In the marketing plumbing business, I often get inquiries that straddle the boundaries of technology, strategy and therapy. One of the most common can be summarized in this mad lib:
How can I configure [piece of technology] to make sure that [group or team] uses [piece of technology] exactly how I want them to?
A good example recently came in on a mailing list I read:
Does anyone have suggestions on processes, automations, incentives, etc. to get sales people to update information in Salesforce.com consistently and proactively? Especially Next Steps and Forecast data.
Have you tried the "make salespeople do what I want" sub-menu? It's in the "customize" section of the admin but available only during the new moon. Unless you have the professional edition, in which case you're pretty much hosed. You could always try saying, "sudo fill in these fields."
Most people on the list responded to that inquiry more constructively than I just did and noted that this issue is really about configuring your sales team and their incentives, not about configuring your sales automation platform. Those folks are not wrong at all, and any good plan should begin with those concerns, but I'm going to play technology optimist and say that there are things you can do in salesforce to increase the odds that your team will use it the way you intend, even if you can't afford a state-of-the-art brainwashing machine.
This is what some of our presidents have called the nucular option. Make the field required and you can't save the record until you fill it in. It's easy to see that this isn't going to get you the highest quality information, but it can work if the required field is super duper easy to fill in, which brings us to the next point...
Field Type Engineering
Knowing that the average sales rep doesn't really like to write an essay on the "next steps" for a deal, consider that you could set up that field as a dropdown, pick list or even a set of fields for the various likely cases. An added bonus of this approach is that you've turned unstructured data into structured data and you can run reports on it more easily. But don't forget to provide some sort of free text field for the inevitable "other" and special cases.
Page Layout & Help Text
Another item on the "make it dead easy" list is to order, organize and prune the fields on your sales reps' screens. The standard layouts contain all sorts of fields that you may or may not use, and as you've created custom fields, you've probably let a lot of them build up on the screens. Think hard about what fields are most important for the rep to see and fill in, sequence them logically, and move the to the top of the screen. Move the other stuff down or even remove it entirely. You can configure different page layouts for different record types or user types. And while you're organizing fields, remember that you can include tooltip style help text with each one, by customizing the field properties. That can only improve compliance, especially when onboarding new reps.
Compliance Reports & Scoreboards
I'm not sure if this qualifies as carrot or stick, but the next thing you can do is set up reports or dashboards that show what portion of each rep's records are fully filled in. Depending on how hot you want it in your boiler room, you can make this info visible to all reps so they can see where they stand against their peers, or just quietly send the report of each rep's stats to that rep (and his/her manager) on a regular basis. Even if data completion doesn't make the comp plan writ large, salesfolks are a competitive bunch and bragging rights or small prizes can move the needle. I suggest a set of steak knives.
It's easy (and fun) to stereotype sales reps as coin-operated knuckle-draggers, but like most employees, they really do want to help move the company forward any way they can. If they're not using salesforce "correctly" you should bring them and their managers into the discussion about why certain fields are important to fill in, make proper use of salesforce an official and documented part of their job, and do what you can with the tool itself to make it easier for reps do the right thing.