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Tim Cynova Post by Tim Cynova

By Tim Cynova on September 26th, 2016

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The Impending Leadership Gap Crisis That Isn’t

Big Ideas | How We Work | Arts | People Operations

A person in silhouette jumping

Over the past ten years or so I’ve heard countless times, and in countless venues, about an impending leadership gap crisis facing the cultural sector. The theory goes, scores of Baby Boomers are getting ready to retire from leadership roles in arts organizations, and we’ve done a poor job building the pipeline to replace them. If we don’t address this crisis, countless organizations will be left adrift without a capable captain, or worse, they’ll disappear entirely. If only we were a for-profit company with the means to create a formal training system we would be in better shape to withstand this sea change. If only we could pay young people better they wouldn’t leave us for those higher paying for-profit jobs.

I’ll grant you we’ve done a relatively poor job investing in our people at all levels of the organization — see also my “Investing In Our People” post — but I don’t believe this is leading to some existential crisis threatening the collapse of the entire cultural sector. Really? Our sector is going to fall to pieces because of something people have been doing for thousands of years — retiring and letting other people take over.

Cemeteries are full of people who thought they were indispensable.

Calgary Cemetery, Queens, NY

Calgary Cemetery, Queens, NY

Growing up the son of a Lutheran pastor in Indiana I spent more than my fair share of time in cemeteries. (When your dad’s occupation includes conducting the funerals for those you know, it makes more than a passing impression on you.) When thinking about whether or not there’s an impending leadership gap crisis, I’m often reminded of the quote, “Cemeteries are full of people who thought they were indispensable.”

The day will come at some point when I cease to work at Fractured Atlas. I hope when that day comes the powers that be don’t hire my carbon copy. What a wasted opportunity. I do a fairly decent job of being Tim Cynova, and have built systems and the position to some extent to adjust to how Tim Cynova works best. I’d hate it if someone tried to step into the role and run it that way.

Someone will take over, and they’ll do things that I might disagree with if I were still at the organization. How many leadership transitions occur and the predecessor says, “That’s exactly how I would have done it.” No? Good! When that happens it’s usually a missed opportunity. Will my future successor nix things that I find important and am hugely passionate about? Perhaps. Will they take my name in vain as they struggle to figure out why I’ve been doing a few things in seemingly so strange a way? Oh, highly likely. (To that person: Sorry about the server closet.)

Will they know everything I do and be able to look at something and quickly understand it? Probably not. But there’s a whole host of things that I don’t know, wouldn’t know, can’t do well, or struggle with that others will be great at.

You know who’s not worried about an impending leadership gap crisis? Young people.

A large crowd of people.

Future leaders. Lots of them. As photographed by James Cridland.

As I pondered the leadership gap crisis argument, I quickly realized something. You know who’s not worried about an impending leadership gap crisis? Young people. And when we were 26, we weren’t either. Chances are we thought we knew all, or most, of the answers or could figure them out when the time came. We were 26. We wanted more responsibility, more autonomy, more fame and fortune-ish.

“The young do not know enough to be prudent, so they attempt the impossible, and achieve it, generation after generation.” — Pearl S. Buck

One needs to possess a certain level of naïveté going into a leadership position. If we, in leadership roles, knew before we got into this what an average day would hold, how many of us would we have leapt at the opportunity? Meeting with disgruntled staff, donors, and board members all day long? Government contract reporting? Sleepless nights worrying about how to make next week’s payroll? HVAC flooding your offices and your relaxing weekend plans suddenly involve a mop, bucket, and large industrial fan? Sign. Me. Up. (I should say for the record, the HVAC system is the only one currently keeping me awake at night.) No, you start off in the direction you think you’re supposed to go and ask for directions along the way when you realize, hopefully sooner rather than later, that you’re in Austin and should be in Boston.

That same naïveté is what allows people to see new solutions to old problems. Or figure out why that thing we failed at a few years ago will work now. Sometimes when people figure things out for themselves, or reinvent the wheel, it produces a better wheel. A wheel better suited for the current situation and environment.

If we want our organizations to look like and operate exactly as they do now then yes, yes there will be some type of leadership gap.

This impending leadership gap crisis theory rests on one very large assumption: that organizations should continue operating and providing their services in largely the same way as they have been. However, organizations, the needs they serve, and how they address those needs are constantly changing. Therefore we need leaders who can change and adapt and build upon what went before them. (Sometimes “building” means taking apart and reassembling to be more efficient and effective.) This is a giant opportunity to question everything from the ways our organizations operate to yes, their very existence.

Success shouldn’t be judged by the number of years an organization has existed. Success should be judged by the impact it makes. Sometimes organizations and leaders can do very bad jobs at that for a very long time. Inertia is a powerful force.

But for-profit companies…

The “successful for-profit company” argument ignores two big points. First, it’s not all that easy these days to land one of those “high paying for-profit jobs,” and two, it neglects that the majority of for-profit employers are small businesses too.

Walter Appliances

Think of all the “Walter & Sons Hardware” stores around the country where the “sons” in question decide they’d rather be a choreographer and arts administrator than take over the family business. Now Walter is in a similar predicament. Oh no, it’s the end of screws, keys, and plungers! Does the store’s closing negate his life’s work, or the decades of assistance he provided to his friends and neighbors? No. Even the best bands call it a day at some point (I’m looking at you Tokyo String Quartet. #tear).

Leadership transitions are an opportunity for fresh ideas to see the light of day unburdened by the past.

Leadership transitions can be like opening the windows and throwing back the curtains. Fresh air rushes in and sunlight bathes the dim parts of our organizations. That thing we’ve been doing for years that is horribly ineffective but there was too much emotion and inertia built into it to stop doing it? Poof, gone. That person who wouldn’t grow their skills to adjust to the new needs of the organization but they’ve just been around forever? Poof, gone. New ideas and new energy are good for everyone, even those people in the latter group who might find themselves without a job. Sometimes we need that push to help us find and reignite our passions.

This is a good thing for all of us. It could be uncharted territory for both the people and the organization. It could shutter what leaders have worked their entire lives building. That doesn’t take away the work that was done. Things evolve into something new and different and build upon the foundation these leaders built. Things serve a purpose for the time they exist and then other things take their place. The Flowbee? One haircut. Then you realize your vacuum cleaner shouldn’t also be cutting your hair.

A flower grows in a sidewalk.

Where are all the leaders of the future?

Great news! We can stop worrying about an impending leadership gap. There are legions of people out there who are skilled leaders in other facets of life, or have leadership potential. People who will quickly rise to the occasion when given the opportunity. Just take a gander at the staff listing on your website to find them. (You’re welcome.) How many times do people surprise us by stepping into the breach during a crisis or a leader’s absence? Leonard Bernstein anyone?

There are plenty of people to fill any valuable role we need. The earth has a billion more people on it then when I joined the workforce twenty years ago. At Fractured Atlas, we routinely have 300+ people apply for one position. Can you imagine how many job seekers want an open position at Google or as the conductor of the New York Philharmonic? I’d wager a lot more than 300 people. It’s less about whether these leaders exist and more about structuring a reconnaissance and matchmaking process to find and place them. Rather than worry about a fictional crisis, let’s spend our time working to identify and connect with those people who are passionate about our work and who don’t find out about us from the ads we place on the NYFA Jobs Board (no disrespect meant to the NYFA jobs board).

There’s an entire cottage industry of arts administration and social impact MBA programs that are churning out graduates with new and different skills than what current organizational leaders had when they joined the workforce (myself included). They don’t need my well-worn copy of Accounting for Dummies to decipher audited financials or oral legend to help them create a marketing plan for their season. I still quibble with freshly minted graduates who think that taking Professor Smith’s fundraising course now qualifies them to be the Director of Development for that $100MM campaign. But the young see only possibilities. That’s more good than not.

Looking for candidates and not finding them? Maybe you’re being unrealistic. God already has a job. Maybe you’re doing a poor job of articulating why someone would want to work at your company? Maybe you’re barking up the wrong tree and need to try a little harder to connect with people who would make better candidates. (Take a look at the book Who if you find yourself in this boat.) Maybe your company’s mission is no longer relevant or its relative importance is not what it once was. The telegraph ceased to be as important when the telephone came into being. The handheld camcorder — may it rest in peace — became obsolete when Apple launched the iPhone.

How much training does a leader need?

How much leadership training did current leaders have before becoming leaders? How much leadership training does one really need before they become a “leader”? Invest in staff regardless. Invest in staff not necessarily so they’ll become leaders but so they’ll be more effective at whatever they choose to do in life. (Not every talented person wants to — nor should they — lead an organization. See the Peter Principle.)

I’m not suggesting here that we just send wholly unprepared individuals into leadership roles. I’m just saying that “prepared” is a relative term that differs from situation to situation. Tomorrow’s leaders shouldn’t be carbon copies of today’s leaders. Nor do we need to train the next leader of an organization to have the skills and knowledge the departing leader acquired over 40 years in order for that new person to be successful. How much and what kind of professional development is the right amount? It depends, right? It depends on the situation, the organization, and the person.

If we hire people for the things that can’t be taught, we’re headed in the right direction. When worrying about the leaders of the future let’s focus on the things they can’t learn from the Dummies book series or Lynda.com. Grit, caring, drive, empathy, integrity, honesty, trustworthiness, openness. The other things can be learned along the way and far easier to retain when they have an actual use case. (Learning about financial statements when you don’t use them on a regular basis is a theoretical exercise until the rubber meets the road.)

Lastly, people of all ages make mistakes. Big mistakes. No one is immune to making mistakes and missteps that they might regret for their careers. Mistakes that inadvertently hurt people’s feelings. Mistakes that might tank organizations. Before we’re too quick to judge and armchair quarterback, pause. People play the hand they’re dealt, when they’re dealt it, and sometimes they find their hand filled with crappy cards regardless of their training or acumen. There are amazing leaders of every age, and bad ones too.

Where to from here?

If you are a leader worried about an impending leadership gap crisis, stop. Just stop it. There are plenty of other things to worry about. Instead, let’s spend our time and energy actively investing in all of our staff. (Don’t have staff? Invest in others through mentoring.) Who’s to say who the next transformational leader will be in our organizations and sector?

Life is short. Let’s work hard, live well, invest in others, and strive to be better today than we were yesterday. We, our organizations, and our sector, all face some very real challenges. Let’s tread lightly on the fictional ones. Carpe diem, and keep an eye on that HVAC unit.

More posts by Tim Cynova

About Tim Cynova

Tim wears a multitude of hats, all in service of creating anti-racist workplaces where people can thrive. He currently is co-CEO of Fractured Atlas (an entirely virtual organization with staff spread across multiple states and countries) and a Principal of the consulting group Work. Shouldn't. Suck. He serves on the faculty of Banff Centre for Arts & Creativity and The New School teaching courses in People-Centric Organizational Design; he's a trained mediator, and a certified Senior Professional in Human Resources (SPHR). Earlier in his career, Tim was the Executive Director of The Parsons Dance Company and of High 5 Tickets to the Arts in New York City, had a memorable stint with the Cincinnati Symphony Orchestra, was a one-time classical trombonist, musicologist, and for five years in his youth he delivered newspapers for the Evansville, Indiana Courier-Press. Also, during a particularly slow summer, he bicycled 3,902 miles across the United States.