Strategic Leadership in Times of Uncertainty: A Guide for Portfolio Managers

Leading with clarity when everything feels unclear

Uncertain times don’t just test business strategies—they test leadership. When markets shift, budgets shrink, and priorities seem to change overnight, teams look to portfolio managers for guidance, stability, and confidence. The problem? If leaders aren’t proactive in how they communicate, align, and motivate their teams, uncertainty turns into hesitation, confusion, and stalled progress.

Gartner’s Program and Portfolio Management Practices for Turbulent Times report highlights a critical truth: successful leaders don’t just react to uncertainty—they navigate through it with clarity, transparency, and adaptability.

The difference between a team that weathers disruption and one that crumbles under pressure often comes down to how leadership approaches communication, goal alignment, and visibility into progress. Let’s break it down.

Transparent communication as a foundation

When uncertainty hits, silence is the fastest way to lose trust. Without consistent, clear communication, teams fill in the gaps with their own assumptions—often imagining the worst. Portfolio managers who keep their teams aligned don’t just share information—they create a culture of open dialogue, psychological safety, and real-time course correction.

But great portfolio managers do more than just communicate—they actively assess risk, surface potential issues early, and ensure their teams are always in the know. They recognize that silence around risks doesn’t prevent problems—it amplifies them.

Transparency doesn’t mean alarming teams with worst-case scenarios. It means proactively acknowledging challenges, sharing insights on potential risks, and providing a clear plan for mitigation. The best leaders don’t pretend everything is fine when it isn’t—they create confidence by showing that risks are understood, managed, and addressed head-on.

This requires a systematic approach to risk assessment, with ongoing evaluation of:

• Portfolio-wide vulnerabilities. Which projects carry the most uncertainty? Where are the dependencies that could cause bottlenecks?
• Resource constraints. Are teams stretched too thin? Will shifting priorities impact workload balance?
• External factors. How might market conditions, budget shifts, or organizational changes affect current initiatives?

When teams see that leadership is actively monitoring risks and adjusting strategies accordingly, they feel more secure—even in unpredictable environments. More importantly, they stay engaged and focused because they understand the challenges at play and trust that their leaders have a plan.

Ultimately, strong portfolio leadership isn’t just about keeping teams informed—it’s about building a shared understanding of risks, decisions, and next steps so that no one is left guessing.

How to lead with transparency:

Uncertainty breeds anxiety, but clarity creates confidence. When teams don’t know what’s happening, they start making their own assumptions—often far worse than reality. That’s why transparent leadership isn’t just about sharing information; it’s about creating an ongoing dialogue where teams feel informed, involved, and empowered to adapt.

Great portfolio managers make transparency a habit by building regular touchpoints, addressing challenges directly, and fostering a culture where feedback flows both ways. Here’s how:

• Hold regular check-ins. Uncertainty thrives in the absence of information. Frequent touchpoints ensure teams stay informed, aligned, and heard.
• Address challenges head-on. Avoiding hard conversations doesn’t make problems go away—it makes them worse. Instead, acknowledge difficulties while reinforcing the team’s ability to adapt.
• Encourage two-way communication. Leadership isn’t just about broadcasting updates. Create space for teams to ask questions, voice concerns, and contribute ideas.

Gartner’s research reinforces that regular feedback loops and transparency are critical for leadership success in volatile conditions. When people understand why decisions are being made, they’re more likely to trust the process—even when times are tough.

Aligning teams with strategic goals

When things change, the worst mistake a portfolio leader can make is assuming their current priorities still make sense. What was strategically sound six months ago—or even a few weeks ago—may no longer be relevant. Yet, without regular recalibration, teams will continue pouring resources into outdated goals, wasting time and effort on work that no longer aligns with the bigger picture.

Strategic alignment isn’t about setting goals once and hoping they stay relevant—it’s a continuous process of reassessment and recalibration. The best portfolio managers treat alignment as an active responsibility, ensuring every project, resource, and initiative contributes to current business priorities, not yesterday’s strategy.

To keep teams focused on what truly matters, leaders need to:

• Revisit strategic objectives regularly. Set quarterly (or even monthly) checkpoints to reassess priorities and ensure they still align with broader business goals.
• Develop clear KPIs. Success should be measurable, not subjective. Establish key performance indicators that help teams track progress and adjust their efforts accordingly.
• Connect day-to-day work with the bigger picture. People work better when they understand why their contributions matter. Reinforce how projects tie into more significant business outcomes to keep motivation and focus high.

Companies that tie portfolio investments directly to strategic objectives consistently outperform those that don’t. But alignment isn’t just about setting goals—it’s about maintaining clear visibility into how work connects to business outcomes. When leadership defines success in concrete terms and tracks progress transparently, teams stay more engaged, efficient, and adaptable.

This is where a Strategic Portfolio Management tool like OnePlan becomes invaluable. By providing a real-time view of objectives, resources, and risks across the portfolio, it helps leaders ensure that priorities stay aligned, teams remain focused, and no effort is wasted on work that no longer serves the bigger picture.

Recognizing progress and maintaining focus

Uncertainty doesn’t just impact business priorities—it affects team morale. When everything feels in flux, motivation can take a hit. If teams don’t see tangible progress, they may start questioning whether their work is making a difference. That’s why celebrating progress—no matter how small—is essential. It reminds teams that, despite external challenges, they are still moving forward and that their efforts matter.

But progress tracking isn’t just about morale—it also helps prevent burnout. In fast-paced, high-stakes environments, teams often push forward without pausing to reflect on what they’ve accomplished. Without visibility into wins—both big and small—teams can fall into the trap of feeling like they’re running on a treadmill, always working but never making real progress.

How to keep teams motivated and engaged:

• Identify and celebrate small wins. Even incremental progress deserves recognition. Acknowledge achievements to build momentum and reinforce confidence.
• Use progress tracking tools. When people can see how their work is moving the needle, they stay more engaged. OnePlan’s Gantt charts provide an easy way to visualize key project milestones across the portfolio, making it easier to see (and share) progress at a glance.
• Create a culture of appreciation. Leadership should actively highlight team contributions, reinforcing that effort, adaptability, and resilience matter.

Visibility into progress isn’t just nice to have—it’s a strategic necessity. Positive reinforcement helps teams sustain focus, adapt more effectively to change, and stay committed to long-term goals. Leaders who make a habit of celebrating progress create an environment where teams feel valued, stay engaged, and maintain momentum—even when the road ahead is uncertain.

Leadership beyond crisis management

Being a strategic leader in uncertain times isn’t just about managing the moment—it’s about guiding teams toward long-term success with clarity, consistency, and confidence. The best portfolio leaders aren’t just reacting to disruption; they keep their teams aligned, focused, and engaged through clear communication, realigned goals, and visible progress tracking. Economic turbulence will always test organizations. But the leaders who navigate it best aren’t the ones with all the answers—they’re the ones who create an environment where their teams can keep moving forward, no matter the conditions.

Interested in learning more? Join our webinar with Brett on Thursday, March 27th!