In a recent LinkedIn post, Cicely Simpson discusses a common pitfall for leaders: making decisions on autopilot, leading to recurring, undesirable outcomes. Simpson, who coaches leaders, highlights how the inability to break free from ingrained decision-making instincts can lead to a series of unexamined choices, rather than deliberate, effective ones.
Simpson argues that when a decision’s outcome feels predetermined before the discussion even begins, the solution isn’t necessarily more effort, but rather adopting a different mental framework. “The cost is never one bad call,” Simpson writes. “It is decisions made on autopilot, stacking up unexamined.”
“If the outcome felt inevitable before you sat down to decide, the fix isn’t more effort. It’s a different framework.”
The Danger of Autopilot Decisions
Cicely Simpson points out that leaders often find themselves in a cycle where their ingrained instincts dictate their choices, regardless of the specific situation. This reliance on habitual decision-making can be detrimental, especially when complex or novel challenges arise. As Simpson notes, this pattern isn’t about isolated poor judgments but a cumulative effect of choices made without deep consideration.
Choosing the Right Framework
To combat this, Simpson introduces seven distinct frameworks leaders can employ to foster more effective decision-making. Each framework is presented with guidance on when it is most applicable.
One such framework is Second-Order Thinking, attributed to Howard Marks. Simpson suggests this involves asking “and then what?” multiple times to understand the cascading consequences of a decision. This is particularly useful, according to Simpson, “when a decision looks good in the short term, but you’re unsure about the ripple effects.”
“Ask ‘and then what?’ 3 times in a row before you commit.”
Another valuable tool Simpson highlights is the Impact vs Effort Matrix. This method helps leaders prioritize by sorting options based on the impact they generate versus the effort required. Simpson advises that “Anything low impact and high effort goes to the bottom of the list,” recommending its use when faced with too many priorities.
Simpson also advocates for Strategic Questioning, suggesting a shift from “How is this going?” to “What are we learning that should change our approach?” She proposes banning status updates in favor of insight-gathering during one-on-one meetings, especially when a team is stuck in reporting rather than critical thinking.
Preventing Failure Before It Happens
The post further details Pre-Mortem Thinking, a concept from Gary Klein. Before committing to a decision, leaders are encouraged to imagine it has failed and then work backward to identify the causes of failure. Simpson’s advice is to “Write down the most likely reason this fails before you launch it,” a practice essential for high-stakes decisions where blind spots can be costly.
“Write down the most likely reason this fails before you launch it.”
Drawing from Jeff Bezos, Simpson explains the One-Way vs Two-Way Door Test. This framework helps leaders assess the reversibility of a decision and adjust their deliberation time accordingly. Simpson emphasizes that if a decision can be undone within a week, it shouldn’t be subjected to lengthy debate.
The 10-10-10 Rule, popularized by Suzy Welch, is also presented. This involves considering how a decision will feel in 10 minutes, 10 months, and 10 years. Simpson suggests trusting the long-term perspective if it conflicts with short-term panic.
Finally, Simpson touches upon First Principles Thinking, which involves breaking a problem down to its fundamental facts and rebuilding the solution from there, rather than relying on existing industry norms. The guiding question here is what one would do if they had never seen anyone else’s approach.
In closing, Cicely Simpson reiterates that applying the same strategy repeatedly will yield the same results. “A different framework, chosen on purpose, is often the only thing standing between you and a different outcome,” she concludes.
📝 About This Content
This article is based on insights shared by Cicely Simpson on LinkedIn.
📅 Originally posted on September 8, 2026 | View original post on LinkedIn →