Questions and Time

September 21st, 2023 | Leadership
Questions and Time

Guest Post by John Dewenter


Have you ever thought about how you may have asked questions of your colleagues or family members as a situation or circumstance evolved over a long period? Or, how a boss may have asked you the same question over and over again?

Much has been written about questions with little said about the relationship of questions or the questioning process with time. Most write about questions in the moment however, questions are rarely standalone events. Questions are typically part of a conversation revealing problems, issues, needs and desires. And, as such, these conversations could take time to reveal these issues or help resolve them.

So, how might the questioning process be impacted by time? How might time be used to allow the questioning process to create resolution or opportunity? The following attempts to explore the relationship of questions to time in two ways. The first reviews how the same question, used or repeated over a period of time, might reveal evolution or growth in either the situation or the respondent. The second looks at how ongoing or evolving situations often create the need to adjust questions to suit.

Same question over time:

As we all know, circumstances, issues and life change over time. With longstanding relationships, we bear witness to how they/we evolve over time. The same can be said about long-lived projects or assignments. Same for the life of a company or a career. How might a question, the same question, be relevant or meaningful in different or new ways as situations and people change over time?

Consider the following:

As a mentor, asking someone the same question at different stages of their career or even at different stages of a project or assignment can generate different responses.

Here is a specific personal example. When our daughters were very young we would ask them: “What do you want to be when you grow up?” Sure many of you parents asked the same question. As children, their answers were often very fanciful. “A princess.” “An actress.” Without much in the way of life-experience or the chance to see where their own interests were going the filters we often apply to questions like this were nonexistent. As they grew up, the question may have evolved a bit but it was essentially the same. “What are you interested in majoring in?”  “What career path do you want to take?” As their life-experience and circumstances advanced the same or similar questions brought new responses.

*Looking back, can you see how you may have asked someone the same question as a situation evolved? Have you listened to how the responses may have changed as the situation changed?

Ongoing situation with questions changing over time:

Situation 1: Often situations take time to fully develop and become clear. In these types of situations, questions can help guide people through an evolving set of circumstances. They can help reveal a direction, after reflection brings clarity.

Situation 2: Question – then answer – then follow-up…repeat:

Questions rarely, if ever, come as a standalone event. One question, then a response, done. More typically, questions can or should come in the context of a conversation that might occur over a period of time.

A question requiring some thought, reflection or research.

A response hours, maybe days later.

Then follow-up questions that dive deeper.

The above is especially true with open-ended, divergent questions that either cannot or should not be answered right away.

Or, we might find a response reveals a misunderstanding of the question and note the need to clarify to get to the “right” issue.

Situation 3: Struggling with a problem – is it the “right” problem?:

What if we have a problem statement the team is struggling with where everyone knows the responses are not going to win-the-day. We don’t really know why we feel it but deep in our gut we know something is off. Then, out of frustration we slam our fist to the table knowing the team is spinning their wheels. We ask the team “what are we REALLY trying to solve?”

We could go back and break the original question apart and see if there are any words or phrases that could be causing the team to go the “wrong” way. Words often carry with them preconceptions and meanings that may not be appropriate to a situation. In these types of situations, it is best to look critically at the words or phrases that make up the question. Frame, reframe and then reframe again until the question better addresses the real issues at hand.

Consider the following example:

Some time ago, I represented an investor who was an owner of a prominent high-rise office building with a retail podium. The asset was 30+ years old and was in need of a major refurbishment and repositioning. As a representative of the investor, I often sat in on project meetings to monitor progress and direction.

During a set of early meetings, the team was struggling to rework the failed retail podium. Often, many of the “solutions” offered were simply different forms of what failed in the past. Replacing shops like a tailor with watch or luggage shops. Trying to take retail and make new retail. After numerous meetings with circular discussions rehashing the same issues over and over I asked a couple of questions:

  • “What is the primary driver of this asset?” Answer: the office tower, by far, brings in the primary cashflow and returns.
  • “If that is the case, then what can we do with the retail podium to reinforce the tower component?”
  • The team immediately and understandably looked for “retail” solutions to the above. Again, these responses failed to create a satisfactory solution.
  • Eventually, this is how we broke the stalemate. “The team is clearly struggling with making ‘retail’ work. ‘Retail’ is forcing preconceived ideas that are limiting. So, how might we look at this differently? How can we reframe this to better address the problem we are trying to solve – namely, keeping the office occupancy high with maximum rents?”
  • Finally, after a long silence, I offered up a reframe by replacing “retail” with “amenity”? What amenity can we offer at the podium that will drive maximum performance from the tower?
  • This reframing of the problem statement drove, at the time, an innovative solution that no other office towers could offer.
  • Sometimes the questions we ask are limiting. And, sometimes they might frame a problem that sets a course to a solution that does not solve the “real” problem. Whenever you are in a situation that might be ongoing continue to explore the questions being asked. Do the questions unnecessarily confine and restrict possible responses? Do the questions and how they are framed need to be broken down, examined and reconstructed to create better questions?

*Have you ever been in a situation where the issues have changed over time requiring you to adjust the questions you ask your colleagues or friends? Have issues become so overbearing and stagnant that your questions helped people see things differently? Questions that have inspired people to shed a funk and become energized to approach a tough situation in a new way?

Sometimes we need to consider how the questions we ask sit in the context of time. Sometimes we need to be aware of the evolution of circumstances to ensure we are asking the “right” questions at the appropriate time. We need to be aware not only of the moment we are in but where the momentum of the past and present are taking us.

John Dewenter


John Dewenter is currently Principal at Dewenter Strategic Advisors advising investors, developers, owners and consultants on real asset issues in today’s turbulent commercial real estate environment. John was previously Head of Development for the Asia Pacific region for the Abu Dhabi Investment Authority (ADIA) from 2011 to 2020 overseeing up to US$5bn in active real estate development works annually along with advising the investment team on asset and operational issues to mitigate risk and reveal opportunity. Positions previously held included senior roles at real estate developers in Asia and the US. Please visit his LinkedIn page (John Dewenter | LinkedIn) and Dewenter Strategic Advisors (01 – Home | Dewenter Advisors) to learn more.


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