Capitalist Note: Throwing a couple of talent/business lessons I was reminded of as I watched the NCAA Men's Basketball Tournament this year. March Madness has something for all of us.
Some organizations/teams play to win. Assertiveness rules the day, which means those organizations and teams are always going to be on the attack, looking to improve their circumstances by being active and aggressive on all fronts (this can be professional in nature, by the way). From the top down, they are always looking to attack. From a corporate standpoint, think Uber as an extreme case of this.
Other organizations are more conservative in nature. These entities generally have already had some level of success and they're looking to remain successful. In the DNA of these organizations, the best way to protect a lead is to circle the wagons and be very pragmatic about the risks they take. These organizations want to win - the risk aversion is more of a stylistic choice on the success they've already had.
But being conservative doesn't mean you've eliminated risk in business - or in basketball, as evidenced by lesson #2 from the first weekend of March Madness 2018:
Talent Lesson #2 from March Madness - Conservative approaches decrease your margin for error. The UMBC upset of Virginia is a great example of this truth. Virginia plays a conservative style on both offense and defense - they aren't incredibly talented, but they execute their base strategy very well. That conservative approach wins a lot - but in a "lose one game and you're out" type of environment, it can be deadly. The other team gets hot, and suddenly you're out. The moral of the story? Even if you have a good to great team, never stop trying to upgrade the talent you have. Conservative approaches in basketball - the grinding out wins mentality - are often there because it is the best way to win with average talent. Same thing is true in business.
Virginia has a very conservative approach. They're a defense-first, grind it out in the half-court type team. They are world class using that system, but playing conservatively means they don't beat teams by large margins to begin with - mainly because the number of possessions in a game goes down as a consequence of their style. That means inferior teams can hang around, if it they hit a couple of shots - watch out. The opposition can get confidence and it can spin out of control into an upset.
The same thing is true in organizations, and happens most often when a company is protecting a cash-cow, dominant position in any marketplace. You're the leader, you're making money and things are great. That means you get away from taking risks, you've probably got a large legal department telling you "no" and the talent on your team is generally poker-faced and unemotional when something goes wrong.
Just play our style. Protect the margin. Don't rock the boat.
Then you look up and the UMBC of your industry or market wins a HUGE deal in a head to head match up with you.
You do a loss analysis, ask the prospect for feedback and it comes back clear - your company was to locked into the way you do it. The upstart was willing to do things outside of scope to customize the solutions.
You just got UMBCed.