Experience becomes leadership development only when challenge, reflection and support are deliberately connected to real work.
Most executives can identify a difficult assignment that changed how they lead.
The danger is concluding that difficult work automatically develops leaders.
It does not.
David Day’s review treats job assignments and action learning as important leadership-development practices because they place people inside real organisational challenges. The accompanying leadership-development material makes the same point: much leadership learning occurs through experience rather than formal instruction.
But the sources also contain a warning. A challenging assignment may produce performance pressure without producing development. If the only objective is to deliver the task, the individual may simply repeat familiar behaviours more intensely.
The Strategic Context
Formal training can transfer concepts, language and methods. It can create a safer environment to practise unfamiliar behaviour.
Yet leadership is exercised in conditions that classrooms cannot fully reproduce: competing priorities, incomplete information, political dependencies, time pressure, stakeholder resistance and consequences that matter.
Work therefore provides something formal training cannot: context.
A stretch assignment may require a leader to build a team, influence across functions, handle unfamiliar responsibility or drive change. These demands expose the limits of existing capability.
The strategic opportunity is to design work so that it develops capability while still producing useful outcomes.
What Leaders Commonly Misread
The first mistake is believing that “more pressure” equals “more development”.
Pressure can reveal capability, but excessive pressure can also push people toward defensive behaviour and short-term survival. Development requires enough challenge to force adaptation without making learning impossible.
The second mistake is allocating assignments based only on availability. If the developmental objective is unclear, the organisation cannot know whether the assignment is appropriate.
The third mistake is assuming that senior leaders will naturally reflect on experience. Busy managers often move from one problem to the next without examining how their judgement operated.
The fourth mistake is treating failure as the only source of learning. Success also contains evidence. Leaders should ask which assumptions were correct, which relationships mattered and which conditions made the result possible.
Reframing the Issue
A developmental assignment has two outputs:
- the business outcome; and
- the capability gained through producing it.
Strong organisations manage both.
This changes the role of the sponsor or manager. The question is no longer simply, “Can this person deliver the assignment?” It becomes, “What will this person need to learn, what support will allow that learning, and what risk is the enterprise willing to carry while they develop?”
Design Challenge, Do Not Merely Add It
Day’s review highlights the importance of matching assignments to developmental needs.
A leader who needs stronger cross-functional influence may benefit from an assignment where success depends on other functions rather than direct authority. Someone who needs strategic perspective may benefit from broader business exposure. A technically strong manager may need a role that requires stakeholder negotiation rather than deeper technical work.
The assignment should create a meaningful capability gap.
If the gap is too small, little learning occurs. If it is too large, the individual may be overwhelmed and the business may carry unacceptable delivery risk.
That makes assignment design a portfolio decision about capability and risk.
Action Learning Connects Development to Enterprise Problems
Action learning uses important organisational problems as the learning environment.
Its strategic strength is obvious: the organisation develops people while addressing issues that matter.
But results can dominate learning. A team may solve the immediate problem without understanding what changed in its leadership behaviour.
The enterprise should therefore protect explicit learning objectives.
What assumptions were challenged? Which relationships became critical? How were disagreements handled? What did the team learn about the system producing the problem?
Without those questions, action learning risks becoming another project with a development label.
Support Determines Whether Challenge Converts to Learning
The leadership-development materials repeatedly connect development with support before and after formal interventions.
The same logic applies to work assignments.
Support can include coaching, mentoring, access to experienced peers, sponsor reviews and structured reflection. It should not remove ownership from the developing leader.
The purpose is to create a learning scaffold.
A mentor may help someone interpret organisational dynamics. A coach may identify recurring behaviour. A sponsor may provide context without solving the problem. Peers may challenge assumptions that the individual cannot see.
Learning Must Be Made Transferable
One assignment can create highly specific experience.
The strategic goal is to convert that experience into judgement that transfers to new situations.
This requires abstraction.
A leader should be able to move from “what happened on this project?” to “what principle did I learn about leading interdependent work?”
For example, the lesson may not be that a particular stakeholder was difficult. It may be that early clarity on decision rights prevents later escalation.
That type of learning can travel.
Decision Framework
Use five tests before assigning a developmental role.
Business relevance: Does the assignment matter enough to create real consequence?
Developmental gap: What capability is the person expected to build?
Challenge level: Is the assignment sufficiently difficult without creating unreasonable enterprise risk?
Support architecture: Who will provide feedback, coaching, context and challenge?
Learning capture: How will experience be converted into transferable judgement?
If the organisation cannot answer these questions, it may be assigning work rather than designing development.
From Strategy to Execution
Immediate action: identify high-value assignments already occurring across major projects, transformations and operational changes. Determine which could serve as deliberate development opportunities.
Medium-term capability building: connect assignments to individual development plans and succession priorities. Add structured sponsor reviews, mentoring or coaching. Require reflection on decisions, relationships, assumptions and outcomes.
Long-term strategic positioning: create a portfolio of developmental experiences across functions, geographies, program environments and levels of uncertainty. Track not just who completed them, but which capabilities they produced.
Related article: Developing Leaders Is Not the Same as Developing Leadership
Related article: Double-Loop Leadership: When Better Execution Is the Wrong Answer
Signals to Monitor
Warning signs include repeated use of the same “safe” people for important assignments, promotions without exposure to broader organisational contexts, talented managers who have never led outside their speciality, and development plans that list courses but no work experiences.
Another warning sign is unmanaged stretch: people are placed into high-risk roles with little support and later judged for failing to learn quickly enough.
Positive signals include deliberate rotation through relevant contexts, assignments matched to known development needs, leaders who can explain what they learned from difficult work, and successors who have already handled meaningful responsibility before promotion.
Questions for the Leadership Team
- Which current business problems could also become leadership-development opportunities?
- Are we matching stretch assignments to specific developmental needs?
- Where are we using pressure without sufficient support?
- What lessons do leaders carry from one assignment into the next?
- Are our best development opportunities distributed fairly, or captured by a small group?
- Which future leadership roles require experiences we are not currently providing?
Closing Perspective
Leadership is developed most powerfully when learning is embedded in consequential work.
But experience alone is an unreliable teacher.
The enterprise must design challenge, support reflection, capture learning and connect assignments to future capability. When that happens, work stops being merely something leaders deliver.
It becomes one of the organisation’s most important development systems.
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