The CEO’s essential checklist: Questions every chief executive should be able to answer

Extractive Summary of the Article | Read | Listen

Agreat aviator is constantly aware of their surroundings. Watching for changes in the weather and in the paths of other aircraft is vital. The same is true for being a great CEO, which is why the business press is full of information about what’s happening in the business environment: geopolitics, regulatory changes, inflation, generative AI, and so on.

Equally important for a pilot’s success is understanding their aircraft and its avionics: checking fuel levels and flight plan progress, testing safety systems, and keeping an eye on engine performance. To ensure a successful trip, pilots utilize checklists before, during, and after the flight. For CEOs, the same should hold true. However, when doing research for their New York Times best-selling book, CEO Excellence: The Six Mindsets That Distinguish the Best Leaders from the Rest (Scribner/Simon & Schuster, March 2022), the authors found that no such checklists existed for the role of the most senior leader. Sure, CEOs have an abundance of financial, operational, and organizational metrics to look at, but what CEOs should be doing to influence those metrics wasn’t exactly clear.

Over the past two years of talking with CEOs about their findings, the authors have been struck by how many have asked for an “in flight” checklist. In response, the authors have crystalized how the mindsets that underpin CEO Excellence translate into practice in each of the six responsibilities of the CEO’s role: setting direction, aligning the organization, mobilizing through leaders, engaging the board, connecting with stakeholders, and managing personal effectiveness. In doing so, theyr have drawn on in-depth interviews with more than 70 of the most successful current and former CEOs of the 21st century, including the likes of Microsoft’s Satya Nadella.  The result is 18-question checklist grouped according to the mindset.

1. Direction-setting checklist: Be bold.  Vision: Do we have a clear and compelling vision that reframes what winning looks like, and is it owned by the whole enterprise?  Strategy: Have we created a short list of clearly defined big moves at the enterprise level that will distance us from our competitors?  Resource allocation: Are we ‘thinking like an outsider’ to actively reallocate resources (such as dollars, people, and management attention) to our highest priorities, even when it’s hard to do?  
2. Organizational-alignment checklist: Treat the soft stuff as the hard stuff.  Culture: Are we targeting and systematically pursuing specific areas of cultural change to further execute our strategy?  Organizational design: Is our organization characterized by a balance of stability and agility that maximizes the speed and effectiveness of execution?  Talent: Are the most value-creating roles in our organization filled with the right talent, and do they have a strong leadership pipeline?  
3. Leadership mobilization checklist: Solve for the team’s psychology.  Team composition: Is my senior team the right size, comprising people with complementary skills and characterized by an ‘enterprise first’ mindset?  Teamwork: Does my senior team effectively use data and dialogue to make timely decisions on topics that only they can take on?  Operating rhythm: Does my senior team have an effective annual operating rhythm and business review cadence that drives execution and minimizes surprises?  
4. Board engagement checklist: Help directors help the business.  Relationships: Have I built trust with my board members by being ‘radically transparent’ and showing an interest in their views?  Capabilities: Do we have the right profiles on the board, and are we sufficiently educating directors and pulling them in to help where they can?  Board meetings: Are board sessions well prepped, effectively run, and focused on the future (going well beyond fiduciary topics)?  
5. External-stakeholder-connection checklist: Start with ‘Why?’  Purpose: Are we clear on the holistic impact we aspire to (our ‘why?’), and have we embedded that into the core of how we run our business?  Interactions: Do we fully understand our stakeholders’ needs (their ‘why?’) and find constructive common ground with them?  Moments of truth: Have we built resilience ahead of any potential crises so that we’ll be able to mitigate their impact and use them to unlock opportunities?
6. Personal-effectiveness checklist: Do what only you can do.  Time and energy: Do I manage my time and energy well, and do I have the right office support in place to help me successfully and sustainably do what only I can do as the CEO?  Leadership model: Am I leading in a way that is authentic to my convictions and values while also adjusting my behaviors to what the organization needs?  Perspective: Do I approach my position with humility, focusing on helping others to succeed and continually improving my ability to do so?