Advice, Mentors, and Questionably Helpful Emails

Let me start by saying: I hate giving advice and I try not to do it. Typically my “advice” falls under two categories (in that order, often deployed together):

1. Telling people that whatever their reaction (stress, sadness, fear…) is understandable.

2. Suggesting books or lines of thinking that I have found helpful in related situations.

Of course the urge to give advice can be overwhelming and sometimes I find myself breaking my own rules. One of my friends was so overwhelmed recently that having had a small degree of success with strategy #1 (see above) I found myself telling her what to do. And then I apologized profusely. But at least she told me afterwards it was helpful.

The thing I really hate about advice, though, is that often people don’t need advice as much as practical help. I would prefer to offer someone practical help than advice, and failing that I buy people books.

That being said – I have a handful of friends who I started interacting with because they came to me for advice. There are people who did this so well they turned me into a mentor, and then a friend. I am fascinated by people who succeed at this approach, because I tend to go the other way. I become friends with people, and then periodically I will ask them a question. Normally just the one. Because I don’t want to impose.

But these people stand out because they are the exception, not the norm. Sometimes I get requests that just sit in my inbox for weeks because I don’t know how – or just plain don’t want to – respond to them.

One thing I’ve taken to doing this year is replying to these requests and explaining that I am never going to get to their request along with some feedback about how they made it. No-one has yet replied to one of these emails, but I like to think that offering concrete feedback on requests is probably more helpful in the long term than some half-hearted and resentful attempt at the request itself.

So what does a bad request look like?

• Large or undefined in size – a vague “help me with X”, or a long email where I need to decipher the question.

• Requires research – asking for something that is not a core expertise. Memorably someone wanted me to watch a (long) video in order to understand their project.

• Impersonal, generic – it’s not clear why they are asking me, or it’s clear they are only asking me because I used to work for $brand-name company.

• Inconsiderate – the best example here is one a friend gave me, people who ask her to travel across town to meet them because they are “too busy” to come to her.

• Entitled – this comes up most frequently when someone who I barely knew or haven’t spoken to in a long time jumps in like we spoke in the last month. Bonus: they introduce me to someone without consent.

Of course no-one goes into these things thinking they are making a Bad Request. And I’ve procrastinated writing this blog post because I don’t want to seem like a monster, and I don’t want the people who send good (we all have off days, including me) requests to feel bad about it.

Note to people I know: if I reply to your emails, we’re good. If you have my phone number, we’re BFFs.

So what makes good requests different?

• Concrete – they ask for a specific thing.

• Concise – it’s a short email, distilling the essence of the problem.

• Small – it’s manageable, doesn’t require me to look stuff up they could easily find using their favorite search engine.

• Personalized – they have done their research on me and their request builds on things that I have written / blogged / tweeted about.

• Builds a connection – they find a commonality and use it to connect us.

• Contextual – they consider the context of what’s going on with me. One, this is a great way to open the email. Two, it’s a way to figure out when to send the email.

• Followed up – they let me know what happened! Periodic updates regardless of whether or not someone wants something is even better.

• Appreciated – there are a number of ways to show someone appreciation. Supporting projects, sharing work, or recommendations. There’s one person who was an absolute pro in turning me into her mentor, and her friend. My favorite thing that she does? She sends me books. Books that aren’t the kind of things I usually read, but that I end up loving.

The word “mentor” gets thrown about like it’s a magical panacea. The original meaning, from Greek, is “wise advisor”. The question of mentoring is not is it good (it is), or how do you find one (anywhere), but how do you get someone to want to be your wise advisor? And the answer, I think, is that you make it very easy and worthwhile for them to do so.

Which is a simple answer, but a lot of work. The thing is though, the people who do that work, are the most worth helping. Because as in so many things, the advice? That’s the least of it. Advice is easy. Execution is hard.

Cate Huston

Cate Huston has spent her career working on mobile technology and documenting everything she learns using WordPress. Now she combines the two as Automattic’s mobile lead. She co-curates Technically Speaking and admins the New-(ish) Manager Slack. You can find her on Twitter at @catehstn and at

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