Blog Post

Getting Comfortable With People Who Make You Uncomfortable

weird_guy If you’re out to create something truly great, you’ll likely need to challenge some widely held — but incorrect — beliefs. Challenging conventional wisdom is much harder than most people realize, and those that do make us uncomfortable. Which is why it’s so important to learn how to identify and embrace people who see the world differently than you do.

Evolutionary Biology and Conformity

Imagine our ancient ancestors out on the savanna in search of food. Chasing a large group of hunters who were running after something out of view was probably a better survival strategy than pursuing animal tracks that may or may not have led to food. Gregory Berns argues that mankind’s propensity to follow the crowd is at least partially a result of evolutionary biology.

Such a propensity is so ingrained in human nature that we will go to ridiculous lengths in order to adjust our beliefs to those of a group, as proven in the series of conformity experiments run by Solomon Asch in the 1950s. According to Wikipedia:


In the basic Asch paradigm, the participants — the real subject and the confederates — were all seated in a classroom. They were asked a variety of questions about the lines (which line was longer than the other, which lines were the same length, etc.) The group was told to announce their answers to each question out loud and the confederates always provided their answers before the study participant. The confederates always gave the same answer as each other. They answered a few questions correctly but eventually began providing incorrect responses. In a control group, with no pressure to conform to an erroneous view, only one subject out of 35 ever gave an incorrect answer. However, when surrounded by individuals all voicing an incorrect answer, participants provided incorrect responses on a high proportion of the questions (36.8%). 75% of the participants gave an incorrect answer to at least one question.”

It’s very challenging to make decisions based on your own information and logic when everyone disagrees with your point of view. We have an urge to conform, as we learn again with each economic boom and bust. Unfortunately, as David Hirshleifer describes in “The Blind Leading the Blind:  Social Influence, Fads, and Informational Cascades,” “If there are many individuals, then…with virtual certainty a point in the chain of decisions will be reached where an individual ignores his private information and bases his decision solely upon what he sees his predecessors do.”

Weird Ideas That Work

The inspiration for the title of this post came from the book “Weird Ideas That Work,” in which Robert Sutton suggests hiring “people who make you uncomfortable.” He argues that employers typically hire people like themselves and that most interviews are more about the social fit between the candidate and interviewer rather than the candidate and the job.

So what can you do to embrace those who make you uncomfortable?

1.  Identify your heroes.

Chances are that the historical figures you hold in high esteem made those around them uncomfortable in their day. Einstein did. Gandhi did. Jefferson did. Apple’s “Think Different” campaign was as much about communicating what the company stood for to its employees as it was about selling Apple products to its customers. An organization that embraces unconventional thinkers has an unfair competitive advantage in a world governed by conformity.

2.  Adjust your hiring process to focus on what really matters.

Jeff Cordova, a former Yahoo colleague of mine, puts all engineering candidates through a code test before he determines cultural fit or the like. He literally sits down in a room with a candidate and spends a few hours coding up an application with them. At the end of the test, he has a very good idea of their software engineering skills and often asks other members of his team to drill down in a particular area of expertise. It’s only after qualifying their skills as an engineer that he allows his team to determine their “fit” within the organization.

While software engineering is relatively easy to test, you can apply a similar type of testing process for just about any role to reduce the impact of social bias in hiring.  Microsoft notoriously put candidates through case study interviews (I don’t know if they still do), as documented by William Poundstone in “How Would You Move Mount Fuji?”

Spend more time thinking about interview-based experiments that you can run on candidates to test what really matters for the role and you might find yourself hiring a different type of person.

3.  If you have a negative reaction to an idea, use the 5 Whys.

The 5 Whys is a method to get at the root cause of a problem. When you hear an idea, before you immediately respond, try to understand the underlying reason for your knee-jerk reaction. You may find that your reaction is more about protecting existing orthodoxy or the source of the idea than it is about the merits of the particular approach at hand.

4.  Consider increasing organizational diversity.

The true benefit of diversity is that it has the potential to produce better results.  Diversity along the lines of age, gender, race, religion and sexual orientation has the potential to make an organization more resilient to conformity. Different people from different backgrounds bring in different biases. And groups that have experienced greater prejudice may have a membership inoculated from group think as a matter of self-preservation — that is, when everyone hates your group, you tend to hold a differing opinion.

It’s not easy working with one of the rare people who is deeply nonconformist. But if your goal is to be innovative, to create something great and to make a difference in the world, you should be prepared to make those around you uncomfortable and recruit others who do the same to you.

Mike Speiser is a Managing Director at Sutter Hill Ventures. His thoughts on technology, economics and entrepreneurship will appear at this time every week.

22 Responses to “Getting Comfortable With People Who Make You Uncomfortable”

  1. Walter Bob

    Good article. When I work with folks I find it more appealing to focus on cognitive and experience diversity instead of diversity along racial, gender, age etc lines.


    Well written article. This approach may work in a larger company. In small companies, startups that I have either worked for or started the demand for talent, scarcity of talent and time pressures forced us hire the best person that we felt could do the job. An interesting reality which I noticed was that the type of person hired varied greatly – the company was a startup during the dot-com days, and with the extreme scarcity of talent we hired whoever we felt could do the job. The distribution of people hired turned out to be more broad than narrow (think normal distribution in statistics, with a wide range of values on the x-axiS). On the other hand a large company that I worked for hired a lot of people out of the Big 6 (at that time there were 6!) – there was less diversity.

    I like the concept but my experience at 4 startups (2 that I worked for and 2 that I started) has shown that it is impractical to implement, even though the unintended result may actually be a diverse pool!!! Strange!

  3. This was such a refreshing outlook into life. I absolutely was intrigued by the title because I do, like many others, become very uncomfortable at times with people around me because I usually don’t agree with what they are saying or I feel that I don’t have much to say about that topic. But, like you said, by really getting at the root of an issue and asking”why?”, it can profoundly affect someone’s thinking. It’s a challenge and a good one and I totally agree that innovativeness and ideas are essential. How else would we move forward? That was also an amazing video, rarely do you see a company or people really making an effort to express those words. You inspired me to add a saying by Robert Sutton into my blog :-)

  4. There’s a tradeoff here. Unconventional and different generates new ideas. Similar thinking makes communication and common work towards a unified goal easier. Both are important.

    Unconventional thinking is difficult to do when resources are tight and everyone has to work efficiently to meet a goal. In that situation, there’s no time to detour into new and unproven ideas. For unconventional thinking to be effective, there has to be enough bandwidth for trial and error, room for mistakes, and time to prove out ideas. Funding some of these unconventional ideas, knowing some of them will work and some won’t, is part of what’s made our VC community so successful. I hope that tradition continues!

  5. Spot on and one of the best post I’ve read. Now if we can just get all the different age groups to use those differences to excel. I’m very concerned about how many new start-ups won’t consider input from older generations. Believe it or not quite a few of the folks in their 60’s, 50’s and 40″s were the people that made the choice to hire folks who made them uncomfortable. That choice helped to make companies like Apple, IBM, Cisco and others successful.

  6. Interesting topic.

    I agree with what you wrote.

    For me it would be better if you replace uncomfortable with challenging or requesting.

    People can make you feel uncomfortable for many reasons: cheating, abusing, harrassing, being overly aggressiv……… people you respect, or yourself. Searching for people that let you feel uncomfortable show that you lack respect for yourself as such feelings are a warning.

    I do agree that it is good to find people which has another set of skills than you. If you are a very organised and logical person a creative person will challenge you to request what you do.

    If you are very analytical you might be challenged by a very intuitiv person.

    While you look for a person that is very different from you make sure that you agree about the core values. That ease to find a productive way to work with each other. I agree dealing with a person that distinguish from you can let you feel uncomfortable.

    Learn to differiate between this feelings. The first is a warning sigh the second is a sign of growing. Be sure to avoid mixing up both of them. Both feel very different for someone who knows what to look for.

    Rev, I agree with you by looking for someone that let you feel uncomfortable this person can hardly feel comfortable itself.

    If you watch out for someone different from you agreeing with the core values you both will grow.

    Embrace the difference and enjoy growing


  7. I think that you are right on the money here. Take VC investments, for example… You find few venture capitalists willing to stray from what makes them comfortable, limiting their ability to find the Dell’s and Apple’s that are out there “thinking different.”

    The result is an an almost universal investment focus on companies that rely solely on advertising revenues, or that provide services for a fee to companies that rely solely on advertising revenues. This can only go so far, as we are witnessing now with ad rates dropping so dramatically.

    You can only increase ad inventory so much before the pressure to bring prices down makes the return on these investments too low to bother anymore. Diversification away from the pure Ad supported model is inevitable and there is a need for diversification into things that “make you uncomfortable,” like say – subscriptions, content, etc…

    Just a thought.

    Lazaro Fuentes

    I am the CEO of a company that VC’s have said they love, but that has not been able to raise a round of capital because they are uncomfortable with content and subscriptions-based companies. [The economy hasn’t helped either. :) ]

  8. Oh, I hade a couple of this kind of schoolmates years ago. But one French woman topped them all: she was tattooed aaaall over her face. I saw her at some modern art museum – she could as well be an exponat there. :-)

  9. marymac


    Easy enough to say, but are you setting your new assistant up to fail? In looking for someone who will make you feel uncomfortable, aren’t you also creating an environment where the assistant cannot possibly BE comfortable?

  10. This article helped me think about why I didn’t fill my outstanding post for an Assistant…I am looking for someone different and willing to challenge the status quo. There were so many nice/qualified applicants…colleagues (and applicants) were confused as to why I didn’t just confirm the appointment. I am now clearer about wanting an assistant who will make me feel uncomfortable in the best possible way! The Think Different campaign has always resonated with me.