Feeding the error messages back into the LLM is the "banging the tv to fix the picture" of our generation.

Lorin Hochstein

Who gets to do strategy?

• 🔑 Strategy is often gatekept — It’s not a skill people inherently lack, but an activity that access is restricted to. This is typically reserved for executives or tenured leaders due to the high cost of failure and the slow feedback loops involved in strategic decisions.
• 🪜 Create a “pyramid” of strategic contribution — Instead of restricting strategy to a select few, leaders should create layered opportunities for practice. This can range from high-level, multi-year vision documents down to project proposals that connect daily work to broader goals.
• 🌱 Develop talent and improves alignment — By providing more “access points” to strategy, organizations can cultivate a larger pool of strategic thinkers. This not only improves the quality of the strategy through diverse input but also ensures more people understand the “why” behind their work, leading to better execution.
• 💪 Treat strategy as a practiced skill, not an innate talent — The core argument is that people become good at strategy by doing it. A leader's role isn’t to find “natural strategists” but to create an environment where this critical skill can be safely practiced and developed across the company.

“You need to be more strategic”

• 🤔 “Be more strategic” is lazy feedback — It’s a vague and unhelpful phrase that places the burden of interpretation on the employee. It often signals a manager's dissatisfaction without providing any clear, actionable guidance.
• 🎯 Strategy is about connecting work to outcomes — Acting strategically isn’t about abstract, long-term thinking. It’s about understanding the why behind your work, prioritizing what will have the most impact, and consciously deciding what not to do.
• 🧑‍🏫 A lack of strategy is often a leadership failure — If an employee isn’t being strategic, it’s frequently because they lack the necessary context that their manager should have provided. This includes clarity on company goals, user problems, and business priorities.
• ✅ Ask three key questions to become more strategic — The article suggests a simple framework for thinking strategically by consistently asking:
  • Why this? — How does this work connect to a specific goal?
  • Why now? — What makes this the most important thing to do right now?
  • What are the trade-offs? — What are we giving up by choosing to do this?

Reducing Power Gradients

One of the most effective levers for increasing psychological safety within a team is flattening the power gradient – the gap between those with the most power and those with the least.

• ⚖️ Power gradients silence people — The perceived difference in status and authority between team members — the “power gradient” — is a major barrier to psychological safety. When the gradient is steep, people with less power are afraid to speak up, challenge ideas, or admit mistakes, which leads to poor decision-making.
• 🧑‍✈️ Leaders are responsible for flattening the curve — Because leaders hold the most authority, it is their responsibility to intentionally reduce this power imbalance. This isn't about giving up leadership but about creating an environment where every voice can be heard, regardless of rank or title.
• 💬 Admit you don't know — A simple but powerful way for a leader to reduce the power gradient is to admit fallibility. Saying things like “I don’t know” or “I could be wrong here” signals that they are open to input and creates space for others to contribute their expertise.
• 🤝 Make it safe to disagree — Leaders should actively invite and normalize dissent. This can be done by asking questions like, “What am I missing?” or “What’s a reason we shouldn’t do this?” and by thanking people who challenge the status quo, making it clear that disagreement is valued, not punished.

Delegating Complex Tasks

• 🧠 Don't just delegate the simple stuff — Many leaders fall into the trap of delegating only simple, transactional tasks while hoarding complex, ambiguous work. The article argues this is a leadership anti-pattern that bottlenecks them and stunts their team’s growth.
• 📝 Define the What & Why — not the How — Effective delegation starts with a clear, written brief that explains the problem, the desired outcome, and the strategic context — the “what” and “why”. It deliberately leaves the “how” for the employee to figure out, fostering problem-solving skills.
• 🧑‍🚀 Empower ownership by asking for a plan — Instead of dictating the solution, the manager’s role is to ask the employee to return with a detailed plan. This creates true ownership and provides a critical coaching opportunity for the manager to review and refine the employee's thinking before execution begins.
• 🗓️ Provide support through structured check-ins — Delegation isn't abandonment. The final step is to establish a clear rhythm of check-ins to offer guidance, remove obstacles, and review progress. This provides a safety net and ensures alignment without falling into the trap of micromanagement.

The 5 Most Difficult Employees (And How To Actually Handle Them)

• 🎭 Difficult behavior falls into archetypes — The article identifies five common patterns of challenging behavior: The Cynic, The Victim, The Brilliant Jerk, The Procrastinator, and The People Pleaser. Recognizing these patterns is the first step to diagnosing the underlying issue.
• 💡 Look beyond the behavior to the root cause — “Difficult” actions are often symptoms of an underlying problem like insecurity, burnout, or a lack of clarity. Effective management requires diagnosing the why behind the behavior instead of just reacting to the surface-level disruption.
• 💬 Use direct and compassionate feedback — The core solution for every archetype is clear, specific, and kind feedback. The focus should be on the tangible impact of the behavior on the team or project, which depersonalizes the issue and frames it around shared goals.
• ♟️ Tolerating bad behavior is a leadership failure — Ignoring a “difficult” employee damages team morale and signals that poor performance or toxic behavior is acceptable. A manager's primary responsibility is to intervene early, set clear boundaries, and hold everyone accountable to the same standard.
• 🎯 How to handle each archetype in one line:
  • The Cynic — Channel their critical eye by asking them to help find solutions, not just poke holes.
  • The Victim — Shift their focus from blame to agency by asking, “What’s one thing you can control here?”
  • The Brilliant Jerk — Set firm boundaries on how they work, making it clear that respect is non-negotiable.
  • The Procrastinator — Break down large tasks into small, concrete steps to help them build momentum.
  • The People Pleaser — Coach them on prioritizing and give them permission to say “no” to protect their focus.

That’s all for this week’s edition

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