Out of Sync with Leadership? — Here’s How Smart PMs Realign (Hint: It’s Not Roadmaps!)
The conference room felt different that afternoon. I sat across from the executive, the tension between us palpable as we attempted to discuss our product roadmap challenges.
“I believe you can make decisions, and you should be able to make decisions in your role,” she said directly, “but I don’t believe you can make the right decisions.”
The words hit me like a physical blow. For months, I’d been working tirelessly to deliver on what I thought were our agreed strategic objectives. I had prioritised features that would increase user engagement, shepherded the team through tight deadlines, and secured enthusiastic beta testers.
I took a deep breath, recalling advice I’d read from Jefferson Fisher about navigating difficult conversations. Instead of becoming defensive, I leant into vulnerability.
“Maybe you’re right,” I said quietly. “Perhaps there is a way I can start making better decisions. Let’s explore that.”
The subtle shift in her expression told me this wasn’t the response she expected. The confrontational energy slightly dissipated as she nodded.
“I’ve been working to deliver what we discussed in our quarterly planning session,” I continued.
She leant forward. “That’s precisely the problem. You’re executing tactically on objectives we discussed three months ago, but our strategic priorities have shifted.”
At that moment, I realised the fundamental disconnect. While I had been heads-down executing explicitly stated goals against the strategy communicated a few months ago, the executive team had pivoted their thinking without communicating those changes. We were operating in different realities, with differing assumptions about what mattered most.
Finding the Path Back to Alignment
That painful conversation became a turning point in my career. What initially felt like a personal failure evolved into one of the most valuable lessons I’ve learned about product leadership: alignment isn’t a one-time event — it’s an ongoing practice that requires deliberate cultivation.
Here’s how I navigated back from the brink of misalignment and how you can, too:
1. Acknowledge the Disconnect Without Defensiveness
Rather than trying to defend my actions or explain away the criticism, I employed Jefferson Fisher’s approach to difficult conversations — embracing curiosity instead of certainty. As Fisher often suggests, the most productive response to criticism isn’t justification but exploration.
“You’re right that I’ve focused on executing the plan we discussed last quarter. It seems I may have missed some signals about how our priorities have shifted. Can we take a step back and realign on what matters most right now?”
Approaching the conversation with humility helped rebuild trust and open a constructive dialogue. Instead of escalating the tension, this response invited collaboration, signalling my willingness to listen, learn, and adjust.
2. Create Visibility into Decision-Making Frameworks
Following our uncomfortable conversation, I worked with my executive to develop a clear decision-making framework that outlined the following:
- The current top three strategic priorities (and why they mattered)
- Key metrics that would indicate success or failure
- Boundaries for autonomous decisions vs. those requiring consultation
- Regular check-in cadence to review and adjust priorities
This framework became our shared language — a north star that prevented us from drifting too far from alignment.
3. Institutionalise Regular Strategic Dialogue
I established a biweekly “strategic pulse” meeting with key executives. These weren’t status updates but forward-looking conversations about market changes, emerging risks, and evolving company priorities. These meetings became early warning systems for potential misalignment.
The format was simple but effective:
- What’s changed in our understanding since we last spoke?
- Are our current priorities still the right ones?
- What new information should influence our thinking?
4. Develop Your Translation Skills
The most valuable skill I developed was the ability to translate between executive strategic thinking and tactical team execution. Executives often communicate in broad strokes and expect product leaders to fill in the details. Learning to ask clarifying questions and restate strategic direction concretely became essential.
When my executive would say something like, “We need to focus more on enterprise value,” I would translate that into specific implications: “So that means we should prioritise the admin console redesign over the consumer features we discussed last month?”
5. Build a Coalition of Understanding
I began cultivating relationships with other leaders who had the executive’s ear. These connections provided valuable context about discussions happening at higher levels and helped me anticipate shifts before they became formal directives.
This network became my early warning system, helping me understand why priorities were changing before they became official mandates.
Keep Alignment a Continuous Practice
Misalignment can creep in when strategic priorities shift faster than communication flows. To prevent this, make alignment a habit — schedule regular check-ins, proactively seek feedback, and create space for ongoing strategic discussions.
The Rewards of Continuous Alignment
Six months later, I sat in the same conference room with the same executive, but the energy had shifted entirely this time. As we mapped out a new strategic initiative, building on each other’s ideas, she paused and said, “I’m so glad we had that conversation. Look at where we are now — we’re truly aligned.”
This moment reinforced a critical lesson: alignment isn’t a one-time event but an ongoing practice. Misalignment often happens when strategic priorities shift faster than communication flows. The best product leaders don’t just execute — they anticipate change, proactively check in with stakeholders, and create space for continuous dialogue.
How Do You Maintain Alignment?
Have you faced a similar challenge? How do you keep your teams and stakeholders aligned when priorities shift? Share your thoughts — I’d love to hear your experiences.
