The Job Interview From Hell

When an interview with a prospective hire ends, “Good luck with your shitty app,” you know there was a wrong turn somewhere. Yesware CEO Matthew Bellows deconstructs a disaster.

The Job Interview From Hell


Matthew Bellows is the CEO of Yesware, an extension for Gmail (and soon, other clients) that helps salespeople track the success of their missives. Bellows is also an expert on another kind of sales–specifically, how a job applicant should not sell himself to a prospective employer. We caught up with Bellows to get the story of a recent job interview gone horribly wrong.

FAST COMPANY: So you came into some funding, and were looking to hire.

MATTHEW BELLOWS: We recently closed a $4 million A round. We want to bring Yesware to mobile phones and many other places, so we’re building up the engineering and product development team. We spend a large amount of time here and don’t like to spend time with jerks, so we’re pretty picky. We have a rigorous interview process, and usually do two phone screens before we bring someone in.

Earlier this month, you brought someone in.

This guy reached out to us. He said, I’m using your product and I think it’s awesome, but I think there are some areas were it could be improved. I love stuff like that–an engaged user, that stuff is so valuable. One of our engineers looked this guy up and saw he was a front-end designer, and his portfolio looked good. We had an opening, so I called him back. We had a nice chat for about 45 minutes. He was working on a startup project that wasn’t going that well, and was interested in a full time job.

So at this point he seems like a normal, good candidate?


He seems like a good candidate. He writes thoughtful comments, we have a good chat. Maybe I had a bit of rose-colored glasses. But I’m excited when he comes in. We have a little chat, and then I leave him with our front-end engineer. The engineer comes and gets me about 30 minutes later and says, “Why don’t you come in? He has some feedback.”

More feedback?

He basically thinks we should completely change the user interface, remove it all, and disappear into Gmail. I was asking, “How would you test that? How would you verify this is a better solution for our customers?” I’m trying to determine, is he an artistic, my-way-or-the-highway, Steve Jobs kind of designer? The more we get into it, I realize this guy has very strong opinions, but he has very little knowledge about how to actually test to figure out which works better for our customers.

But at least he has a bold vision.

At this point I’m still kind of on board. He’s talented, he’s smart, he’s got a ton of experience. I’m thinking, he may be hard to work with, but this actually might work. For me, though, the final straw was when he started talking about another company. He’s going on and on about how great they are and how much money they’ve raised. I get a little bit annoyed and say as gently as I can, “We’ve had some news recently, too? Have you seen that?” He was like, “Nope. Haven’t done it, haven’t seen it.”

Just brusque and dismissive?


Like, “It’s just not worth my time. It’s irrelevant. Why are you asking me?” Maybe he was embarrassed, so he put a front up. Either way, it didn’t matter. He hadn’t even looked at our blog to see we had raised a Series A round from great investors, Google Ventures and Foundry Group. That this guy could come in, tear up our UI, recommend completely changing the look of the app, and then not have even taken the time to look and see what’s up with the company before a two-hour interview with me and my front-end engineer–just drove me batshit. I contained myself. I said as politely as I could, “I don’t think this is gonna work out. I appreciate your time.” And I reach across the table and shook his hand. He looked at me like he had been smacked across the head with a two-by-four.

And was his response polite?

In my mind it’s all fine at this point–we’re gonna end this amicably, with no hard feelings. Like a date, you want to maintain a sensitivity so both people can emerge with their dignities intact. I go to open the door, I’m going to walk him out, and he says to my engineer, “Good luck with your shitty app.”

That contradicted his previous claim to be a fan.

I say, “What did you just say?” He says, “I said, ‘Good luck with your app.’” I say, “That’s not what you said. You said, ‘Good luck with your shitty app.’” He says, “I’m giving you gold and you’re throwing me out the door!” I say, “I wasn’t throwing you out the door before, but now I am.”

I’ve had interviews that didn’t pan out, and they more typically ended with polite nothings. Why’d you think it was best to cut to the chase?


In subsequent interviews I’ve tried to be more gracious in ending them. It was something about his overall egotistic approach which got me angry. The last thing I wanted to do was waste any more time with this guy who couldn’t be bothered to spend five minutes of his time before the interview. The investment a candidate makes in the job before going in is a great indication of the investment they’ll make at the actual job. If someone can’t be bothered to make a cursory examination of your blog posts, or your background, it means they just don’t care.

What are the lessons to be learned here?

For applicants, the obvious one is: Do your homework. On the interviewer’s side, maybe I could have detected the arrogance earlier, if I hadn’t really been hoping it would work out.

What do you think he’ll be doing in five years?

I hope he achieves his dream–that he finds a great startup where he can contribute, or that his startup catches on. That’s what I hope for him. There are plenty of arrogant people who are very successful in business. I’ve met a lot of people like him in consulting, or in banking, or in the venture capital world. Those industries are much more accepting of and interested in strong opinions, regardless of whether there’s data behind them. Those businesses seem to be full of people who just are sure what’s gonna happen in the future, even though none of us actually know.

Good luck with your app.


It’s free to try.

This interview has been condensed and edited.

For more from the Fast Talk interview series, click here. Know someone who’d make a good Fast Talk subject? Mention it to David Zax.

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[Image: Flickr user kellbailey]


About the author

David Zax is a contributing writer for Fast Company. His writing has appeared in many publications, including Smithsonian, Slate, Wired, and The Wall Street Journal