What is your goal? Depends on the stage of the company… you might be working with a five year roadmap of value extraction activities, but if so I can’t really help. I’ve always left companies when they hit that stage. What I’m much more used to is active value creation. That will translate to a six to twelve month roadmap of what we’re doing now and what we’re thinking about doing next. This kind of roadmap is a conversation, not a schedule.

Before you do anything else, prepare your note taking system. Your goal is to acquire knowledge of your customer’s needs, and the best way to serve your team is to get it in writing.

Step one is to prepare with the sales team: get fifteen to thirty minutes with the account manager (might be called an executive or representative), technical representative (might be called a sales engineer or technical account manager or customer success manager), and project manager if there is one.

• Does the customer and account team realize that we’re not giving five year projections? This isn’t a blatant question, but something to listen for in your conversation. There are vendors who are working to a very long term plan, and there are other vendors who pretend to be… if you’ve hired account managers or won customers from either, their expectations may not be aligned with the more discovery-driven approach of a small and agile enterprise software vendor.
• What does the customer want to hear about? Product they own? Product they’ve heard about? Is there a competitive product they’re interested in dumping? A recent problem they need to solve?
• What hot buttons should you be aware of? Bugs, of the production impacting or annoying variety? Personnel changes? New partnerships or competitors?
• Who will be on, what are their roles, and do they like to talk or not? The worst roadmaps are you talking to dead air. If the customer won’t engage, might as well play them a recording or send them a PDF of your deck.

You’re the voice of the company presenting on the future; let sales guide, but watch out for common traps like the unattainable goal or the revenue recognition blocker. Not every account manager can recognize when they’re in these traps, and you might just save them (and everyone else) a lot of pain.

Discuss the company’s goal and strategy (in terms of value delivery, goals like leadership quadrant positioning are expected to come from that naturally). This slide is usually a geometric metaphor for what you build. A platform with capabilities on it? An ecosystem in which you provide specific features? An exponentially improving workflow that you make possible? Something like that.

Discuss how those goals inform features. This slide is your top three focus areas, icons backed with two to four words each. What are you doing this year? A partner ecosystem? A UX refresh? This would be the stuff your executives talk to your board about, not specific features or specific products.  

Stop and ask if you’re on the right track. Give them time to unmute. If you only get a monosyllabic answer after the account rep gets uncomfortable at the long silence and prompts them, this call is probably not going to get you anything valuable, so you can probably speed up.

Cover recent deliveries first — most customers weren’t paying attention to the things you thought were dreadfully important.

Then focus on your current top line deliverables, the most important things you’re working on. You know you’re pretty likely to actually deliver them after all. If your product portfolio is really broad, you may not know all the details… that’s okay, just skip what you don’t know anything about. They’re not going to enjoy you reading slides at them. If they care about one of those bullet points, they’ll unmute and ask. If you don’t know anything about it, admit that and commit to getting answers.

By now, if a customer is engaged they will have commented or asked a question. If you haven’t heard anyone else talk, stop and ask a question. “Would that feature be useful to you?” “I forget, do you use us for that today?” “Have you got any Grey Poupon?” If you still can’t get any engagement, you might be dealing with a cultural difference, or you might be dealing with a customer who doesn’t want to share any details. Whichever it is, there’s no winning by trying to drag words out of them — you might get lucky and inspire conversation, or might just as well create bad feelings or friction. If there’s still no engagement at this point, I’ll skip any remaining slides and go to the last part.

The end of the deck is blue sky ideas. This is the stuff that you’d like to do but haven’t got clear plans for; adjacent markets, new tech, moonshots. Talk about your favorite one or two, then ask if there was anything the customer missed or expected you to touch on. An engaged customer might go into a new idea, or they might want to talk about bugs in a product they’ve got, or they might want to talk about your competitive situations. 

Time’s up, if the account manager hasn’t already taken the talking stick back, hand it off. The customer may ask if they can have your slides; that depends on your company’s culture, so make sure you know the answer before you get on the call. If you’re responsible for that answer… there’s two major risk paths to consider.

• One is that your own people will do their own variations on the roadmap presentation. As companies scale, the PM team invariably grows more slowly than the field does, and it can be difficult to get calls scheduled. It’s not uncommon for authorized or unauthorized roadmap calls to get delivered by the field, and maybe even edited in the field to tell customers what they want to hear. While that’s hardly ideal… it’s also not something you can personally stop. So, own what you can control and let go of what you can’t.
• Second, anything you hand out has a chance of ending up in a competitor’s hands, who frankly probably won’t care. The competitors that you should worry about are too heads down on their own work to spend time worrying about yours. All that said, the default position should be don’t share the roadmap deck. Keep it separate from your field team’s deck, and if you do share with the customer, make a copy watermarked with the customer and date and PDF that for them. Doesn’t prevent bad outcomes, but it makes leverage if they occur.

Final step: while the account team is wrapping things up or maybe during the first few minutes of your next meeting, you need to review your notes, fill them in with anything important that didn’t get written down, and then share them to the team. Maybe that’s entering them into a system, maybe it’s a Google document you maintain, maybe it’s just a Slack room, but get this material off your laptop and into the company’s shared domain before your attention moves to the next problem.