or a transit snafu won’t completely derail your arrival. If you’re going to be late, let your advisor know. On the other hand, don’t arrive too early – especially if you’re meeting at your mentor’s home or office. Alex Taub of Dwolla has a solid post on why earlier is not always better (but late is never good).

Be prepared

I’ve had meetings with people who’d obviously forgotten my name. This is…not a good look. Always have a clear objective for your meetings with your mentors and advisors, and make specific requests. Avoid: “I’d really like to meet people and media”. Prefer: “Would you be able to introduce me to XXX editor at YYY newspaper? I’m interested in an internship there over the summer.”

Offer to pay for the coffee or meal

Your mentor or advisor will appreciate the gesture, even if s/he declines. But always offer. And be sincere.


At the very least, send a thank you email within 24 hours of the meeting. Ensure you send your mentor any information or details s/he requested – like a PDF of your CV. And if the interaction involved career advice or introductions, keep your advisor informed of your progress .

Here’s a real example of how to fail at following-up:

– Ask your mentor or advisor to recommend you for an internship.
– Secure an interview for said internship; fail to let your advisor know of your progress.
– Secure said internship
– Allow enough time to elapse that your advisor first hears that you’ve started the internship from a third party
– Entirely fail to send your advisor a thank you note or update of any kind

Don’t embarrass your mentor

When you asked your mentor or advisor to introduce you to someone, you are effectively asking him/her to trust that you will not abuse the privilege. You can bet that if you annoy the person to whom you have been introduced (or, and sometimes worse, if you fail to follow-up on an email introduction, for instance) you will undermine your relationship with your mentor.

Don’t embarrass yourself

Spell check your emails. Get names right. Don’t show up for a meeting hungover. Etc.

Have you had an excellent or awkward mentor/mentee relationship? Weigh in with your suggestions for avoiding embarrassment and ensuring good relations in the comments

Startups 101: Pitching and Presenting


2 thoughts on “Startups 101: How not to lose mentors and irritate advisors

  1. To the first point, I’d add be opened to rescheduling, possibly with little notice if the mentor is in a much higher position than yours.

    Regarding follow-up, if during a conversation with the mentor you discuss a book/report s/he seems interested in but isn’t familiar with, send a link/pdf in the follow up email.

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