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44 Questions For Business Leaders

Can you imagine your tombstone having your company’s performance results carved in it? Of course you can’t. (I hope.) So what would you like on the tombstone? Why do you keep discussing numbers instead?


How would you explain ‘why you do’ - what you do to your 10-year-old daughter? (Aim for 25/50 words or less.) 


How would you explain your most recent major decision to your 10-year-old daughter? (Aim for 25/50 words or less.) 


Did you miss half your 13-year-olds soccer games or school plays this year? (I’ll guarantee that if you live to be 109, you’ll never forgive yourself no matter how many zeros in your net worth.) 


What does this really say about your priority setting, time management and leadership?


Are your training courses so damn good that they make you feel ‘future ready’? 


Can every employee, when stopped by you in the hall, describe her or his personal development strategy for 2014? (Is it radical?) 


Is your CTO/Chief Training Officer on a par (e.g., pay, perks, pecking order) with your CFO/CIO/CMO? 


Have you (I HOPE) read Forbes publisher Rich Karlgaard’s superb … 

The Soft Edge?  


Do you have enough freaky customers in your portfolio, pushing you to the limit day in and day out? 


If you got run over by a bus, could you guarantee that your successor is BETTER than you are? 


Have you thanked 10 people for SOMETHING … today? 


At year’s end do you call 25-50 people to thank them for their support during the prior 12 months? (Inspired by Hank Paulson) 


Is EVERY meeting a Paragon of Excellence? (To a large extent, like it or not, meetings are ALL that you do.  Sadly but Truly.) 


Do you ever act like an asshole? (Guess what, dude, you can’t get away with it—you are NOT Steve Jobs.) 


Do you have an implicit bias for capital investments over people investments? (Think VERY carefully about this.) 

Are you a good listener? (Odds are VERY high that you are not—AND that you’re getting worse. Nothing is more important. It is a subject that can be studied and mastered.) 


Are you a PROFESSIONAL … listener? 

Are you a PROFESSIONAL … at hiring? 

Are you a PROFESSIONAL … at evaluating people? 


How many-off-the-charts crazy new people have you had lunch with in the last 90 days? (Inspired by FedEx CEO Fred Smith.) 


Do you read enough? (THE answer is “No.”) (Inspired by one of USA’s top 10 investment bankers who said not reading enough is the number ONE failing of CEOs.) 


If all of your traditional marketing programs were shut down tomorrow, would your extant Social Media programs carry the load? 


Do you think the whole “social media”/“social employee”/“social business” “thing” is overblown? (It may be, but are you sure? Good chance it’s “underblown.” How do you plan to test the overblown/underblown hypothesis?) 


Do you insist on too much data too have a discussion or to make decisions? Sure enough you want facts. But are you so lazy and grounded in your chair that apart from that data, you have very little conviction about whats going on?


Do you make eye contact 100% of the time? 


Do you meet your customers every week?


To what degree can you say you are honestly (regularly, intensively) in touch with folks three levels “down” in the organisation—where the real work gets done? 


Are you over-reliant on email, or do you still use the phone regularly? 


Do you reward imaginative failures that lead to significant learning? (Courtesy a successful Aussie exec who says his philosophy is, “Reward excellent failures, punish mediocre successes.”) 


Do you have a rigid/near-religious routine of calling a key contact at each of your top 10 (25?) customers once a month? 


Are you sure that you are not so intimidating that you cause people not to share priority problems with you early on when they are fixable? (Hint, you think you are approachable—odds are you are alone in that assessment) 


Women buy the lion’s share of retail AND commercial goods. Does your top team reflect that? (If it doesn’t, you’re outdated.) 


Is your top team a paragon of diversity? Or do they all have SIMILAR backgrounds with SIMILAR education, coming up with SIMILAR ideas and SIMILAR problems?


Have you read and attentively studied and widely shared Daniel Kahneman’s book Thinking, Fast and Slow? (It will shake your confidence in your and your colleagues’ judgment/decision-making skills—that’s a good thing.) 


Do you think your intuition is good? (I don’t think so —and I don’t even know you.) 


Is 50% of your time unscheduled? (Courtesy Intel superstar Dov Frohman’s book Leadership the Hard Way. Frohman says over-scheduling and failure to “daydream” are CEOs’ two top failings.) 


Is your full cadre of 1st-line bosses staggeringly talented and well trained/mentored/compensated? (The population of 1st-line bosses is unmistakably the #1 determinant of productivity/employee retention.) 


Do you have an implicit bias toward noisy, aggressive people? (You probably do. Read the book Quiet—and realise that shortchanging introverts is a strategic mistake.)


Do you acknowledge that failed cross-functional communication/cooperation/ synergy is the #1 cause of delays of … EVERYTHING? (It is.) Do you work VISIBLY on this EVERY day? (Inspired by Mayo Clinic—MC fires top docs who fail to buy into team medicine.) 


Do you acknowledge that there are about 500 ways to de-motivate people, and about 5 ways to motivate them—and act accordingly? 


Do you quickly get tired of people who constantly say “the sky is falling”? (Well, I do, too. But sometimes it is falling. I pray you are an optimist; I pray that you have a few pessimistic pals whom you do not dismiss out of hand.) 


Do you acknowledge that acquisitions rarely live up to their billing—the billing that was so gloriously touted by you? And do you acknowledge that when acquisitions blow up it is usually courtesy a “culture clash” which you didn’t look at hard enough during the vetting process? (If you don’t acknowledge that, you are wrong. PERIOD.) 


In presentations you review, is there as much/more text devoted to implementation as there is to problem/opportunity analysis? 


In presentations that you review, are you more worried about ‘what went wrong’ versus ‘what are you going to do about it’? Where does you time go?

Is your strategic plan > 2 pages? (If yes … shame on you) 

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