100 Great Questions Every Entrepreneur Should Ask

Do we have bad profits?Jonathan L. Byrnes, author and senior lecturer at MIT 
Byrnes explains, “Some investments look attractive, but they also take the company’s capital and focus away from its main line of business.”

What counts that we are not counting?Chip Conley, founder of Joie de Vivre Hospitality and head of global hospitality for Airbnb 

Conley explains, “In any business, we measure cash flow, profitability, and a few other key metrics. But what are the tangible and intangible assets that we have no means of measuring, but that truly differentiate our business? These may be things like the company’s reputation, employee engagement, and the brand’s emotional resonance with people inside and outside the business.”

Who uses our product in ways we never expected?Kevin P. Coyne and Shawn T. Coyne, authors and strategy consultants

Is this an issue for analysis or intuition?Tom Davenport, author and professor at Babson College

Davenport explains, “If it’s a decision that’s important, recurring, and amenable to improvement, you should invest in gathering data, doing analysis, and examining failure factors. If it’s a decision you will only make once, or if for some reason you can’t get data or improve the decision-making process, you might as well go with your experience and intuition.”

Who, on the executive team or the board, has spoken to a customer recently?James Champy, author and management expert

Did my employees make progress today?Teresa Amabile, author and Harvard Business School professor 
Amabile explains, “Forward momentum in employees’ work has the greatest positive impact on their motivation.”


What am I trying to prove to myself, and how might it be hijacking my life and business success?Bob Rosen, executive coach and author

Do we underestimate the customer’s journey?Matt Dixon, author and executive director of research at CEB 
Dixon explains, “Often, companies don’t understand 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 first, pokes around but can’t find the answer to their question, and then tries to start up a chat with an agent, only to get frustrated by the delayed response. Only then do they go to the Contact Us tab and call. From the company’s perspective, the call is square one. The customer sees it as, you’ve already wasted 15 minutes of my time.”
What would have to be true for the option on the table to be the best possible choice? –Roger Martin, professor, Rotman Business School 

Martin uses this question when members of a group bring diverse opinions to a decision. It allows people to step back from their strongly held beliefs and contemplate a range of circumstances that might–or might not–support each option.

Is our strategy driving our strategy? Or is the way in which we allocate resources driving our strategy?Mark Johnson, co-founder, Innosight 
Johnson explains, “You might think you have a strategic plan, but your people may be doing things on a day-to-day basis that are undermining it. It’s essential that people believe in the strategy so they can make the daily decisions that support it.”

Why don’t our customers like us?James Champy

Do you keep 50% of your time unscheduled?Dov Frohman, engineer and executive, author 

The 50% stat may be somewhat arbitrary. But Frohman’s point, laid out in his book “Leadership the Hard Way,” is that leaders should make sure they maintain sufficient “slop” in their schedules to allow space for reflection and the assimilation of lessons learned from experience.

What kind of crime could a potential new hire have committed that would not only not disqualify him/her from being hired by our organization, but would actually indicate that he/she might be a particularly good fit?  -Pat Lencioni 

Lencioni explains, “In this case “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 beliefs or blowing the whistle on something. A particularly competitive organization may be okay hiring someone who in prior positions was reprimanded for being overly arrogant or difficult to work with.” 

Do you have an implicit bias for capital investments over people investments?Tom Peters 

Peters explains: “Capital enhancements are important. They’re also cool. You can get your picture taken next to a new robot. People investments are invisible and hard to measure. The tendency is to favor the hard stuff over the soft stuff. But the soft stuff is invariably more related to long-term strategic success than the hard stuff.”

How will you motivate the dishwashers?Bill 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 correct answer to this question, posed to manager candidates in a hotel chain, is “If they are overloaded I would roll up my sleeves and start washing right alongside them.” That speaks to the candidate’s ability to create employee engagement. Turned inward, however, the question reveals even more about culture. Ask yourself this: Are we the kind of company that cares whether our dishwashers are motivated?

Would you rather sell to knowledgeable and informed customers or to uninformed customers?Don Peppers, founding partner, Peppers and Rogers Group 
Partly it’s a matter of values: uninformed customers can be easy 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 customer references are not the ones who spend the most, but the ones who have the most expertise and authority. That gives them credibility with their peers.”

Whose voice (department, ethnic group, women, older workers, etc) might you have missed hearing from in your company, and how might you amplify this voice to create positive momentum for your business?Jane Hyun and Audrey Lee, partners, Hyun & Associates

What successful thing are we doing today that may be blinding us to new growth opportunities?Scott D. Anthony, managing partner, Innosight