Executive and board member meetings don’t just present opportunities for reflection and review. They also present chances to ask key questions that can help you know if an organization is on the right track to adapt, innovate, and stay ahead of its competitors. While it’s important to use these occasions to explore strategic direction, new initiatives, and overall organizational performance, it’s also crucial to use them as opportunities to get a sense of where a company is headed, and how well equipped it is to get there. Put the following queries to your colleagues, and you’ll get a much better sense of how things look to shake out:


Q: Studies recommend that the right way to approach emerging technology is as a strategic imperative, not just an operational issue. One of the pitfalls of this principle is fixation on the technology, not the value to the customer. How does the company plan to take a strategic, customer-focused approach to digital transformation?


Q: Another common pitfall that we see in business is when companies take on random acts of digital innovation that don’t necessarily add value. How are you thinking about the balance of going all in versus acting incrementally with regard to digital transformation to make sure the businesses is headed toward the appropriate future state?


Q: It’s also important for an organization to have the right people and the right culture in place. How are you providing oversight in this area to ensure the company is ready to greet the challenges that tomorrow’s working world and marketplace will bring?


Q: Digital transformation presents both an opportunity and a risk. What are we doing to ensure that digital transformation is accompanied by an appropriate level of risk oversight, striking a balance between opportunity and risk?


Other Questions to Ask:


• Directors demand frequent and forward-looking reporting on technology-related initiatives. What are we doing to successfully track and provide it?

• Hiring a CEO is the #1 job of boards. Should directors be thinking about a CEO’s track record in or aptitude for digital transformation when hiring, and, if so, even in “traditional” industries?

• How can the board maintain the focus on a long-term digital strategy instead of on realizing immediate returns and easy innovation wins?

• How do we build trust in a digital economy/business?

• How can a company strike the right balance and avoid under or over investing in digital transformation?