Hi Naina, I am reaching out to you for advice and guidance for my girlfriend X, who’s very passionate about Photography. I saw you as part of my network and also browsed through your website and profile, and figured you would be a great mentor for her as she wishes to pursue Fashion Photography.

I also see we have a <B-School name> connect 🙂 and would really appreciate if you could take out some time to evaluate her profile and CV to see how best you could help her out.

If you could share your email id, I will ask X to send across some of her work and her CV.

Just wanted to ask, are you based in Mumbai?

Look forward to hearing from you and your support and guidance will go a long way in helping her gain much needed confidence in this field.


How Not To Ask For Help

01. Be a complete stranger – I don’t know you from Adam, I’ve never interacted with you previously ( in any way / shape / form ).

02. Miss the fact that I’ve stated on my profile that email is the best way to get in touch with me. And I’ve shared my email ID publicly everywhere. If you’ve seen my blog / website / social channels, ALL of them display my email ID. But you send me a LinkedIn Private Message. Which is by far, the worst way to get in touch with me because I visit the platform maybe twice a month and all my notifications are off. “If you could share your email ID.” Tells me all I need to know about how much of my work you actually researched online.

03. Make your girlfriend sound like a low on confidence silly girl who needs her boyfriend to write messages to strangers. If you can write to me – as a stranger – so can she.

04. Ask me to evaluate you CV. Why don’t I evaluate your life choices too while I’m at it? Yikes. ( The last time I saw a CV was when I had one – a decade ago. I don’t even know what CVs looks like anymore or why anyone even needs them. )

05. Be completely vague. What does “evaluate her CV”, “Helping her gain much needed confidence”, “figured you’d be a great mentor”, “see how best you could help her out” really mean anyway? No. She needs to figure out how best to utilize my help and in what areas. I’m not going to first tell you what the right questions to ask are and then proceed to answer them as well. ( I might write about what’s wrong with the email / approach, but I’ll assume you can figure out what the right approach might be. That is, if you’re reading my blog in the first place. )

06. “see how best you could help her out” Why in the name of Hood will I do that?  This ticked me off way more than anything else in that message. How is it my responsibility to figure out how I can help someone when that someone doesn’t even have the professional approach to ask me for help in the first place?! What a clusterfuck of a message this is.

07. Ask where I live. You’re assuming I’m going to take time out and actually meet your girlfriend? Watch me snicker. I have no problem meeting with someone who wants help. But not someone with these preemptive assumptions and feeling of entitlement. In any case, if you had actually seen my blog – the home page has a small FAQ section at the bottom, which specifies my current location. Duh.

08. Mention how we have a “B-School” connect. Are you suggesting same-college so nepotism? WTF. Who gives a rats ass what college you’re from? Are you a decent human being? Nothing else really matters. We have a “Earth Planet” connect, so what does that mean?

09. “send across her work and her CV” Please don’t ever send .JPG files of photos from your portfolio. Send a link to your portfolio website. If you don’t have one, first make one. JPG files eat up my GMail space and I will have to delete the entire email to make room. You don’t need to ask permission to send me an email or a link – just include the link in the email. Sending an email to ask whether you can ask a question is a bit silly.

10. “figured you’d be a great mentor” Maybe. But it’s a bit presumptuous of you to assume I WANT to be a mentor. To anyone. It depends on the relationship, how much time both parties have, my inclination to take time out to help someone else’s career, etc. Or, I might be a terrible mentor – how would you know ‘O stranger from the Internet?

I get it that he was probably trying to help out his girl and go the extra mile, etc. Road to Hell paved with good intentions and all that.

If she writes to me, with a specific set of questions, I will of course respond. Maybe even suggest a phone chat depending on how the email chat goes. I try not to spend too much time doling out advice – unless I can make a blog post out of it – like this one you’re reading!


More anecdotes and stories in the #WTFNaina series. ( These are all inspired by true stories. Some written emails, some from face-to-face meetings. They have all been piling up for years now and I’ve decided to put them to use! )




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