The Stretch Assignment Myth - When Challenge Becomes Harm
Stretch roles only develop people when paired with adequate support. How to spot when 'development' is actually setting someone up to fail.
I need to tell you about a role I said yes to, years ago, that taught me something I couldn't have learned any other way.
I was working in higher education. I'd been performing well, building a reputation as someone who could hold complexity, manage difficult situations, and lead teams through change. So when my role was expanded through a change management process - bigger scope, larger team, responsibilities I hadn't held before - I went through the application process and backed myself.
What followed was eighteen months of the steepest learning curve of my career. Not steep in the way that builds you. Steep in the way that wears you down so gradually you don't notice until you're sitting in a car park at 7pm, wondering why you can't make yourself drive home.
This isn't a story about being let down by my leaders. They weren't absent or uncaring. They were, in many cases, navigating their own stretch, managing their own ambiguity, making decisions with incomplete information, and leading through change they hadn't experienced before either. The idea that there's always a senior leader somewhere who has the full picture and simply needs to share it is one of the quieter myths in organisational life. Often, nobody has the full picture.
No, the real problem was something more subtle and, I think, more common. I didn't know what I didn't know. And because I didn't know what I needed, I couldn't ask for it.
I didn't know that what I was feeling wasn't failure - it was the predictable result of operating beyond my zone of capability without scaffolding. I didn't know that the exhaustion wasn't a sign that I needed to try harder, but a signal that the conditions around me needed to change. I didn't have the language or the self-awareness to say ‘I need a thinking partner for this’ or ‘I need someone to help me see the patterns I can't see from inside them.’
So I did what many high-performing people do. I worked harder. I stayed later. I said yes to more. I built the systems around me that I didn't know I was missing. And I told myself that the exhaustion and self-doubt were the price of growth. The price of senior leadership. That this was what development felt like.
Growth requires discomfort. I'd always known that. What I hadn't understood was that I'd been using resilience as a reason to absorb things I shouldn't have been absorbing. The damage wasn't dramatic. It was quiet, incremental, and easy to mistake for the cost of doing the job.
It took me a long time to see the line between stretch and strain clearly. And the distance between the two is almost never about the person's capability. It's about what's been built around them, and whether anyone helped them see what they couldn't yet see for themselves.
The incomplete truth about stretch
The idea that challenging assignments develop leaders is one of the most well-established findings in leadership research. The Centre for Creative Leadership's foundational work, grounded in McCall, Lombardo, and Morrison's The Lessons of Experience (1988), found that effective leaders attributed most of their growth not to formal training but to on-the-job experiences that pushed them beyond their comfort zones.
This is powerful research. And it has been powerfully misapplied.
What gets quoted is that ‘stretch builds leaders’. What gets left out is awareness and understanding of the full picture. CCL's own framework makes clear that developmental experiences require three conditions working together: challenge (the stretch itself), assessment (understanding the gap between current capability and what the role demands), and support (the scaffolding around the person). Remove any one of those three, and the experience ceases to be developmental.
Lev Vygotsky's Zone of Proximal Development, first described in the 1930s and still foundational to adult learning theory, draws the same line with even more precision. The ZPD is the space between what someone can do independently and what they can achieve with guided support. Within that zone, learning happens. Below it, boredom. Above it, overwhelm. When we place someone beyond their ZPD and provide no scaffolding, the stretch stops being growth and becomes survival.
But here's what I've come to understand, both from my own experience and from sitting with hundreds of leaders since. The scaffolding problem isn't always a failure of the organisation or the senior leader. Don’t get me wrong, sometimes it is, but often, it's a failure of visibility. The person being stretched doesn't know what support they need because they haven't been in this territory before. And the leader offering the stretch may not know either, because they're navigating their own uncertainty at the same time.
This is the ambiguity problem that sits underneath most stretch assignments. We act as though the person assigning the role has a clear view of what the role requires and can articulate it precisely. In reality, especially in complex environments, the person assigning the role is often making their best guess in shifting conditions. The expectations aren't withheld. They're genuinely unclear.
Research published in the Academy of Management Journal (Dong, Seo & Bartol, 2014) examined 214 early-career managers and found that stretch assignments amplify emotional reactions in both positive and negative directions. The determining factor was not the person's talent or resilience. It was the support structure around them. But what the research also implies, and what I see in practice, is that building that support structure is harder than it sounds when neither party can fully see what's needed until the person is already in the middle of it.
What I see now as a coach
Over time, the role shifted again as the structure evolved. It grew to include crisis response, complex change and student transition and engagement programs, and I was able to reshape the structure to better match the complexity of the work. The challenges were just as deep, but something had changed. By then, I had started to understand what I needed to ask for. The difference wasn't the difficulty of the work. It was my ability to see my own gaps and name them.
That experience is why I coach the way I do now.
When a client sits across from me saying, ‘I think something's wrong with me,’ I don't rush to reassure them. I help them see clearly what's actually happening. Almost always, when we unpack the situation, the problem isn't that something is wrong with them. It's a gap between the challenge they're facing and the support around them. But the more interesting conversation, the one that changes things, is helping them see what they don't yet know they need.
Because that's the real scaffolding gap. Not the absent mentor or the missing check-in, although those matter. It's the self-awareness to recognise where you are, what's beyond your current capability, and what kind of support would actually help. Most high-performing people have never been taught to ask those questions. They've been taught to figure it out.
These are the signs I watch for when a stretch assignment has stopped being developmental:
- The person was chosen for capability, not readiness. They were talented and willing, but nobody mapped the distance between where they were and what the role actually demanded. And the person themselves couldn't see that distance, because they'd never been in that territory before.
- Support exists in theory but not in practice. ‘My door is always open’ only works if the person knows what question to walk through it with. When you don't know what you don't know, an open door is just a door.
- Asking for help feels like an admission of failure. In environments where self-sufficiency is rewarded, stretch assignments become endurance tests. The person focuses on appearing competent rather than becoming competent, which is the opposite of development.
- Ambiguity is treated as something to push through, not name. When neither the person in the role nor the person who assigned it can clearly articulate what success looks like, the stretch becomes shapeless. You can't grow toward a target you can't see.
What I wish I'd known
If I could go back to the version of me who said yes to that role, I wouldn't tell her not to take it. The learning was real, even if it came at too high a cost. What I'd tell her is this:
You don't need to know everything. But you do need to learn to see what you can't yet see. Find someone, a coach, a mentor, a trusted peer, whose job it is to help you notice what you're missing. Not to give you answers. To help you find better questions.
I'd also tell her to stop wearing the exhaustion as a badge of honour. And I'd tell her something I now say to every client in the same situation: the gap between who you are and what this role demands is not evidence of your inadequacy. It's information. And with the right support, it's the starting point for some of the most important growth you'll ever do.
For leaders who assign stretch roles
If you're in a position to offer someone a stretch assignment, I want to say something you might not hear very often: it's okay that you don't have the full picture either. Leading through ambiguity means sometimes offering opportunities you can't fully define, in conditions you can't fully predict. That's honest. That's real.
But you can name it. You can say, ‘This role is going to stretch you, and I want to be honest that I can't tell you exactly what it will demand because some of it is still unfolding. What I can do is make sure you're not navigating it alone.’
That means building in structured support from day one. A coach, a mentor, a thinking partner. It means checking in at two weeks, not two months. It means creating the conditions in which the person can say, ‘I don't know what I need yet, but I know I need help figuring it out,’ without that statement costing them anything.
Stretch is one of the most powerful developmental tools we have. It is also, when handled without care, one of the fastest ways to damage a capable person's confidence and career trajectory. The difference between the two has very little to do with the person and almost everything to do with what's built around them - including the permission to see clearly what they don't yet know.
I know, because it took me years to learn that for myself. And it's the reason I do what I do now.
If this resonated, I'd love to hear from you. Have you experienced a stretch assignment that genuinely grew you, or one that crossed the line? What made the difference?
References
Dong, Y., Seo, M. & Bartol, K. M. (2014). No pain, no gain: An affect-based model of developmental job experience and the buffering effects of emotional intelligence. Academy of Management Journal, 57(4), 1056–1077.
McCall, M. W., Lombardo, M. M. & Morrison, A. M. (1988). The Lessons of Experience: How Successful Executives Develop on the Job. Lexington Books.
Vygotsky, L. S. (1978). Mind in Society: The Development of Higher Psychological Processes. Harvard University Press.
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