Great Management Questions

What questions should entrepreneurs ask themselves if they want to improve their companies?” Earlier this year, business thought-leaders including Jim Collins, Marshall Goldsmith, and Gary Hamel were asked this question and their responses were published in Inc. magazine.9762662-question-marks-background

The compiled list of questions was fascinating and far-ranging – from the esoteric (“What is our question?” by Dev Patnaik, CEO, Jump Associates) to the pragmatic (“Do I make eye contact 100 percent of the time?”  by Tom Peters, author and management expert).  I categorized the questions into several topics and found nearly half of them had to do with the company strategy and competitive positioning.  The categorization looked like this:

  • strategy and competition – 43 questions
  • leadership – 21 questions
  • managing people – 14 questions
  • customer – 9 questions
  • other – 13 questions

The following are the questions that resonated most strongly with me:

strategy and competition

What is our Big Hairy Audacious Goal? -Jim Collins, author and management consultant

This question is from the seminal text by Collins, Built to Last.  I find it inspires and challenges my clients to think beyond the day to day and identify a purpose worthy of their people and their customers.

What should we stop doing?Peter Drucker, management expert and author

This is a particularly effective question to ask start-ups and small businesses, when opportunities abound but resources don’t.

Who have we, as a company, historically been when we’ve been at our best?Keith Yamashita, author and founder of SYPartners

I like how this question grounds people in reality (vs. possibility) and focuses them on what their companies do best – both points are key when trying to re-discover or re-define the core of their brand.

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.”  I couldn’t agree more.

Who are you going to put out of business, and why?Brad Feld, managing director, Foundry Group and How can we become the company that would put us out of business?Danny Meyer, CEO of Union Square Hospitality Group

These two questions together produce a revealing perspective on competition and sustainability of your competitive advantage.

What are the rules and assumptions my industry operates under? What if the opposite were true? Phil McKinney, innovation expert

Truly disruptive innovations come when challenging the status quo like this.

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.”  I sympathize with Conley’s point whenever people ask me to prove the ROI of brand-building.  Just because it’s difficult to isolate a quantifiable value doesn’t mean that value isn’t created.


Why should people listen to you?Dave Ulrich and Norm Smallwood, co-founders, The RBL Group

I like to ask leaders, “Why should people follow you?”  If their answers indicate a combination of confidence and humility, I think their people are in good hands.

Do I know what I’m doing? And who do I call if I don’t?Erin Pooley, business journalist

Knowing what you don’t know is one of the most critical leadership qualities.

What are the implications of this decision 10 minutes, 10 months, and 10 years from now? Suzy Welch, author

I like how this helps leaders very quickly consider the short-, mid-, and long-term before making a decision.

managing people

Do we have the right people on the bus? -Jim Collins

Another gem from Collins.  A good corollary would be “Am I willing to get the wrong people off the bus?”  I find too many leaders recognize the deficits in their teams but they don’t have the courage or commitment to make the necessary changes nor do they realize the toxic environment they create by letting the wrong people stay.

How will you motivate the dishwashers? -Bill Keena, independent casino consultant

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?


Why don’t our customers like us?James Champy, author and management expert

I like this question because it causes people to not take their customers for granted.  Even if someone is buying from you, it’s likely that there are things you could do better for them.  Delivering a truly extraordinary experience is the best way to earn customers’ loyalty.

Are your clients Pepsi or Coke drinkers? –Marcy Massura, a digital marketer and brand strategist at MSL Group

Massura explains: “This is a symbolic question that gets at how deeply you have researched your target clients.”  I’ve found some of my clients think they know their customers when they really don’t.  A question like this would really open their eyes to the level of customer intimacy they need.


The “other” category of questions ended up containing a potpourri of intriguing ones.  This one from Tony Hsieh seemed particularly eye-opening:

If energy were free, what would we do differently?Tony Hsieh, CEO of Zappos

Hsieh explains, “This is a thought experiment to see how you would reconfigure the business if you had different resources available or knew that different resources would one day become available. Another question might be, what if storage was free? Or what if labor costs half as much or twice as much?”

I encourage you to take a look at the complete list and do two things:

  1. pick out your favorite(s)
  2. provide your own question

Please share in the comments section below!

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