If your company sells products in different tiers (Basic, Professional, Premium etc.) how easy is it for your prospects to understand the difference in the tiers both in terms of functionality and price? If you put on the hat of a prospect, how easy will it be for you to figure this out. Have you done usability testing to determine if this is easy for a prospect to figure it out? If not, you have created a big stumbling block preventing your prospects from giving you money. 
Here is one from my experience last night. I am a Dish Network customer. I am also a Charter Communications customer for my internet and phone. Charter offers a nice bundle if I buy cable, internet and phone – sweet – but this is the good news and the bad news.
I currently have a HD DVR. When I ask them about it, all the options kick in and there is a myriad of options – for HD it is $5/month, for DVR it is $15/month but then they have a promotion where if you buy another couple of options, they give you HD for free and the DVR for $8/month. I had a headache listening to all of this. It was so complicated that after couple of attempts to understand this, I decided not to switch.
Think about this – I initiated the call to find out how to buy – the prospect walked in and said this is my need. You had everything that your prospect needed, but your pricing was so complex to understand, your prospect just walked away. You essentially created a huge stumbling block that you lost the money that the prospect was about to hand over.
Does your product pricing have the same problem? If you do, stop all those feature enhancements you are working on, stop all those marketing campaigns you are working on to create awareness and bring more prospects into the funnel and fix this leaky bucket right now – you are essentially TURNING YOUR BUYERS AWAY.
Image: Courtesy of Triangle.com
Software Product Manager by Gopal Shenoy 