Our roadmap has three columns and no dates. Here is how I sell that to sales.

Every quarter someone from sales asks me for "the roadmap with dates," and every quarter I give them the same document: three columns called Now, Next and Later, with no dates on anything past the current quarter. It took a while to make this work politically, so here is what I've learned.

Why no dates

A date on a roadmap item six months out is not a plan. It's a guess that becomes a promise the moment it leaves the building. Sales forwards it to a customer, the customer puts it into their own planning, and now an estimate my engineers made with 20% of the information is treated like a contract. When it slips, which it will, everyone loses trust in the roadmap instead of in the guess.

What the columns mean

• Now: committed and in progress. These have dates, because the team has broken the work down and we know enough to be held to them.
• Next: the problems we expect to work on after Now, in rough priority order. Written as problems, not features. "Managers can't see who is out next week" rather than "team calendar view."
• Later: things we believe matter but haven't investigated. Explicitly allowed to move or disappear.

Every item also carries a confidence level: high, medium or low. Sales cares about that more than I expected.

How I sell it

The trick was to stop framing it as "we won't give you dates" and start framing it as "we'll never make you walk something back." I showed our account executives two years of slipped dates from the old Gantt-style roadmap and asked how many of those customer conversations had been fun. That was the whole argument.

Then I gave them something in exchange:

• A monthly 30 minute call where they can ask about anything on the board.
• A promise that when an item moves from Next to Now, they hear about it before customers do.
• One approved sentence per Next item that they are allowed to say out loud. Customers rarely need dates. They need to know you understood their problem.

Where it breaks

Large deals with contractual commitments still happen, and I won't pretend otherwise. When leadership decides a feature is a condition of a deal, it goes into Now with a date, and something else leaves Now. Making that trade visible, in the same meeting, is the most useful thing the format does. Nobody gets to add without removing.

If you try this, expect the first quarter to be uncomfortable. By the second, our sales team had stopped asking for dates and started asking which problems were in Next, which is the conversation I wanted all along.