If your messaging isn't landing, how do you know if it's because it needs to be reworked or because sales has poor delivery?

When your messaging needs to be reworked there are typically multiple signs pointing this way. Not only your reps may not be getting traction, but your competitive losses start climbing, fewer qualified leads enter the funnel, and when talking with customers you start hearing more “you were cheaper than the competition” instead of “we saw greater value in your product”. Analysts (Gartner, Forrester, etc.) can also help serve as early warning signs that your messaging needs work, as they will flatly tell you that you sound just like everyone else. I’ve been there and it hurts but is a great wake-up call.

This why it is so critical for product marketers to conduct win/loss analysis and also to occasionally sit on sales calls. Now, if you see that leads are coming in, the pipeline is growing but deals are getting stuck, this could be an indicator that the sales team is not being able to convey your value prop or that they are having difficulty in clearly articulating why your solution is different. In this case, more training or enablement can help.

The biggest risk we have is waiting too long to diagnose the problem. The ideal scenario is when you can intercept the problem before it becomes too big, and this is where sales enablement tools like MindTickle come into place. They can help you identify if reps are able to deliver your message by providing virtual role-plays and allowing you to measure their effectiveness before they even start talking to customers. Using tools like Gong or Chorus can also help as you are able to listen to call recordings and identify patterns that might be hindering a salesperson's effectiveness. 

I often see marketing spending a lot of time understanding the customer - doing customer research, and interviews, but completely bypassing understanding sales and their interaction with customers. 

Sitting in, and/or listening to recorded calls can really help inform - not only if your messaging is working, but also if it's not - what is working? This level of visibility into sales calls will help evaluate how sales pitches the messaging and if this was what was invisioned by marketing, and ultimately if more training is needed or message tweaking.

Another way to get ahead of this is to work closely with Sales at the start of creating messaging - and testing it along the way so there is not a metaphorical wall where messaging is created and then thrown over

I'd watch some recorded sales rep calls to form my own opinion on what's going on. I'd also follow up with the rep to get their perspective on challenges. Once you've diagnosed the problem, there's a few steps you can take:

• Is the rep nailing your talk track but the customer just isn't convinced? If so, this is definitely a messaging problem.  
• Is the rep doing their own thing, for example using old messaging or just skipping straight to a demo? Here, the rep isn't sufficiently trained on the messaging or hasn't received a strong enough mandate to change from their leadership. They may have tried your messaging but then given up because it was hard to use, here's where I'd work closely with them to troubleshoot. Why was it hard to use? Is it clunky or are they just unsure?
• Maybe the rep is trying to use your messaging but just struggles to deliver? Here again, it could be clunky messaging or an untrained rep. I'd ask their help in diagnosing the problem and also look to see if other reps are having the same issue.

So if the main problem is: The message isn’t resonating with our audience, what should we do? I would break this into two separate pieces, similar to what you already have thought of above.

• Does messaging need to be reworked?
• Are my sales reps delivering this adequately?

Does messaging need to be reworked?

If the messaging isn’t resonating with your target audience, regardless of delivery, then you have a messaging problem. A messaging problem requires a messaging solution.

Some ways to figure out if you have a messaging problem:

• If you have a sales team, get feedback from QBRs, individual sales area leaders, or from a range of several mid-to-high performing sales reps. Their collective feedback should give you a good idea if it’s the message or if what you see is just from an individual (or set of individuals) that need more practice.
• Listen to a few of live pitches by becoming a fly on the wall of some those sales calls.
• If you have paid digital campaigns that represent your messaging, how are those performing relative to past campaigns or other benchmarks?
• If you have online conversions that are driven largely by your messaging, how are those performing relative to past landing pages or other benchmarks?

Are my sales reps delivering this adequately?

If your sales team isn’t delivering the message adequately, then it could be a sales training problem. A sales training problem requires a training solution that partners with sales.

Would advise to get feedback and gain alignment from your sales leaders if they think sales training is an issue and the specific needs for sales training. A sales leader's resposibility is to make sure that their teams are adequately trained. If they are aligned, you can work with them on structured trainings that focus on specific sales needs based on past learnings.

Some possible areas to learn from:

• Previous Trainings Were Unclear - Previous trainings may not have been adequate in introducing and explaining the message. Even though reps went through the training, people just didn’t get it.
• Unclear Assets - There may have been something in the assets produced that ultimately confuses a sales rep or the target audience when delivered.
• Practice and Coaching - There may not have been enough practice and coaching to really get reps ramped up in the new message and materials.
• Enforcement - People are busy. Some reps may not practice unless it’s mandatory (i.e. certifications) and enforced by their sales leader.

I think Dave's answer covers a lot here, so consider me co-signed. I do want to add a few things though: 

1. The problem is almost always the messaging. If you have developed a clear narrative and messaging for the customer segment, it would take an extraordinarily untalented sales rep to mess it up. 

2. The best way to evaluate your messaging is by sitting in on a live demo or sales call. Where is the customer falling off track? Do they have trouble understanding the value prop? Are they stuck comparing you to a competitor? Are they unable to follow along with the features you're explaining? These are all things keeping them from having their "aha" moment - and that means it's definitely a messaging problem.

3. Consider whether your core website marketing and live demo/sales pitch are inconsistent - and therefore confusing people. In my experience, a lot of salespeople who are really good at what they do often run into problems because marketing has inadequately prepared the customer for the call. Remember that something like 70% of buyers do their research online before they're willing to talk to a sales rep. So if sales is selling/communicating product differently from the marketing, then your inconsistency is leaving your customers with big question marks over their heads.

Your goal should be to have an aligned narrative that both sales and marketing can use and riff off of as they pursue customers together and separately. Because sales spends so much time with customers, I recommend doing deep dive interviews with your sales reps - they will often point you in exactly the right direction. 

When you do develop new messaging, definitely keep sales actively in the loop. You want to work together to develop both the messaging and language that feels effective both in writing and for in-person sales meetings. 

The first question I'd ask is how the messaging seems to be resonating in the market otherwise. If consistent messaging is used both by sales and with your other marketing programs, then you can better gauge differences in how customers react to the messaging when delivered each way. 

If you find that the two are received differently, your job still isn't over, as it might make sense to ensure there isn't something else responsible for the differential. However it will be a big clue.