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Leading with Questions:
Relieving the Pressure to Have All the Answers

805 words/3.5-minute read

In today’s tech-driven leadership environment, CIOs and CTOs are often expected to have immediate answers to a constant stream of challenges: staying ahead of trends, balancing innovation and risk, navigating security, aligning with business goals, and leading digital transformation. But what if the real power isn’t in having the answers—but in asking the right questions?

Here's a few thoughts on ways to consider your own leadership in both today and tomorrow’s ever-changing environments no matter what leadership position you manage.

1. Stay Ahead of Tech Trends by Leading with Curiosity
The rate of change is almost more scary than the capabilities coming to market and becoming commonplace. Instead of scrambling to stay on top of every trend, focus on creating a learning organization. Think about how you play with technology in your home and your transportation and more. Why does that have to be only during personal time? Bring those same lessons into the workplace. Your customers are going to expect your operations to work the same way their personal activities are run, so why not encourage that same application of your staff for the good of the organization and its customers?

Encourage questions like, 'What problem are we solving with this trend?' or 'How could this apply to our strategic goals?' This fosters a mindset where learning is valued over knowing, and discovery becomes a shared effort.

2. Balance Innovation and Stability Through Experimentation
Now discovery and exploration promote excitement in some, but nervousness in others as you navigate an uncertain adventure. However, doing what you’ve always done in today’s age, will not only give you what you’ve always gotten, but worse – it can leave you behind. But especially for those in the business of security and mitigating risks, navigating unknowns can be risky business.

You don’t need to lead with certainty—lead with permission. Allow teams to test ideas in controlled ways. Ask, 'What’s the smallest thing we can try safely?' or 'What guardrails help us innovate without breaking critical systems?' Give space for solutions. Articulate the needs clearly – define the “why” – but then leave plenty of space for “how.” Create space for collaborative discussions on the “what” so that definition of success is mutually defined and agreed upon. Then encourage what is possible within that space. That’s where smart innovation lives.

3. Manage Cybersecurity Risks Through Collective Intelligence
Now top of mind in our technology evolutions is how to ensure smart, secure investments in all we do. But security isn’t a solo responsibility. This is the shift from applications and products to collaboratively built solutions. Lead by asking, 'What risks haven’t we thought of?' or 'Who else should be part of this conversation?' Engaging a diverse set of minds builds stronger, more resilient solutions. And that approach allows security to be built INTO solutions, not an afterthought. And the sooner the conversations start, the sooner the risks can be identified and discussed.

4. Align Tech Investments with Business Outcomes
And the value of your hard work does not simply wait until projects are completed and changes are delivered. Value, even more than security, should be discussed from the beginning, defining what success looks like – and from all stakeholders’ perspectives. Always asking if we’re still adding value throughout any initiative. And then asking what can we do to add more value will make you think about the goals and strategically tie your decision-making to value-based outcomes.

Reframe the pressure to justify every spend. Ask, 'How does this investment get us closer to our business objectives?' and 'What does success look like for this solution?' Questions like these help bridge the gap between strategy and execution.

5. Drive Digital Transformation with Curiosity and Flexibility
Throughout your work, the shift to questions is what breeds opportunity.  It softens the pressure to have all the answers and worry about if you are making the right decisions. Surround yourself with smart, curious, and collaborative teams so that you can seed their curiosity with good questions. What could you ask that would get them excited to research and explore in search of a good answer? YOU ask the good questions while THEY create amazing solution options. 

Transformation can feel overwhelming—but asking the right questions creates clarity. 'What’s one outdated process we can redesign?' or 'What’s stopping us from moving forward?' Small, smart questions shift mindsets and mobilize teams. While defining the value that can be delivered is important, creating actions that fuel the value delivery is the most important direction you can encourage while steering the ship in the right direction.

Conclusion
Relieving the pressure to know everything frees you to be the kind of leader who inspires innovation, builds trust, and creates space for teams to thrive. Ask more. Answer less. That’s where great leadership begins. And great solutions and value can be delivered.