How to do the blandest and most irrelevant press conference of the event season

My diginomica series on surviving enterprise events covers a lot of ground. We go from how to make sure your customer panel is boring and stale, to how to screw up a vendor analyst day. It's not just a snark festival - I also share feedback from customers on how to make an enterprise event better.

Vendors have a golden opportunity to save enterprise events from themselves. Alas, bloated keynotes will be the norm:

Stale slide decks, boring panels and cheesy motivational speakers have obscured the essence of enterprise events: peers learning from peers.

The enterprise press conference - twelve ways to yawn it up

But there's hope. We don't have to throw all event traditions our the window. One of those fine traditions is the press conference. The press conference is typically for media and analysts (customers who show up are *usually* welcome to attend).

If the so-called pundits do our jobs right at the press event, we should surface a juicy nugget or two - items that customers can use for roadmap questions and product evaluations.

Alas, many things can also go wrong at a press conference. If you want your "presser" to be inconsequential and irrelevant, there's absolutely a proven playbook for that. So here's my satirical tips - all based on real-life situations. Follow these, and your press conference will go into the event dustbins as a yawner for the ages.

In no particular order:

1. As per tradition, let the first question go to the poor sod who has been covering the company the longest. They can always be counted on to throw a nice PR meatball over the plate.

2. Schedule the press conference immediately following the keynote. If possible - and it shouldn't be hard - make sure that keynote runs long. Enjoy the mad scramble that ensues. Make it even more interesting by switching up the location due to these time conflicts. With any luck, some of the media hotheads will give up - and head for Starbucks.

3. *Never* stream or record the press conference. If no one is listening, it's not on the record.

4. Always spend the first 10-15 minutes of the press conference rehashing the keynote, preferably with a beefy Powerpoint deck on hand.

5. Make sure whoever moderates the press conference is fully prepared to praise the executive team for their terrific keynotes, their leadership during this time of incredible transformation, and their "great answers" to each question.

6. Make sure the press conference is during a fiscal "quiet period." No need to provide historical performance data either - just punt all financial questions to kingdom come.

7. If you've made an acquisition recently, don't have the CEO of the acquired company present to answer questions. Stoked with cash and stock options, they might be a little too honest about the hard work ahead integrating the acquired product, and so on.

8. NEVER, ever share the actual number of customers who have migrated from on-premise to your SaaS solutions. For press conference purposes, your total number of "cloud customers" is: anyone who accesses your software through a browser, VPN, or a managed data center.

9. If a member of the media inconveniently brings up a prior customer count mentioned publicly in the past, explain that number is now out of date. An updated number will (hypothetically) be provided (someday).

10. Make sure each executive panelist answers each question, whether or not the question pertains to their focus. Ideally, each tag team answer should run about ten minutes.

11. You have a "we'll follow up with you on that" you can use. That's your get-out-of-this-squirmy-question card, which you can play a couple of times in each presser. Remember, "we'll follow up" isn't an absolute promise, it's a good intention in the moment.

12. Yes, a press conference is about as pleasant to your executive team as a dental filling. Assure them that if they do this one chore, they won't have to deal with any 1:1 or small group media meetings, as there will be no need.

Pro tip: Brian Sommer is likely to ask how you stack up to the rule of 40, Holger Mueller about your Hadoop and big data strategy, and Vinnie Mirchandani about why you're slow on vertical functionality.

Media and analysts do their part to make yawners yawn

It's only fair for media and analysts to do their part to make the press conference forgettable and irrelevant. Here's some ways we can - and do - help out.

1. Start a gladhanding competition. The goal? Who can compliment the CEO most profusely for their terrific keynote, before asking the obvious?

2. Don't just ask one question, ask several - in one run-on sentence. Make sure your question structure is elaborate enough that they'll have to come back to you several times, e.g. "what was your other question?"

3. It's important everyone at the press event understands the breadth of your knowledge. Please share some deep context about you and your expertise, before asking your question.

4. Never follow up on a question that wasn't sufficiently answered at the last show. If the vendor has let the issue go, so should you.

5. If you have that nervous feeling in your gut, you know, that feeling you get when you are about to ask a question that can get you in hot water, just be patient. Wait a bit longer. Raise your hand near the end, when it's highly unlikely you will be called upon. That way you'll know you tried.

6. Don't miss the chance to ask the executives, "What's on your summer/fall/winter/spring reading list"?

7. There's always the incisive "Which leaders do you admire?", ready for the asking.

8. If both those are taken, "What keeps you up at night?" will suffice.

And yeah, I've made some of these mistakes. I'm not proud of it either.

The wrap - press conferences don't have to be brutally bland

If press conferences are as predictable and bland as I've implied here, why not just put them out of their misery?

A good executive team can win transparency points by answering questions in an authentic/forthright way. Product leaders can earn roadmap trust with expert answers. Even the occasional  "We made a mistake, and here's why" can speak volumes.

Executives are understandably more cautious in a large, on-the-record session with media and analysts (you can get more revealing comments in 1:1 sessions). But: you can learn a LOT about a company from the facial expressions after pointed questions, pregnant pauses, and how questions are answered directly, or diverted. Even the chemistry amongst on-stage executives can be revealing. When I go into 1:1 interviews after the presser, if I hear answers that deviate, that is cause for concern.

Press conferences might be our only opportunity to hear questions from outlets across the globe. Hearing the questions of Chinese journalists, for example, can shift our thinking. It's a bonus if there are financial analysts around. The best financial analysts comb the quarterlies, and can pose technical financial questions about EBITDA and non-GAAP earnings. Yep, executives love answering those!

A press conference is no substitute for candid, on the record sessions with smaller groups, or one-on-one interviews. But if transparency is a priority, press events are a useful benchmark.

If we serve the enterprise customer better with our questions and answers, I like our chances of avoiding a yawner. And yes, crappy press conferences keep me up at night.

This piece is part of my ongoing enterprise event survival guide.