What are the biggest obstacles you typically encounter in implementing new messages for a product or service?

In the B2B space, getting Sales to fully adopt new messaging is almost always a challenge, especially for a product or service that has existed for quite some time. In many cases, you’ll find that even after extensive training, they may end up reverting back to their standard discovery and pitch.

Old habits are hard to change but there a couple of tactics that typically work out well:

• Ensure you have alignment and buy-in with Sales leadership. Sales reps trust their managers and leaders more than you, so having strong alignment with leadership and a few influential sales reps can go a long way.
• If your sales team is small, having quick 15 min chats to address individual problem points and questions can be very effective. Time consuming, yes, but effective. For larger sales teams, attending their team meetings (smaller group settings) and conducting surveys can help you get down to the root of the problem quicker.
• A single sales training is very rarely enough, especially for a large enough messaging shift, so temper your expectations accordingly. Coming up with creative ways to instill the new messaging over a quarter or two may be required.

New messaging for a product is always both challenging and fun. But the obstacles tend to be unique to each situation. Let me explain through a few scenarios.

1. Evolving product line: Your product used to be a widget, but is now much broader with a lot of new features that were added along the way. The biggest obstacle is to put new contours and define this product. Everyone agrees it isn't just a widget anymore, you need new positioning to stop looking like a niche player in the market. The biggest obstacle often is convincing the insiders (Product Managers, Engineers, Founders) that you are now a platform or a system or similar. In the course of coming up with this new messaging, you will have to downplay somebody's favorite feature because you realized your prospects care more for dependable feature X vs. jazzy feature Y.
2. Net new product: The challenge in messaging a net new product is more external to your firm than it is internal. At this stage in the game no one knows who you are or what you do. You will have to start with a hypothesis and test it in the market. Getting market traction will be more difficult. Maybe you got the category right, but it was too competitive. Maybe you thought you had 'named' a category, but it was too niche to get buyer attention. There will be a lot of learning and adjusting in this scenario.
3. Same product, new market: Amongst the scenarios listed here, this is probably the most simplest messaging excercise. If your product already has a specific target market, buyers and sales motion, you will have a good understanding of the value proposition. The challenge here will be to understand the peculiarities of this new market better. Perhaps security and compliance are much bigger needs for them, or perhaps their budgets are far smaller. However, once you've gone through this process, the next time around it will look pretty much the time. Even if the answers/decisions differ.
4. Same product, same market, new positioning: This one can be more challenging. The very fact that this is a "thing" might mean something is not working. Maybe as a startup, you've fallen into the proverbial chasm. Maybe a market event has changed the dynamics for your product. Harder still, this could just be a case of a broken sales motion which is pointing to messaging as the problem. The answer here really depends on first doing a true organizational root cause before proceeding and aligning with your internal stakeholders. A lot may depend on the outcome of your work, and it will take focussed execution with constant alignment to deliver on this project.

Most importantly, every situation is unique. It is always prudent to not jump to conclusions about the "right solution". Spending more time in discovery and alignment always helps. 

What has been challenging for me in the past is not having a ton of reference customers and/or data to back up messaging for a new product launch. This is a delicate balance between making sure that you have product-market fit before a major launch, having those reference customers with some data and wanting to wait before you have "enough." Depending on the market conditions, you may just need to ship and launch and then work to really target early adopters, get some good data validation and then refine your messaging over time. I always try to err on the side of having data / validation with at least 5 customers before launching vs. going out with hollow messaging, however.