Welcome to the assessment! There are 20 yes/no questions and it will take 5 minutes to complete. If you feel like you fall somewhere in the middle, choose the answer that you feel best reflects what's true in your business today.

QUESTION 1

Do you have a clear digital transformation strategy aligned with your business goals?

A successful digital transformation starts with a well-defined strategy. This means having documented objectives, timelines, and success metrics that connect technology initiatives to actual business outcomes. Without this foundation, digital projects often become disconnected from what truly matters to your organization.

QUESTION 2

Do you have a process for evaluating and adopting new technologies?

Shiny object syndrome is real. Without a structured approach to evaluating new tools against actual business needs, organizations either adopt too many disconnected solutions or miss opportunities that could provide real competitive advantage.

QUESTION 3

Is leadership actively championing and participating in digital transformation efforts?

Digital transformation fails without executive sponsorship. When leaders delegate without engaging, initiatives lose momentum and resources. True transformation requires leaders who understand, advocate for, and model digital-first thinking.

QUESTION 4

Do you have clear KPIs to measure the success of your digital initiatives?

Without defined metrics, it's impossible to know if your digital investments are paying off. KPIs should connect technology initiatives to business outcomes—revenue, efficiency, customer satisfaction—not just adoption rates.

QUESTION 5

Are your core business processes documented and regularly reviewed for optimization?

Before automating or digitizing processes, you need to understand them deeply. Many organizations rush to implement new tools without first mapping their workflows, leading to digitized inefficiency rather than genuine improvement. Documentation also enables easier onboarding and knowledge transfer.

QUESTION 6

Are repetitive manual tasks in your organization being automated where possible?

Every hour spent on repetitive data entry, report generation, or manual transfers is an hour not spent on high-value work. Modern automation tools can handle these tasks reliably, freeing your team to focus on what requires human creativity and judgment.

QUESTION 7

Do you have integrations between your key business systems to avoid data silos?

When systems don't talk to each other, data gets duplicated, errors creep in, and teams waste time manually transferring information. Integrated systems create a single source of truth and enable end-to-end process automation.

QUESTION 8

Do you have a documented disaster recovery and business continuity plan?

As organizations become more dependent on digital systems, the cost of downtime increases. A robust DR/BC plan ensures you can recover quickly from technical failures, cyberattacks, or other disruptions without catastrophic business impact.

QUESTION 9

Do you have a centralized system for managing customer data and interactions?

Customer data scattered across spreadsheets, email inboxes, and disconnected tools creates blind spots. A unified CRM or customer data platform ensures everyone has access to the same information, enabling consistent experiences and data-driven decisions.

QUESTION 10

Is your customer journey mapped and optimized across all digital touchpoints?

Customers interact with your brand across websites, emails, social media, and more. Understanding and optimizing this entire journey—not just individual touchpoints—is crucial for delivering experiences that convert and retain.

QUESTION 11

Do you have a mobile-friendly or mobile-first approach to customer interactions?

More than half of web traffic comes from mobile devices. If your website, emails, or customer portals aren't optimized for mobile, you're creating friction that drives customers to competitors who've prioritized the mobile experience.

QUESTION 12

Are you actively gathering and acting on customer feedback through digital channels?

Digital channels make it easier than ever to understand customer needs and pain points. Organizations that systematically collect, analyze, and act on this feedback can iterate faster and stay ahead of changing expectations.

QUESTION 13

Do you regularly collect and analyze data to inform business decisions?

Gut feelings have their place, but sustainable growth requires data-driven decision making. This means having dashboards, reports, or analytics tools that surface actionable insights—and leadership that actually uses them to guide strategy.

QUESTION 14

Do you have visibility into your key business metrics in real-time or near real-time?

If you're waiting for monthly reports to understand performance, you're always reacting rather than proactively managing. Real-time dashboards enable quick course corrections and help identify opportunities before they pass.

QUESTION 15

Are you leveraging AI or machine learning in any part of your business operations?

AI isn't just hype—it's increasingly table stakes. From chatbots to predictive analytics to content generation, AI tools can augment human capabilities significantly. Organizations not exploring these technologies risk falling behind competitors who are.

QUESTION 16

Is your website generating leads or revenue effectively for your business?

Your website should be your hardest-working employee. If it's just a digital brochure rather than an active lead generation and conversion engine, you're missing one of the most cost-effective growth channels available.

QUESTION 17

Is your team actively using collaboration tools beyond email for daily work?

Email alone can't support modern collaborative work. Tools like Slack, Teams, or Notion enable real-time communication, async collaboration, and transparent project tracking. If your team still relies primarily on email, important context gets lost in inboxes.

QUESTION 18

Do you have cloud-based systems that allow your team to work from anywhere?

Cloud infrastructure isn't just about remote work—it's about flexibility, scalability, and resilience. Organizations locked into on-premise systems often struggle to adapt quickly to changing circumstances or scale operations efficiently.

QUESTION 19

Is cybersecurity a regular topic of discussion and investment in your organization?

Digital transformation expands your attack surface. If security is an afterthought or only addressed after incidents, you're taking on significant risk. Proactive security investment protects not just your data, but your reputation and customer trust.

QUESTION 20

Are your employees receiving regular training on digital tools and best practices?

Tools are only as effective as the people using them. Ongoing training ensures your team can leverage technology fully, while also building a culture of continuous learning that's essential for long-term digital success.

You're all done!

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