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Question #1. Are you automating a productive process?
Adding technology to a broken sales process simply makes the process more broken. And adding technology to an organization that lacks a sales process is simply throwing money away. Before adding any technology to a sales environment, it's essential to have core processes in place. For example, it's useless to give a marketing team a lead-generation tool if the team members have not yet gotten agreement from the sales team on what constitutes a qualified lead. Until such agreement is reached, it's impossible to know how to apply the technology in an effective manner.

Question #2. Have you properly prioritized the functionality?
Sales managers sometimes buy technology because they heard it was good or because a competitor has purchased it. That's a big mistake. Every technology purchase should be carefully vetted to ensure that it will increase sales. The best way to do this is to have the team that will be using the technology participate in the prioritization. This is important because to achieve sustained benefits, a Sales 2.0 application must be adopted, and it's not likely to be adopted unless it can provide real value. So get your team to think through the issues, define usage requirements, and pick the tools that will serve your sales needs the best.

Question #3. Will the next technology work well with your infrastructure?
New technology always adds new complexity to the work environment. That's especially true when the technology is completely separate from the technology that the team is already using. Sales professionals want to spend their time selling, not learning a new interface or copying data from one application to another. A Sales 2.0 tool is far more likely to be used – and used frequently – when it presents a familiar and natural environment. It should therefore integrate well with your CRM (at the very least) and ideally with a wide range of office automation and personal productivity tools, such as email and voicemail.

Question #4. Have you articulated the benefits of the new technology?
Whether you're implementing a Sales 2.0 tool for the first time or simply upgrading your existing sales technology, you must carefully and believably explain the benefits – to both the sales team and the company at large. Explain how the requirements evolved, how the new technology solves problems and creates opportunities, how it will change the measurement schemes and resulting compensation, and (most importantly) how it will help sales reps to sell. If you ensure that people understand how important the new technology is to the company's success, chances are that people will do everything possible to make the tool a success.

Question #5. Have you budgeted appropriately for user training?
While software vendors always claim that products are intuitively easy to use, most tools require some kind of training before employees can use them effectively. While it may not be necessary to provide classroom training, there should be an easy way, such as e-learning or video training, for employees to get up to speed. This training process can be made easier by introducing new technology as a pilot project or in-house evaluation. That way a core of early adopters can help to train the rest of the sales team.