Giving good context · for leaders
Giving good context as a leader
A model knows a lot about management in general. It knows nothing about your company’s strategy, last quarter’s board discussion, or why a past initiative failed. Without that material, it writes advice that would suit any company and fits none.
Giving good context means selecting the material a trusted new executive would need before writing. That includes the current plan, recent decisions and their reasons, confirmed figures, and the concerns of the people who will read the output. It also means leaving out material that is stale or sensitive.
Where it comes up
A quarterly board update
Provide the agreed metrics, the previous update, and the questions directors raised last time. The draft can then show progress against what the board already expects, rather than starting from nothing.
A strategy memo for the leadership team
Give the model the current strategy document, the market facts you trust, and the constraints, such as budget and headcount. Mark which assumptions are confirmed and which are still open.
A hiring rubric for a new role
Supply the job’s actual responsibilities, the skills the team lacks today, and your company’s rules on fair hiring. A rubric built from this reflects the real job, not a generic job listing.
What it looks like at each band
E1 · Foundational
Gives the task and a line of background. Output reads as generic management writing. Does not yet connect the generic result to the missing material.
E2 · Proficient
Includes the relevant plan, figures, and prior documents. Pastes the source material rather than summarizing it from memory. Output reflects the organization’s real situation.
E3 · Distinguished
Chooses context for each task with care. Removes outdated plans that would mislead, labels which figures are final and which are estimates, and states what the model should not assume. Keeps a current briefing document ready for recurring work.
E4 · Exceptional
Maintains shared context the leadership team uses, such as current strategy, approved metrics definitions, and decision history. Updates it when plans change. Others get accurate output because the source material is reliable.
Common mistakes
Relying on the model’s view of your industry
Training data may describe your market as it was some time ago. Supply the current facts you rely on, with dates.
Pasting the whole data room
Hundreds of pages bury the material that matters for this decision. Select the documents that bear on the question you are asking.
Mixing drafts and final figures
If an early forecast and the approved budget both go in unlabeled, the model may quote either. Mark which version is final.
A worked example
A strategy memo recommending whether to enter a new regional market next year.
Write a memo on whether we should expand into the Nordic market. We are a mid-sized software company.
The model has no facts about the product, the finances, or the leadership team’s concerns. It will produce a general list of pros and cons that could apply to any company.
Draft a two-page memo for our leadership team. Attached: our current three-year plan, last year’s results for our two existing regions, and notes from three customer calls in the target market. Confirmed: we have budget for two hires next year. Not confirmed: whether our product meets local data rules. The CFO’s main concern is payback time. Recommend a course of action, and list what we would need to learn first.
The model has the plan, real results, customer evidence, a confirmed constraint, an open question, and the main reader’s concern. The memo can address this company’s decision.
The full study guide for this skill, for every role, is Giving good context. The other five skills for leaders are on the AI skills for leaders page. A one-page summary is in the AI context checklist.
See where you stand
The free check grades giving good context and the other five skills in about fifteen minutes. Nobody sees the grade but you.
Then build the skills and prove it. The three steps for leaders list the courses and templates that fit the work.