I sat across the enormous desk from my boss, Modesto Bee Publisher - and industry legend - Orage Quarles III and wrung my hands in my lap. I'd just told him that, uh, I had an offer to run online news for The Sacramento Bee, McClatchy's flagship paper. And, uh, I was very appreciative that he'd given me the chance to build ModBee.com, but, uh, this was a good offer, and, uh, I didn't want to seem ungrateful and -
Orage held up his hand to silence my ham-fisted attempt at being a grown-up executive. I was 30.
"Not only do I think you should take this job," Orage said, "but if you don't take it, you're fired."
I gaped at him. This was not how the three business books I'd read said this would go.
"Because if you don't take it, that tells me how little you think of your own value. And I don't want that person working for me."
It was the second time Orage taught me a great lesson as a manager. First, when he'd plucked me out of the reporter ranks to build the company's digital future, he taught me that great leaders see more in their team members than their team members see in themselves.
The second was knowing when to fire yourself.
In the 20-plus years since Orage taught me that amazing lesson, I've exercised it a few times. Each time was bold, scary, honest and ultimately the moment that propelled my career - and personal life - forward. And, rising in the ranks of the media industry, I've also seen plenty of examples of executives and CEOs who never learned that lesson.
The water coolers - or Slack channels - have plenty of unkind phrases for such a leader. Out of touch. Out of step. A great leader for last century. Waiting until he can retire. Hiding out. Rudderless. And, if your industry is facing secular changes, extreme market pressures and total disruption - as the local media industry is - those phrases come with a salty spin, but that would make this post NSFW.
Firing yourself, to me, never has been an admission of failure but an acknowledgement of reality. Of fit. Of recognizing that all things have their season. It's also not a rash decision - my wife and I have one child out of college, three in and one in the wings. We have extended families and the financial obligations that come with those blood entanglements. Nothing is a rash decision.
Firing yourself takes ownership of who you are, what your contribution is and what the organization needs. If those things are not in alignment, firing yourself should come as no surprise to anyone paying attention.
But all of us can get distracted and not look for the breadcrumbs. That's why I keep a file in Evernote and add to it as other crumbs occur to me. They include these questions:
Did I accomplish what I wanted to in this position? If not, stay. If yes, and you can't see the next hill to take, don't. Picnics are for parks.
Do I reflect the culture of my boss/board/ownership? These change over time, and so does the culture. If it doesn't align with your own mission, character or values, beware.
Do I have credibility with my team? Being an executive means making difficult and sometimes painful decisions. The best handle them with grace and dignity. The worst just look like shills.
Does this still excite me? Does it make my brain itch? Or has it become a job? Because you're not very good at hiding that.
Have I ever thought - let alone said - "I'm just holding out until ..." (I used to think this was only time based or had a specific dollar amount until I heard an exec tell me he was waiting until he received a specific accolade. Seriously. A plaque.)
When attending industry conferences, have I sat in a session covering the same topic featured in the past three conferences, with no new information presented? Bonus points if I was the presenter.
Do I have a gag reflex every morning before going to work because what I'm being asked to do compromises my integrity? This is your body telling you what your brain won't admit. (Personal experience, sorry to say.)
Have I created a business that will sustain and thrive without me, or have I made it solely dependent on me? Codependency doesn't look good on anyone.
Do I have a personal line? I generally have two: A red line I will not cross (lie to the team) and a finish line (landing on the moon). It's why in business coaching for entrepreneurs, my first challenge to them is to define their exit strategy. (You wouldn't believe how confrontational that can be. I didn't, and, hell, I've done knockoff courses of Werner Erhard's EST.)
I have others that are more personal, and have studied others by better business thinkers. Perhaps you have your own. Maybe it's time to review them.
A footnote regarding Orage: I saw him years later, when he was Publisher of the News & Observer in Raleigh. We would have lunch whenever I was in town, which was frequent. At one lunch, I did what business people do too rarely: I told one of my mentors how much he meant to me, and retold the story from his office, and how he'd taught me two of the best leadership lessons of my life.
He blinked slowly, then said, "I don't remember doing that, but you're welcome." And then he finished his meal - and taught me a third great lesson in leadership:
You never know when you're going to change someone's life.