Everybody wins when somebody is put in a stretch role. Whoever does the hiring - a manager naming a first time tech lead or a board hiring a first time CEO - has propelled somebody's career. The investment in that person's success implies a commitment to a very active mentoring relationship. The person being asked to stretch is being given the opportunity to learn and mature, with a tacit expectation that they have freedom to try and fail while they are honing new skills.
We like seeing people in stretch roles, we like what it says about us as leaders that we put people in them, and we like the possibility that one day we, too will be given an opportunity to stretch.
A stretch role creates a halo effect for the person doing the hiring and the person being hired. For the management doing the hiring, it's a sign that the company is investing in the next generation of leaders, and that the firm demonstrably offers opportunity for advancement. For the individual being hired, it signals satisfaction of performance and expectations for great things. And, because everybody is taking a chance, it communicates an element of "risk", even in otherwise risk-averse corporate cultures.
But the halo reflects little brilliance. Stretch roles are too often made because there aren't any other viable choices. We rarely get to hire our ideal candidate, so we're going to have to settle in one way or another. Scarcity is a factor: in tight labor markets, availability becomes a skill. Plus, the longer a position goes without being filled, the worse the manager responsible for filling it looks - and the more likely that somebody higher up will conclude the position isn't all that necessary and will remove it from the budget. The decision to put somebody in a stretch role is very often simply that we can't think of any reason not to put you in this job. This is easily rationalized: emotionally, the benevolence of offering somebody a stretch role more than compensates for the risk that the person will not work out.
In the right circumstances, stretch roles grow people and businesses. They give a person license to test his or her boundaries, the freedom to experiment, and the opportunity to develop a unique style at something. But success depends on the circumstances: a short honeymoon period, being kept on a short leash by management, pressure to underwrite risks they don't completely understand, a "we never fail" corporate culture, no critical assessment of the person's areas of weakness, an absentee mentor or, worse, an incapable mentor, each stack the deck against the stretch candidate. A newbie in the job will not recognize the factors working against their success.
Throwing somebody into the deep end of the pool in their first swim lesson isn't enabling, it's overwhelming. Having somebody claw their way into a state where they can perform at a rudimentary level isn't professional development: it risks developing the wrong "muscle memories" for the job, and denies them the opportunity to achieve the meta-awareness they need to master their new role. It's also short-term career fatal: perpetually chasing responsibilities, constant drama and few successes alter the perception of the person from "aspirant stretchie" to "unqualified leader".
There is also the potential for long-term career damage. Over-promote somebody into a leadership role and they'll forever think they're leadership material. It may be that they simply aren't, but the stretch candidate is not likely to recognize this before or after being asked to take a stretch role; once invited, they've made the grade. The person who was on a stable career path ends up making frequent job-hops across firms just to maintain the same level of seniority.
Teams and departments suffer, too, not only from weak leadership at the helm but from the damage done to the confidence and trust among everybody else in the business. Plus, it sews seeds of doubt with the management who put the person in that role in the first place, often with damaging consequences (recall that Bill Ackman was ousted from the JC Penney board for having hired Ron Johnson as CEO).
Worse, the time spent with the wrong person in the role is time the business prolongs its people problems. Some years ago, I worked with a firm that had a strong tech culture but a weak sales one. There was high turnover of salespeople, and frequent vacancies in the sales team. A manager in the tech organization asked for a position in business development. Because of his credibility in tech delivery twined with an extrovert personality, management saw no reason not to give him the job. His lack of knowledge of business development, his lack of empathy for non-technical business buyers, and the absence of any strong sales leaders to mentor the new hire contributed to a disappointing year, culminating with his being asked to leave the sales organization and return to tech. Tainted by this failure, the would-be BDM left the company soon after. The company had not only engineered the loss of a respected member of the tech organization, it was no further along solving it's sales problem one year on.
(As to the person in question, his resume ticked technology, management and sales boxes, he already had a general management position at another tech firm in hand at the time he left. It was a short-lived gig as it became obvious very quickly that his capability did not live up to his resume.)
There's a simple litmus test we can apply to any organizational leader: would this person hold a comparable position in a comparable organization? An established leader capable of redefining and reshaping role clearly passes this test. An emerging leader who quickly takes to their new role while also disrupting conventional understanding of it will also pass this test. An aspirant leader being chased by demands and relegated to rote execution under constant direction of his or her superiors will not.
Every business has people in stretch roles. What are you doing with yours?