Ask A Manager


Last summer, my little corner of the Internet blew up with a post on Ask A Manager, a workplace advice column by Alison Green. The letter writer said that 10 years ago, he’d ghosted on his girlfriend of three years. While she was visiting her family, he moved out—not just of the home they shared together, but of the entire country—without so much as a Post-It note. And then, as karma would have it, he learned that his ex-girlfriend was about to become his new boss. Oof. Alison responded with her trademark thoughtfulness and honesty:

I don’t know that you can salvage this! It’s not reasonable to ask Sylvia to manage someone who she has this history with. You can try and see what her take on it is, but I’d be prepared to have to move on, whatever that might look like for you. I get that it’s going to be inconvenient — maybe even quite hard — but there may not be an alternative here.

I got hooked on Ask A Manager with this post, but I’m a relative latecomer to the party. Alison’s been dispensing workplace wisdom for a decade now and today she launches a new book that provides practical advice for how to talk to managers, employees, and coworkers about a huge range of topics, from asking for raises or promotions to handling awkward social situations at the office. On the latest episode of Rework, I interview Alison about how she became an advice columnist, how she’s cultivated a community of surprisingly nice commenters, memorable letters (like the ghosting ex), and more.

Advice to a younger me

Go Cubs Go

Someone recently asked me advice I’d give my younger self. Well, here are three things of an endless list 🙂

Don’t be embarrassed

I think I’ve done a relatively good job putting myself out there in the world, but I can still point to many moments where I should have done one thing, yet did another. I didn’t release that app. I didn’t start that blog. I didn’t go to that audition. Because I was too embarrassed.

That fear of embarrassment is the key thing holding most of us back from the stuff we really want to achieve. The best of us are out there trying as hard as they can without fear of embarrassment, and yet they screw up constantly. They just deal with it. And quickly move on.

I bet there’s something you’re considering doing right this very second but keep putting off just because you fear what others are going to think. I know I am.

Become a better storyteller

I’m obsessed with becoming a better storyteller. Not just in words and articles, but now especially with video. How can I better inspire/captivate/motivate people through my content and ideas?

One of the key lessons there is to think about how an article or video or whatever leads people from one end of the spectrum in a strong human theme to another (hate/love, fear/security, despair/happiness, failure/success, embarrassment/pride, ignorance/genius etc.) Show people how the hero struggled to find love from a hateful place, or overcame great odds to go from failure to success, etc.

And it doesn’t always have to go from “negative” to “positive”. People crave authenticity. It’s ok to show people an autobiographical story of you moving from something good to something bad. Of course, they’ll probably love to tune in again to see how you can reverse that course.

A book I’m hooked on right now is Story. It’s about screenwriting, but really it’s universal. You want to write a blog post that keeps people’s attention, figure out how screenwriters and movies get people to stay in their seats.

Learn what really makes “good design”

Sounds like you’re focused on being a great developer. That’s awesome. But I wish my younger self also spent more time early on figuring out how to be at least a moderately ok designer. Too many people think they can’t design, just because they suck at things like picking aesthetically pleasing colors. They feel like, “I can’t make things that look good. Shit, I can’t even pick nice furniture for my home. I can’t design.”

Yes, there are some ridiculously good designers and their talents should be employed and not taken for granted.

But as a solo developer you don’t want yourself stuck in a spot where you can’t get a project out the door because you can’t find someone else to craft something that you think is “good design”. Figure out some basic principles of what makes great design.

Here’s one: writing.

It’s similar to watching video. Sure viewers want great visuals, but if the sound is terrible you’ll walk out. The opposite isn’t true. People watch poorly taken video all the time as long as the sound is good.

Same goes for writing. The “aesthetic” design can lag, but the copy can’t. It needs to be engaging, helpful, clear.

And there’s some great resources that can help you see a few basic principles to making good design. One of my favs is Bootstrapping Design.


I could go on and on.

P.S. If you enjoyed this article, you should follow my YouTube channel, where I share more about how history, psychology, and science can help us create better businesses. And if you find yourself overwhelmed while organizing your own small business or customer feedback, check out how Highrise can help!


It never hurts to ask


A simple, effective piece of advice from Jason Fried

A couple of years ago, Jason Fried gave me the simplest, most effective advice I’ve ever received:


It seems so obvious, something you’ve probably heard before: it never hurts to ask. But when you actually put that advice into practice, the results are rather amazing.


In 2014 we sponsored a project management conference. As sponsors we got all the usual promotion: our logo on some slides, some tweets, email callouts, etc.

We wanted to get the most out of our sponsorship, so Jason encouraged me to get creative with what we could do. Here’s what I said:


Jason completely agreed, but I couldn’t think of a good way to pull this off. How could we clearly announce who we were and give them a sense of our friendly personalities? 😁


Aha, what a great idea — that would accomplish exactly what we wanted!

But…stage time wasn’t part of any sponsorship package they offered. And as one of the world’s worst negotiators, I was hesitant to ask for something outside of the existing options. 😶

But I needed to learn. I got over myself. I sent an email to the organizers asking nicely and explaining why it was so important to us.

You can probably guess what happened next. We got our stage time. The organizers were happy to accommodate us. It wasn’t a big deal at all.

And from that one success, I burned Jason’s advice into my brain: it never hurts to ask.


Since then, I’ve had plenty of success with Jason’s advice. Yet I’m still fascinated by how well it works.

Last week I was reminded how simple and powerful “just asking” can be.

I’d written an article about how I built my first Android open source library, and was looking for ways to share it beyond our normal blog audience.

I’m a big fan of The Practical Dev, and I figured the article might be of interest to their audience. But how could I get them to share it?

I remembered Jason’s advice — it never hurts to ask. So that’s exactly what I did. I sent them a link to my article and politely asked if they’d consider sharing it. A couple of hours later they were nice enough to do so. Success!


Perhaps unsurprisingly, this advice can also apply to product design.

In the Basecamp 3 Android app we recently added a “what’s new” dialog. This lets customers know what new features we added, but also gives us a chance to ask for their review.


Any idea when we started asking for reviews? 😏

I fully admit I was skeptical that a simple “rate us” button would have any impact our ratings.

Wow, I couldn’t have been more wrong. Our positive ratings and reviews skyrocketed! 🚀

Once again Jason’s advice held true — all we had to do was ask for reviews, and people were happy to do it.


I can’t tell you how many times “it never hurts to ask” has turned out positively for me. Even if I don’t end up getting what I hoped for, it’s still nice to know that I at least asked. Nobody gets offended or upset by reasonable requests. ¯\_(ツ)_/¯

I think this comes down to one fundamental truth: people want to help you.

Sure, not everyone is super generous. But as a rule I think most people try to be. If you ask for something in a nice, humble, and confident manner, they’ll try to find a way to help you.

So the next time you want something, remember: it never hurts to ask!


If you liked this article, I’d really appreciate if you click the heart button down below. And if there’s anything I can help you with, just ask!

We’ve been hard at work making Basecamp 3 and its Android app the best way to run your projects and small business. Won’t you give them a try? 😀

I’m New Here…

A couple of months ago, I made a big decision. I joined Basecamp as its first-ever COO. Once I came aboard, I was immediately reminded what’s tough about joining a new company.

There’s a lot about the company you don’t know.

And one of the hardest things is where to start.

Especially when you’re in a new role for a company like Basecamp.

I had a head start. Jason and David were clear and unwavering about the charter from the outset: We want to operate the company with as much love and attention and care as we already put into building our products. We want Basecamp the company to be outstanding at every level.


That still leaves a lot of wiggle room. Where do you start with a company that is already so great to begin with? A company that trusts its employees to choose and figure out what to work on. How I can I do that when I’m new?

But that’s the magic. I’m only going to be new once. Being new wasn’t the predicament, it was the breakthrough.

I came in with fresh eyes and an open mind. It was like wearing 3-D glasses. Everything was intensified. I had no pre-conceived notions and plenty of room for new thoughts. I had the gift of fresh perspective.

So what did I do with this gift?

I spent the first week going through our company basecamps. Luckily it was all waiting for me: The marketing basecamp, the team OMG (our support team) basecamp, the data basecamp and many others. They were all there with their to-do’s, message boards, documents and threaded discussions. It didn’t matter how long ago my colleagues commented in these basecamps. It was all there for me to see, review and learn from.

I asked for and received written responses from almost everyone in the company to a message I posted seeking advice for newbies. My colleagues were helpful, generous, funny and a little irreverent in their responses — just like our culture. Advice ranged from …and never, ever, drink the Malört to drink the Malört, it’s totally fine. It’s only gross when you can smell it, are drinking it and for a few short hours afterwards.

I was in several hang outs with my colleagues. Each hang out was different. I listened to their questions and asked where they thought I should start.

I went to our meet up. I got to meet almost everyone in the company face-to-face. It was great. I tried to speak everyone personally and asked them what they thought I should focus on first.

After that I asked questions. A lot of questions. Some were in one-on-one pings and others were in response to threaded discussions about specific topics.

I read books that were recommended to me.

I helped answer support tickets for our customers.

I listened in campfires and piped up when I had a question.

Then something magical happened. Big rocks (from Rockefeller Habits) started coming into my field of view. All the interlocking pieces came together in my mind’s eye. I chose (with a little help from Jason and David) and figured out which big rocks to focus on for Basecamp.

I’m new here and that’s a good thing! 😀

A few words of advice to brain pickers

A few times a week I get an email from someone asking if they can pick my brain for 15 minutes. I appreciate their interest in what I might have to share, but when it’s pitched as a brain pick they’re making it hard to say yes.

I’m all for giving back, and I try to do it as often as I can, but I wanted to extend three quick points of advice to people who ask to pick people’s brains.

1. Picking someone’s brain sounds like an entirely one-sided appeal. Give me what’s in your head. That’s a hard sell — especially when you are pitching someone who’s busy and occupied with trying to focus on their own business. Whenever you ask someone for something, always ask yourself what’s in it for them? What can you do to fill their brain rather than pick their brain? So, rather than pitching it as all-take, try pitching someone some give, too. “I’d love to ask you a few questions about X, Y, Z, and at the same time share some perspective I have on A, B, an C.” Everyone has perspective, everyone has experiences that are unique to them. The more you can suggest that it’s a give and take, and that the person you want to talk to could learn something from you too, the better the chance of lining up the opportunity.

2. There’s no such thing as a 15 minute call, or coffee, or meeting with someone you don’t really know. It takes 5 minutes just to say hello and warm up. It takes another 5 minutes just to begin to get into a conversation. And then you’re left with 5 minutes — which is never really enough time to have a substantive conversation (which is the kind of conversation you really want to have). So just be honest and set the expectation clearly, because surely the other person doesn’t believe you’ll only be taking 15 minutes of their time. Suggesting it’ll only take 15 minutes either says to me you’re being disingenuous, or you aren’t sure what you really want to talk about. “I was wondering if you might have a full hour for an in-depth conversation about this product problem I’m struggling with… It’s…” makes me take you more seriously. I still may not have an hour, but I know you understand what you’re asking for.

3. Offer to come to them. When you are pitching someone, and asking for their time, you want to make it as easy as possible for them. And one of the best ways is to offer to come to them. Don’t pick a lunch spot or a coffee shop. Don’t even suggest a time (“lunch” is a time, “coffee” is a time). First suggest that you are willing to come to them or meet them wherever and whenever they prefer. That shows you’re courteous, concerned with their time (when they don’t have to go anywhere they save travel time), and it shows you are willing to make more of an effort to make the meeting happen. “If it would be easier, I’d be happy to come to you or meet you wherever is most convenient for you”.

If you follow these three simple rules, I think you’ll increase your odds of landing a meeting with someone. The odds may still be slim, but at least you’re setting yourself up to show that you 1. know what’s in it for someone else (you’re asking but you also have something to offer in return), 2. respect the true time involved to have a substantive conversation (and that that’s what you want to have), and 3, that their location and time is easier for them (and if it’s not, they’ll tell you).

Hope this helps!