Successful Transitions Rule #3: Ask Smart Questions

After you’ve put together your personal board of directors and received valuable feedback on you, it’s time to look outside to gather information on where you think you may want to go.  Be a detective, be curious, be open and be strategic.

When I lecture graduate students about their next career steps, I advise them to get as much insight as possible from people who have real experience in the companies, sectors or countries where they think they may be headed.  The good news is, the older one gets, the broader the network and thus potential sources of information. 


After you’ve made a list of key contacts, come up with a script for the call or meeting.  You will be leading the conversation so you need to be prepared to make it worth everyone’s precious time.

Smart questions are ones that get at the deeper (non-Google-able) issues that can make or break success and happiness. They include, but certainly are not limited to: 

  • Why did you choose this company/industry/position?   Has it met your expectations? 

  • What are the ingredients of success here?  How is effort rewarded?  How long do people tend to stay?

  • What are some industry trends you see and how might they affect this organization?

  • How well aligned is the culture with the stated strategy and vision?  What are the key elements of the corporate culture in your experience?

  • Is authority aligned with responsibility?  (this is huge for senior positions)

  • How would you describe the leadership and management style of the c-suite (or board if it’s the top position)? How does this filter down throughout the enterprise?

  • What kind of boundaries exist and/or how are they honored?

  • [For entrepreneurial searches] Where do you see gaps in this industry/sector? Who is doing a great job of providing products or services?


Questioning is a uniquely powerful tool for unlocking value in organizations: It spurs learning and the exchange of ideas, it fuels innovation and performance improvement, it builds rapport and trust among team members. And it can mitigate business risk by uncovering unforeseen pitfalls and hazards.

Harvard Business Review, The Surprising Power of Questions

The last two questions of any information interview are always: 

  • Is there anyone you recommend I connect with to further my inquiry?

  • May I stay in touch with you in case I have additional questions or have news to share?

Not only are these “smart” they are essential to keep the process moving forward and growing strategically.   


If you do this well, it will not only be informative, it will be fun and will lay additional groundwork for future networking once you’ve inked the last sentence on this new chapter.