Leaders who have thrived in structured, predictable environments are now grappling with the dynamic, ever-shifting landscape of generative AI. It can be destabilizing - and disorienting. Detailed analysis and scenario planning is difficult, if not impossible. The uncertainty isn’t just due to a lack of information or knowledge - it’s inherently unknowable.
Unexpected outcomes are becoming the norm, not the exception.
Yet, in most industries, avoiding the integration of AI into the way we work is no longer an option. While we may hesitate to embrace it, rest assured - some of our competitors won’t.
The challenge: How then do we make strategic decisions and inspire aligned and committed action amidst such uncertainty, especially when our credibility and the organization’s success is on the line?
It’s the ultimate paradox - how to be decisive enough to move forward, but agile enough to adapt.
This was the challenge my client Ray faced as we began our executive coaching engagement. He was excited about embedding generative AI into his organization. He had a strong track record of delivering results with a structured approach—breaking down challenges into clear goals, metrics, timelines, and contingency plans. In many ways, Ray exemplifies the Planner stage of game-changing strategic leadership. But now, the familiar benefits of his methods were colliding with the unpredictability of AI.
The feedback was becoming clear: his tried-and-true methods were no longer sufficient.
Yet he didn’t know another way. Collectively, he and the organization need to navigate rapid technological shifts, data privacy, workforce transformation, emerging regulations, ethical implications and evolving customer expectations - to name a few. The only thing for certain is that the landscape will be different in a year, a quarter, a month …but the time for clear direction and action was now.
The Practice of Decisive and Adaptive Leadership
When leading through the “fog” of the generative AI landscape, we must expand our strategic leadership capacities to help our organization thrive. This requires getting comfortable with discomfort (yours and others) and learning to strategically navigate through a complex and dynamic environment.
Here are three practices that strategic leaders like Ray can integrate to balance decisiveness with adaptability in inherently unpredictable environments, such as AI.
1. Know your Habits and Tendencies
Every leader has certain tendencies they lean on more than others - habits that become second nature, especially under pressure. How can we expand our range to be a more versatile leader that adapts to what the situation demands in complex contexts?
The first step is developing awareness - because without awareness, there is no choice. So, ask yourself: What is your default tendency in the face of not knowing? Then consider what the situation truly requires - even if it makes you feel uncomfortable.
- Do you default to research and analysis mode, like Ray (and me)? While thoughtful action can prevent costly missteps, it can also lead to over-analysis, delayed decisions and a lack of clarity for an organization that needs to act now.
- Do you prefer to take action swiftly? An action-oriented approach can be powerful - but it risks misalignment without a clear framework or guiding principles that orient teams to a shared endpoint. Without that different teams will likely take actions that lead in conflicting directions, creating inefficiencies and confusion.
- Are you too attached to your decisions? While clarity can come from decisiveness, rigidly clinging to a course of action can prevent you and the organization from adapting when new, relevant information emerges.
- Are you too adaptive, constantly changing course? While flexibility is essential in complex environments, being overly adaptive can create instability and undermine your credibility. If teams feel like priorities and approaches are always changing, they may lose trust in your leadership – struggling to feel a sense of momentum or impact on longer-term goals.
Strategic leadership is learning to actively manage these polarities - shifting from an either/or approach (thoughtful or action-oriented, decisive or adaptive) to a both/and mindset, like the natural rhythm of inhaling and exhaling. We’d never choose just one.
By identifying our natural patterns and actively managing these seemingly contradictory approaches, we can more effectively navigate inherently unpredictable environments like the AI landscape. This is the first step to developing beyond our proven leadership strengths and becoming more adaptive in our leadership approach.
2. Prioritize Clarity of Direction over a Detailed Plan
When leading in complex systems, we can no longer plan our way through a multi‑year transformation—we must lead our way through it.
Rather than rigid planning we need more robust strategic thinking. That helps us make strategic bets and guide the organization’s evolution. Instead of relying on detailed, fixed plans, create a flexible framework built on key assumptions about the future. A clear strategic direction - a “north star” - that should guide decision-making without being overly rigid. Like design principles, this guiding framework helps next-level decisions stay aligned even as circumstances change.
In contrast, a long-term plan focused on revenue growth alone won’t help you make decisions when ‘what can’t be anticipated’ occurs. As Michael Mankins points out in an HBR article, we must evolve from a static, plan-then-do process to a dynamic and continuous approach to strategic decision-making and action.
3. Embrace Iteration: Experiment, Test, Learn, Adapt
Mankins continues, “rigid plans — based on deterministic forecasts — must be discarded and replaced with a more dynamic and decision-focused approach. Flexibility and adaptability must move to the forefront of leadership’s thinking.”
Rather than trying to control every variable, focus on creating the conditions for adaptive learning. Lead with a mindset of continuous iteration, embracing shorter cycles of decision-making and action, with a greater emphasis on ‘learning by doing’ - experiment, test, learn, evaluate and adapt. It’s the practice of day-to-day strategic leadership - creating the future through day‑to‑day actions and decisions.
Leading through the Complexity of the AI Age
If you feel as if you are leading through a high stakes fog - you are.
AI technology is often described as the “wild west” - much like when the internet transformed the way we work and live. We are all pioneers in the industry - even your competitors. None of us can fully anticipate what’s to come - not the technology itself nor its broader effects on how we do business. An uncertainty that works against our biology and can be especially difficult for a strategic leader in the Planner stage, who thrives on structure, predictability and consistently delivering results.
Yet, in this rapidly evolving and complex landscape, the core principles of strategic leadership still hold true. Establishing a clear “north star” for your organization provides the steady direction amidst inevitable change. While the routes may shift, the general direction remains constant. By embracing this leadership mindset shift, you can practice being both decisive and adaptive in your leadership to effectively navigate this uncharted territory while maintaining momentum and alignment. Your organization depends on this evolution in your leadership.
The complexity "out there" demands that you evolve "in here."
This is part of the transition from Planner to Creator on the journey to becoming a Game-Changing Strategic Leader. If you are in the Planner stage,
- Can you identify a situation where your need for predictability and control might be limiting your ability to lead or influence a robust and adaptive strategy?
- What’s one practice that you could implement to step into the Creator stage, expanding your capacity to lead with both clarity and flexibility?
