Over the twenty years I’ve spent implementing organizational initiatives, I’ve uncovered a secret weapon for project success. Someone who asks great questions. Great questions are thought-provoking. They initiate dialog. They catalyze learning. They are essential to the development of shared understanding and trust. In short, great questions are the gateway to great answers and great project performance.
While it’s helpful to project teams when anyone asks good questions, it’s particularly impactful when they come from leadership. Someone with power, who is invested in the effort, but removed from the day-to-day activities of the initiative. While project managers and teams often look to leadership as a source of answers, executives have an important role to play in spurring innovative thinking and creative problem-solving by asking thoughtful questions. Unfortunately, my experience has been that many organizational leaders in the role of project, program or initiative sponsor do not know what questions to ask and/or do not invest in the necessary dialog to reach good answers. (This is especially true as projects or initiatives get larger and more complex.) As a result, disconnects can begin to develop exactly where the glue of shared understanding and trust is most needed.
So, what are good questions to ask? There are many, but in this post I’ll focus on those related to four topics:
What does success look like?
When will we be done?
What will go wrong?
What do you need from me?
These are not the only topics worth asking about, of course. Rather, they represent areas that I find are too commonly overlooked or given cursory attention when they deserve much more. Below, I offer a variety of example questions for each topic, which with a little rewording to fit your specific situation, may help you to spur good conversations. (Please share your ideas about other important topics and questions in the comments section— I’d love to hear them!)
A few additional thoughts, before I get to the details of the questions.
If you are a project sponsor or other executive…when you ask about these topics, you are signaling to your project managers and teams that these are important and expected areas for conversation. So, it’s best to ask early and often. When you do, you should expect that your team will already have great answers for or ideas about some of these questions. However, you should also expect that they won’t for others. (Neither will you.) That’s not failure. That’s the purpose and opportunity of asking questions. That’s where good conversations begin.
If you are a project manager who is reading this and thinking, “My sponsor will never ask me these questions”…it may be an opportunity for you to manage up. You can ask these questions of yourself and/or your team and share the outputs with your sponsor as a means of initiating a conversation.
Regardless of who is asking the questions, it will take a combined effort from all parties to answer them effectively. Developing a habit of dialog that produces actionable understanding is worth the effort (and it does take effort.) Done right, it can become your team’s secret weapon for project success.
Now, on to the questions…
What does success look like?
Answers to this question should create shared understanding of how success is defined, how it will be measured, and how it will be monitored throughout the life of the project. Time spent probing at this question to ensure you’ve gotten to the essence of success and how you’ll gauge progress is never wasted. More tactically, it’s important to develop shared expectations about best available data to use for measures and the appropriate level of effort to invest in capturing and monitoring data and discussing progress. This agreement can ensure success measures are a value-add tool throughout the implementation effort, not a burden or paper-pushing exercise.
Some questions that can help to spur conversations on this topic include:
Paint me a picture of what things will look like when we are finished with this effort. What can people do? How can they do it? How do they feel about it? What difference has it made?
Based on what you’ve heard from me (project sponsor) to date, what do you think is my definition of success? What questions do you have about why I have defined it this way?
How do you (project manager) define success? Why? How does your team define success?
How will we know we’ve been successful or that we’ve fallen short? What specific measures do you suggest we use to monitor our progress?
How much effort do you estimate data collection and monitoring will take? Do you think it’s worth it?
Do you think our efforts, as currently planned, lead us on a path to our desired outcomes? Why? Are there any gaps, or areas of concern for you?
How and how often will we discuss progress? Who will be involved? How we will communicate progress to others?
What have we learned so far? What should we do now to act on that learning?
When will we be ‘done’?
My work in the last decade has focused on large-scale, multi-year implementation efforts within organizations. This has taught me that shared expectations about when “full implementation” will be achieved, and the time it will take to get there, is hard-won and demands commitment to sustain. Discussions on this topic should result in clarity about how the effort will be phased and a practical understanding of what will be produced in each phase. (A common error is to adopt generic phases and assume everyone is on the same page about what will actually result from each.) Particularly for larger efforts, conversations on this topic should ensure that transition to normal operations is thoughtfully integrated into plans from the outset.
Questions about timing and phasing relate to success measures (see above) and at some point the two topics can come together (e.g., success measures by project phase.) However, at the outset, it can be helpful to segregate questions/discussions about each topic to better clarify positions on each.
Questions that may help to create good dialog on this topic include:
If you were a journalist reporting on the project, what would your headlines be to communicate what will be achieved in each project phase?
What should I expect to see from the project in 3 months? 9 months? 18 months?
Assume we are asked to rank in priority order speed vs. quality/scope vs. cost? What would the rank order be? (Note: An easy and unacceptable answer is that they are all equally important.)
How realistic are my expectations (as project sponsor) related to pacing and timeframe? (Too fast; too slow?) What are my expectations impacting the team?
When will this effort be fully integrated into normal operations (i.e., no longer a “special” project or initiative)? How have we prepared for that transition to ensure it is smooth and productive? What does sustainability look like?
What will go wrong?
Every effort has an Achilles' heel. If you don’t talk about it, you can’t mitigate it. A sponsor's willingness upfront to converse about potential blind spots and shortcomings can open the door for honest communication throughout the life of the project. Setting expectations for mitigation efforts and active learning when missteps happen can also strengthen team performance. Particularly for larger efforts, holding a formal, pre-mortem can also be a useful.
Questions to start conversations on this topic include:
What about this project makes you most uncomfortable? Why? What actions can we take right now to start to change that?
What cushion or contingency have we built into our plans? How will we decide when and how to use it?
What red flags will we use to warn us that we are on the wrong track?
If there is one thing that you (as project manager) think will make this project fail, what is it? If I asked the full team the same question, what do you think their answer would be?
What mechanisms have we set up to ensure we are learning as a team? How are they working?
What have we learned to date that calls into question our original assumptions?
What, specifically, do you (project manager/team) need from me (project sponsor/executive)?
Most project managers and teams adjust to accommodate the style and preferences of the project sponsor. While this is appropriate (to an extent), it does not necessarily lead to the most effective team operations. As a project sponsor, ensure you understand with some specificity what your project manager needs from you to be successful. With this understanding, you’ll be better positioned to execute the most important part of the project sponsor's role – to be an effective and committed advocate for the project and team.
Questions that can initiate good conversations on this topic include:
What am I doing that’s most helpful to you and the team? Least helpful?
Where do you need more clarity from me? From other members of organizational leadership?
Who do you need me to talk to, because you can’t get access to them?
What do you know right now the you are reluctant to tell me — or think I don’t want to hear?
If I could do one thing differently, what would you want it to be?