what are the top 100 most common questions entrepreneurs ask to themselves and others
100 Great Questions Every Entrepreneur Should Ask
Paul Graham, Jim Collins, Tony Hsieh, and other business leaders share the questions you should be request if you lot want to ameliorate your company.

There'south no Superman versus Fe Human being confront-off between questions and answers over which is the meliorate tool for innovation. But if there were, questions would be winning. Questions ignite imaginations, avert catastrophes, and reveal unexpected paths to brighter destinations. Jim Collins, Marshall Goldsmith, and other thinkers have compiled their own stocks of questions, which they urge leaders to pose to themselves and their teams. The right questions don't allow people to remain passive. They require reflection, followed by activity.
Warren Berger, writer of A More Beautiful Question, praises inquiry's ability to trigger divergent thinking, in which the listen seeks multiple, sometimes non-obvious paths to a solution. Asking good questions and doing so often "opens people to new ideas and possibilities," says Berger.
To compile this list of provocative questions for business owners, we reached out to entrepreneurs and management thinkers, scanned blogs, and revisited our favorite business books. (Though we tried to identify the origin of each question, some had competing claims of authorship. In those cases, we made our best phone call.) Accept you lot got a great question that yous use at your company? We welcome yous to add your own to the listing via the annotate box below the story. Rigid mindsets are unsafe things. We hope the following volition keep your mind supple.
- How can we become the company that would put us out of business organization? -Danny Meyer, CEO of Wedlock Foursquare Hospitality Group
- Are we relevant? Will we be relevant 5 years from now? Ten? -Debra Kaye, innovation consultant and author
- If energy were free, what would we practice differently? -Tony Hsieh, CEO of Zappos
Hsieh explains, "This is a idea experiment to see how yous would reconfigure the business if you had different resources available or knew that different resources would one mean solar day become available. Some other question might exist, what if storage was costless? Or what if labor costs one-half equally much or twice as much?" - What is it similar to work for me? -Robert Sutton, author and direction professor at Stanford
- If we weren't already in this business, would nosotros enter information technology today? And if not, what are we going to practise about it? -Peter Drucker, direction good and author
The late Drucker posed a variation on this question to Jack Welch in the 1980s. It inspired General Electrical's "fix, sell, or shut" strategy for exiting or restructuring unprofitable businesses. - What trophy do nosotros want on our mantle? -Marcy Massura, a digital marketer and brand strategist at MSL Group
Massura explains, "Not every business concern determines success the aforementioned way.Is growth most important to you? Profitability? Stability?" - Practice we take bad profits? -Jonathan L. Byrnes, author and senior lecturer at MIT
Byrnes explains, "Some investments expect bonny, but they as well take the company's upper-case letter and focus away from its main line of business." - What counts that nosotros are not counting? -Chip Conley, founder of Joie de Vivre Hospitality and caput of global hospitality for Airbnb
Conley explains, "In any concern, we measure cash flow, profitability, and a few other key metrics. But what are the tangible and intangible assets that nosotros have no means of measuring, but that truly differentiate our business? These may be things like the company's reputation, employee date, and the make'south emotional resonance with people within and exterior the business." - In the past few months, what is the smallest change we have made that has had the biggest positive issue? What was it about that modest modify that produced the big render? -Robert Cialdini, author and professor emeritus of marketing and psychology at Arizona State University
- Are we paying plenty attention to the partners our company depends on to succeed? -Ron Adner, author and professor at Tuck School of Business concern
Adner explains, "Even companies that execute well themselves are vulnerable to the missteps of suppliers, distributors, and others." - What prevents me from making the changes I know volition make me a more than effective leader? -Marshall Goldsmith, leadership coach and author
- What are the implications of this determination 10 minutes, 10 months, and 10 years from now? -Suzy Welch, author
- Do I make middle contact 100 pct of the fourth dimension? -Tom Peters, writer and management practiced
- What is the smallest subset of the trouble we tin can usefully solve? -Paul Graham, co-founder of Y Combinator
- Are we changing every bit fast as the world around us? -Gary Hamel, author and management consultant
- If no ane would always detect out virtually my accomplishments, how would I lead differently? -Adam Grant, author and professor at Wharton
- Which customers can't participate in our market because they lack skills, wealth, or user-friendly access to existing solutions? -Clayton Christensen, author, Harvard Business School professor, and co-founder of Innosight
- Who uses our product in ways nosotros never expected? -Kevin P. Coyne and Shawn T. Coyne, authors and strategy consultants
- How probable is information technology that a customer would recommend our visitor to a friend or colleague? -Andrew Taylor, executive chairman of Enterprise Holdings
"Taylor'due south utilize of this question at Enterprise Rent-A-Car inspired Fred Reichheld to create the Net Promoter Score, a widely used metric for customer loyalty. - Is this an upshot for analysis or intuition? -Tom Davenport, author and professor at Babson College
Davenport explains, "If information technology's a decision that's important, recurring, and amenable to improvement, you should invest in gathering information, doing analysis, and examining failure factors. If it's a decision you volition only make once, or if for some reason you can't become data or improve the decision-making procedure, you might likewise become with your experience and intuition." - Who, on the executive team or the board, has spoken to a client recently? -James Champy, author and management expert
- Did my employees make progress today? -Teresa Amabile, author and Harvard Concern School professor
Amabile explains, "Forrard momentum in employees' piece of work has the greatest positive impact on their motivation." - What one word do nosotros desire to own in the minds of our customers, employees, and partners? -Matthew May, author and innovation expert
May explains, "This deceptively uncomplicated question creates utter clarity inside and outside a company. Information technology is incredibly hard for well-nigh people to answer and difficult to go consensus on--fifty-fifty at the highest levels. Apple = unlike. Toyota = quality. Google = search. It'south taken me 3 years to become one of my clients, Edmunds.com, to observe and agree on their word: trust." - What should we stop doing? -Peter Drucker, management expert and author
- What are the gaps in my knowledge and experience? -Charles Handy, writer and management expert
- What am I trying to prove to myself, and how might information technology be hijacking my life and business success? -Bob Rosen, executive coach and writer
- If we got kicked out and the board brought in a new CEO, what would he do? -Andy Grove, onetime CEO of Intel
In 1985, with the company's memory-scrap business organisation under siege, CEO Grove famously posed this hypothetical to Intel co-founder Gordon Moore, leading them to ditch retentiveness for microprocessors. - If I had to go out my organization for a year and the simply communication I could have with employees was a single paragraph, what would I write? -Pat Lencioni, author and founder of The Table Group
Lencioni explains, "Determining the substance of this paragraph forces yous to identify the company's core values and strategies, and the roles and responsibilities of those hypothetically left backside." - Who have we, as a company, historically been when we've been at our best? -Keith Yamashita, author and founder of SYPartners
- What exercise we stand for--and what are we against? -Scott Goodson, co-founder of StrawberryFrog
- Is there whatsoever reason to believe the opposite of my current belief? -Flake and Dan Heath, authors who teach at Stanford'southward and Duke'southward business schools, respectively
- Do we underestimate the customer'south journeying? -Matt Dixon, author and executive director of research at CEB
Dixon explains, "Often, companies don't empathize the entirety of the customer's experience and how many channels may have already failed them. They don't understand that the customer goes to the website outset, pokes around just can't discover the respond to their question, and then tries to kickoff up a chat with an agent, just to get frustrated by the delayed response. Only so exercise they go to the Contact Us tab and call. From the company's perspective, the telephone call is square one. The customer sees it every bit, you've already wasted fifteen minutes of my time." - Among our stronger employees, how many run across themselves at the company in three years? How many would leave for a 10 percent heighten from another company? -Jonathan Rosenberg, adviser to Google management
- What did we miss in the interview for the worst hire nosotros e'er fabricated? -Alberto Perlman, CEO of Zumba Fitness
- Practise we have the right people on the motorcoach? -Jim Collins, author and management consultant
- What would accept to be true for the choice on the table to be the best possible choice? -Roger Martin, professor, Rotman Business concern School
Martin uses this question when members of a group bring various opinions to a decision. Information technology allows people to step back from their strongly held beliefs and contemplate a range of circumstances that might--or might not--support each option. - Am I failing differently each time? -David Kelley, founder, IDEO
- When data truly is ubiquitous, when reach and connectivity are completely global, when calculating resources are infinite, and when a whole new set of impossibilities are non only possible, merely happening, what volition that do to our business? -Jonathan Rosenberg
- Do we aggressively reward and promote the people who have the biggest impact on creating fantabulous products? -Jonathan Rosenberg
- What is our Big Hairy Audacious Goal? -Jim Collins
- Is our strategy driving our strategy? Or is the mode in which we classify resources driving our strategy? -Mark Johnson, co-founder, Innosight
Johnson explains, "You might recall you have a strategic plan, just your people may be doing things on a day-to-twenty-four hours footing that are undermining information technology. It'south essential that people believe in the strategy and so they tin can make the daily decisions that support it." - How is the way you lot as the leader call up and process information affecting your organizational culture? -Ari Weinzweig, co-founder Zingerman's Community of Businesses
Weinzweig explains, "Describe the civilisation you'd love to have in your organization. And so cheque the desired characteristics of the culture against the fashion you think and procedure information. Are they congruent? Do you want collaboration but think in isolation? Practise you lot want a flat organization only think hierarchically? - Why don't our customers like u.s.a.? -James Champy
- How can we become more high-tech but even so be high affect? -James Champy
- What do we need to start doing? -Jack Bergstrand, CEO, Brand Velocity
- Whom among your colleagues practice y'all trust, and for what? -Charles Handy
Handy tells this story: "One CEO had a trouble with his all-time subordinate, who was very good at his chore. Just he was also personally ambitious, then the CEO could not trust him to exist totally loyal. The dilemma was whether to keep him because of his abilities or lose him because he couldn't be sure of him. The reply was for the CEO to either assign the subordinate jobs where his loyalty wasn't relevant or to confront him with his feelings. After some pushing from me. the CEO did the latter, and information technology cleared the air." - Are yous satisfied with your electric current office? If non, what is missing from it? -Charles Handy
- Practice you keep 50% of your fourth dimension unscheduled? -Dov Frohman, engineer and executive, author
The l% stat may be somewhat arbitrary. But Frohman'southward point, laid out in his volume "Leadership the Difficult Style," is that leaders should make certain they maintain sufficient "slop" in their schedules to let space for reflection and the assimilation of lessons learned from feel. - What would I recommend my friend practice if he were facing this dilemma? -Chip and Dan Heath
- What kind of offense could a potential new hire have committed that would not only not disqualify him/her from being hired past our system, but would actually point that he/she might exist a particularly good fit?-Pat Lencioni
Lencioni explains, "In this example "crime" is a metaphor. This question speaks to values. A particularly idealistic organization may be okay with hiring someone that was previously reprimanded for standing up for his behavior or blowing the whistle on something. A particularly competitive organization may be okay hiring someone who in prior positions was reprimanded for being overly big-headed or hard to work with." - If our customer were my grandmother, would I tell her to purchase what we're selling? -Dan Pinkish, writer
- If our company went out of business tomorrow, would anyone who doesn't get a paycheck here care? -Dan Pinkish
- What is something you believe that about no one agrees with yous on? -Peter Thiel, partner, Founders Fund
- Do you have an implicit bias for upper-case letter investments over people investments? -Tom Peters
Peters explains: "Capital enhancements are of import. They're too cool. You tin get your picture taken side by side to a new robot. People investments are invisible and hard to measure. The tendency is to favor the difficult stuff over the soft stuff. But the soft stuff is invariably more related to long-term strategic success than the difficult stuff." - Exercise we have enough freaky customers in our portfolio pushing u.s.a. to the limit day in and solar day out? -Tom Peters
- Who are you going to put out of business, and why? -Brad Feld, managing manager, Foundry Group
- What happens at this company when people fail? -Bob Sutton and Jeff Pfeffer, Stanford professors
- How volition y'all motivate the dishwashers? -Pecker Keena, independent casino consultant
Job interview questions comprise a genre unto themselves, so we chose not to include them in this article. With one exception. Keena says the only right respond to this question, posed to director candidates in a hotel chain, is "If they are overloaded I would roll up my sleeves and start washing right aslope them." That speaks to the candidate'southward ability to create employee engagement. Turned in, withal, the question reveals even more about culture. Ask yourself this: Are nosotros the kind of company that cares whether our dishwashers are motivated? - Do your employees have the opportunity to do what they exercise all-time everyday? -Marcus Buckingham, author
- Where is our petri dish? -Tim Ogilvie, CEO. Peer Insight
- What Microsoft is this the Altair Basic of? -Paul Graham
- Do we say "no" to customers for no reason? -Matt Dixon
Y'all may have created your client policies at a time when you lot lacked resources, technology wasn't up-to-snuff, or low service levels were the industry norm. Have those circumstances changed? If so, your customer policies should change too. - Instead of going to electric current contacts for new ideas, what if you reconnected with dormant contacts--the people you lot used to know? If y'all were going reactivate a fallow tie, who would it exist? -Adam Grant
- Practice you see more potential in people than they exercise in themselves? -Adam Grant
- Are yous taking your company in the direction of better and revenue or cheaper and cost? -Michael Raynor, director, Deloitte Services LP
- Would you rather sell to knowledgeable and informed customers or to uninformed customers? -Don Peppers, founding partner, Peppers and Rogers Group
Partly it'southward a affair of values: uninformed customers tin exist piece of cake targets who swallow your pitch without pushing back. Selling to knowledgeable customers, by contrast, "is a mark of a trustable firm--one that is working to advance its customers' best interests," says Peppers. And there's another benefit: "Your most valuable client references are non the ones who spend the most, but the ones who accept the most expertise and authorisation. That gives them credibility with their peers." - What are we challenging, in the sense that Mac challenged the PC or Dove tackled the Beauty Myth? -Marking Barden and Adam Morgan, founders, eatbigfish
Barden and Morgan explain that for companies challenging market leaders with greater resources, competing on the status quo is death. Instead they must attack the dynamics of a category (the dominance of PC) or a cultural meme (what society defines as "cute" in women). - In what fashion can we redefine the criteria of pick in our category in our favor, equally Method introduced style and pattern to cleaning and Virgin America returned glamor to flying? -Marker Barden and Adam Morgan
- In the by yr, what have you done (or could yous have done) to increment the accurate perception of this company/make as ethical and honest? -Robert Cialdini
Cialdini explains: "Of course, the preferred fashion to increase the perception of a visitor as ethical is to foster ethical practise within the organization. However, sometimes a company can be ethical without a corresponding perception in the marketplace that this is indeed the example. Therefore, companies should strive not only to raise and reinforce an ethical culture merely also to arrange for a warranted perception of that ethicality to be part of their brand." - To whom do you add value? -Dave Ulrich and Norm Smallwood, co-founders, The RBL Group
- Why should people mind to y'all? -Dave Ulrich and Norm Smallwood
- How would our PR, marketing, and social media alter if nosotros did not employ outside agencies? -Guy Kawasaki, founder, Garage Engineering Ventures and Alltop
Kawasaki explains, "Permit's see what happens when a company tin can't abdicate these functions to hired guns. I'd bet that employees, considering they know and love their product more than any agency, can exercise a much better chore at less expense to kick." - What was the last experiment we ran? -Scott Berkun, author
- Are your clients Pepsi or Coke drinkers?" -Marcy Massura
Massura explains: "This is a symbolic question that gets at how deeply yous accept researched your target clients. Business concern leaders tin discover out more about their customers than e'er before thanks to the ability to collect information on a grand calibration. Such detailed information allows the visitor to interact with targets in new ways and to assess electric current production development and marketing roadmaps." - What is your BATNA (best alternative to a negotiated agreement)? -Roger Fisher and William Ury, negotiation experts
- What's the best design framework for an organization in a post Industrial-Age if the top-down, command and control model is no longer relevant? -Traci Fenton, CEO, Worldblu
- Who are 4 people whose careers I've enhanced? -Alex Gorsky, CEO, Johnson & Johnson
- Where can we break convention? -Shane Snow, co-founder, Contently
- Whose vocalism (section, ethnic group, women, older workers, etc) might you have missed hearing from in your company, and how might you dilate this phonation to create positive momentum for your business? -Jane Hyun and Audrey Lee, partners, Hyun & Associates
- In retrospect, of the projects that nosotros pulled the plug on, what percent do we wish had been immune to keep going, and what pct do nosotros wish had ended earlier? -Ron Adner
- Practice y'all, equally a leader, bounce back quickly from setbacks? -Bob Rosen
- Who do we call back the globe wants us to exist? -Geoffrey Moore, organizational theorist and management consultant
- How volition we build a 100-yr startup? -Phil Libin, CEO, Evernote
- What successful thing are we doing today that may exist blinding the states to new growth opportunities? -Scott D. Anthony, managing partner, Innosight
- If yous could go back in time five years, what decision would you brand differently? What is your best guess as to what conclusion y'all're making today you might regret five years from now? -Patrick Lencioni
- What stupid dominion would we almost like to kill? -Lisa Bodell, CEO, FutureThink
- What potential megatrends could make our business concern model obsolete? -Michael A. Cusumano, professor, MIT
- What information is critical to our arrangement that our executives are ignoring? -Max Bazerman, professor, Harvard Business organisation Schoolhouse
- What have we washed to protect our concern from competitive encroachment? -Tom Stemberg, managing full general partner, Highland Venture Upper-case letter
- If you lot had to rebuild your arrangement without any traditional competitive advantages (i.east., no killer a applied science, promising enquiry, innovative product/service delivery model, etc.), how would your people accept to approach their work and collaborate together in order to create the necessary conditions for success?" -Jesse Sostrin, founder, Sostrin Consulting
- What are the rules and assumptions my manufacture operates under? What if the opposite were truthful?Phil McKinney, innovation expert
- Do the decisions we brand today help people and the planet tomorrow? -Kevin Cleary, president, Clif Bar
- What is your theory of homo motivation, and how does your bounty program fit with that view? -Dan Ariely, professor, Duke University
- How practice you encourage people to take command and responsibility? -Dan Ariely
- Who do we want out customers to become? -Michael Schrage, professor, MIT
- How do I stay inspired? -Paul Bennett, main creative officeholder, IDEO
- Do I know what I'1000 doing? And who do I call if I don't? -Erin Pooley, business journalist
- Exercise they use it? -Howard Tullman, CEO, 1871
- What is our question? -Dev Patnaik, CEO, Jump Assembly
- How is business organization? Why? -Thomas A. Stewart, executive director, National Center for the Centre Market
From the April 2014 outcome of Inc. magazine
Source: https://www.inc.com/magazine/201404/leigh-buchanan/100-questions-business-leaders-should-ask.html
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