Successful product leaders use workshopping to develop strategy, roadmaps, and anything else where input and feedback are valuable. A workshop can set a group on a great path forward, but it can also suffer from tangential conversations, people who don’t participate, or disrespectful behavior. Encourage frank but respectful engagement by setting ground rules beforehand.

Welcome to 2025! Here’s a resolution: If you are starting this year with a product roadmap (or at least working on one), update regularly throughout the year. No matter how well you plan, conditions inevitably change. Regular roadmap updates set the expectation within your organization that you are constantly learning and adjusting accordingly.

But how often should you update your roadmap? Here are some guidelines:

Some stakeholders seem like Grinches. Nothing is good enough and you have to make a business case to play with your toys. When the Grinch comes around, try to discover their intrinsic motivations to see if you can turn a negative relationship positive.

Some Grinches may simply be very passionate about a particular issue, and may not see their behavior as “difficult,” rather as simply the best way to get results.

Roadmaps are a team sport. If you include sales, marketing, finance, and others in your roadmapping process, you’ll get a better roadmap, and better buy in. But should you include everybody?

Test stakeholder alignment on your roadmap by asking a trusted outsider’s opinion before you finalize. Bring someone in with fresh eyes who may spot holes or problems the group missed. Do this with the whole group present and it may prompt deeper discussion of the thorniest issues as they hear their own private doubts expressed by someone they respect.

When decisions are made slowly (or not at all), when they seem to change from week to week, it’s often because it’s simply unclear who makes these decisions and how. The DACI (Driver, Approver, Contributors, Informed) framework can help by designating clear decision roles….

Roadmap alignment naturally decays. Stakeholders forget what they agreed to and even the overall goals of your team. To avoid this, frequent communication is key.

A good roadmap is a statement of strategy that helps stakeholders understand the destination and the obstacles along the way. It provides guidance for navigating those hurdles without prescribing an exact route. Yet, like a GPS, it recalculates as needed rather than a fixed set of turn-by-turn directions.

As product people, we often find ourselves trying to handle difficult stakeholders. I once had a colleague, a brilliant software architect, who objected (loudly) to any new idea. She disrupted several planning sessions, so I finally invited her to lunch. I said open debate between the two of us was confusing to the team, and we should meet one-on-one before team meetings.

For Halloween, here’s a frighting topic: quitting. Humans don’t like to quit. Our brains are wired for loss aversion and focus on sunk costs, among other things. How to make a smart, rational decision?

When you have to say “no” to a stakeholder, ideally you arrive at that answer together. If that’s not possible, use what you know about your stakeholder to craft a narrative that will help them understand why “no” is the right answer.

What to do when your boss starts talking about "Founder Mode?" Some founders think they are the next Steve Jobs, but are they? Or when they invoke "founder mode" are they just micromanaging things they no longer understand? I’m leading a CPO online discussion: Founder Mode: Poison Pill or Silver Bullet? Thursday, November 7 @ 9am PT / 12pm ET / 5pm GMT / 6pm CET. Register

When you learn something about your organization and your stakeholders, write it down in a super secret document. Keep it to yourself, because people may not appreciate your judgments about them (even if they’re true).

When building rapport with stakeholders, bring your actual human self. In one product job, coach Melissa Appel created a monthly “Women in Warehousing” brown bag lunch. There was no agenda, just an opportunity to connect. With the natural work-related lunch banter, Melissa often learned valuable new information. More importantly, she developed relationships that made work easier.

Sharing your experience helps establish trust with stakeholders. When they realize you’ve done this before, they will be more likely to trust your advice.

Asking about the perspectives and motivations of your stakeholders will help too. Acknowledging their fears and concerns — added to your expertise — show that you can provide good solutions to their problems.

Great roadmaps are the result of hard decisions, of deciding what you will do and what you will NOT do. By making hard choices public, you make your strategy really clear. And clear strategy helps the entire organization execution in alignment. Coach Phil Hornby will lead a CPO online discussion on Roadmaps: the Key to Great Product Decisions. Thursday, October 10 @ 9am PT / 12pm ET / 5pm GMT / 6pm CET. Register.