The best outcome for you is not a long sit-down meeting. If you can have a 20 minute session that the CEO actually remembers, terrific...particularly if she's actually asking for a follow-up session. One of the tricks I use is to create a personalized feature that answers a very specific CEO question in a simple, usable way.
If you possibly can, have four or five of these goodies at the ready, so you can deliver information and functionality in bite-sized chunks. What you don't want to do is deliver them all at once: less is more. Keep some dry powder, and have a planned sequence of "bright shiny objects" for the boss.
Beware Dangerous Sizzle
It's tempting to focus your opening gambit on some piece of CRM tech that gives great demo, but involves risk (either of uncertain results or of losing control of the conversation). Let's look at some examples of dangerous sizzle:
• Dashboards would seem a natural for showing off to the CEO: they're the top-down view of key success factors in the business, right? Problem is, dashboards are dependent on correctly constructed reports (particularly the filters and joins), and it's all too easy to show some report that leads to bogus conclusions. Perhaps more importantly, dashboards expose (or even magnify) problems with data quality and semantics. If your data has dupes, dashboards will show double-counting. If the data is incomplete (or has blurry semantics), the dashboards will show holes.
• Mobile apps certainly check the "sizzle" box, but they can only look as good as the platform they are on. While an iPhone mobile CRM app usually looks great, if your corporate standard is Windows Mobile, the story won't be so pretty. There's an additional twist: as most serious mobile CRM apps involve extra charges per user, they risk some optics that backfire.
• The Latest Greatest CRM Features also check the box for sizzle, but they can be high risk territory. The slickest demo of cool Social CRM goodies can be beautiful, until you discover that the demo shows stuff that isn't really part of the product. Setting expectations around something cool that actually requires a $100K consulting engagement in order to work is not likely your best move.
The key to an effective CRM training session for CEOs is to keep it at a high enough level that the conversation is around business value and board-level topics. Anything you talk about in the training session must be bullet-proof (and idiot proof) — so you need to do some homework and careful orchestration.
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