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How to Benchmark Your AI Confidence: Bridging the Gap Between Knowing and Using
- Janine Dormiendo
- Nov 4
- 4 min read
Many leaders today can describe what AI is. Fewer can describe how they personally use it. That gap — between knowing and using — is where confidence is either built or eroded.
This guide is for senior leaders and department heads who want to assess their organisation’s AI readiness — not in terms of tools or code, but in mindset, confidence, and strategic alignment. From that benchmark, you can begin to build the fluency that enables meaningful, people-centred transformation.
Why Benchmarking Your AI Confidence Matters
Organisations don’t transform simply because they have AI.They transform because leaders use AI well - with clarity, judgement, and cultural alignment.
And that starts with assessing your own starting point.
Confidence with AI isn’t about having all the answers. It’s about moving purposefully from awareness to application. This shift often reveals itself not in dashboards or data, but in how you work, lead, and influence others.
Recent research reinforces this. According to the 2025 “People Readiness Report” by Kyndryl, while 95 % of enterprise leaders say they’re already using AI across multiple areas, 71 % admit that their workforce is not yet ready to harness AI’s full potential. Kyndryl
In other words: adoption of tools is high — but readiness, culture and leadership fluency are lagging.
Step 1: Locate Your Mindset Starting Point
Before you focus on capability, assess your current mindset.
Consider the following spectrum:
Cautious CuriosityYou’re interested in AI but unsure how it applies to your role. You might delegate AI exploration but don’t yet use it directly.
Pragmatic ExperimentationYou’ve started to test AI for basic tasks — notes, summaries, outlines — but usage is still ad hoc. Confidence varies with context.
Purposeful IntegrationAI is a consistent part of your workflow. You use it to inform decisions, clarify communication, and model learning for others.
💡 You don’t need to be in Stage 3. You just need to know where you are — and where you want to go.
Step 2: Reflect with These 3 Coaching Questions
To deepen your self-assessment, use these reflection prompts. They’re designed to surface unseen blockers or opportunities:
Where in your current workflow do you avoid using AI — and why?Is it trust, ethics, discomfort, or lack of clarity? Identifying resistance points helps guide your next steps.
How often do you use AI to support a decision — not just a task?Confidence grows when AI supports thinking, not just doing. Are you using it for synthesis or communication strategy?
What would your team say about your example?Your AI usage sends signals. Are you modelling curiosity, discernment, and a people-first approach to transformation?
These questions aren’t about evaluation — they’re about alignment, and alignment creates momentum.
Step 3: Move from Insight to Integration
Once you’ve benchmarked your confidence, the next step is to build a structured pathway forward.
At Envisago, our AI Coaching Accelerator™ helps leaders make this shift over six weeks.
The journey starts with a diagnostic and builds toward a tailored playbook for leadership-aligned AI use — and this matters because research shows many organisations are stuck in the “adoption” phase but still lack workflow integration and culture change. For example, a BCG study found that while more than three-quarters of leaders and managers say they use generative AI several times a week, regular usage among frontline employees remains at just 51 %. Boston Consulting Group
The gap isn’t about tools — it’s about leadership clarity, culture and strategic alignment.
Here’s a simplified version of our six-week structure:
Week 1: Define success and assess mindset
Weeks 2–3: Apply AI to productivity and decision-making
Weeks 4–5: Identify use cases and enable others
Week 6: Integrate learning into your daily leadership rhythm
What matters is not just knowing how — but knowing how to embed what works, and leave behind what doesn’t.
Step 4: Translate Confidence into Culture
Benchmarking your own AI confidence is a valuable first step.But leadership doesn’t end with personal clarity — it extends to how you coach, communicate, and cultivate fluency in others.
Leaders who model thoughtful experimentation accelerate cultural readiness.In the same BCG study above, this gap in adoption among frontline employees demonstrates the critical role of leadership modelling and enabling structures. Your example isn’t just symbolic — it influences whether AI becomes embedded or remains superficial.
That’s how AI becomes a leadership capability, not just a technical upgrade.
In Summary: A Practical Path Forward
Benchmarking your AI confidence begins with four steps — which is vital in a moment where many enterprise leaders say adoption is high, yet readiness is uneven. According to the Kyndryl “People Readiness Report 2025”, while 95% of leaders say they’re using AI, 45% of CEOs report that employees actively resist it. Kyndryl
Identify your current mindset: cautious, experimental, or integrated
Reflect on your relationship with AI through targeted coaching questions
Structure your next steps through a guided, outcomes-focused pathway
Model confidence and curiosity to influence your wider culture
Next Step: Build Leadership-Aligned AI Capability
Where are you starting from — and where do you want to lead next?
Book a 20-minute Discovery Call to see where your leadership team sits on the AI Confidence Benchmark, or Explore the AI Coaching Accelerator™ to turn insight into integrated action.
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