Navigating the Pivot: Using Product Strategy to Communicate, Plan, & Execute Major Changes - DockYard

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DockYard Team


DockYard Team

You and your team are knee-deep in product development when you realize that some element of your roadmap needs to change. Whether it’s a change in stakeholder agendas or the departure of a valued team member, you’ll need to change your roadmap to ensure it reflects current dynamics.

Pivoting requires conversations, which can be difficult when there are deadlines to meet, investors to keep happy, and teams to keep moving. No matter what kind of pivot you’re eyeing, having tough conversations needs to start sooner rather than later. Here are three bases we recommend you cover before you begin making major changes to your product strategy:

1. Make sure your stakeholders are focused on the right things

Sometimes your pivot will start from the top and require a quick shift from your product team. In other cases, it’s your product team who needs to communicate up the chain of command. In either case, the first step is ensuring everyone is focused on the right thing.


In our experience, it is typical for a CEO or other top executives to struggle with taking a step back. It’s their baby, from idea to rollout, and they can find it difficult to loosen the reins. Product ownership can trump product strategy in this case, making it easy for execs to stay in a micromanaging comfort zone.

Teaching executives to become executives can be an unwritten part of the product strategy, and it’s an especially important base to cover when you’re executing a pivot. There is typically no playbook or HR manual to tell the executive what to do and how to do it, especially for product strategy.

That’s why pivoting their time and attention away from product details to business strategy is an enormous leap best accomplished by someone outside of the company who knows how to support the transformation of the “entrepreneur” to “executive leader.”

Whether it is a formal business coach, valued friend, or third-party vendor who knows the ropes, executives must shift from doing it all to doing the right things.

One of the biggest challenges executives will face is knowing when and how to share top-down pivot communications. M&A changes, leadership or stakeholder changes, and shifts in the business environment can all affect business strategy, products, and team direction.

These changes should be shared with the product team sooner rather than later. But if an executive isn’t focusing on the right things, they may fall into the trap of keeping a change to themselves and assuming they can navigate the necessary product changes.

Often, this information is confidential or legal in nature, and requires a structured communication approach. Balancing transparency, urgency, and importance are critical for executive communications, especially those that impact product strategy and by default, company revenue.


Likewise, bottom-up pivot communications from product teams keep executives involved in product decisions. It can be difficult to wean an executive off of hourly texts and scrum meetings because they’ve built up a habit of being fed detailed data from day one.

Switching from daily details to summary reports is one of the biggest pivots in bottom-up communications a company will face. So how do you keep executives involved, but not immersed in product team decisions?

Start by setting team goals that release executives from the product team’s day-to-day activities. For example, set a goal to replace daily meeting with weekly status reports. These reports are a great place to start, along with dashboards indicating product strategy success measures, and help build trust in the product team and their process.

Frequent report-outs that show team successes enhance the CEO’s confidence in the team’s progress without texting them five times a day for an update. They also give the product team an avenue to communicate pivots up to executives in a consistent way and keep everyone on the same page.

Whether you’re facing top-down or bottom-up communication issues, an objective third party will tell an executive what they should do and where their time is most valuable while navigating communication challenges.

Then, they can refocus the executive’s energy on connecting with customers and vendors, setting strategic goals, and directing team leaders. Over time, the exec will transition to managing from the 50,000-foot strategic level instead of the 50-foot daily grind.

2. Establish common ground

Your existing product strategy may be quite detailed, or it might be scrawled on a few sticky notes around the office. The product team tries to follow the strategy but they’re often in the weeds sorting out user requirements, technical issues, and sprint schedules. Meanwhile, a new stakeholder enters the picture, bringing market intelligence and preconceived notions on how to execute the product strategy. Where do you begin?

Start by establishing common ground. Product teams, executives, third parties, and other stakeholders need to understand:

  • What was the original vision for the product?
  • Who is the user, and what job are they hiring us for? (We recommend using the Jobs-To-Be-Done (JTBD) approach.)
  • Does the product align with our business objectives?
  • Is the product both technically and financially feasible?

Focusing the conversation on the user and business objectives is essential to validate an existing product strategy or create a new roadmap. For instance, using the JTBD framework can help the entire group explore who the customer is, what “jobs” they need to fill, and how your product can solve user problems better than your competitors.

But conversations can get heated. Stakeholders may insist their needs are more important than user needs, and teams may just want to get things done. Creating a safe space for everyone to discuss the issue is essential so no one dominates the conversation. One way to achieve this is to bring in an objective third party who is not afraid to have an honest conversation and kindly challenge assumptions.

3. Conduct a product team checkup

A healthy team is a happy team. But change can be tough for everyone to navigate, and executing a pivot comes with plenty of change. When your formerly productive team starts missing deadlines, has open conflicts, or can’t decide what to do next, it may be time for an intervention. These are all signs of a team that has lost their direction, or worse yet, lost their passion for the product.

First, you’ll need to get your team’s concerns on the table. For example, do they understand the roadmap, what the priorities are, and have confidence that they can meet their deadlines in their day-to-day activities? If not, you may need to dive into their work processes to see which bottlenecks are slowing them down. Do they have the right technology? Are there repetitive tasks? Identifying workflow issues can be a simple way to regain productivity.

Second, does your team have a regular cadence, or do they deliver whenever convenient? Reinstating a structure—like two-week sprints—can put them on a regular schedule and set expectations for routine deliverables and major product launches.

Finally, if there are personnel problems, it is time to be honest about them. If your team members show signs of fatigue and burnout, it is time to break. Your product will never be successful if it destroys the team who created it. It might be time for vacations, more resources, reassignment to new areas, and conversations about what will reinvigorate your team’s passion.

How an outside perspective can help

At DockYard, we help companies pivot operations in ways that support growth, improve processes, and align the team towards success.

We’re skilled at making sure companies focus on a higher vision—serving customer needs—while challenging executives to focus on making the bold decisions necessary to scale their company. We aren’t afraid to have honest conversations about what hinders your growth because we’re experts and putting companies on the right track and building a team culture that translates to long-term success for our partners.

For more insights on making your product strategy successful, download our Ebook, So You Built the Right Product the Wrong Way. And subscribe to our monthly newsletter to learn more about how we handle product strategy pivots, engineering innovations, and more.


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