We’re pivoting our product, and it’s difficult to plan the roadmap too far out. How do we reset expectations on what product communicates?

I've had to manage a couple different pivots like in my product career. What's worked best in terms of communicating is the following:

• Making clear the "why" behind the pivot, and the risk associated with not pivoting
• Stating clearly the underlying first principles or vision for the pivot that exists today (it doesn't have to be super detailed - but this more about acknowledging what you do know or what you believe should be true)
• Acknowledging clearly that the roadmap will be in flux for some time, and the short-term is around building learnings and certainty around a long-term strategy
• Committing to some series of regular updates (I like every 2 weeks - if you're not learning enough worth sharing in 2 weeks, you're not pivoting fast enough)
• Following through on those updates, and keeping them as crisp and simple to understand as possible. Bulleted lists usually work well for me.

I’m wishing you a successful product pivot! You got this!

In this situation, you have your internal stakeholders (sales, marketing, GTM, etc) and you have your customers you need to reset expectations with (mostly for B2B products, less so for B2C)

For your internal stakeholders, the best thing you can do is be transparent and bring them as close as possible to what’s happening. For example, share the challenges, the tough trade off considerations, data you are using to drive your decisions, etc. This builds trust and partnership. Once you do that, sharing a short term roadmap will be more understandable and you can always provide a DFAD (date for a date) on when you expect to know more or have more things planned (milestones).

For your customers, also be transparent about the pivot and why you are making this change. Hopefully this pivot is ultimately for the best interest of your customers. Also, what works really well is if you take the opportunity to solicit feedback from your customers about the pivot and get some insights from them. This builds trust and a stronger partnership with your customers. And since you can’t share plans too far out, a DFAD is also good to manage expectations with your customers.

I think you say exactly that!

"We're pivoting our product. There are a lot of unknowns. It's hard to plan our roadmap too far out. We're resetting expectations on how much we can communicate..." THEN, I would add this...

"We are focusing on these 3 themes in this priority - 1... 2... 3...Our goal is to deliver these X, Y, and Z customer outcomes by pivoting our product. We plan to have an update on these themes in ABC timeframe."

It's ok not to have all the answers in times of big change and ambiguity. If you did, you'd probably be guessing at best! And that's the fun - figuring it out.

Say exactly that "We're pivoting our product. There are a lot of unknowns and it's difficult to plan too far out." It's perfectly fine to communicate honestly. If there's a good reason for the pivot, no one will fault you for it. 

If you're able to have direct conversations with customers, it's important that you set up these conversations. Having open and honest conversations is important to build trust despite the pivot. It is also an opportunity to solicit feedback and listen to your customers.

Resetting expectations internally within your company will be much easier if you have already held conversations with customers. You can leverage these conversations to prove that the new direction has been validated by your customers.

In any case, pivoting a feature or a product can be stressful. But it's also fun.  

If you are unable to have a longer term roadmap view: then proactively reset expectations while increasing the cadence of communication. 

There may be a number of reasons why you are in this state: product pivot, external event like global pandemic happening that changes customer and market dynamics beyond your control. Switch your roadmap in these scenarios to focus on assumptions you are looking to quickly prove/disprove before more additional investments. Then provide an accelerated pace of communication that shows how you are making progress towards validating in the market and what decisions you are taking with the feedback. For example, if you are used to communicating your longer-term roadmap quarterly, move to a monthly read-out instead. 

A roadmap is a conclusion to a story that starts with a mission and then continues with a vision, strategy and goals. If you're pivoting, I presume you've already shared why that's happening and the new vision you're pivoting towards. If not, then that's what you need to do first.

After that you need to get the strategy and goals updated before roadmap matters. Bring your company along on that journey and you won't need to worry about expectations

It sounds like you're probably concerned about pushback from stakeholders for whom longer-term planning is highly beneficial, e.g. sales and marketing. Having a "plan for a plan" could help here – in other words, "we're pivoting and we don't want to plan more than 3 months out because we need to reach X, Y, Z milestones or answer questions A, B, C". Provide a timeframe / conditions under which you'll start to plan further out could help build trust and confidence. In the meantime, you might also need to provide more support to those functions, e.g. enablement, talking points for customers, while they have less visibility into the product roadmap.

Ultimately, communicating about your product should tie to the outcome that you hope to drive. When pivoting a product, I've found it's most helpful to be honest about the process the team is going through. Sharing less information with higher quality is far more valuable than any other course of action in these scenarios.

For example, when our team was stuck in a rut due to poor Org Design and a mountain of tech debt, we went to our executive team with a clear message. We needed time to unravel and unwind much of the legacy issues from the past. We believed that by taking this time, we would be able to position our teams in a way that would allow an exponential increase in our teams ability to solve their core issues (around interwoven code and tech debt).

We did not have an explicit understanding of exactly how long this shift would take, or what the outcome would be, but we did commit to regular updates on our progress. Setting these very vulnerable expectations and committing to continuous communication brought our customer (the leadership team) along on our journey.

Pivoting a product is typically a very difficult time for everyone involved. I feel for you! Depending on who has these expectations and the reasons why it is difficult to plan too far out (and what "too far out" means to you), there are several things that you can do. Some of them are pre-requisites before you actually try to set expectations.

1. Have a vision for where you want the product to go.

   • If you are pivoting, you need to know what you are pivoting to. If you don't have a vision for your product, setting expectations on what you communicate won't be worth much, since you won't really have anything to communicate. If you are struggling with this, how did you decide to work on the current items in progress? Even if it isn't written down, you likely have an idea of where you want to go. You may not know all the details, but you don't need details to have a vision.

2. Have a strategy for how you are going to achieve the vision.

   • This doesn't have to be specific items on a long-term roadmap, but, once you have a vision, you should begin piecing together the general idea of what will make your product successful. Plan the roadmap for the next quarter, keep talking to your customers, and do market research. Define the jobs to be done for your product. Figure out the broad strokes of what your users will need to be able to do with your product in order to reach your vision.

   • If there is something blocking your ability to know what needs to happen to achieve your vision, have a strategy for remedying that problem. Do you need more knowledge about the market? Does engineering need more experience with the technologies they are now required to work with? Come up with a plan to unblock the team's ability to execute on the vision.

3. Have a solid roadmap for the next quarter (or the next month, if quarterly planning is too ambitious for you right now).

   • Planning quarterly can be a great way to provide enough detail to satisfy expectations, while still allowing for adaptability. As the product manager, you and your design team should be working on the details for the next three months while engineering is executing on the current quarter's plan. This gives you enough time to solidify plans, while being flexible enough to react to customer feedback, changes in the market, or evolving business priorities.

Once you have these things in place, you are ready to set expectations and communicate your roadmap.

1. Be transparent

   • Tell people your vision and strategy. Let them know that this is where you want to go, but the details past the next few months aren't completely clear yet. Let them know why it isn't clear and what you are doing to remedy the situation. If it is difficult to plan too far out because your engineering team has had enough experience with the features or technologies you are pivoting to, give them confidence that the team is working through the unknowns and that you will have a more solid plan soon. If it is difficult to plan too far out because you don't know the market you are pivoting to well enough yet, tell them what you are going to do to work towards gaining the knowledge that you lack. This is a temporary situation and everyone needs to know that. You can't be constantly pivoting your product or you'll never have something that is that useful to anyone. If the people you are talking to know that you are executing on a plan to address the challenges, they will be more willing to give you a bit more space to do what you need to do.

2. Schedule updates

   • If you can only communicate what you are going to do a quarter at a time, let your audience know when to expect the next update. For example, if you have a quarterly roadmap, schedule monthly updates. If you only know what the next month looks like, schedule weekly updates. Even if the next update is that you are still working on the same things and you aren't any closer to the details of the next roadmap item, at least people will have confidence that when something changes, they will know about it. You want to have frequent, consistent, transparent communication, even when nothing has changed. Frequent communications will ease minds that you have things under control. Of course, tailor your communication to your audience, as customers generally don't need to know as many details as executives do. But, giving these updates will let people know that you care enough about the situation and their being informed that you will take the time to communicate with them.

3. Solicit feedback

   • Involving people in the process can help them understand the difficulties you are facing. It also may make things a bit clearer to you, if they give you some good ideas. Moving from away from you talking at people to an inclusive discussion helps to give everyone a sense of involvement. If they understand the difficulties and are involved in helping to solve them, many people are more willing to give you a bit more leeway in how much you communicate.

To reiterate, this shouldn't be a permanent situation. Bring your audience along with you for the journey, be open and transparent with them, but give them confidence that you have a vision and a strategy for moving forward. This should set expectations that they will know as much as you can possibly be confident about right now and that you will constantly be updating them as you get new knowledge or information.

Navigating a product pivot involves recalibrating communication with stakeholders, including customers, investors, and internal teams. The primary goal is to build trust. I recommend transparently communicating the rationale behind the pivot and framing it as an opportunity for innovation and growth. At this phase, shifting your team's focus from long-term planning to short-term goals is crucial. Your ability to demonstrate tangible progress toward these short-term goals will deepen trust and reinforce confidence in the new direction. Finally, I'd recommend maintaining an "adaptability mindset" and iterating on the roadmap as you discover new insights.

Good luck!

In terms of how to communicate with your internal organization, partner teams, and stakeholders during a pivot, I'd make these internal partners and stakeholders a participating part of the pivot planning process. Once you're through that process and back to executing, then you can communicate timelines and project status internally just like before.

How to communicate with an external audience (e.g. clients in a b2b business or consumers in a b2c business) is a decision that usually gets vetted all the way up to the C-level. I've worked in major companies that shared almost no forward-looking roadmaps (either due to the risk to b2b relationships when product plans change, or because of bottoms-up product development culture that's inherently chaotic and hard to communicate to consumers). Some companies also worry about adverse press reactions or competing companies learning about your future plans and competing with you more effectively. But many other companies build strong communities of fans/supporters/customers by communicating somewhat openly about work-in-progress and future releases.

Whatever the appropriate amount of future-plans-communication for your business and customers, I'd expect you'd communicate less openly when you're less certain internally about your future direction.

E.g. if your customers love something in your future plans, but you're pivoting and may not follow-through, the risk of disappointing these customers and even undermining their trust in your business/brand increases. If your customers hate something about your announced future direction and write-off your business as likely to meet their needs, but you're pivoting and may veer back in an earlier direction... then you may scare off customers that you'd ultimate end up serving.

Net-net I think you need a kind of customer strategy for your pivoting. Do you know for sure how your target audience is changing? Can you predict whether part or all of your current customer base is also in your new target audience?

This is a common case scenario. Here are the few things I would take into account when providing a reset of expectations:

1. For the items too far out in the roadmap should be provided with an asterix and tentative disclaimer

2. Ensure that as soon as you know that there is a possibility of a pivot, start communication informally with the primary stakeholders to avoid surprises and backlash

3. Once there is clarity on the pivot, come up with a plan to explain the following things in the communication -

   1. Why did we pivot and the data behind it

   2. Potential benefit with the new route or the pitfall with the old route

   3. New plan

For a product pivot with unpredictable directions, aligning stakeholders' expectations around flexibility and frequent updates is key. Here’s how to approach this:

1. Adopt a Rolling Roadmap: Shift from a long-term fixed roadmap to a shorter, rolling roadmap that focuses on the immediate few months. Emphasise that the roadmap will be revisited and adjusted as insights from the pivot emerge.

2. Introduce Themes Over Features: Communicate high-level themes or objectives rather than specific features or timelines. This way, stakeholders understand the direction without expecting a concrete feature set or release date.

3. Increase Communication Cadence: Set up regular updates (e.g., monthly or bi-weekly) to share the latest insights and shifts in focus. This keeps everyone in the loop and shows responsiveness to the evolving strategy.

4. Educate on Agile Methodology: Reinforce an agile mindset, explaining that the pivot requires iterative learning and adaptation. This could mean frequent course corrections, and regular feedback will guide these changes.

5. Define Success Metrics at Each Stage: Instead of committing to feature delivery, focus on metrics that showcase learning and customer validation, which are crucial during a pivot.

The question underscores the challenges which POs experience while attempting to clarify reasons behind product pivot. However, the reason to pivot the product must be first clear enough to the product team such that they can subdue any background cacophony which often becomes too much time consuming and is un-productive.

Triggers to pivot a product might be the result of market reciprocation, but the narratives become stronger if the reasons are supported by data and information of associated or complimentary businesses which has an indirect impact on the product. At times such impact the outweigh the direct reasons. E commerce pre-existed prior Covid but the pandemic simply fueled it further.

Disruptions, often perceived as driven by Technology is actually a reflection of extreme volatile business situations that demand immediate navigation; a digital product is just the means, as I see it. If the general business situations are clarified, along with how users/market is behaving, how cost and overall finances are getting impacted it can provide a more holistic vision to the stakeholders.

POs are not fortune tellers. Short term product vision is more realistic than long term, often which is a red herring, based on assumptive judgements stemming from overconfident past experiences (mostly). Resetting expectations can be easy.

• Avoid sudden surprises. Share regular market and product insights.

• Create an equitable participative environment. A disciplined cadence of 'sense check' sessions with stakeholders helps.

• Craft Role Play sessions such that stakeholders play the role of PO/PM and provide them with enough information such that they can come up with strategies for product roadmap. DevOps; bring the philosophy back minus the tools/platforms.

There will always be background cacophony, negative sentiments when product pivot happens. Especially confidence level on the team takes a nosedive. Investor aspirations pivoting on an unidirectional and fixated product roadmap is a clear symptom of upcoming challenges for the product team.

Pivoting products which are designed to lead the business on its own 'product led growth' is a lot difficult. A multi-tiered target market may help steer the wheels of the product roadmap.