Balancing flexibility and predictability

Running a business would be so much easier without customers. At least without them bugging you all the time.

If you have ever sold software to larger companies, you know what I mean. The requests never stop. They want to know what is coming next quarter, next year, sometimes even two years out. They need slides for their own leadership teams, budgets to defend, resources to plan, and marketing campaigns to lock in. Meanwhile, you are trying to build something valuable without painting yourself into a corner. You want to adapt to what you are learning, change priorities when something breaks or a new opportunity shows up, and keep your team focused on what matters now.

That tension between giving your customers a clear view of the future while also keeping that future flexible is real. The world changes faster than you expect, and the best features usually come from insights you did not have when you were drawing up last year’s plan. At the same time, if you sell to enterprises, saying “we do not plan that far ahead” can kill deals or stall adoption. Predictability is part of the product they are buying.

It is tempting to look at companies like 37signals, who openly run their product process in six-week cycles and happily start fresh every few months. They famously avoid long-term roadmaps and it clearly works for them. If you sell to small businesses or consumers, you can often get away with that. If you are working with enterprise customers, it is harder. Their flexibility has limits. Your nice, clean, self-directed roadmap will quickly collide with their budgeting and planning cycles.

That is why I liked the approach Varun Paramar (then at Miro) described on Lenny’s Podcast a while back. Miro uses a six-month rolling roadmap with decreasing levels of certainty the further out you go. It is a way to give customers enough predictability without locking your team into bad bets.

Here is the simple version:

• Next 3 months: about 80 % certainty. These are the things you are actively building or are confident will ship.
• Following 3 months: about 50 % certainty. These are your intended priorities and bets, but they can still change if you learn something new or a bigger opportunity appears.

Beyond six months you might still share a vision or themes, but you stay clear that these are not commitments.

This model nicely balances the conflicting needs of customers and product development. Sales and customer success teams can show something concrete to customers. Finance and operations on the client side can plan with enough confidence to allocate resources. At the same time, product and engineering keep the option to stop, pivot, or even kill when reality changes. You have enough predictability to be credible without painting yourself into a corner.

A few things make it easier in practice:

• Keep an internal roadmap that is more detailed and a customer-facing version that is simpler and less committal.
• Use clear confidence language on the public version: “Committed” versus “Exploring” works better than pretending everything is locked.
• Review and update every quarter. Rolling means you are always adding a new three-month window and revisiting the next one.
• Avoid false certainty. If something is a bet, say so. Customers usually appreciate honesty if you frame it as a chance to influence priorities.

When you work like this, you can have meaningful conversations with your customers instead of always being on your back foot. You are not promising a perfect map of the future, but you are not refusing to give them anything either. They get enough stability to plan their side of the table and your team keeps enough freedom to do the job well.

I you do it right, it should give you a nice balance between certainty and flexibility. A six-month rolling roadmap with clear confidence levels gives both sides enough to work with. It is not perfect, but it beats a static year-long plan that is outdated after a month and it beats the chaos of “we will see what happens” when you are asking someone to invest serious time and money in your product.