DEVELOPMENT for different types of support? What external pressures are becoming more frequent topics?
Creating space for strategic thinking The biggest gift you can give your executive right now is protected time for deeper thinking. Not just 15-minute gaps between meetings. We’ re talking about substantial blocks where they can step back from immediate pressures and consider bigger questions.
Schedule regular‘ thinking time’ in their calendar and defend it as fiercely as you would a board meeting. This isn’ t empty time; it’ s when breakthrough insights happen. They may resist this initially, feeling guilty about time that isn’ t visibly productive, but the results speak for themselves.
Make sure to use this time strategically. Beforehand, provide the pattern summaries you’ ve been tracking. Include relevant articles about industry changes, competitor moves or emerging trends that connect to what you’ re seeing internally. Frame questions rather than providing answers:‘ Given what we’ re seeing with client requests, what might this mean for our service delivery next year?’
Building organisational awareness Your access across different levels of the organisation puts you in an ideal position to help your boss understand what’ s really happening beyond the senior leadership bubble. Employees often see changes coming before those above do. After all, they’ re closer to customer interactions, operational challenges and day-to-day market shifts.
Create informal channels for this intelligence to reach your executive. This might mean brief conversations with other EAs about what their executives are prioritising or noting themes from company-wide communications. When you’ re coordinating with different departments, listen for concerns or opportunities that haven’ t yet made it into formal reports.
Present this information thoughtfully. Your executive doesn’ t need every detail, but they do need to understand patterns that could affect strategic decisions. Frame insights in terms of potential impact:‘ The operations team has mentioned three times this month that clients are asking about sustainable options – this might be worth exploring.’
Supporting adaptive leadership In uncertain times, your exec needs to make decisions with incomplete information. They need to be comfortable with changing direction when new information emerges, rather than sticking rigidly to original plans.
You can support this by building flexibility into how you manage their commitments. Instead of packing schedules with fixed commitments months in advance, leave space for emerging priorities. Create systems that allow for quick pivots, whether that’ s having backup plans for key meetings or maintaining relationships that can provide rapid market intelligence.
Help your boss stay connected to diverse perspectives. This might mean expanding the range of people they meet with, attending different types of industry events or connecting with peers facing similar challenges. The goal isn’ t networking for its own sake but ensuring they hear weak signals before they become obvious trends.
The confidence to act differently Perhaps most importantly, your exec needs confidence to act on emerging insights rather than waiting for certainty. In rapidly changing environments, the biggest risk often comes from waiting too long to respond to new information.
Your role here is to help them process and test new ideas. When they’ re considering a significant change in direction, help them think through implications. What would this mean for current projects? Which stakeholders would need to be consulted? How could they test the idea on a smaller scale first?
Create space for experimentation. Many breakthrough strategies start as small tests that prove successful before being scaled up. Your executive needs permission to try new approaches without the pressure of getting everything right immediately.
You can help your executive navigate uncertainty by creating the conditions for adaptive thinking. By protecting time for reflection, providing pattern intelligence, and building flexibility into how they operate, you’ re not just supporting their current success – you’ re helping them prepare for opportunities that others won’ t see coming. S
thehupersonproject. com
THE EXPERT
Jill is co-founder and CEO of The HuPerson Project and former CEO of Burgerville. With experience leading three businesses through significant change, she specialises in helping leaders develop the awareness and flexibility needed to navigate uncertainty.
Building your intelligence system
n Track patterns: Note recurring themes in meetings, correspondence and stakeholder conversations. Look for shifts in the types of questions people ask or problems they raise. n Monitor externally: Subscribe to industry publications and competitor updates. Share relevant insights that connect to internal patterns you’ re seeing. n Listen across levels: Use your interactions with different departments to understand ground-level changes that haven’ t reached senior leadership yet. n Frame questions: Instead of just reporting what you observe, help your executive think about implications by asking:‘ What might this mean for our strategy?’
Spring Issue 2025 | Executive PA 57