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Five and a Half Habits of Highly Effective Designers

We have theories about everything: why the sky is blue, why apples fall, why bees buzz (and do other unmentionable things), why my boss said a certain thing, why that girl in the restaurant looked at me, why didn’t that girl in the restaurant look at me…. We’re wired to theorize. Theories make us feel secure. We can wrap our heads around them and explain them with little diagrams on whiteboards, or with equations, or even graphs. We give theories fancy names like “The Classical Elemental Theory” and “The Flat Earth Hypothesis.”

The bottom line is: we humans love theories. Yet as a wise person once said, “In theory, theory and practice are the same. In practice, they are not.” This article is about practice. It’s about five and a half — yes, half — habits that highly effective designers tend to share and which I’ve observed first-hand in the complicated, non-theoretical, absolutely real world. If practice is your thing, keep reading.

5 1/2 Habits of Highly Effective Designers
This article doesn’t provide an ultimate medicine for becoming a highly effective designer, but it might help you achieve a better workflow.

They Know When To Quit Link

Some of you might know Vince Lombardi as a football legend. I know him as the guy who ruined the world by uttering seven simple yet lethal words: “Winners never quit, and quitters never win.” You’ll find this unassuming little quotation’s fingerprints all over tragic events worldwide: co-dependent lovers who implode their relationships, leaders of warring nations who refuse to compromise for peace, CEOs who won’t back down from flawed strategies to save their company from bankruptcy, and blackjack players who double-down instead of retreating to their rooms.

Admittedly, Vince wasn’t the real offender. He was just a messenger for the real culprit: our humanness. The urge to persevere despite seemingly unconquerable conditions is as human as opposable thumbs. We’re so awful at cutting our losses that there’s even a technical term for this tendency: loss aversion. We strongly prefer to avoid losses than to achieve gains. It’s central to our inability to quit. Quitting has a bad rep, but it’s often the most rational option.

Jerry Maguire’s quitting scene1
Quitting doesn’t necessarily mean pulling a Jerry Maguire2, although it did work out well for him in the end.

As Seth Godin writes in a little book about quitting called The Dip, “Winners quit all the time. They just quit the right stuff at the right time.” It’s worthy, practical advice that can curb the runaway idealist in every designer. Bear in mind, we’re not just talking about quitting your job. We’re talking about quitting things on a daily basis. This entails: picking your battles at work; discerning not just your design goals, but your non-goals; relenting to client needs when necessary; and trading off some design idealism for business karma.

Ironically, quitting can be good for your career. So, that’s the first habit: learn to quit. Let things go. Kill your darlings.

They Redesign Processes Link

I remember when Agile software development methodologies were all the rage. I was working at Amazon as a program manager at the time, and our team was the first to adopt Scrum. Scrum was going to enable us to ship early, with twice the features and zero overhead (at least, that’s how we interpreted Ken Schwaber’s words3).


It would have been nothing short of a miracle, but then again, most of us were fresh out of school, and miracles, free pizza and unicorns were part of our reality. In the end, we shipped almost a year behind schedule, with fewer than half of the planned features. Worse, over 75% of the team quit within 90 days of launch (which is not necessarily a bad thing, as we just learned). Yippee ki-yay!

What’s most worrisome about failures such as these, though, is that they so often occur despite “gold standard” processes. It happens all the time.

Tomes have been written about why our best practices fail so frequently. For a literary (even theoretical) overview, I direct you to two books: The Design of Design4 by Fred Brooks, author of The Mythical Man-Month5 and recipient of the 1999 Turing Award6; and The Black Swan7, by the brilliant, Larry David-like Nassim Nicholas Taleb.

A Website Named Desire8
A Website Named Desire119 illustrates (see the screenshot above) the non-linear and highly erratic nature of the web design process in the real world.

To understand such failures from a practical standpoint, we must turn to another book: Predictably Irrational10, by behavioral economist Dan Ariely. Ariely’s research confirms that predictable irrationality is often the root cause of process failures. Indeed, as A Website Named Desire119 illustrates, our biases, prejudices, quiet agendas, irrational actions and diverse portfolio of imperfections are more often to blame than the processes themselves.

Formal processes work when we accept the irrational nature of people and make room for those imperfections. Thus, the key to successful processes lies in how practically we implement and execute them, not in how well we adhere to an ideal.

Highly effective designers embrace and learn processes — and then tweak them to work well in reality.

They Combat Distortions Of Reality Link

Picture this. You’re reviewing final comps with a set of stakeholders. After multiple iterations, you’re finally feeling great about the design. Then, out of nowhere, a senior manager says, “I think we need to change the blue on the top bar. It doesn’t feel right. I showed it to my wife, who’s pretty good at picking colors, and she felt the same way.” He continues, and then delivers the final blow: “I know you worked hard to find the right color scheme, but picking colors is pretty subjective, right? It’d be worth taking another pass at this.”


How a Web Design Goes Straight to Hell by The Oatmeal12
“How a Web Design Goes Straight to Hell,”13 a classic post on Matthew Inman’s “The Oatmeal”, humorously depicts distortions of reality.

“Design is subjective” is one among many prevailing distortions of reality — ideas that have gone unchecked for so long that they parade around as facts — in our organizations. You might recognize these other distortions: “Data and logic trump intuition,“ “Design is decoration,” and “More feedback leads to better designs.” Then there are those that hit closer to home, like “The page has a fold,” and (everyone’s personal favorite) “Make the logo bigger.” (Note that there is now much14 evidence out15 there16 against distortions like these.)

These clichés seem benign but, in fact, are extremely harmful. They are the proverbial elephant in the room at the heart of dysfunctional organizations. Highly effective designers work to resolve these distortions in their organizations.

They Find The Right Environment Link

People are brilliant scavengers. In a world of a million choices, we know exactly where to look when we need something. We’re good at identifying environments that meet our demands, almost without thinking. We instinctively know how to find certain things (keyword: certain).

When it comes to finding slightly more intangible things — true love, a good job, a great employee — many of us spend a lifetime searching awkwardly and failing repeatedly. We can’t wrap our minds around such abstract pursuits. God knows we try, though; how many times have you heard someone proclaim that they have made a spreadsheet to determine a life choice or a good partner?

Identifying a good work environment falls into the same category. We’re usually terrible at it. Here’s a little secret: highly effective designers are most often products of a good work environment and know how to seek them out.

What does a good work environment look like?

The answer is hidden in a brilliant presentation on clients17 by Michael Bierut. I recommend watching the whole thing, but if you don’t have the time, then watch the four-minute section from 13:00 to 17:00. In it, Michael answers the questions “What do I look for in a client?” and “What should I look for in a work environment?”

Trust, passion, courage and brains.18
Michael Bierut’s presentation on clients19 also answers the question “What should I look for in a work environment?”

The simple answer is trust, passion, courage and brains. Each quality has obvious benefits. In a trusting environment, stakeholders can rely on their designers’ gut instincts20. Where there is passion, the will to make meaningful progress will flourish. Courage enables designers to take risk and bring cutting-edge designs to market. Brains — not genius, but real-world, common-sense brains — bring it all together.

All four of these qualities must exist simultaneously to make a good environment. Take one away, and the environment will eventually become dysfunctional. For instance, take away trust, and you end up testing 41 shades of blue21 to find the right one.

They Habitually Rewrite The Habits Link

In the software industry, we strive to build “perfect” (read: bug-free) things that can’t be improved. This is a worthy goal, but it can have negative side effects. For example, we often conclude that certain practices, processes and lines of thinking have reached their zenith and can’t be modified. We start treating real life like a line of code — a meticulously crafted string, neatly concluded by a semicolon, that reaps a perfect, logical result (needless to say, I’m not referring to Web development here).

Reality — or should I say practice — proves that this kind of thinking is a mistake.

If this article were written a decade ago, it would have listed different habits. A decade from now, I expect some of the habits will have changed; for example, eventually we’ll all agree that “Design is subjective” is a distortion of reality. Heck, if you had written this article, you might have listed completely different habits.

Highly effective designers are aware of this. They’re always questioning, rethinking, improving and refining the dogma. Their methods are best captured by an old Chinese proverb: “All things change, and we change with them.”

There you have it: the final habit. It’s one and a half times as important as the other habits.

Now you know what the “half” means.


Footnotes Link

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Nishant Kothary lives and breathes the Web at Microsoft. When unplugged from the Death Star, he writes at Rainypixels, takes the occasional shot on Dribbble, and etches away at MINKY. He doesn’t tweet much.

  1. 1

    Thanks, I think I need to learn these habits.

  2. 2

    Do you believe you have sufficient understanding of the context of Lombardi’s “winners” statement to draw your conclusion?

    If so, how can we understand Lombardi’s own resignation as Head Coach of the Green Bay Packers after the 1967 season?

    If not, the following may be of interest:
    “When Pride Still Mattered”, David Maraniss
    “Run To Daylight!”, Vince Lombardi
    “Instant Replay”, Jerry Kramer

    • 3

      Nishant Kothary

      February 18, 2011 12:29 pm

      Thanks for the links, Cort. That’s definitely an interesting point about his own resignation.

    • 4

      Who cares, don’t change the subject. If taken at face value, then yes, that phrase blows. Don’t get all into Lombardi like he’s being “misunderstood”. And please relate 1967 football (yawn) to modern web design.

      I would quote Gretzky… you know, about missing 100% of the shots you never take.


  3. 5

    “distortions of reality” – Slam dunk.

    Thanks for the great read.

  4. 6

    The wise man quoted at the beginning of the article was apparently Yogi Berra. He does have some good lines!

  5. 8

    This was a great read! I appreciate the many great references to books, videos and websites, and I just wanted to point out that I’ll be referencing this article many times in the near future. Thanks!

  6. 9

    since you work at MS, can you please tell your engineers to stop IE6 support already?

  7. 10

    I second that Chris, give us a break!

    Why do they insist on using technology from 2002?

  8. 11

    Thank you for a wonderful read.

  9. 12

    The quitting aspect is sound advice…but it’s also a scary situation. If I hadn’t have quit a certain job in the past that was slowly poisoning my career and portfolio (not to mention driving me crazy on a daily basis) I wouldn’t be where I am today: in a great company where your talent is not only appreciated but relied upon. I quit abruptly from that previous job. I finally had reached my wit’s end. I didn’t have anything else lined up and it was a frightening time trying to pick back up some freelance clients to make ends meet until I found a new job. I’d recommend having something else lined up…but sometimes rash decisions end up working out for the best in the end.

    • 13

      Nishant Kothary

      February 18, 2011 12:34 pm

      Great points, James. Turns out that you and I share this experience. My first job sucked in a way that only randomly strung-together profanities could articulate. Much good came out of it, though (fodder for another post). And rash decisions definitely seem to have a way to turn into the best decisions of ones life. Funny how that works.

  10. 14

    Andy Reid-McGlinn

    February 18, 2011 8:00 am

    My favourite article for a while.

    A third party that we’ve employed where I work use the Agile system. I’m not entirely sure if it’s supposed to be an ironic name, as it’s one of the least flexible systems I’ve ever witnessed at work. It also provides a way out for the third party who just bump problems to different Stories and then claim they’re out of scope!

    Every time they’ve handed us work, we amend it using our own process which we call ‘Off the cuff but infinitely more sensible: The Organised Communication Strategy’. Works like a charm.

    • 15

      Nishant Kothary

      February 18, 2011 12:38 pm

      Lol. What a coincidence… I am a big advocate of that process as well (though, your name for it is infinitely more awesome).

  11. 16

    Great article, Nishant. I agree on all points. “They Know When To Quit” is a hard one to overcome. This goes back to the mind does not thing creatively when burned out and when it has tunnel vision.

  12. 17

    “since you work at MS, can you please tell your engineers to stop IE6 support already?”
    I liked wat Cris told..

  13. 18

    Awesome read!
    Great references…

  14. 19

    I was all ready to roll my eyes at yet another amatuerish and blatantly traffic-seeking Smashing “list” post, but was pleasantly – very pleasantly – surprised.

    Thanks for this. It’s not the list that inspires me (it’s fine, but I agree with #5), it’s the way you look at things, the way you express yourself, and the amazing tidbits you link off to along the way. You are everything a great web writer should be, and obviously have the “talent, training, intuition and experience” to speak intelligently and wisely about design and the web.

    Also, I found it gratifying that you are with Microsoft. I’m really sick of the mythical dichotomy of Mac (beautiful, smart, modern, good) vs PC (utilitarian, dullard, outdated, evil). People who need to reduce the world into camps like that are what’s wrong with the world.

    • 20

      Nishant Kothary

      February 18, 2011 12:44 pm

      Thanks for the kind comments, Mave. (FWIW I plead guilty on charges of having a pandering article title and format.)

    • 21

      I wouldn’t compare the Mac/PC debate to “what’s wrong with the world”. Either you work industry standard or don’t. I’m not knocking the PC, but good luck working for a design firm/news/print/anyone and telling them that you use a PC. Unfair? No… just reality. Mac vs. PC isn’t just some internet argument, it’s how the design world works. Be careful with that knowledge my son.

      • 22

        Nishant Kothary

        February 21, 2011 12:01 pm

        I certainly think there’s a preference for designers to be on a Mac, but it’s tough for me to agree that it’s the standard. I know way too many people in the industry (and in education) who design primarily on a PC. Especially if you start talking about outside the US. In any case, I agree with Mave’s general sentiment that the polarization can be annoying (like watching the news these days) and isn’t very representative of how people truly feel…

        In my own case, Microsoft actually bought me my first Apple product ever (a Macbook pro) when I joined the company three years ago. In all my past jobs, it was always Windows/Unix/Linux PCs.

  15. 23

    Thanks for sharing.
    Your statement on knowing when to quit was very helpful. I get asked to do projects all of the time and never turn them down or delegate then, even when I know time is against me. Also I really loved the Oatmeal comic. Clients can be so frustrating; they seem to always want a bigger logo in primary blue.

  16. 24

    This one went over my head – I am moderately successful designer and I am definitely not that disciplined or capable. I do make a good living.

    I don’t even have 5-steps I am more like three:

    1.) Keep your skills current and well practiced
    2.) Learn form both good and bad design
    3.) Be industrious

    The rest is all business and marketing – after that, I suck at most stuff

  17. 26

    Real nice insight into the design of design… The ‘half’ is certainly a valid paradox!

  18. 27

    “Winners never quit, and quitters never win” You never know what should be possible. And is really bad habit to quit something just only 3 steps before gold.

  19. 28

    Satish Chathanath

    February 20, 2011 1:11 am

    I liked the ‘Distortion of the Reality’ the most. I couldn’t agree more with you on the usual manager’s response – ‘Design is subjective’.

    I’d like to add a bit on this…” and the manager thinks that his feedback is very ‘objective’.” When it comes to forms, the same manager wants the entire demo details about the end-users… as many fields as possible. After all, end-users spend time in a site to give you enough details about them ;)

  20. 29

    sushil bharwani

    February 20, 2011 3:36 am

    I like the flow of your content specially starting with “We like to theorize …and theories makes us feel safe”


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