How to Improve Your Projects with 25 Simple Questions

As I wrote in a post a few years ago, project management is not for the faint of heart! Projects can be very complex and stressful.

Besides managing scope, schedule, and budget, project managers need to manage relationships with staff, customers, contractors, vendors, community leaders, and many others. Much of this project management is now done virtually as the project team, contractors and customers can be spread in multiple locations over multiple time zones, cultures and languages.

This is a daunting task!

Even more daunting is the task of a person responsible for the oversight of multiple projects. How can one person possibly stay on top of all the details from multiple large projects?

The answer is that they cannot and they should not even try!

So, what can a leader who is responsible for oversight of multiple large projects do to ensure the projects are on track and delivered successfully?

Ask Questions

In that previously referenced post, I shared a list of 23 questions that I would ask project managers each month to understand the state of their projects. I find these questions draw out quite a few insights that you simply don’t get by having the managers present a standard set of slides.

I still like having the standard slide set that can be used as a reference point but it must not be a canned presentation. The project review must be a two way conversation in order to draw out the level of detail that is needed by the organization’s leaders.

I have since transitioned into a multi-business consulting role and that caused me to update my list of 23 questions. I have added two open ended questions that cause the project managers to look at their projects in a different light and help them open up about how their projects are really going.

25 Questions for Project Managers

  1. NEW – If you were the customer instead of the project manager, would you be happy with the results you have seen so far?
  2. NEW – “What is not going well on your project?” or “Why is your project not going well?” (even if everything is basically on track, it is a good practice to start with a question like this to see what the answer draws out.)
  3. Do you have the correct resources with the proper skill sets allocated to your project in the correct time frames? Is this captured in your project schedule?
  4. Do invoices to the client match with the Purchase Orders (POs) received from that client and is this in alignment with the contract?
  5. Do invoices from vendors line up with the PO submitted to that vendor?
  6. Do your change notices have liquidated damages associated with them? Will the change note result in enabling a liquidated damage clause in the contract?
  7. Does your project have a business plan or a Project Execution Plan?
  8. Does your project have ALL deals with the client in writing (i.e., travel time, per diems, uplifts, markups, etc.)
  9. If your Estimate At Complete Gross Profit and Incurred To Date Gross Profit are different, do you have an explanation?
  10. Is there a difference between invoiced to date and collections to date and if so, why?
  11. Is there a difference between current PO amount and total potential PO amount, if so why?
  12. Is there a difference between current cost budget and total potential cost budget, if so why?
  13. Do the margins on labor properly reflect; labor burdens for employees, uplifts, overtimes, contractors and agency personnel.
  14. Is the project risk register up to date? Are the risk mitigation costs and expected cost outcomes included in your cost budget?
  15. Where are the project contingencies located….do these match your risk register?
  16. Where are the funds for project warranties located? Are the warranty terms clearly defined in the contract?
  17. Is there work being completed or items procured for which your project does not yet have an approved budget, and if so why? Are Change Notices being used, if not why?  Is there an funds approval authorization in place authorizing the expenditure of associated funds without a Change Notice in place?
  18. What is in place for your quality management system? How many quality audits have been done to date and what issues have been identified?
  19. What methods are being used to track changes in scope, schedule, budget, specifications and deliverables?
  20. If there is a difference between baseline budgets and Estimate At Complete budgets, what is this this caused from?
  21. Do you prepare a detailed cost report for your client each month on a per task code basis? If not, why not?
  22. What feedback have you received from the client? What is your latest Customer Satisfaction Survey score?
  23. Do you have a team meeting (or team lead meeting) each week? Is a safety topic discussed during this meeting?
  24. Does your percent complete estimate for each task code line up with what your team leads’ assessment would be for the same tasks?
  25. How does your project compare to the original estimated revenue, cost and GP predictions.

Take Action

The challenge to those of you responsible for multiple projects is to start asking deep, probing questions of your project teams. Look for areas of concern or weakness. Don’t stop the questioning until you have an answer that can be validated or until there is a set of actions in place to get a validated answer. When you uncover areas of concern, don’t be aggressive but rather be supportive and work with the project team to uncover and then resolve the issue.

Spend some time this week and create your own set of questions that will help you manage your project portfolio. Start by downloading the 25 Questions Word document from the Business Tools page.

Finally, take a look at these related posts for more details:


My greatest strength as a consultant is to be ignorant and ask a few questions.Peter Drucker


What questions do you use to draw out the best from your project managers? Leave your comments below!


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