1. How do you define and measure change that is happening as a result of technology?
How do you know whether or not your brand is doing better from a digital perspective than your nearest competitor? What is the set of metrics that allow you to determine that you are successful? Technology has the capability to change the foundation of everything you do as a business. It has the capability to destroy your business if you do not do anything. To know where you are headed you must be able to measure how you're doing.
If you are in the B2B market space, if you are an asset producer, how do you know whether or not certain prospects can absorb the technological changes you are implementing? Which prospects do you go to first? These questions must be answered by having sound analytics.
2. What are you doing to fuel the transformation?
Are you actively pursuing technology investments as part of your merger and acquisition strategy? Are there startups in the technology space that can disrupt existing processes, services or interaction with customers. If that is the case, you need to pursue a strategy of 'techquisition' – technology acquisitions that change or add to your business process. Some industries are doing this well today, like the banking industry.
Someone at board level needs to own the responsibility to challenge the organisation and the executive suite to be aggressive on the change.
3. What are you doing to shift leadership mindsets?
Many people define the world at the moment by projects. And therefore everything has an end date. Leaders have been driven by projects or end of financial year cycles. How can you get leadership talent that still gets those cycles, but is also creative, agile from a business perspective and user-centric in terms of how they think. They are leaders that are both good at operating at scale, keeping large systems moving, but can also destroy whatever is passed its use by date and recreate it quickly.
What have you done over the last two years to make sure you have the right leaders at your organisation to make that change?
4. Can you pre-empt the next challenge?
It is highly likely that 12 months from now, or 18 months from now, you will go into the 'trough of disillusionment' regarding digital. Large parts of your organisation will be frustrated with the speed of change and start to argue there is nothing to profit from this. As a great leader, you have to recognise that is what always happens when change comes. How do you pre-empt that? What is the structure you are building on the other side of that trough of disillusionment?
Does your leadership team stand up in that period when what they are doing will be questioned?
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