What are the common mistakes you see product marketers making when they launch new sales enablement programs?

I see a few issues:

(1) not think about the sales process and the customer journey (CS version, not the marketing version). You need to think about when they will need collateral and what kind of collateral. This will help you with effectiveness. 

(2) build persona and product messaging without context, meaning just shipping an internal guide without thinking about the situations and scripts will not land. Anything you send out needs to be actionable and in the context of reps workflow (SDR, CS, and Sales) 

(3) not partnering and testing with a few higher-performing reps for new collateral. You need to make sure your best reps like and will use your collaterals, otherwise, you will land flat 

(4) not getting alignment from SDR, CS, and Sales leadership on any programs.

The most common mistake I see is PMM / Sales enablement positioned as a reactive team that is creating content and collateral for sales without a clear understanding of what problem (within the sales cycle) it is solving for, and how it will be measured for impact. 

This can lead to endless content creation, that is not always valuable or solving real pain points, and puts PMM/enablement teams on the constant backfoot. 

The biggest mistake I’ve made is not involving Sales at the ideation stage. Too many times, I’ve thought I had a great idea for a new program or piece of content, only to find upon rolling it out that I was solving a problem nobody had.

It’s always good to have a few “friendlies” on the sales team who you can bounce early-stage ideas off of. If they think you’re onto something, you can get sales leadership involved. There’s no better way to make an enablement program work than for the Head of Sales to make it a priority.

At a more tactical level, I’ve learned a ton over the years about delivering sales training, due in large part to mistakes I’ve made. There are two common themes:

1. It’s not interactive enough. Sales professionals talk to people for a living, so sitting there and watching a slideshow for an hour (or longer) tends to be an exceedingly boring activity for them. They want to practice things as they’d do them in real life so that they aren’t winging it when they get the big meeting. That means live pitches, role plays, and objection handling –– or at a minimum, open Q&A. The sales leadership team will have useful ideas about ways to make your training valuable for their teams.
2. Too focused on features / functionality. I can see the survey feedback from a former Head of Sales like a blinking red sign in my head: “Help us learn how to sell it, not how it works.” Those two concepts are of course related, but sales needs the details woven into a bigger story that they can use with executives who won’t care about a new button or report you’ve added. They want to know how it leads to more revenue, time saved, lower expenses, better decisions, and all the usual types of business impact.

• Simply put, I think focusing on the outputs (e.g., collateral/content creation) instead of understanding the problem and building a solution for that problem. But in order to understand the problem, you have to understand how your sales team operates...you need to be on calls across the entire funnel and especially post-close. 
• Instead of focusing on outputs, focus on how to achieve outcomes. If you’re standing up a sales enablement team, then the business is probably needs enablement as a strategic function that helps the sales teams with process optimization and foundational onboarding/training work to drive better outcomes (e.g., better win rates, shorter sales cycles, higher deal sizes, increased cross-sell/product adoption, etc.)

Making the program without adequate sales buy in or guidance. 

There's an important balance to strike here: The product marketer should be focused on anticipating the needs to a sales team and solving the problems at hand, rather than reactively responding to inbound requests from the sales team. That means you can't execute on everything your sales team requests the exact way that they want. But that doesn't mean your sales team shouldn't help shape what your enablement program looks like. If they don't, the program becomes something you made yourself that you're asking sales to execute on, rather than something that they're creating with you and committed to. 

I've seen product marketers put a lot of hard work into an enablement program and roll it out to the sales org, only to get a lackluster response or, worse, hear about all the ways it won't work for the team. The issue here is not that the marketer created a poor program, it's that they didn't put the work in up front to get sales leads onboard with the plan or get enough feedback on the program to ensure it'll work for the team. To get into the brass tacks, the process that I've seen work well is something along the lines of: 

1.  Loop in sales leads just as you start thinking about your program to talk about goals and listen to their needs and insights. This way, you're shaping the idea and focus behind the program but still getting their thoughts and feedback on priority, pain points, structure, etc that will help you create a program that works well. This meeting should be mostly you asking the leads questions and bringing up topics for discussion, not you showing a full plan that you've already made. 
2. Once you've taken that feedback and turned it into a plan, get back in a room to discuss and get their thoughts. That way, the sales leads can pinpoint any problems in your plan and give feedback before you start executing. It also has the added benefit of truly making them stakeholders and making them feel like you're listening to their feedback. The more inovlved they are, the more it's on you and them to make the program succeed together.
3. When you're starting to execute on work and have drafts of deliverables, make sure that key sales contacts are reviewers on the materials. That way, you can pinpoint any feedback or edits early so you can talk about it, make changes or explain your POV before you're trying to roll it out to the broader team. No one likes watching a sales person's hand go up while you're just starting a program rollout with feedback or thoughts that could have helped 5 weeks ago but are no longer helpful. Get that feedback here, and get it from the right sales leads. 
4. To launch the program, have a sales lead help with the team rollout. That can be them introducing the program before you talk through it in specifics to talk about why this is so important and help the team feel like this is something they need to buy into or sending an email after the training reinforcing how important this program is for the team. I had a sales lead once reply all to an email I sent saying "If you do not do this, you will not make President's Club, guaranteed" - turns out, people really bought into that program :) No matter how skilled and sly a product marketer is, a sales team is always going to listen to their lead more than they'll listen to you. If you can get them to be the one to say 'Hey this is important, we've put work into it, and we feel strongly about this program' it makes your life way easier. 
5. Get continuous feedback on the program. Make clear that you'd like sales feedback on how the program is working (and make clear how you'd like that feedback delivered so you're not fielding desk drive bys or a million Slack messages about it). Set expectations about what you'll do with that feedback, and discuss it with your sales leads. Sales teams should feel like they have enablement that works for them but that doesn't work if you give them a program and then walk away from it. You don't need to do every single thing that a sales person asks of your team, but you DO need to make them feel heard and give them a forum to make suggestions. Turns out, some of the suggestions can be really useful.