October 12, 2009
Demystifying the Internets: Tips for Talking to the Boss

If you read this blog, I’m going to assume you’re tech-savvy. So, for the purposes of this post you new name is “Savvy.” Those that aren’t tech-savvy, I will call “Boss.”
I’m talking to you, Savvy. I want you to know something: Boss reads articles that mention microblogging, SNS and iPhone apps every morning in the Wall Street Journal. Every single morning. They understand the basic concept (which for some is enough) of these “new” technologies because their kids talk about them, or they request casual elevator speeches from employees. But yet, they still remain both intrigued and discomfited by how these technologies add value and profit to their company as opposed to traditional means. They also want to know what’s under the hood.
Savvy, share what you know. Don’t watch Boss retire to the Hamptons with their decades of experience and deep Rolodex (it’s a swivel thingy that holds business cards) without investing in you. They will invest in you, personally and professionally, once you showcase your ability to instruct them effectively with an approach that is void of entitlement. Now, think of Boss. What is the best way to approach him/her to create a learning environment for both parties?
In my own personal approach with Boss over the past couple years, I started jotting down all the mistakes and successes I experienced,which were enough to fill a moleskin. So, if Boss asks, “What's this Twitter business?” here are a few tips to keep in mind.
Pre-meeting:
- Learn the background of the topic at hand. If the topic is “search engines”, then know who the players are in the space, who each are owned by, who is their audience, current news and top level financial information.
- Understand these new technologies are another medium, not THE medium. Be able to explain how they fit into the entire spectrum.
- Prepare yourself to learn something new, rather than purely to instruct.
Meeting:
- They control the mouse (if at a computer) and are seated in front of the computer to drive.
- Never point at the monitor to where they should click (unless asked). Allot them enough time to find it for themselves. Their eyes don’t process information as quickly as yours on a computer screen. Your goal should be that when you leave their office they will be able to retrace every step.
- Have them set up their own log-in instead of using your account. Start them from scratch.
- Avoid acronyms and unfamiliar lingo, but introduce words after explaining the concept behind them (i.e., “tweet”).
- Ask how these new technologies would’ve changed their high school, college, dating (or as they refer to it, “courting”) and early career experience.
- Address the chief issue that Boss has: security.
- Publish their own work using new technologies (one time, I assisted a Boss to post a :30 commercial spot he created in the 80’s and you should’ve seen his eyes light up).
- If you note that the number of questions being asked by Boss has dwindled, then they are not getting it. You’re now speaking Russian, stop! You’re glazing their eyes over with your lack of listening skills and will not be invited back for another discussion.
- Record the ideas that start to flow from discussions. You’re tapping into someone who will be able to supplement these new technologies with their vast experience. Bring a pen and write everything down.
Post-meeting:
- Send a thank you note or email, including an overview of the discussion.
- Offer to hold regular sessions, but let them decide when and how often. If you are invited to return do not move onto a new concept or technology until the previous discussion fully understood.
- If you come across articles that pertain to your discussion, send them along (brownie points if you cut the article out and leave it on their desk).
- If Boss isn’t interested in moving forward with additional discussions, that is OK. Thank them for the opportunity and assure them you’re always available.
Stay flexible, as each individual is unique, but these tips will help. I promise you will be shocked at what comes out of this dialogue if you engage appropriately. Good luck, Savvy! Let me know how it goes, and what other tips you would add to the list.
- Mike Matthews


