A very interesting thread.

My tuppence worth

One day workshop, four themes, 2 hours per theme, in each using bicycling as a metaphor for commercial decisions involving risk

1 Calculation. R+ and R-, risk and reward, making a decision to operate only in the zone of potential gain. Don't do anything you can't do. Don't ride bikes unlit in Manhattan, don't do a ride in Arizona summer without planned water stops, understand your present strength and fitness, don't borrow at 8% to open 5% roi businesses. Do the sums, honestly and accurately.

2 Anticipation. Understand traffic patterns on your route, don't ride on the school run or commuter traffic, don't ride (here in August in Bahrain) after 8.00 am, don't ride at sundown into the sun when traffic from behind will be dazzled by low sun in front. The Motorcycle Safety Foundation advises "Think 6 seconds ahead - and think six seconds ahead for everyone you can see, who aren't thinking 6 seconds ahead". Avoid routes (or commercial ventures) where the biggest risks (semi trucks, cash rich competitors) might prowl.

These two themes are about "Is it worth it". The next two are about "How to do it".

3 Mitigation. Tool kit and the ability to use it? Water stops, food stops, power bars, cell phones, loved ones warned and agreeing to be a sag wagon? Planned "quit" decision points? Go/no go points within the commercial project plan? Sponsor agreement to each of these "Continue/Quit" milestones?

4 Preparation. Have you gained the required levels of skill, commitment and fitness? Have your companions (staff)? Are you planning something that your necessary collaborators (staff, financial backers, technical and financial collaborators) consider daft? Does your sag wagon driver have a liking for a frothy one after 5.00 pm, when you're going to be out after 8.00? Have you done this before? Have you benchmarked the skills and endurance required against others who have?

Hey, sorry but I got interested!

>>> a workshop on risk-taking for the executive team in an organization

My Inner Uber Cybic trembles at the thought of taking on such a project. Any 'team' with sufficiently low time stress to attend a seminar is by definition not about to take the slightest risk. Risk-taking is borne of desperation. In addition, executives do not retain 'execution' privilege past the point of their first failure . .implicit in the risk concept.

Cycling implications? If executive's advancement** were contingent on the risks associated with cycling, they'd contract it off-shore.

** - The only significant metric you're dealing with here and the only one you can use to keep them awake.

Many people who are adverse to risk have difficulty managing more than one plan at a time. Good risk takers have alternative actions planned in advance for when a less than optimum plan must be abandoned.

For example, the military trains for many eventualities because theirs is a risky business. The ability to shift into an alternate path is a necessity.

Most of inhabitants of "cubical land" that I observe have only one plan. If and when it goes bad they have inadequate fall back routes prepaired for use.

Whe you approach an intersection on your bike where you have the right of way do you have an alternate plan for what to do when that car at the stopsign ignores you and pulls out anyway. Most of us have learned to deal with physical problems like this almost automatically. Alternate plans are a good survival trait and minimize the bad side of risk.

Risk taking in the business world however is not something we practice every day while just walking around breathing. Plans for how to deal with the upside or downside of risk need to be put in place alongside the original plans to ensure best results.

Risk is the area that makes the successful what they are. If you do what everyone else does, you will always be like everyone else. The "trick" is knowing when to take risk and having the forsight to plan for the outcome.