Jensen Harris Profile picture
Father, engineer, designer, 🏳️‍🌈, co-founder and CTO of @textio.
Vedhavyas Singareddi Profile picture gkrasadakis Profile picture Laust Rud Jacobsen Profile picture scott young Profile picture 4 added to My Authors
28 Jun 18
We’ve all felt the anxiety of trying to choose a next job. 😱

Whether starting out in a career, moving to a new company, or choosing a new role/team inside of a megacorp, fear and confusion can reign.

Don’t despair! Here are 4 tips to make your decision easier:
1) Always, always, always choose the people.

The people you work with every day will be by far the biggest factor in your work happiness. This isn’t measured just by whether they’re good happy hour companions or quick with a witty joke, however.

(Though that can't hurt.) 🍹🤭
Great people will be invested in your success. They will celebrate your triumphs and help you through mistakes. They will offer to teach you and mentor you (and it’s mentorship you want!)

Surround yourself by people who you click with, who you admire, who share your values.
Read 21 tweets
20 Jun 18
The concept of work/life balance is wildly outdated.

A holdover from the 20th century, in which work at home meant a briefcase full of legal pads or someone calling your landline, it makes no sense in today’s world.

Work/life balance has outlived its usefulness. Here’s why:
The term “work/life” itself has a bunch of wrong assumptions baked into it.

First, that work is separate from (and not a part of) life. Two, that work and life together comprise the totality of human existence. Three, that achieving balance between them is important/desirable.
This anachronistic idea of “work/life balance” was popularized in the 1970s and 1980s to clarify expectations about what hours workers were expected to be in the office at IBM/GE/AT&T-style megacorps.

In patriarchal terms, during which hours did you have to wear a tie? 👨🏼‍💼
Read 14 tweets
13 Jun 18
Many people working at startups change jobs frequently, while employees of big companies may toil in the same place for decades. 😢

If you work at a megacorp today, how do you know if you’re ready to make the big leap to the startup world?

Here are 5 questions to ask yourself:
1) Are you capable of working in an unstructured environment?

Here’s the thing, even in well-run startups, there’s nothing like the command structure, hierarchy, and clear roles of a huge megacorp.

Big companies thrive on deep layers of people and titles and information.
Startups require you to make progress despite ambiguity. Often times deep ambiguity.

Features aren’t in planning for months. There’s no internal handbook describing exactly how your role works. Every “first” has to be invented.

You kind of have to figure it out on your own.
Read 22 tweets
7 Jun 18
Product design best practices dictate that you should ask what customers need and build that.

But a product that you don’t deeply want to use yourself won’t have a soul. Most of the world’s great products were born of personal passion.

Build for yourself first. 4 reasons why:
1) When you are designing for you, the customer is not abstract.

So many bad products have been designed based on generic business plans or analyses of “unmet customer needs.” Yes, there are ways to get great customer signal but that is always one layer abstracted from yourself.
Facebook started because… well, you've seen The Social Network. The Uber guys wanted to tool around in fancy black cars. @stewart + the Slack team started building a game and instead realized what they cared about was the chat software they were building for themselves to use.
Read 19 tweets
30 May 18
The “Minimum Viable Product” (MVP) is the most well-known, admired concept in early startup product development.

Unfortunately, MVP is often misused in a way that actually harms early-stage startups, leading them to create needlessly bad products.

4 thoughts about better MVPs:
1) MVP doesn’t automatically mean “ship a bad UI.”

The word MVP can end up being used as a battering ram against people who argue to flesh out the product design more, to make the user experience more complete.

Instead, the barebones-ness itself becomes a badge of honor.
The key misunderstood word in MVP is “viable.”

@ericries writes about this pretty clearly. Simplifying, you want to, in the quickest possible way, get to a product you can learn from and then measure if users are finding value in it. Only then should you invest more in the idea.
Read 19 tweets
23 May 18
It seems like every company is tripping over themselves in a rush to say their software is “powered by AI.”

But saying “powered by AI” is like saying you’re “powered by the internet” or “powered by computer code." By itself, it means nothing.

Here’s how I think about it:
1) Most “now powered by AI!” is just a rebranding of the same heuristics and rules engines software has used for decades.

When your email program keeps track of what folders you use most often and magically offers to file mails to them, that’s a simple algorithm, not “AI.”
Software has been adapting to users for decades.

The old Microsoft Office “smart” menus and toolbars rearranged based on your usage (“powered by AI!”) as early as 1999.

Learning spam and antivirus filters have been around for more than 20 years.
Read 15 tweets
22 May 18
Startups are exponential. There's an enormous mountain to climb from founding to success.

In the spirit of the famous "Powers of Ten" film by the Eames Office, here's an exponential look at startups. Each step is a 10x increase beyond the previous one.

Startups by the numbers:

The number of chances you get to choose your founders.

Select right and you have a chance to make it big. Choose wrong, and no matter how great your idea or technology or product is, you will eventually fail.

The number of employees you'll have before you don't fit into someone's apartment anymore.

Someone will be constantly filling up the coffee machine's water reservoir, and you'll have the first instance of someone leaving something bad in the bathroom that no one owns up to.
Read 14 tweets
18 May 18
As a founder, meeting with a VC can be intimidating. It can seem like the VC has all the power, your dream's future at stake.

Yet, it doesn't have to be this way; pitching can be respectful and mutually useful, even if it's a no.

Here's a Simple Guide to Being an Empathetic VC:
1) Offer constructive feedback.

In one of the first meetings for our seed round, a highly-respected seed VC (who passed on us and probably doesn't even remember this) asked what our go-to-market plan was.

We thought for a minute and said "well, I guess build it and sell it?”
Without being disrespectful, he gave us gentle but clear feedback in the moment that our answer wasn't actually a go-to-market plan, and offered a framework for how we might think about one.

Though he doesn't know it, that small kernel of advice took root.
Read 21 tweets
16 May 18
There are certain behaviors in a job interview that cause automatic disqualification. Earlier in my career, I made several of these mistakes myself.

Unfortunately, I see these pretty much every week. Here are 5 of the worst behaviors that everyone should avoid when interviewing:
1) Don’t talk bad about all of your previous managers.

Yes, it's true: many managers are mediocre and some are outright terrible. I have no issue with someone relating that they worked in a hard or unstable environment, as long as they do so respectfully.
But when I hear constant blame, that every single thing that went wrong was because their manager was stupid, bad at decision making, inept, etc., I can't help but think "this is how you'll talk about me in 18 months when you're at your next job interview.”
Read 17 tweets
11 May 18
Whiteboard coding is a pretty broken way to gauge developer skills.

For years, companies have "proven" that they hire only the best and brightest by putting interviewees through rigorous algorithmic puzzle solving on the whiteboard.

It's kind of dumb. Here's why:
1) Whiteboard coding is literally never a skill you need in real life as a software engineer.

Judging a developer by their ability to code on a whiteboard is like deciding to draft an NFL quarterback because of how many points he can rack up on his Xbox playing Madden.
That's not to say that knowing how to sketch ideas, data structures, architectures, or bits of code on a whiteboard isn't a useful arrow to have in an engineer's quiver; it definitely is.

But daily coding rarely involves writing functions longhand in a high-pressure situation.
Read 16 tweets
8 May 18
There’s no such thing as a “startup inside of a big company.”

This misnomer actively misleads both big company employees working in such teams as well as people toiling in actual startups.

Despite all best efforts to create megacorp “startups”, they can never exist. Here's why:
(And, by the way, I ran one of these “startups inside of a big company” myself and at the time thought it was basically a startup.

We had a cool name. We were small, lean, and agile and dreaming about the future and had a $50,000 3D printer. This was not a startup. I was wrong.)
1) The most fundamental, pervasive background thread of an early-stage startup is that when it fails, everyone has find a new job. The company is gone, kaput, relegated to the dustbin of Crunchbase.

The company literally lives & dies on the work every employee does every day.
Read 18 tweets
5 May 18
While Microsoft officially stopped putting "easter eggs" into their software around the year 2000, harmless little eggs still made their way into Microsoft Office.

Some of these were intentional, and some were not.

Here are 3 of the eggs that I know about in Microsoft Office:
1) The fountain in the Insert Caption tooltip in Microsoft Word.

In Office 2007, we added what we called "Super Tooltips", basically extra informative descriptions of the feature that could include an illustration.

We were excited about this, but hadn't planned it end-to-end.
When I asked the UA team (in charge of UI text) to write all of these descriptions, they came back and said they only "had budget" to write about 12 of them across the entire Microsoft Office suite.

We had a set of incredulous meetings but it became clear they weren't budging.
Read 22 tweets
4 May 18
Interviewing at a startup can be totally perplexing. Some startups pride themselves in having "no processes", leading to a confusing, inscrutable experience. Don't lose hope! 😕

Here are 4 warning signs that you may want to steer clear of the startup at which you're interiewing:
1) Repeated misfires on communication. This can be anything from the recruiter calling you Cindy when your name is Stacy (a mistake we made with a candidate early in our company) or making an appointment for a chat on the phone and then you never get the call.
People do make mistakes from time to time, but if you've started the process with an initial conversation (doing an informational with a recruiter or member of the team) and then don't hear anything for a long time, it probably means they are not into you. It's ok... move on!
Read 20 tweets
25 Apr 18
When you're leaving a big company to interview at a startup, there are some hidden questions you might not know to ask.

Not all startup jobs are created equal; without the right info, you could make a bad choice.

Here are 4 questions you should ask in a startup interview loop:
1) How much money does the company have in the bank?

OK, yes: this sounds super crass... an embarrassingly direct question. But it is also incredibly crucial, because without this info, you have no idea what kind of situation you are potentially walking into.
You would never ask this question at a megacorp because, well, the answer is usually "infinite money." The cash position of a public company is also usually freely available. Besides, you probably wouldn't be talking to someone who could give you a direct answer anyway! 🤑
Read 20 tweets
23 Apr 18
As I detailed a few days ago, there was a secret, unsolved puzzle quietly embedded into default Windows wallpapers.

It was misinterpreted as an advanced "anti-leak" security measure by many users, leading to all sorts of craziness.

I also promised you the solution. Here it is:
If you need to catch up on the original story, you can find it all here:
One of the most interesting thing that popped up in the discussion was that not only did users outside of Microsoft believe the wallpaper was some form of security, but the Xbox team also did and copied a version of what they thought it was for Xbox:
Read 7 tweets
21 Apr 18
Here's some puzzle solving fun for a Friday night.

As we developed Windows, one of the minor decisions we had to make was what wallpaper to use for various internal builds.

These builds always leaked outside of Microsoft, so we knew that the wallpapers would also end up public.
Traditionally, these wallpapers included text embedded in them threatening to throw people in jail if they leaked the build, blah blah, substantial penalty for early withdrawal, not all coins go up in value (some go down!), etc. etc.

We wanted to try a more elegant tact.
So early in Windows 8, we created a wallpaper that was a combination of the text the lawyers wanted us to use with an attempt to appeal to people's better nature...

...thus the "shhh... let's not leak our hard work" series of wallpapers was born.
Read 13 tweets
12 Apr 18
Leaving a big company job for a startup can rejuvenate your career and make you love work again.💖

But landing a startup job requires relearning some things, especially if (like me) you logged years and years at Microgoogfaceforceazon.

Here are six things I wish I'd known:
1) At a startup, you will probably make less money at first.

Yes, if you join the perfect startup early enough, your equity may someday turn into a private island and 200 foot yacht. But, in the meantime, your take home pay is likely going to be a bit less than it is now.
The so-called “golden handcuffs” that big companies give you in stock grants/bonuses that vest over time are because those companies need to overpay you in order to get you to stay.

Think about the metaphor for a second: You don't have to handcuff people to things they love.
Read 19 tweets
22 Mar 18
A few days ago, I wrote about the self-loathing I feel when I get “twitchy Slack finger” and impulsively switch to a channel to read something funny/interesting in Slack and, as a result, lose whatever I was previously reading forever.
There’s nothing easier (or really more cowardly) than poking holes in someone else’s user interface if not paired with constructive thoughts on how it might be improved. So, as promised, here are a few thoughts about some ways forward for Slack’s UI.
Read this for context if you missed the original conversation the first time around:

Ok. Let’s start with just 3 ideas for tonight.
Read 25 tweets
14 Mar 18
My day is spent in mortal fear, worrying that I'm going to accidentally click away in Slack and forget what channel or DM that last important thing I forgot to mark for follow up was in.
As the first Slack-native companies without internal email cultures get larger, Slack will need to grow up to solve their problems the same way email had to grow up two decades ago.
When I led the redesign of the Outlook user interface in 2003, we felt similar growing pains: people were getting 5x, 10x, 100x more mail than they ever got before. Users felt out of control; they lacked the tools and affordances to manage this constant deluge.
Read 17 tweets