5 Ways to Master the Art of Asking Questions

Turning your problems into solutions with help from the Project Management Institute.

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It’s not that they can’t see the solution. They can’t see the problem.

— G.K. Chesterton

When I started out in my publishing career some 40+ years ago as a textbook sales representative, I was lucky to learn the value of asking questions early on. Questions such as: “Are you looking to change textbooks?” “What topics in a new textbook are you looking for?” “When would you be making a change in textbooks?” These were questions which saved lots of time making sure that I was on the right track and in the right place at the right time.

One very successful sales rep mentored me and recommended that in addition to the above such questions, I should also ask every professor “So, are you interested in writing a book?” Answers to this question were likely to get noticed by the home office and maybe offer up a promotion to the coveted position of editor.

As a sales rep, editor, and publisher — asking good questions has been an essential responsibility. It helps people see the problems so that they can find the solutions.

The Project Management Institute has developed five different phases of Agile Project Management that generally occur within a project. Below is a description of these phases as well as some questions that I try to ask during each phase of a project — along with some reasoning for asking such questions in the first place. Here are a dozen or so questions to ask both yourself and your team during each of the phases:

Phase 1 — Envision: After approval of a business case or when a project officially begins, the project leader and team members are involved in the initial phase where they collaborate to create a compelling vision for the project.

  • What are the goals?
  • What are the short-term and long-term opportunities?
  • What are the biggest risks?
  • What is the best way to add value to this project?

When people want to accomplish something new, they tend to have a very general sense of exactly what that is such as: Grow revenue from x to y. Publish 25% more books in 3 years. Develop new series and ebooks.

The keys in asking questions during phase 1 are to clarify the general into the specific and come away with a few solid expectations for what you really what to accomplish.

Phase 2 — Speculate: A product vision is translated into an understanding of how to meet the requirements as well as the overall approach to meet the requirements along with priorities:

  • What are the deliverables for the project?
  • What elements need to be delivered for the project to be considered “done”?
  • Who is the key person for communication?
  • What are the top priorities?

The keys in asking questions during phase 2 are to agree on a few priorities and action items as well as understand the best ways to communicate throughout the project.

Phase 3 — Explore: In this phase the team begins to build the deliverables of the project and make sure that they are on track to develop what is really necessary.

  • Is the project progressing in an honest, fair, responsible, and respectful manner?
  • Are team members mindful about not crossing organizational boundaries?
  • Is this what you were looking for?

The keys in asking questions during phase 3 are to make sure that things are progressing well in a logical fashion, there is process to follow to get things done, and it is going well.

Phase 4 — Adapt: In the adapt phase, the team reviews the results of the project and the performance of the project against the plan and then makes changes as appropriate.

  • What is the process for review and to implement changes?
  • Is the project meeting the objectives as outlined in the original vision?
  • What changes do you recommend?

The keys in asking questions during phase 4 are to understand feedback, acknowledge it, and adapt to the feedback as appropriate.

Phase 5 — Close: This phase concludes the project in an ordered manner capturing the project’s key lessons.

  • What would you do differently as a project manager?
  • Is the project complete and are you as a project manager able to turn it over to the team?
  • Did/will the project make a difference to the organization?

The keys in asking questions during phase 5 are to finish things up, “let it go,” and most important — reflect on things and be thankful for the opportunity to learn something new.

I tend to write down my questions at the beginning of each project and divide the questions into the appropriate phases. For a start, you can create a template of questions in phases such as Beginning, Middle, and End and then refine these phases as the project progresses. I leave space in the template to carefully record the answers to each question and the notes that come as a result.

Next, I have learned to prepare the template in a professional manner and send if off to a client with questions such as: “Am I missing anything here?” “Is this what you and your team were thinking too?” “Is there anything else that you would like to add?” This also helps to have things in writing so that you do not have to reinvent the wheel down the road.

Best wishes for success with using questions and turning your problems into solutions!