Summer field trip 2.2: Strategy theatre at Google: was I the hero or the fool?

Sorry for the delay in part two of my summer field trip (part one here). In trying to summarize twenty years of strategic planning stories, my first draft was a billion words long and read like a bad business-school case study full of petty score-settling. So I had to scratch it all and start over. I ended up with something more like a memoir than my usual position papers. Please let me know how you like it at [email protected].

If you like superheroes but haven’t seen the 1999 cult classic Mystery Men, you really should. It stars a group of marginal heroes who somehow end up saving the day. William H. Macy plays The Shoveller, whose power is hitting people with a shovel. It’s dumb and borderline useless, but he takes pride in it. As he tells his wife, “I shovel well. I shovel very well.”

My version of shovelling at Google was strategic planning. This was the annual process of figuring out the best projects for our teams to work on, calculating how much money they would make, and asking our overlords to give us the permission and budget to proceed. Done right, it took months and involved a bunch of written documents and high-stakes presentations. This meant extra work, travel to offsites, and stress. But as a former theatre kid who also grew up loving school projects, strategic planning season was my idea of heaven. Every year was another chance for my big break. I just had to land the right slide, the revelatory data point, or the perfectly-timed comment during a group session, and I could change the world. Or at least get the part.

I fell in love with strategic planning from the start. Hellman and Friedman took DoubleClick private in mid-2005, just as the online ad business was coming back after the dot-com crash, and our leaders brought in a brilliant consultant named Dwight Porter to guide us through his proven approach to strategic planning. This was fertile ground for my A-student attitude – Dwight’s process was clear, my product had a ton of obvious problems to solve, and I had an endless appetite for building Powerpoint slides. Every year I came into strategic planning HOT. Sometimes too hot – one year, I talked for so long over my allotted time slot that they moved me later in the day in every subsequent session so I couldn’t ruin the schedule again. But people seemed to like my team’s plans, and we got most of what we asked for.

The plot thickened when we were bought by Google in 2008 and had to redo all of our strategic plans. It turned out there was another team at Google doing more-or-less the same thing mine had been doing at DoubleClick, and they assumed they’d be in charge going forward. [Ad Tech historians: this was how DFP Small Business and DFP Premium ended up being same-same, but different, but still same.] I cared deeply about my product, and at least as deeply about holding on to my precarious new job at Google, so I wasn’t about to make room. I fought like a demon at every planning session after the deal closed. More data, more multi-paragraph emails, more emotional monologues about the future of the publisher business. I have no idea if I actually persuaded Neal Mohan and Susan Wojcicki that I was the right man for the job, or if they just figured it was easier to keep me on than to fight about it any more. Either way, like Henry Fonda in 12 Angry Men, I got everyone on board with the verdict I thought was just.

My run of success ended when the ad business changed. At DoubleClick and post-acquisition Google, our plans had big stakes because we were breaking new ground. DoubleClick needed to pull off a turnaround, and Google was trying to become a success in display ads when Yahoo!, AOL, and MSN were the huge incumbents. But by 2014, once Google pulled ahead as the display leader, strategic planning stopped being about change and became an exercise in protecting our gargantuan business.

I couldn’t adapt. I was wired to find drama – looming threats, exciting opportunities, and radical approaches. Nobody wanted that any more. They wanted steadily growing revenues and profits with minimal risk. That didn’t mean there weren’t crises and urgency [ad tech historians: think retargeting or header bidding], but leadership wanted plans to restore calm, not a large bald man rocking the boat.

I didn’t get the memo, and kept trying to sell big, disruptive ideas to an indifferent audience. The rise of Facebook and other walled gardens was a threat to the open web. Large publishers were pivoting away from ads toward consumer revenue. New companies building in the cloud wanted modular ad serving and usage-based pricing. And so forth. I fell flat year after year. I distinctly (and painfully) remember trying the old “sell my ideas emphatically” trick once in front of a group of vice-presidents, and bombing so badly that Neal had to stand up and join the presentation to bail me out. My team and I were still succeeding operationally, but strategically, I felt my credibility slipping away. To abuse famous lines from Death of a Salesman, I was liked, but not well-liked, and after Neal left for YouTube, there was nobody to insist that attention must be paid.

After I left Ads, I kept chasing the old high of a successful strategic planning cycle, and did have a few wins. In particular, I am grateful to the leader of the Google Core organization, Jen Fitzpatrick, for investing in my team’s ideas around better appeals handling and transparency reporting. More often, though, I felt like Sam the Eagle, shouting “you are all weirdos!” as a bunch of chaos muppets ran riot around me.

At one role, I remember spending multiple sessions getting aligned around common priorities as part of a pitch to grow our small organization by 25-50%. In the end, we received one new headcount, which my boss gave out based on a gut feeling. We would have saved time and gotten the same result if we’d done no planning at all.

A couple of years later, a group of 20+ leaders overseeing thousands of Googlers convened at a luxury strategy offsite that probably cost hundreds of thousands of dollars, and at least as much in opportunity cost of pulling us all away from our day jobs. Partway through, the organizers decided over lunch to cut the actual strategic planning sessions to a minimum, in order to give hours of extra time to a wildly eccentric outside speaker they thought was really fun.

None of it mattered. As teams that were cost centers instead of money-making businesses, the most important strategic decisions had little to do with the quality of our plans or the persuasiveness of our case. The company’s top priority, like in late-period Ads, was minimizing risk. This meant mission-critical concerns like security and child safety were well-funded and led by the world’s best experts. But if something equally vital wasn’t at stake, decisions were driven as much by regulatory pressure, personal ambition, and internal politics as the topics at hand.

All of my experience and passion for strategic planning (and, I arrogantly assert, talent for it) had become about as relevant as The Shoveller’s shovelling.

My devotion to strategic planning continues. I recently started helping my town’s news organization, Montclar Local, with their next three-year plan. I am in a new role as a board member instead of a business leader, but so far it’s been rewarding and seems to be going well. The old sense of uncertainty is back, as we figure out how to build a durable institution that can serve our community for decades to come, even as media consumption patterns continue to change rapidly. Our next board meeting is in October, so I’ll know better by then whether the result is drama, tragedy, or farce. Fingers crossed.

In the meantime, if any of you out there in Platformocracy-land want help with your own strategic planning challenges, drop me a line at [email protected] and I’ll come running. I love this stuff. Strategery!