One gray ceiling is one gray floor

5 min read

One man’s ceiling is another man’s floor.
– Paul Simon

At the beginning of my talk on leadership to NH&RA’s Next Generation Leadership group in November here in Boston, my glib self-description (“either the room’s youngest old person or its oldest young person”) unwittingly voiced a generational paradox of our industry: what seems to older executives a gray floor seems to their younger colleagues a gray ceiling.

I know this from personal experience: I started in this business in 1975 (twilight of the Don Draper era) as the lowest of the low, a temporary typist, amidst a severe recession, in a company that before my arrival had shed half its executive staff, barely avoiding being shut down by its primary lender. Crisis proved opportunity: problems were plentiful, solutions were scarce, urgency was paramount, and there was nobody standing in the way. Learning was doing, doing was learning.

Forty-plus years later, I’ve never stopped either. But over those four decades, while I and many others were growing careers even as we collectively grew an industry, two things happened to my generation: we grew old, and we forgot that the business had ever been other than thus. It’s long past time we remembered.

In recent years, among our work at Recap have been two meta-specialties:

1. Intra-partner valuations, particularly for executive buy-sell and retirement transfers.

2. Business strategic planning, including de-risking from overdependence on a handful of quirky Federal programs and identifying major housing challenges that need new solutions.

Both of these specialties confront the gray floor and gray ceiling:

  • To the older generation looking for equity buyouts and transition to a less-frenetic but not-idle retirement, the org-chart floor below is a gray fog from which no leaders are emerging.
  • To the younger generation seeking career paths, promotion, and equity buildup, the C-suite ceiling above is a gray cloudbank that squelches innovation and risk-taking.

Even as Next Generation members are looking for mentorship, innovation space, and opportunities to do things differently, those who mentored me (the ones still in the business) are looking at precisely the same problem but call it succession planning, knowledge transfer, and leadership development.

In truth, all of us are Dorian Gray. Youth is a shiny costume that devalues intelligence, aspiration, and courage. Age is a baggy ill-fitting suit that obscures the soul and clouds the judgment. Senior executives do not see in their current staff their past selves, though they absolutely should, because when my peers were inventing today’s affordable housing world we were children too, and somehow it didn’t stop us.

In my career, nobody taught me … or perhaps everybody taught me, some more consciously than others. No matter your age, role, platform, or seniority, as an affordable housing executive you must always be both a mentor and an apprentice. Apprenticeship – yours or your colleagues’ – is your R&D. Your next breakthrough business lines will come not from industry gatherings but from the light of conviction in your ambitious colleagues’ eyes; that flame must burn brightly or die trying.

Wisdom is good; so is courage and, gerontocratic though human societies may be, any business, any industry, needs both. Especially now: double-bottom-line investment banking – which is what we do, never let anyone belittle it – is all about inventing and demonstrating viable transactions for urgent housing-related problems by stretching existing paradigms or creating entirely new ones. Its essential skill is rigorous creativity, or creative rigor – analysis and imagination in equal measure.

For four decades, our industry has existed on the ever-shifting intersection between political will (as expressed in subsidy and resource flows) and capital-markets viability. We have to out-think the political markets, and for that we need innovative courage: to stop thinking about where the subsidy currently is and how to capture more of it. Instead, think about what urgent housing problem isn’t being solved now, design a solution for it, and the solution will summon its own resources.

Via the Affordable Housing Institute, I work on affordable- housing-related topics all over the world, from Abu Dhabi to Zimbabwe, and speak on these topics in gatherings large and small; nevertheless, that two-hour talk to the Next Generation audience just down the street from my office was among the most personally moving I’ve given in the last year and a half, because it reconnected me to our industry’s leadership challenge: if you don’t help the next generation up, then the current generation has nowhere to step down.
Leadership is demonstrated; trust is granted before it is earned because it can be earned only after it has been granted; learning requires permission to risk and to fail; and delegation takes the courage not to busybody afterwards.

Dissolve the gray ceiling, cut through the gray floor.

Always be teaching. Always be learning. Always be delegating. Always be aspiring.

Your career, your business, and our industry, depend on it.

David A. Smith is founder and CEO of the Affordable Housing Institute, a Boston-based global nonprofit consultancy that works around the world (60 countries so far) accelerating affordable housing impact via program design, entity development and financial product innovations. Write him at