Starting Out At A Company — Questions To Ask Executives

Todd
2 min readDec 26, 2023

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When meeting with the CEO and other leaders to understand the long-term vision of a company, it’s essential to ask insightful and strategic questions. Here are some questions you can ask:

  1. “Where do you see the company in 1 year; in 3 years; in 5 years?” This question aims to understand the short, medium, and long-term goals and the trajectory the company envisions.
  2. “What is your plan for getting there?” Asking this follows up on the first question takes you into the strategies and steps the company intends to take to achieve its vision.
  3. “How do you anticipate market trends and customer needs changing over these periods, and how is the company preparing to adapt?” This question will give you insight into the company’s adaptability and foresight in planning for future challenges and opportunities.
  4. “What are the biggest challenges you foresee, and how is the company planning to address them?” Understanding potential obstacles and the company’s strategies to deal with them can reveal a lot about its resilience and strategic planning.
  5. “How do you define success for the company, and how do you measure it?” This question helps clarify the key performance indicators and goals that are prioritized at the highest level.
  6. “What role do you see [your department/position] playing in achieving these long-term objectives?” Tailoring a question about your specific role or department shows your interest in how you can contribute to the larger vision.
  7. “How does the company’s culture support or drive the achievement of these long-term goals?” Understanding the interplay between culture and strategy can provide deep insights into the company’s operational philosophy.
  8. “Can you describe any upcoming projects or initiatives that are critical to achieving these long-term objectives?” This gives a more tangible sense of what’s currently in the works and how it ties into the bigger picture.
  9. “How does the company plan to evolve its products/services to meet future demands?” This question focuses on innovation and adaptation in the company’s core offerings.
  10. “What can employees do to best align their efforts with the company’s long-term objectives?” This shows your proactive stance in wanting to contribute effectively to the company’s success.

Asking these questions not only provides you with a clearer understanding of the company’s future direction but also demonstrates your strategic thinking and genuine interest in aligning with the company’s vision.

Photo by Joshua Earle on Unsplash

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