Listening to a sales call can be excruciating when you’re not allowed to interject. I suggest you do it today.

I have many not-so-fond memories of listening to salespeople pitch my product badly. Sometimes they focused too much on features instead of the value proposition. Other times they got the value proposition wrong altogether. They’d forget how to demo the tool and get lost, or they’d just avoid demoing altogether because they weren’t confident enough.

Knowing it’s your fault as the product owner is what makes those moments so painful.

Whenever Bill Parcells used to see one of his assistant coaches chewing out a player who’d screwed up a play, he’d remind the coach that he obviously hadn’t coached well enough. That’s the mentality you should have when it comes to training anyone responsible for your product’s sales and renewals, from salespeople to account managers to CSRs.

Why Commercialization Is Hard

The fanfare and external marketing activities around a big launch can be fun, but you win long-term in the enterprise business by adjusting the the right levers in the organization. The people, processes and systems that turn your product into revenue all need to be tuned just so. It’s more slog than sizzle.

Unfortunately, many teams underestimate the work involved, under-invest in the associated activities (especially training), and end up frustrated with under-performance. So what is it about commercializing B2B products that makes it so deceptively challenging for product teams?

Salespeople are busy. Yeah, I know, so are you — but they’re not asking you to stop making money and listen to you, are they? They’re always traveling, on calls, in the car, at a meeting, you name it. Multiply that level of activity by the size of the sales force and you’ve got a serious shortage of attention span. (Did I mention the not-making-money-while-they-sit-and-listen-to-you part?)

They’ve heard it all before. After a while, new products and features start to sound the same. Every new addition is a “game changer” or killer feature or whatever. Salespeople who’ve been around have had underwhelming products foisted on them from above before. It’s not easy to stand our in their minds. Repetition matters more than sizzle for your message to sink in.

You’re busy. Let’s face it, you’re probably under pressure to get rolling on the next feature/product too. Whether you’re training the sales force yourself or training the trainers, your schedule may not have much room. Add in the fact that you’d probably rather be designing products…you can see where the schedule casualties are going to be.

Products are complicated. Just because you live and breathe this stuff doesn’t mean everyone else does. You’ve been able to get a bottom-up understanding of your product as it’s been assembled byte by byte. Even if a new feature is on the small-ish side, you’re just adding one more dollop of complexity to something that’s already complex.

You need to sell them on it. Can you honestly say you’re going to make their job easier, improve their customer relationships, or make them more successful? If not, why should they bother? And don’t forget, the sales folks tend to have good B.S. radars.

Sales training can go south fast if you’re not paying attention to these factors. Here’s what I’ve seen work well.

How to Train the Organization without Getting Frustrated

1. Expect 3x whatever you’d expect for time investment on your part. There’s a rule of thumb in blogging that you should spend three times as much time promoting content as you do writing it in order to get traction. I recommend a similar mindset for commercialization. You’ll better manage your own expectations your managers’.

2. Don’t expect overnight success. The “big-bang” kickoff and training might be satisfying, but you should expect to do this over and over again. Offering training sessions regularly and just making it part of every month beats stressing out over a big internal launch, only to find the training didn’t sink in. Again, repetition beats sizzle.

3. Video is your friend. Not everyone likes reading, so record every training session and demo you give. Even if they’re repetitive, make the videos available to the sales team online. Let them consume everything their time at their own speed, and you’ll all be happier.

(I also like “organic FAQs” – where instead of sharing everything over emails, the team creates an internal webpage for people to ask questions and get answers that everyone can benefit from.)

4. Reach out to the hardest-to-reach. The best salespeople are often the hardest to reach. It may be annoying, but do whatever you have to in order to make sure they get what they need. They’re the tone-setters, and others will follow their lead. We all have to cater to the influencers sometimes.

5. Get the incentives right. If you need to work with your CFO and/or head of Sales to re-work the sales compensation plan to incorporate your new product, give yourself plenty of time. It’s one of those things that’s so obviously important yet easy for the product team to forget. If the incentives aren’t there to sell your product, all the training in the world won’t help you.

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