Five Essential Questions for Digital Health Leaders

The old line about brevity being the soul of wit certainly applies to Peter Drucker’s classic 2008 publication, “The Five Most  Important Questions You Will Ever Ask About Your Organization.” The book distills critical organizational guiding principles down to bite-size essentials that anyone leading an organization or major initiative can quickly  absorb. The five questions are:

  1. What is our mission?
  2. Who is our customer?
  3. What does the customer value?
  4. What are our results?
  5. What is our plan?

Working out the answers to these seemingly simple questions can help chart a course for a business or organization; revisiting them regularly can help a team stay on message and keep the customer and business end-goals in sight. The simplicity, focus, and clarity of a
short list of good questions is a great catalyst for leadership teams and professionals in every domain —especially in the face of change and complex challenges.

Central to Peter Drucker’s work, and what makes the five questions so powerful, are the concepts of innovation and entrepreneurship. Drucker contrasted efficiency (business as usual but with lower effort and cost) with effectiveness —setting goals and building an organization that can transform to withstand or even thrive when conditions change.

As digital health professionals, we all work in a sector experiencing enormous, rapid change. You are probably aware of major shifts precipitated by powerful new entrants in health service delivery sectors in North America. Google’s AI and machine learning capabilities position it as a powerful healthcare innovation leader. Walmart Heath Centres are transforming access to care. Amazon and Best Buy both see healthcare and healthtech for an aging population as a growth area. And Apple products are creating a space in the clinical research and health data field.

Digital health incumbents must shift focus, ask new questions, and look closely at what retail and tech companies are seeing and hearing from their customers — and what traditional healthcare may be unable to deliver.

I thought it might be helpful to take a page from Peter Drucker’s book and come up with Five Important Questions that leaders of organizations involved in delivering health in a digital world (read: our members!) should be asking.

1. What is your vision for the future of health in a digital world?
It is critical that leadership teams develop a clear and vivid picture of the future state of their organization, their teams, and their audience. This vision should be firmly rooted in the future needs and interests of the people you serve, while still considering context of macro trends and industry shifts. To many stakeholders, the future feels uncertain and distant, even though key components of the future state — AI, robotics, virtual care, digitized physiology — are already here (thank you, William Gibson). Visionary leaders must conceptualize, construct and communicate the vivid imagery toward which others will align and build.

2. What is your organization’s role in this future scenario(s)?
Think about how you can create clarity around the role your organization will play in the broader ecosystem(s). What partnerships will you form? What will that look like? The digital health leaders who make up the membership of the CHIEF Executive Forum generally agree that the complex challenges they face will be solved by partnerships and organizational collaboration (rather than as single organizations working individually). Understanding partners’ and competitors’ goals and roles — and developing leadership alignment and agreement on vision — within the context of the future state must be addressed early and revisited frequently on the journey. Only then can leaders clearly and confidently move forward with a relevant organizational agenda that delivers value within the broader ecosystem.

3. What value do you deliver, and to whom?
Know Your Customer. Successful organizations can clearly articulate the value they provide, to whom they provide that value, and how it is delivered. As new entrants engage in the future of health and care delivery, those traditional players that adapt and participate in new value chains and ecosystems will flourish. The challenge? Engagement is moving away from a one-to-one relationship between a single entity delivering health and/or care to an individual. Increasingly, organizations must gain key insights within a many-to-one relationship where the patient is receiving healthcare or support from multiple providers. Defining the details around your value is a critical leadership conversation.

4. What results do you expect?
Define your desired results. What does success look like to you? We all share a goal of advancing health and healthcare for Canadians. But how will you sustain the growth and vitality of your organization in a field crowded with players with undifferentiated strength and skills? By focusing on and working toward your own unique results within a partnership framework, you can define what success looks like for your organization and your partners and create a plan to achieve it together.

5. What is your plan?
Crafting a plan might sound simple — but it’s not easy. Future-focused digital health leaders may find they need to adapt the metrics they are using now, or identify new indicators altogether based on their vision for the future of health in a digital world. Building an operational plan to deliver on your vision requires a unique set of indicators for each organization and its partners.

Here’s the key: figure out what other leaders you should be working with today to help answer the Five Important Questions. Choose a tight- knit group of partners to work with, and stay true to the original spirit of brevity, focus, and clarity. I suspect both Drucker (and Shakespeare) would be proud.

This is only a starting point. What are your questions? Reach out to continue the conversation at

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