23 Questions To Improve Project Delivery

Project management is not for the faint of heart. Projects can be very complex and stressful especially as the project size grows.  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 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 can be 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. So, what can a person responsible for oversight of multiple large projects do to ensure the projects are on track and delivered successfully?

A number of years ago, I was responsible for a large portfolio of projects. In an effort to stay on top of these projects, I started out doing reviews once a month with each of the larger projects. We were using a standard set of project reports that each project manager was responsible to prepare in advance and then present during the review. The result? This review process was helpful but there were still projects that ended up in trouble even though they looked good during the review.

So, I tried changing the review format, splitting the review into operations and financial reviews and many other little tweaks. However, we were still seeing some projects “slip through the cracks”. I finally realized that the solution was quite simple. Rather than have the project managers methodically run through a preset presentation each month, I needed to shake things up a bit by asking questions that probed deep below the surface of the information on the slides.

In taking this approach, the project managers needed to understand their projects in detail or face a very daunting meeting. I always asked the questions in a challenging manner but it was done in a way that assistance was provided when an area of weakness on the project was uncovered. I believe this got the project managers more engaged and created a work environment where they were willing to ask for help before it was too late. This resulted in fewer projects going “off the rails.”

I have shown a small subset of the questions that I would ask during a typical project review meeting. Note that I would not methodically work from the top to the bottom of this list. Rather, I would ask one pertinent question which would then lead to multiple spin off questions as the deep dive process unfolded.

My list of 23 questions:

  1. 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?
  2. Do invoices to the client match with the Purchase Orders (POs) received from that client and is this in alignment with the contract?
  3. Do invoices from vendors line up with the PO submitted to that vendor?
  4. Do your change notices have liquidated damages associated with them? Will the change note result in enabling a liquidated damage clause in the contract?
  5. Does your project have a business plan or a Project Execution Plan?
  6. Does your project have ALL deals with the client in writing (i.e., travel time, per diems, uplifts, markups, etc.)
  7. If your Estimate At Complete Gross Profit and Incurred To Date Gross Profit are different, do you have an explanation?
  8. Is there a difference between invoiced to date and collections to date and if so, why?
  9. Is there a difference between current PO amount and total potential PO amount, if so why?
  10. Is there a difference between current cost budget and total potential cost budget, if so why?
  11. Do the margins on labor properly reflect; labor burdens for employees, uplifts, overtimes, contractors and agency personnel.
  12. Is the project risk register up to date? Are the risk mitigation costs and expected cost outcomes included in your cost budget?
  13. Where are the project contingencies located….do these match your risk register?
  14. Where are the funds for project warranties located? Are the warranty terms clearly defined in the contract?
  15. 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?
  16. What is in place for your quality management system? How many quality audits have been done to date and what issues have been identified?
  17. What methods are being used to track changes in scope, schedule, budget, specifications and deliverables?
  18. If there is a difference between baseline budgets and Estimate At Complete budgets, what is this this caused from?
  19. Do you prepare a detailed cost report for your client each month on a per task code basis? If not, why not?
  20. What feedback have you received from the client? What is your latest Customer Satisfaction Survey score?
  21. Do you have a team meeting (or team lead meeting) each week? Is a safety topic discussed during this meeting?
  22. Does your percent complete estimate for each task code line up with what your team leads’ assessment would be for the same tasks?
  23. How does your project compare to the original estimated revenue, cost and GP predictions.


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 23+ questions that will help you manage your project portfolio. Start by downloading the 23 Questions Word document from the Business Tools page.


“My greatest strength as a consultant is to be ignorant and ask a few questions.”

Peter Drucker

Please note: I reserve the right to delete comments that are offensive or off-topic.

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