Red teaming is a structured way to challenge plans, assumptions, or strategies before they fail in practice. It creates a disciplined environment to test ideas from different angles—exposing blind spots, uncovering risks, and strengthening decision-making.

Most strategy tools are built on clean lines and rigid boxes (e.g., OKRs, SWOT, five-forces diagrams). But the real world bends, warps, and shifts in unpredictable ways. What if our strategies need to stretch just as flexibly?  AI will tell us all pretty quickly.

What’s so hard about strategy? Everyone claims to have one. There’s no shortage of books, articles, videos, advisors, and strategy-creating courses. But guidance on evaluating a strategy’s effectiveness or its long-term impact on organizational performance? That’s far rarer.

What’s so hard about strategy? Everyone claims to have one. There’s no shortage of books, articles, videos, advisors, and strategy-creating courses. But guidance on evaluating a strategy’s effectiveness or its long-term impact on organizational performance? That’s far rarer.

Time pressure drives companies to fast-track strategy development, viewing assumption testing as an unnecessary delay. Executive teams, eager to show progress to boards and investors, often conflate speed with decisiveness. Many times, executive teams are too busy doing and fail to carve out enough time for thinking. This urgency creates a false choice between thorough validation and timely execution, leading to strategies built on untested hypotheses.

Boards may accept outdated strategies without probing whether market conditions, technology, or competition have changed. For example, BlackBerry’s board failed to question management’s reliance on enterprise hardware while Apple redefined consumer mobility. Similarly, Kodak’s board didn’t press for urgent action despite signs that digital photography would disrupt film. More recently, Boeing, Bed Bath & Beyond, WeWork, and Credit Suisse boards arguably failed to question assumptions, adapt to changing environments, or hold leadership accountable:

Red teaming is a structured way to challenge plans, assumptions, or strategies before they fail in practice. It creates a disciplined environment to test ideas from different angles—exposing blind spots, uncovering risks, and strengthening decision-making.

Most strategy tools are built on clean lines and rigid boxes (e.g., OKRs, SWOT, five-forces diagrams). But the real world bends, warps, and shifts in unpredictable ways. What if our strategies need to stretch just as flexibly?  AI will tell us all pretty quickly.

What’s so hard about strategy? Everyone claims to have one. There’s no shortage of books, articles, videos, advisors, and strategy-creating courses. But guidance on evaluating a strategy’s effectiveness or its long-term impact on organizational performance? That’s far rarer.

What’s so hard about strategy? Everyone claims to have one. There’s no shortage of books, articles, videos, advisors, and strategy-creating courses. But guidance on evaluating a strategy’s effectiveness or its long-term impact on organizational performance? That’s far rarer.

Time pressure drives companies to fast-track strategy development, viewing assumption testing as an unnecessary delay. Executive teams, eager to show progress to boards and investors, often conflate speed with decisiveness. Many times, executive teams are too busy doing and fail to carve out enough time for thinking. This urgency creates a false choice between thorough validation and timely execution, leading to strategies built on untested hypotheses.

Boards may accept outdated strategies without probing whether market conditions, technology, or competition have changed. For example, BlackBerry’s board failed to question management’s reliance on enterprise hardware while Apple redefined consumer mobility. Similarly, Kodak’s board didn’t press for urgent action despite signs that digital photography would disrupt film. More recently, Boeing, Bed Bath & Beyond, WeWork, and Credit Suisse boards arguably failed to question assumptions, adapt to changing environments, or hold leadership accountable:

Red teaming is a structured way to challenge plans, assumptions, or strategies before they fail in practice. It creates a disciplined environment to test ideas from different angles—exposing blind spots, uncovering risks, and strengthening decision-making.

Most strategy tools are built on clean lines and rigid boxes (e.g., OKRs, SWOT, five-forces diagrams). But the real world bends, warps, and shifts in unpredictable ways. What if our strategies need to stretch just as flexibly?  AI will tell us all pretty quickly.

What’s so hard about strategy? Everyone claims to have one. There’s no shortage of books, articles, videos, advisors, and strategy-creating courses. But guidance on evaluating a strategy’s effectiveness or its long-term impact on organizational performance? That’s far rarer.

What’s so hard about strategy? Everyone claims to have one. There’s no shortage of books, articles, videos, advisors, and strategy-creating courses. But guidance on evaluating a strategy’s effectiveness or its long-term impact on organizational performance? That’s far rarer.

Time pressure drives companies to fast-track strategy development, viewing assumption testing as an unnecessary delay. Executive teams, eager to show progress to boards and investors, often conflate speed with decisiveness. Many times, executive teams are too busy doing and fail to carve out enough time for thinking. This urgency creates a false choice between thorough validation and timely execution, leading to strategies built on untested hypotheses.

Boards may accept outdated strategies without probing whether market conditions, technology, or competition have changed. For example, BlackBerry’s board failed to question management’s reliance on enterprise hardware while Apple redefined consumer mobility. Similarly, Kodak’s board didn’t press for urgent action despite signs that digital photography would disrupt film. More recently, Boeing, Bed Bath & Beyond, WeWork, and Credit Suisse boards arguably failed to question assumptions, adapt to changing environments, or hold leadership accountable: