Beware the 11th-Hour CEO

During the dot com 90s, when money was cheap and rivers flowed in champagne, we used to do these things called ‘press tours’. In person. We were speeding in a Manhattan taxi running behind time to get to PC Magazine offices. Wait-for-the-last-minute CEO was working on his Powerpoint slides while the yellow cab dodged bicycle messengers and pedestrians, when suddenly the CEO hurled on his laptop and Italian silk necktie.

Beware the Didactic CEO

We worked with a CEO from a Midwestern company once. Let’s call him Doug. A nice enough family man, kind and considerate. We usually like to put new CEOs in front of research analysts well before putting them in front of the press. I like to hear how spokespeople speak. I analyze their delivery, their tempo, their nuances. I gage the mood of the recipient. (Interested, engaged, or bored to tears?) By the time an individual’s career has topped at the CEO level, they will have collected hours of interview experience. But I can usually catch mistakes that can lead to mis-judgments, which can lead to mis-quotes. Most CEOs are talented frontmen and frontwomen. They get the whole picture and can talk big picture. By now I must have hit the 1,000 mark for number of press interviews and analyst briefings done over the past 20 years. Every CEO spokesperson has a lesson or two to learn. But Doug had a severe case of bad CEO speak. He approached each interview as though from a podium. He spoke on the phone as though addressing a congregation. He delivered a monologue that bordered on a diatribe. It was didactic in tone and sentiment. His style was so offensive, that we decided to hire a freelance reporter with New York Times street cred. Then got a hotel room. We put this CEO inside the hotel room with the reporter, who conducted a mock interview. Then we watched the whole affair unfold. After an hour interview, we gave the CEO feedback. The exercise paid off. It made a huge difference in his approach and interview style.

Beware the Fire-Hosing CEO

Let’s call our CEO Keith. Keith was an affable, young and energetic CEO with an easy smile. His startup was based in Mass with about 50 employees. A native New Yorker, when we let him know how we caught the attention of Bob Tedeschi at NY Times for an interview, Keith got so excited he practically kissed me. Heck, I too was excited. Interviews with the former “grey lady” are few and far between. But the interview was a disaster. (Keith had not undergone my “Interview Tips & Tricks” training.)  What happened was this. Keith launched into a virtual verbal assault, talking non-stop for an hour. He didn’t obey the basic rules of conduct, namely 1) conduct a dialog and 2) service the article/reporter, not your business. Interviews should be primarily about helping the reporter write the best article he or she can. If you prove you are worthy to that end, the reporter will view you as an asset and resource for future articles. Reporters do not live to be sold a bag of goods. They are not a potential end user or customer. A few times Mr. Tedeschi tried to interject a question, but each time Keith could not hear him. Keith never paused after making a point. He never did a check-in to judge whether he was serving the article at hand. His was a monologue. He fire-hosed the reporter so badly that after an hour of non-stop rapid fire, Tedeschi said, unenthusiastically, “Wow. That’s a lot of information.” The end result was a one word mention of the company and no quote. The marketing director called to ask what had happened. Why didn’t Keith get a quote? I had to think about it. (This was in 1995, when I didn’t have my trusty “Interview Tips & Tricks” PPT on the ready.) I slept on it. Conclusion? The CEO fire-hosed the reporter. (Company eventually went out of business.)

Beware the Hidden-Closet CEO

If you read the NY Times Sunday Business from January 8, 2006 you will see a “Boss” profile write up not about the CEO from Wal-Mart or Whole Foods but from a tiny, no-name private startup with 19 employees (at the time). I was scratching my head, trying to get press for this SaaS (software-as-a-service) time & billing web 2.0 services company. They had some customers, but no household brands. They were not solving a specific IT problem that would lend interest to an IT pub. Six months into the relationship, and we had no news to tell. I mused, I pondered. Then I thought about asking the CEO for his back-story. Come to find out, this CEO had an amazing back-story that started as a Miami Herald reporter, then to Harvard Law, then to the NY prosecutor’s office, then as the legal counsel for the Department of Justice at the US Embassy in Bogota, Columbia, fighting drug trafficking. I couldn’t believe it. Fighting Pablo Escobar? When he arrived to Bogota, he was given a bodyguard and an armored car. He told me the cartel could’ve easily blown him up. Instead, they tried to discredit the office by implicating him in some drug trade, or with prostitution. It was so colorful. I immediately thought of the NY Times “Boss” column. I wish I had more pitches like that one. Never back down from the back-story. Ask your client about their past.

(This company was eventually acquired.)


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