Trial and Error Expert: Alison Green

Alison Green knows a thing or two about trial and error.

She’s become known as a go-to advice writer for work issues, and her audience writes in from around the world to ask her about everything from salary negotiations to unbearable coworkers on her blog Ask a Manager.

She responds with headlines that grab your attention, and her straightforward advice cuts right through the clutter to capture the essence of any complicated problem. She has been one of my favorite writers for years, and I’ve loved witnessing her success. Chances are, you’ve read her column in The Cut, or maybe stumbled across her work in Inc, Business Insider, or US News & World Report. Maybe you’ve even read one of her two books or listened to her Ask a Manager podcast. If you haven’t, today’s your lucky day… Check out her four questions to my most pressing questions below.


In less than a decade, you’ve become a national thought leader in writing about career advice, especially when regarding the job search and conflicts in the workplace. Not only does your Ask A Manager blog receive more than 2 million visits each month, your weekly column in New York Magazine’s The Cut is an absolute hit. What has been one of your proudest moments when you reflect on the past ten years?

It’s funny — when I first started Ask a Manager, I figured hardly anyone would really read it. I thought I’d do it for a few months for fun, and that would be it. So it’s been amazing to watch it grow.

But the thing I’m proudest of is when I hear from people that my advice worked for them — whether it’s that they successfully negotiated a raise, or left a toxic job for a much better one, or just spoke up and advocated for themselves in a situation where they’d been hesitant to do that. I feel really lucky to have a platform that lets me connect with people like that and help them get good outcomes for themselves!


One of my favorite aspects of the way you write is how you offer your readers straightforward answers to complicated, convoluted questions. What does your writing process look like when responding to reader’s questions? Can you think of a time when you were truly stumped by a work-related situation submitted by a reader or in your personal career?

Most of the time, I treat letters the same way I’d treat it if a colleague walked into my office with a problem — in this case, the discussion is just in writing and it’s usually one-sided.  But I write pretty much the way I talk, so what you see at Ask a Manager is pretty similar to what you’d get if you walked into my office agonizing over a problem.

I definitely do get stumped sometimes! Depending on the question, it might mean that I put it aside and let it percolate in my head and come back to it later. This is an example of a letter like that ( — I had to put real thought into figuring out how to advise navigating that situation. But other times, if I’m stumped, it means that the question goes in the pile of questions I don’t answer. I get way more mail than I have time to answer, so there are a lot of questions that do end up going unanswered.


I just recently graduated from college and am beginning my career after years of summer jobs and internships. Your advice articles have been infinitely helpful, and it’s honestly tough to think of questions that you haven’t discussed and answered expertly. I’ll ask you to synthesize some of your own advice instead. So, if you could go back and tell your newly-graduated, young professional self only three pieces of advice, what would they be?

One, choose your battles! Not everything that’s frustrating is worth taking a stand on. Two, you can learn a ton from bad managers. Pay attention and watch where they go wrong; there are free management lessons in there. And three, always ask for more money when you’re getting hired or promoted. Well, almost always.

What major lessons have you learned from your professional success?

For me, as a writer, one big lesson has been about following your instincts. I’ve always followed my instincts about content on my site. I’ve never done any SEO or marketing; I’ve just written content that I would want to read — things that I’d find interesting, entertaining, amusing, or useful, and I’m convinced that’s what readers have responded to. I think it would be a very different (and less enjoyable) site if I’d followed all the SEO advice that you’re supposed to follow.

Another one is, sometimes you have to turn down work in order to make room for even better things to come your way. As someone who’s self-employed, I used get really anxious about turning down work — because what if nothing else came along to fill that space? And so I ended up way over-scheduled and overworked, because I didn’t want to turn anything down. I finally realized I couldn’t say yes to everything and got comfortable with turning things down, and it’s allowed me to still have breathing room available when something really cool comes along that I really want to say yes to.

Other lessons … Can I repeat “always ask for more money”? Always ask for more money! You’ll often get it.


Be sure to check Alison’s blog out the next time you’re stumped at work or in the mood for an entertaining story, and I promise you won’t be disappointed.

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