Risk is good. Not properly managing your risk is a dangerous leap.
- Evel Knievel
"The Strategy Paradox," Michael Raynor's classic book, 
should be required reading for executives interested in understanding the connection between risk and return in strategic planning and decision-making.
Raynor’s basic premise is that almost everyone, because of how human beings are fundamentally wired, over-rate the consequences of “things going bad” and consequently too often default to seemingly safe strategies.
Raynor goes on to make the point that while this may be fine from a personal health and safety perspective, it is quite sub-optimal when it comes to strategic decision-making.
The reasons, he cites, are both subtle and obvious.
The obvious reasons revolve around classic “agency” challenges - namely that there are a different set of incentives in place for owners versus operators of businesses.
The owners - i.e. the shareholders - main goal is investment return. As such, they usually evaluate strategic decisions through the dispassionate prism of expected value.
The operators of businesses, in contrast, usually act as who they are - emotional, empathetic, and personal-safety focused human beings.
And while, as professionally trained managers, they are of course aware and focused on expected value and shareholder return, their analysis of those rational probabilities often get overshadowed by more "human" concerns.
Like friendship. Like the stable, comfortable routine of a job. Of co-workers. Of a daily, comfortable work rhythm.
And the result of this natural human bias toward "the comfortable" is executive decision-making that defaults too often to the seemingly (that word again) conservative option.
Now as for why this conservatism is a strategic problem, Raynor delves into the concept of survivor bias and how it pertains to traditional studies of what factors separate successful companies from the unsuccessful ones.
Survivor bias can be best illustrated by all of those statistics that too many of us unfortunately know by heart regarding the abysmally low percentage of companies that make it through their 1st year of business, those that make it to 5 years, to 10 years, etc.
Now most of us naturally interpret these statistics as to mean that the leaders of these failed businesses were too aggressive, that they took too many risks, made too many big bets that didn’t pan out.
But Raynor's research actually demonstrates the opposite.
As opposed to Jim Collins’ famous (and famously flawed) Good to Greatanalysis, Raynor found that when the full universe of companies were surveyed – not just those that survived– that there was a direct negative correlation between those that didn't make it and the relative conservatism of their leaders and their pursued business strategies.
Or from the other perspective, the successful businesses were led and managed far more so by leaders who could be described in those "seemingly"pejorative terms - "aggressive,""risk taker,""bet the house" types.
So what does this all mean for the executive / entrepreneur interested in making quality higher risk / higher return strategic decisions?
Well, to quote the title of a famous self-help book: "Feel the Fear…but Do It Anyway."
Accept that as human beings, we are wired to be afraid.
BUT to prosper in modern business we must push through this and trust that the riskier choice far more often than not is...
...the strategically correct one.