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Leadership Development

Develop Leaders Who Put the Enterprise Before Their Function

KEEN SIX Advisory Practice · October 18, 2026 · 4 min read

Bottom line

Functional excellence does not prove that a leader can make sound trade-offs for the whole business. Use the remaining 2027 planning decisions to develop that capability through real work, explicit authority and direct feedback—not another leadership course.

Make planning a leadership development assignment

As 2027 budgets and operating plans move toward approval, CEOs have a practical development opportunity. Put senior leaders into decisions where protecting their own function would weaken the business.

Consider a commercial leader seeking more sales capacity while customer implementation is already constrained. Or a technology leader protecting a platform investment while operations needs funding to address service failures. Each proposal may be defensible on its own. The leadership test is whether the executives can resolve the competing claims.

This is different from asking people to collaborate. Collaboration can produce cordial meetings and a longer list of requests. Enterprise leadership requires a choice: what gets funded, what waits, who absorbs the cost and what the business gains.

Research discussed in Harvard Business Review’s “Cross-Silo Leadership” emphasizes the importance of building connections across organizational boundaries, understanding other perspectives and bringing different expertise together.[1] Those capabilities develop through practice, not simply through exposure to colleagues.

For the CEO, the implication is direct. Treat a consequential cross-business decision as a development assignment. Make the required behavior explicit before the discussion starts.

Give leaders a real trade-off, not a simulation

Choose one unresolved issue with material consequences for revenue, cost, cash or execution. Keep the scope narrow enough for a decision within the current planning cycle.

Pair leaders whose responsibilities create legitimate tension. Ask them to produce one joint recommendation, not two functional presentations followed by a request for the CEO to arbitrate.

Their recommendation should state:

  • The business outcome they are protecting.
  • The options considered and the constraints that matter.
  • The cost imposed on each function, including work that must stop.
  • The assumptions that could make the recommendation wrong.
  • The person who will decide and the people who will execute.

Do not require consensus. A joint recommendation can include a clearly documented disagreement. The purpose is to improve the quality of judgment, not conceal differences.

Give the leaders access to the same operating evidence. If finance, sales and operations use incompatible definitions of profitability or capacity, resolve that problem first. Otherwise, the assignment tests who can defend a preferred spreadsheet.

The work also needs a clear purpose, workable structure and adequate support. These are among the conditions described in “The Secrets of Great Teamwork.”[2] Development is not an excuse to leave authority or resources ambiguous.

Observe how they reason under pressure

The final recommendation matters. So does how the leaders reach it.

Watch whether they can explain the other function’s constraints accurately. Notice whether they acknowledge a cost to their own area without immediately asking for compensation. Look for willingness to change a position when operating evidence changes.

Also examine what they escalate. A useful escalation identifies the unresolved choice and its consequences. An unhelpful one transfers the entire problem upward.

After the decision, hold a short review with the leaders involved. Ask each to identify an assumption they changed, an impact they initially missed and a commitment they now own. Use specific examples from the work. Avoid broad labels such as “not strategic” or “needs more presence.” Those descriptions provide little direction for improvement.

Separate decision quality from immediate results. A sound decision can encounter an external setback. A weak decision can benefit from favorable conditions. Review the evidence available at the time, the alternatives considered and the follow-through.

Then assign another decision with a different counterpart. One successful negotiation does not establish a durable capability. Repeated practice shows whether a leader can apply the learning beyond a familiar relationship.

Stop rewarding the behavior you want leaders to outgrow

Development will stall if the operating system punishes enterprise-minded choices.

Suppose an executive agrees to slow bookings because implementation capacity cannot support additional customers. If the company later criticizes that executive solely for missing the original sales target, the lesson is clear: protect the function next time.

Before approving a cross-business trade-off, document any changes to commitments, resources and performance expectations. Keep accountability intact, but align it with the decision the business actually made.

“The Leader’s Guide to Corporate Culture” describes how culture shapes behavior and how leadership actions and organizational practices help reinforce it.[3] A speech about shared responsibility will carry little weight if budget reviews reward only local wins.

The CEO has obligations here too. Set the strategic priorities. Define which trade-offs leaders may make and which require approval. Do not ask executives to resolve contradictions that only the CEO or board has authority to settle.

This week, select one live planning decision. Name the participating leaders, the decision owner and the deadline. Afterward, review both the business choice and the leadership behavior. That makes development part of running the company—not an activity postponed until the plan is finished.

Key takeaways

  • Use live planning trade-offs as leadership development assignments.
  • Require a business recommendation, not competing functional requests.
  • Give feedback on observable reasoning and follow-through.
  • Adjust performance expectations when approved trade-offs change commitments.

Questions to ask this week

  1. Which unresolved 2027 planning decision would require leaders to think beyond their own functions?
  2. Have we made decision authority and strategic priorities clear enough for them to act?
  3. Where would our current performance expectations punish an enterprise-minded choice?
  4. What specific behavior will we review after the decision?

Sources

  1. [1] Cross-Silo Leadership — Harvard Business Review, 2019
  2. [2] The Secrets of Great Teamwork — Harvard Business Review, 2016
  3. [3] The Leader’s Guide to Corporate Culture — Harvard Business Review, 2018

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