The exit interview
After a fourteen-year run with the company, I wasn’t offered a final interview. So I opted to conduct my own.
Thanks for coming in to talk with HR today. We want you to know that we valued your contribution here at the Tribune Publishing Company and simply want to ask you a few questions about your experience before your services conclude.
Can you start by stating your name and how long you have been with the company?
My name is Chris Courtney. I’ve been employed by the Tribune Company for close to fourteen years.
And how would you describe the time that you spent here?
Incredible.
Yeah, I would probably say that it has been an incredible journey.
I’m lucky in that I spent that time bouncing around the Tower trying to reinvent a company. That alone would have been enough to call the time spent memorable. But I got here at the very moment that old guard media establishments like the Tribune would begin their long decline. Every job was really about the restoration of the Tower. Every task an attempt to make the company more nimble in an era of rapid change.
That sounds like a very exciting environment to be working in. You talk about ‘bouncing around the Tower’. What exactly do you mean.
Well, in my time here I have worked on nine different floors of this tower and split my time across four distinctly different parts of the company. That exposure to the different arms of the company provided me with a unique picture of the inner workings of the organization in a way that most wouldn’t really be able to see.
What would you say was the greatest advantage to having such a unique view of the company?
When you spend all of your time sitting inside of a division like editorial or tech, it becomes easy to assume that there is a dullard in another division that is messing up what could be a great opportunity for the organization.
In short, because we keep these people apart from one another it encourages people to adopt tribe mentalities. ‘Our tribe understands the mission of journalism or business or whatever, and the others do not.’
However, when you go work with people from different divisions what you find is really smart people working hard on all sides of the company. The only division between them is the false ones imposed by the floor you sit on and who you report to. This has provided fertile ground for fiefdoms to develop throughout the organization.
The continual decline of the company has only entrenched the fiefdom mentality because at our base, humans are trained to do whatever they can to survive. If survival to you means that you keep pushing print ads long after it is a useful tool to reach customers, so be it. If it is forcing content into non-personal buckets to make it easier to put a bunch of remnant advertising around, so be it.
So are you saying that management of the company was inhibiting employees from getting their jobs done?
That really depends on the situation. I think the editorial newsrooms that I was able to work with were all well organized and happy to assist anyone who was there to collaborate with them. Whether it was Newsday’s editor John Mancini coming out to help get RedEye off the ground in 2002 or Jonathan Ozeran and I working with the Los Angeles Times to get their first apps out the door in 2009, all parties seemed happy to work with one another.
The issues always seemed to originate at the higher levels of the organization. During my tenure here, we’ve had little to no consistency at the top. I know fourteen years is quite the span of time, but to run through 6 different leadership structures is to ask a lot of a company (Dennis Fitzsimons, Randy Michaels, the weird Four Horseman leadership panel, Eddy Hartenstein, Peter Liguori and Jack Griffin).
That sort of turnover doesn’t encourage any accountability or give any value to the long-view, which is required to rebuild or sustain a company. Everything just becomes a game of hit a short-term bonus or get a parachute or both. I have a hard time fathoming how cutting jobs to save money for a company that is struggling to find a way to survive should turn into million-dollar bonuses or parachutes for executives who aren’t delivering long-term value to the company. I understand we live in a selfish world that only Ayn Rand would love, but I think even she would balk at the taking of things that were not actually earned.
So are you holding the current executive leadership accountable for the ‘mistakes’ of the last decade?
No, but fourteen years with the company doesn’t give me much confidence that they will pursue anything beyond keeping the new stockholders happy from quarter-to-quarter.
I wish Jack Griffin and this current group of executive leadership the best. They deserve an opportunity to prove themselves. That said, anything less than a long-term commitment with measureable goals should be viewed with caution.
And any plan created in 2014 that has print as the core profit center is not a plan at all. It’s an obituary.
Are there any bright spots in the company that you see?
Of course! The newsrooms still have magnificent people doing journalism that matters to the communities that they serve. I would be shocked if Peter Nickeas didn’t generate half of the traffic that finds its way to chicagotribune.com. Personalities like Melissa Harris are a big reason that the business section can carry weight against focused competitors like Crain’s. In a city of foodies, Kevin Pang’s coverage is unrivaled. Lenny Gilmore might be the best photographer in Chicago and he’s hidden away at RedEye, which is to say nothing about the video talents of Sean Ely.
There are literally a dozen other people I could throw out right now. What makes all of these people so special is that they have no playbook. No map guides their creations. They are pirates. The same type of people who created any innovation that you’ve seen over the history of the Tribune Company.
Just a short time ago, I could have thrown out a hundred of names. We’re running out of the pirates that marry themselves to the art of storytelling. We need more people who are willing to invest themselves to make unforgettable art and take amazing risks that will reinvent the company.
Why do you think these ‘pirates’ are leaving?
The same reason they leave any corporate job. They realize that no matter how hard they work, they will never be able to change the course of the company.
The goal is always to make a dent.
People who are great at what they do could work anywhere, but they choose to work here because they believe in the mission of the organization.
Unfortunately, their mental picture of that mission and the actual ‘mission’ are often quite different. Once they realize that the legacy giant isn’t going to change course, they bolt and increasingly we see them ending up at new startup media organizations that are simply more nimble. Without the weight of a century of bad debt and bad deals attached to them, the pirates will be free to create their own world while further disrupting and plundering the media giants of old.
Ok, I think we need to wrap up. Is there anything else you would like to add before you turn in work laptop and work ID?
Where do I begin?
I’ve grown enough over the past fourteen years to realize the bad deals and decisions that have accelerated the Tribune’s decline were in motion before I ever fathomed coming to work here. So I come back to the people that are working hard in spite of that. These people give everything for the craft of journalism and the communities that they serve.
Even today, the Chicago Tribune is producing high quality journalism that would rival its best work from any era.
So the problem here isn’t quality.
It’s platform, politics and a business ledger that will always favor a corporate-level executive over anyone else in the company.
That’s not a flaw unique to the Tribune, that’s just office politics in the modern American workplace.
Much akin to the journey of Christian the pilgrim or Dove Linkhorn, friends and enemies both have appeared along my path. It is striking how often those friends and enemies have ended up being the same people — just at different points in time.
I might say that lesson was the most important thing I learned in my time at the Tribune, but that would sell short the time so many people spent molding me into the person that I have become.
Every significant person who has shaped me has one fundamental thing in common.
In one manner or another, they are all pirates.
Without the approval of Ryan Smith, I’m not employed by the Tribune and none of this ever happens.
Mike Kellams taught me what it was like to create anything on a tight deadline with pure instinct. Did I say tight deadline? I meant five minutes past deadline.
Joe Knowles showed me how to lead. Jane Hirt and Jesus would soften the approach over the years, but any leadership qualities I managed to cultivate over time started with those three.
It is an unfortunate flaw that I naturally take the minority position on whatever is being debated at the time. All three of my mentors should not be faulted for that flaw.
Being an art student, I couldn’t copy edit my way out of a paper bag until Jane and Tran Ha got their hands on my work.
Please don’t hold this interview against them, they did their best.
Tran would later skillfully guide Mash out of the lab that Jane and I created it in. In the process I would discover that Tran is the happiest pirate you will ever encounter.
I would thank Chris Malcolm for bestowing upon me his knack of comedic timing, but it didn’t stick. Sorry about that.
Without the help of Wendy Pierro and Chase Agnello-Dean, I would never have successfully found the boundaries for the proper use of a photo studio. Powdered sugar and glue will make an amazing mess. The things we learn.
Mike Rich was my first hire. It was his teamwork that taught me how to delegate, but it’s easy to delegate when the person backing you up is amazing. It was the success of our initial collaboration that allowed me to gather the greatest collection of design talent that the Tower ever saw. ToRex Chekal, Kris Karnopp, Trent Koland, Mike Morgan, Jessica Randklev, Victoria Rodriguez, Drew Sottardi, Sara Stewart, Brandon Stuck — thank you for pouring yourselves into RedEye. That was amazing while it lasted.
If you sit very still you can actually hear Mike Morgan laughing right now. It doesn’t really matter where you are.
That other sound is Jane laughing.
In 2007 when I started foaming at the mouth about the impact that the iPhone was going to have on news (and my career) Scott Kleinberg was the person I could consistently count on to discuss my latest prototypes and pipedreams.
The friendship of Alberto Trevino. What do I even say? He accurately predicted the writing of this note a decade ago.

It was John Trainor who pulled the trigger and got me involved in the rebuilding of Hoy. And no amount of credit could ever reflect the work that Fernando Diaz and Rodolfo Jimenez did to establish the brand and publication as a true strength of the company.
I would have never navigated from print to digital without the guidance of Brad Moore. No single person did more to look out for my professional welfare in the Tower.
I am still growing from the time spent working with Jonathan Ozeran. It was Jonathan that provided me with the basic blueprint for how to successfully build digital products long before I was ever able to read it. He’ll often say that I helped him with design. Maybe, but he helped me with everything else. My most productive time in the Tower was spent working with him in Marc Chase’s version of Trib Tech.

The team that Ozeran constructed in tech was so far over my head that it all seemed like magic at the time. It’s nearly 2015 and I still see digital echos of the work that Claudiu Colteu, Bill Desmarais, Nemanja Stefanovic, Guy Umbright and David Wisti were churning on in 2009.
When I wasn’t strong enough to stand on my own, these are the people who stood my me.
When I couldn’t stand anymore, it was Bill Demarais who visited me in ICU. Alberto Trevino was there while I still had a collection of tubes protruding from my right ribcage.
The people you can count on in life appear on their own when you are in need. They opt in without you ever asking. They are present.
I don’t know if I would ever recognize the importance of pirates in my life without my bout with cancer, but that experience made it possible for me to appreciate the pirate mentality when life reintroduced the idea to me in the form of Brian Boyer, Joe Germuska, Chris Groskopf and Ryan Mark.

Their grunge band, also known as the NewsApps team, presented in itself a vision for what would later begin the reformation of media in America.
It was Boyer who accurately predicted that in 5 years either the pirates are running things in the Tower or we’re all gone.
It’s notable that only a handful of individuals named in this note are still with the company, but that’s a story for another time. Perhaps never.
The thing to remember is that no one was pushing forward with the intention of leaving. We were pushing forward with the hope of restoring the Tower and its place in the media landscape as our focus.
Paired with Michael Cahan, we spent eighteen months banging our head against the wall in advertising trying to coax a company drunk on the sales of print ads that mobile was important.
Michael got no support from the Tower but he always gave me his and he was the only person who thought me learning to code was a good idea.
It was that move that paved my path to join the NewsApps team.
Not that I was ready for that. But under the tutelage this diverse band of pirates, growth came.
Ryan Nagle is the most patient person on the planet. Trust me. I have tried to frustrate him in every way possible. Luckily, I took notes along the way.
Programatically or socially, if there was a problem then David Eads would have a take on it. For me, David is the model that socially-conscious modern hackers are aiming for.
It was Ryan Mark that made it ok to focus on being a designer again. Without his guidance, I’m still busy abandoning the skill that has visually defined my time at the Tower.
While I was lucky enough to collaborate some with Heather Billings, Andy Boyle, Abe Epton, and Jennifer Linder I know I didn’t collaborate enough with them. Each are amazing, creative people.
I have worked with Ryan Asher off and on since he was an intern at RedEye. We both did tours in the slightly different parts of the basement at the Tower while working for Interactive/Tech. No single person I know has been more responsive in working with the everyday user of the products we make. He really gravitated toward those issues and solved real problems for real people. That’s the sign of someone who gets it.
In this chaotic incubation chamber of application development people like Alex Bordens and myself could do nothing but grow.
Keeping the whole NewsApps team spinning forward would have been a task for anyone, but Kaitlen Exum did it all while showering the newsroom in sass and glitter.
But the glitter is gone.
And most of the pirates are gone as well.

The pirates that remain are scattered about in the Tower and Tribune editor Gerold Kern is leading those that remain to produce amazing work in the midst of legacy media’s darkest hour.
Why do I call it the darkest hour?
Because so much of what has been done over the past decade has been focused on short-term gains at the cost of the long-term health of the company. The quick wins that are achieved by mass layoffs are clearly in favor with bonus-hunting corporate executives but they fail to meet the needs of the communities they serve.
But let’s be honest — this is not a journalism problem, it’s an American one. We pay executives to hit their numbers. That’s what any MBA program in America would teach you to do.
How you hit the numbers is where the notion of ethics should play a roll. Extract value and move on to the next opportunity is the American way. But maybe that’s not the way we should be running our businesses if we hope for them to be lasting institutions.
As a person who builds products for a living, I recognize that I am responsible for the things that I build. I only ask that the executives that enter the boardrooms of our media institutions hold themselves to the same accountability.
Here are two questions that I would like every media executive to ask themselves.
First question Am I personally invested in the communities I serve?
Having trouble answering that? I suggest a visit to an after-school program for troubled teens or a homeless shelter. Your answer shouldn’t be measured in the amount of money you donate, but in the time you physically spend helping others that are less fortunate.
And no, time spent working on a junior executive’s yacht doesn’t count.
Second question How much money do I really need to make?
Having trouble answering this one reasonably? Get out of media and go into banking.
Moving forward, my goal will be to have a positive impact on the people and communities that I work for and with.
We all have a choice of where we work and the world needs your decision to be based on more than a paycheck.
Corporate executives can’t collect their bonuses off your back if you don’t work for them.
The world doesn’t need another person that just keeps their head down and draws a paycheck.
The world wants all of us exercise the God-given gifts that we were blessed with.
To best do that in this world, you have to be willing to stand your ground.
You have to question those that have been put in charge.
You have to be willing to create without a map.
And to do all of that, you only have to do one thing.
You have to be a pirate.
This item was originally published on designhawg.com in December 2014