The Two Questions That Improve Your Upstream Thinking
Explore the importance of upstream thinking in navigating crises and anticipating future challenges.
I posted on this topic after the attempt on former President Trump’s life at a Pennsylvania rally, and other failures in anticipatory (upstream) thinking keep hitting the news. The fallout at Delta Air Lines after the abortive CrowdStrike, a cybersecurity firm, update and the Trump campaign’s flailing after President Biden dropped out of the race are among the latest examples of failures to think ahead. Vice President Harris’ deft exploitation of Biden’s withdrawal shows the power of anticipatory thinking.
To CrowdStrike’s credit, the CEO took responsibility for the error and began corrective and remedial action. Most airlines recovered quickly, but Delta struggled to right the ship over a week later and plans to sue CrowdStrike.
Meanwhile, the Democratic party’s ouster of President Biden from the 2024 race was a slow-motion strike that anyone could see coming after his disastrous June 27th debate. The only ones who seemed surprised were Biden’s inner circle and the entire Trump campaign, both high on their own supply.
The Trump campaign assumed the most advantageous future—that a deteriorating Biden would stay in the race and stumble to defeat. Wrongfooted by Biden’s ouster and the rapid coronation of Vice President Harris, the Trump campaign remains unable to adapt.
Vice President Harris, meanwhile, anticipated and exploited the opportunity created by Biden’s withdrawal, rapidly consolidating support for her candidacy. Had she been content with reactive thinking, she would likely have faced a bruising primary.

Anticipatory Thinking Begins with Two Questions: What If and How Would
“What if” prompts people to consider alternative scenarios. What if this update contains a bug? What if our systems go down for several hours? What if Biden steps aside?
“How would” encourages people to think about the actions to take in the alternative scenarios. How would we prevent a bad update from damaging our customers and reputation, for example, might have prompted more vigorous testing from CrowdStrike (preventive action).
How would we motivate companies to switch, on the other hand, might nudge Apple to “promoting action” that highlights most viruses are built for PCs and not Macs, and “exploiting action” that subtly invites people frustrated by the abortive update to switch systems.
How would we adjust our strategy if Biden steps down and Vice President Harris replaces him should have been a conversation within Team Trump.
Holding an upstream or anticipatory discussion quarterly using what if and how would helps you prevent problems from arising, prepare contingencies if they do (like getting the proper insurance and building resilience in your systems), promote ways to increase market share, and exploit fleeting opportunities.
Would you like someone to facilitate this discussion? Getting outside support for these discussions can boost their effectiveness, and I’d be delighted to help you think through the best approach for your company. Book a call.

