The 3 Strategy Questions Every CEO Should Ask Regularly

Only through strategy can an organization establish a lasting competitive advantage that enables it to capture the Big Opportunities ahead of competition, namely.

Whether the strategy will actually achieve this, however, depends on how well it is aligned with the actual business environment, how accurate its change management plan is, and how well this change management plan is executed. This is why it is imperative that CEOs actively engage not only in Strategy Formulation, but also in Strategic Planning and Strategy Execution.

Considering the demands on a CEO’s time, it can be challenging to fit these activities into the CEO calendar. To keep things simple, CEOs should start with regularly asking their organizations the following 3 strategic questions.

“Welcome the identification and communication of threats to plan execution. Don’t criticize managers for fearing the future.

1. Where are we today? Every organization will focus on the things it believes its leader is focusing on. Consequently, if the leader shows no interest in the execution of plans, the organization will not focus on this task either and none of the things that were agreed during strategy will get done. For this reason, regularly ask your organization about the progress of Strategy Execution: “Where are we today and how does this compare to the targets we set ourselves?”

2. Are we ready for the next steps? Organizations that manage Strategy Execution solely through asking backward-looking questions will always be reactionary. Since “an ounce of prevention is better than a pound of cure”, you should also drive a forward-looking mindset in your organization. This can be accomplished by regularly asking: “Are we ready to execute the next phase of the strategic plan and what could cause issues?” Key here is to welcome the identification and communication of threats to plan execution. Don’t criticize managers for fearing the future. Criticize them if they are not getting ready for it!

3. Do we still want to take the next steps? The global business environment today is characterized by continuous fast-paced and unpredictable change. Every strategy therefore runs the risk of being overtaken by time. If the real world does not change in accordance to what was assumed during Strategy Formulation, it is most likely the identified Big Opportunities will never materialize. In such a situation an organization would just be wasting time and effort if it continues focusing on executing the strategic plan. Such “strategic tunnel vision” can be avoided if you regularly ask your organization to challenge the strategy it is working under: “Do we still want to take the next steps of the strategic plan, or has the world changed in ways that necessitate a change in strategy?”

With this 3-step strategy, CEOs can very simply stay on top of his or her company’s priorities.

Andreas de Vries

Andreas consults on strategy and strategy management in the oil & gas industry. His articles have been featured in the LNG Journal, OilVoice, European Energy Review and The Innovation Enterprise.

Share
Published by
Andreas de Vries

Recent Posts

Gallagher Insurance Exec Shannon Gallagher: ‘Give Your Employees Life’

According to Gallagher, mentorship starts with curiosity: 'Get to know people, be present. This is…

3 hours ago

After Tariff Whiplash, EarthQuaker Devices CEO Keeps Playing Offense

From weekly war-room meetings to testifying in D.C., Julie Robbins has spent the past year…

21 hours ago

Manufacturing Confidence Rebounds In Face Of Global Volatility 

Despite stressors associated with heightened global risk mounting since early 2026, U.S. manufacturers express increased…

4 days ago

The Surprising Reason Successful Founders Feel Overwhelmed

Most entrepreneurs expect uncertainty to fade as their businesses succeed. More revenue, more experience, more…

5 days ago

Your Books Are Lying To You

What CEOs don’t know about their own financials—and what it’s costing them.

7 days ago

Three Lies Leaders Tell Themselves That Never Stay Cheap

How short-term leadership relief turns into high-interest debt.

1 week ago