Leadership Development
Develop Leaders Who Can Put the Enterprise Before Their Function
KEEN SIX Advisory Practice · November 5, 2026 · 3 min read
Bottom line
A leader who consistently wins resources for one function may still be unprepared to lead the enterprise. Use 2027 planning decisions to develop a harder capability: making, explaining and executing trade-offs that benefit the business while imposing a real cost on the leader’s own team.
Make planning a test of enterprise leadership
As 2027 budgets and operating plans move toward approval, CEOs have a practical leadership development opportunity. Watch what happens when a business priority requires a capable executive to accept less funding, share scarce expertise or absorb work that benefits another function.
The issue is not whether that executive agrees quickly. Fast agreement can conceal weak analysis or an intention to resist later. The issue is whether the leader can distinguish a legitimate business constraint from a preference to protect their own territory.
Functional excellence and enterprise leadership are different jobs. Michael Watkins describes the transition from functional manager to business leader as a series of shifts, including moving from specialist to generalist and from analyst to integrator.[1] Those shifts become tangible when executives must reconcile competing needs rather than optimize one function.
For development, choose a live decision with material consequences. It might involve moving experienced staff to a product launch, changing customer service commitments or funding a shared capability. Do not manufacture an exercise when the operating plan already contains the work.
Require an enterprise case, not a loyalty test
Before the decision meeting, ask each participating leader to prepare a short account of the trade-off. What enterprise outcome matters? What does their function contribute? What cost would their preferred option impose elsewhere? What evidence would change their recommendation?
Require leaders to explain the strongest alternative to their own proposal. This is not a performance of agreement. It tests whether they understand another function’s economics, obligations and operating constraints well enough to make a responsible decision.
Research discussed in HBR’s “Cross-Silo Leadership” emphasizes capabilities such as asking questions, taking others’ perspectives and connecting across organizational boundaries.[2] Apply those capabilities to the actual work. A commercial leader should understand delivery capacity. An operations leader should understand the customer consequences of a capacity limit.
Do not equate enterprise thinking with surrendering resources. Sometimes the executive defending an unpopular requirement is protecting the business. A control obligation, critical maintenance need or contractual commitment cannot be dismissed as territorial behavior.
The development standard is a defensible enterprise case. Leaders should make the benefit, cost and uncertainty visible, including the consequences for their own teams.
Clarify authority before judging behavior
An executive cannot learn sound trade-off judgment inside a decision process where everyone has an informal veto and nobody owns the outcome. That environment can teach negotiation for advantage, not enterprise leadership.
For the chosen decision, identify who develops the recommendation, who contributes relevant evidence, who makes the final decision and who must execute it. Where formal approval is required, make that explicit. HBR’s “Who Has the D?” offers a useful foundation for separating decision roles rather than treating participation as shared authority.[3]
Then make the CEO’s role equally clear. If the CEO invites challenge but privately rewards agreement, the exercise will produce compliance. If the CEO repeatedly reopens settled choices after private lobbying, leaders will learn that the meeting is not where decisions are made.
Once a decision is made, ask the executive absorbing the largest cost to state three things: what will change, what risk remains and what support is needed to execute. Ask the benefiting executive to acknowledge any reciprocal obligations.
Record the consequence for existing commitments. If resources move, delivery expectations may need to move too. Leaving those expectations untouched turns an enterprise decision into an unacknowledged burden on one team.
Develop through execution, not just the meeting
Review the decision after enough operating time has passed to observe consequences. Examine both the business result and how the leaders executed it.
Did the executive explain the decision accurately to their team? Did they transfer the agreed resources on time? Did they surface an emerging problem early, or use it to reopen the original dispute? Did the receiving function deliver its side of the agreement?
Use that evidence in a direct development conversation. Identify one behavior to repeat and one to change. Give the leader another real opportunity to practice, with a specific expectation and a review date.
Keep room for correction. Enterprise commitment does not mean defending a poor decision indefinitely. If assumptions fail, leaders should bring evidence and propose an adjustment without rewriting the history of what was agreed.
For CEOs and boards, the succession implication is clear. Evaluate more than functional results and personal influence. Look for evidence that a leader can protect the whole business, carry a difficult decision through execution and remain accountable when their own function does not receive the immediate benefit.
Key takeaways
- Use live planning trade-offs as leadership development work.
- Test the enterprise case, not the speed of agreement.
- Clarify decision authority and adjust commitments when resources move.
- Evaluate execution after the meeting, including reciprocal obligations.
Questions to ask this week
- Which 2027 planning decision would require an executive to accept a real cost for an enterprise benefit?
- Can each leader explain the strongest alternative to their preferred option?
- Where are unclear decision roles or private lobbying undermining accountability?
- What execution evidence will we review before drawing conclusions about a leader’s readiness?
Sources
- [1] How Managers Become Leaders — Harvard Business Review, 2012
- [2] Cross-Silo Leadership — Harvard Business Review, 2019
- [3] Who Has the D? How Clear Decision Roles Enhance Organizational Performance — Harvard Business Review, 2006
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