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On Boarding – Questions to Ask During Learning Plan

The following information is taken from:  You’re in Charge – NOW WHAT by Thomas Neff and James Citrin and The First 90 Days by Michael Watkins. 

Based on your role and objectives, select from the group directly below the top 5 questions you will ask of the Team during your learning plan.  Ask everyone these same top 5 questions.   Your boss may want a recap of your findings.  This can be a good discussion topic for one of your early meetings.

What about the Company Culture do you want to preserve and why?

What are the top three things we need to change and why?

What do you hope I do?

What are you concerned I might do?

What advice do you have for me?

What is your most important tool for figuring out what the customer wants?

What are the biggest challenges the organization is facing (or will face) in the near future?

Why is the organization facing (or gong to face) these challenges?

What are the most promising unexploited opportunities for growth?

What would need to happen for the organization to exploit the potential of these opportunities?

If you were me, what would you focus attention on?

The following include the Questions the Team will have about you.  They may not verbalize them, but they are thinking them.  Answer the questions for them in one on one or group meetings.

Who are you?

Where do you come from?

Why am you here?

What do you plan to accomplish?

How do you hope to do it?

The following group of questions may be used to build your learning plan.  As you are interviewing internal and external stakeholders, shorten your learning curve by focusing on these key questions. 

Crucial Conversations / Interviews:

Questions About the Past


  • How has this organization performed in the past?  How do people in the organization think it has performed?
  • How were goals set?  Were they insufficiently or overly ambitious?
  • Were internal or external benchmarks used?
  • What measures were employed?  What behaviors did they encourage and discourage?
  • What happened if goals were not met?

Root Causes

  • If performance has been good, why has that been the case?
  • What have been the relative contributions of the organization’s strategy, its structure, its technical capabilities, its culture, and its politics?
  • If performance has been poor, why has that been the case?  Do the primary issues reside in the organization’s strategy?  Its structure?  Its technical capabilities?  Its cultures?  Its politics?

History of Change

  • What efforts have been made to change the organization?  What happened?
  • Who has been instrumental in shaping this organization?

Questions About the Present

Vision and Strategy

  • What is the stated vision and strategy of the organization?
  • Is it really pursuing that strategy?  If not, why not?  If so, is the strategy going to take the organization where it needs to go?

The Markets

  • What are the markets you serve?
  • What are the issues facing the company in those and in new markets?
  • What do you have to do to be successful?
  • How are we really different from our competitors?
  • Who are the most innovative competitors?
  • Why are our competitors so successful in their core areas of strength?
  • Are we setting the right goals?
  • Are those goals consistent with the external environment?

The Product

  • How are we going to deliver a service to customers that people value and want to buy?
  • What is our product’s unique selling proposition?
  • What is the pricing strategy?

The Finances

  • How do we fund our efforts?
  • Where does the business create profits?

The People

  • Do we have the right people to address the issues and implement the strategy?
  • Who are the “gatekeepers”?
  • Who are the people who really make things happen?
  • What do the people who are most successful share in common?
  • What are the common traits among those who have failed?
  • Who are the “five” most respected people in the organization and why?

The Processes

  • How do people tend to work together?
  • How do decisions get made and implemented?
  • What are the key processes of the organization?
  • Are the processes performing acceptably in terms of quality, reliability, and timeliness?  If not, why not?

Land Mines

  • What lurking surprises could detonate and push me off track?
  • What potentially damaging cultural or political missteps must I avoid making?

Questions About The Future

Challenges and Opportunities

  • In what areas is the business most likely to face stiff challenges in the coming year?  What can be done now to prepare for them?
  • What are the most promising unexploited opportunities?  What would need to happen to realize their potential?

Barriers and Resources

  • What are the most formidable barriers to making needed changes?  Are they technical?  Cultural? Political?
  • Are there islands of excellence or other high-quality resources that you can leverage?
  • What new capabilities need to be developed or acquired?


  • Which elements of the culture should be preserved?
  • Which elements need to change?


At the conclusion of each work week, ask yourself the following questions.  The information you uncover may be good discussion topics for early meetings with your manager or mentor.  Following this plan weekly will help ensure you get off to a good start.

Guidelines for Structured Reflection

What do you feel so far?

On a scale of high to low, do you feel:

Excited? If not, why not? What can you do about it?

Confident? If not, why not? What can you do about it?

In control of your success? If not, why not? What can you do about it?

What has bothered you so far?

With whom have you failed to connect?   Why?

Of the meetings you have attended, which has been the most troubling? Why?

Of all that you have seen or heard, what has disturbed you most? Why?

What has gone well or poorly?

Which interactions would you handle differently if you could?  Which exceeded your expectations? Why?

Which of your decisions have turned out particularly well?  Not so well?  Why?

What missed opportunities do you regret most?  Was a better result blocked primarily by you or by something beyond your control? 


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