If at first you don’t succeed, step back and try to understand “Why.” As well, follow some of the other suggestions this regular IBJ contributor has for executives.

Executives will find Malcolm Gladwell’s new book, Outliers, (Little, Brown and Company, 2008) a very good use of their very scarce reading time. The book not only offers a number of thoughts useful to running a good business, but is also marvellously written, full of interesting and useful anecdotes and just plain a lot of fun.

I have used this space to recommend Malcolm Gladwell’s two previous books to executives. Same basis for this recommendation: high value-to-time-invested ratio. The Tipping Point (Little, Brown and Company, 2000 – reviewed in the July/August 2004 Ivey Business Journal) describes the nature and importance of how things become critical and gradual change becomes radical. That a business can be just fine one moment but be heading into the abyss the next moment seems nonsensical. But it is a notion executives must get their minds around. Far more than they would wish, it is an executive’s reality. Executives need to manage and drive change and that is Gladwell’s wheelhouse in The Tipping Point.

Blink (Little, Brown and Company, 2005 – reviewed in the May/June 2005 Ivey Business Journal) is Gladwell’s take on decision-making, especially hunches, snap judgements and instantaneous choices. Blink asks “Why are some people brilliant decision-makers, while others are consistently inept? Why do some people follow their instincts and win, while others end up stumbling into error?” Executives make decisions. That is what they do. Recommending Blink to executives was a no brainer.

In Outliers, Gladwell analyzes success. The appeal to executives is obvious. What executive or organization does not aspire to success? What executive or organization would not welcome insights and hints on being successful? That is what you get in Outliers. The philosopher David Hume was reputed to have loved curious facts. Outliers is one curious fact after another about success. Read it and you will never look at success the same way again. Your chances of success may even go up; they sure won’t go down.

Gladwell sets Outliers up this way. “What is the question we always ask about the successful? We want to know what they’re like – what kind of personalities they have, or how intelligent they are, or what kind of lifestyles they have, or what special talents they might have been born with. And we assume that it is those personal qualities that explain how that individual reached the top … In Outliers, I want to convince you that these kinds of personal explanations of success don’t work … The people who stand before kings may look like they did it all by themselves. But in fact they are invariably the beneficiaries of hidden advantages and extraordinary opportunities and cultural legacies that allow them to learn and work hard and make sense of the world in ways others cannot… It’s not enough to ask what successful people are like, in other words. It is only by asking where they are from that we can unravel the logic behind who succeeds and who doesn’t.”

Here are just a few things that I think will resonate with executives if they take a trip through Outliers. First, success for an individual, and by extension for an organization, is an extraordinarily complex phenomenon. It is far more than it seems and sometimes not remotely what it seems. Executives would do well to put some serious time into getting to the bottom of why they are successful or not. Is it brains, education, personality, family, relationships, skills, luck, etc.? If you do not know why you are what you are, being what you want to be is going to be a lot harder.

Executives should also ask why their organizations are successful or not. Is it management, the competition, buying and selling of assets, that elusive luck again, etc.? As with executives, organizations that do not know why they are what they are will have a tough time being what they want to be.

Second, timing really matters in success. I have always liked that classic investment line: “Don’t tell me what to buy; tell me when to buy it.” Gladwell offers two examples that make the timing/success connection. Example 1. Success for youngsters in age-group hockey correlates strongly with being born in the first three months of the calendar year because January 1 is the birthday cut-off. If you are born January 1 you play with youngsters born until December 31 of that year, which means that in the early years if you are born in the first few months of the year you are likely to be bigger, stronger and more coordinated than those born in the last few months of the year. This gives the early month youngsters a big edge. They get noticed more, they get more ice time and the path to success becomes easier and reinforcing. I note that I was born in February and got nowhere in hockey; but no theory is perfect.

Example 2. Just when you were born in the last two centuries correlates with the probability of achieving super wealth. Gladwell lists the 75 richest people of all time and finds, for example, that a staggering 14 were Americans born in a nine-year span between 1831 and 1840. He explains: “In the 1860s and 1870s, the American economy went through perhaps the greatest transformation in its history. This was when the railroads were being built and when Wall Street emerged. It was when industrial manufacturing started in earnest. It was when all the rules by which the traditional economy had functioned were broken and remade. What this list says is that it really matters how old you were when that transformation happened. If you were born in the late 1840s you missed it. You were too young to take advantage of that moment. If you were born in the 1820s you were too old: your mind-set was shaped by the pre-Civil War paradigm. But there was a particular, nine-year window that was just perfect for seeing the potential that the future held.”

Timing should be on the front-burner in every executive decision. Executives should not only ask if the decision is right but if the time is right for the decision to be made. The need to think about timing should be on every executive’s checklist.

Third, it will come as no surprise to executives that work is important to success. But what Gladwell does is quantify the relationship for the general public by citing the neurologist Daniel Levitin: “The emerging picture from such studies is that ten thousand hours of practice is required to achieve the level of mastery associated with being a world-class expert – in anything. In study after study, of composers, basketball players, fiction writers, ice skaters, concert pianists, chess players, master criminals and what have you, this number comes up again and again… It seems that it takes the brain this long to assimilate all that it needs to know to achieve true mastery.”

Executives manage their own careers and the careers of others. The ten-thousand hour rule is an important insight. To be good, you have to work. So do the people you manage.

Fourth, executives will find Gladwell’s development of psychologist Robert Sternberg’s concept of “practical intelligence” useful and interesting. Gladwell quotes Sternberg on practical intelligence as including things like “knowing what to say to whom, knowing when to say it, and knowing how to say it for maximum effect.”

Practical intelligence is good old fashioned street smarts usually learned in that well- known institution of higher learning, The School of Hard Knocks. This is where you develop good judgement from the experience of having used terrible judgement. Another management one-liner I like: The difference between a great career and a bad one is a couple of things every so often you elect to say or not say or do or not do.

Success as an executive is about playing the executive game well day after day. Read Gladwell on “practical intelligence” and you will get some ideas on how to play the game better. It is all about developing the “kind of savvy that (allows you) to get what (you want) from the world”. Savvy is such a splendid quality in an executive.

Fifth, a big part of being an effective executive is dealing with things that go wrong, or better still, stopping things from going wrong. Using plane crashes and industrial accidents as examples, Gladwell shows that big things that go wrong is “much more likely to be the result of an accumulation of minor difficulties and seemingly trivial malfunctions.” It is the cascading spiral, not the big bang, which gets organizations. The idea for executives is that success is doing a lot of little things well all the time, and when a little thing goes sideways, getting a hold of it fast so that it does not trigger a catastrophic chain of events. Outliers is a good reminder to executives to get into the details and deal with small problems.

Finally, Outliers will give you a different perspective on your own success. It’s not just you that made you what you are but all the help and luck along the long-forgotten way that came together and made all the difference.

No executive can read Outliers and not come away humbled by his or her own success. A bit of humility is a good thing in executives. That well-known thinker and Hall of Fame baseball player Yogi Berra said “In baseball, you don’t know nothin.” Executives will sometimes be further ahead if they see themselves the same way in the practice of their profession.

To executives, I would say it will not take you long to read Outliers. You will be glad you did.

About the Author

John S. McCallum is Professor of Finance at the I. H. Asper School of Business, University of Manitoba, and former Chairman of Manitoba Hydro. Contact John.McCallum@umanitoba.ca.