Risk comes from unknown and uncertainty. Therefore, the questions should around those two topics: 

• What do we don't know and what are the major sources of uncertainty in future?
• What are the external risks (e.g. economics impacts, competition, reorganization)? and the internal risks (e.g. team dynamics, lack of knowledge or experiences, logistics, office politics)?

We find the "Delivery 6" concept brought by Brendon Baker worth looking at when exploring new strategies or evaluating change proposals in organizations.

• ​What exactly are we doing?
• How will we do it?
• How much will it cost?
• Who will we need?
• What could go wrong?
• When will we do it?

In other words, before starting any project or change management plan, these questions remind us to let go of our own agenda, listen, and be open-minded. ​

After identifying people with common interests or attributes, people form a group or circle for comfortable interactions. Within the group, we trust, help, and share information. Outsiders are typically excluded, which causes the problem of missing opportunities, such as creative thinking.

To avoid group biases, we should start getting to know people by asking the following questions:

• Do I belong to the group the person is in?
• What are their interests and background?
• How can I become part of their inner circle?

Before tackling difficult problems, it's crucial to establish a connection with the person we're dealing with and become a part of their "we". We can accomplish this by learning about their background, including where they grew up, what language they speak, their hobbies and interests, what motivates them, their career objectives, the subjects they enjoy working on, and their past accomplishments. By obtaining this information and establishing a connection or belonging, we can be more effective in addressing their challenges. We need to be ally first. 

The boiling frog is a fable describing a frog being slowly boiled alive. The premise is that if a frog is put suddenly into boiling water, it will jump out, but if the frog is put in tepid water, which is then brought to a boil slowly, it will not perceive the danger and will be cooked to death". The one thing we learned from this is how to interact with individuals during change management: make small tasks one at a time to progress in the desired direction. 

Case Study - Meeting Reduction
Let's look at a case study. When we observe project managers join too many dev team meetings, we decide to make the change to pull the PMs out of the unnecessary dev meetings to focus on projects.

The change management strategy incorporates the following: (1) reducing attendance from one meeting at a time, letting people get used to not having PMs on the call first, and then pulling the PMs out completely. (2) breaking down the stakeholder alliance by asking questions like, "Why is the meeting is required? Are the objectives of the meeting?". Then, figure out which stakeholder to start with and start from there. ​

The process turns out to be effective, but it requires patience and carefully plotted changing paths. Do you have any examples or more thoughts on this? ​

Confirmation bias is a common tendency involving disregarding or discounting evidence that contradicts our beliefs or viewpoints. To avoid others imposing their biases on us, it's crucial to understand their beliefs and views:

• Do we have the same background, such as gender, race, education, or age? 
• Do we have prior errors known to others that they expect us to repeat the same mistakes? 
• Do we value the same beliefs as them as ideas, race, and political affiliation? 
• Do I agree with others? 
• ​Is the topic within comfortable zone of the audience? 

If the answer is no, we must proceed cautiously and ensure we set up the conversation creatively.

​Do you feel like you’re not getting the guidance, clarity, or feedback you need from your manager in your one-on-one meetings? If so, redirect the focus by asking the right questions. The following is quick reading note: 

Ask for guidance on tasks and projects:

• I’m having some challenges with X. Can you help me think about how to navigate it successfully?
• What do you think of my idea Z? Do you have any suggestions for how to improve it, or an alternative idea I should consider?

Clarify priorities and expectations:

• Given what’s on my plate, what should I be prioritizing right now, and can you help me understand why?
• As you review my workload, am I taking on the right projects?

Align with the organization and its strategy:

• To help me better understand the big picture, how does the work I’m doing fit into the company’s broader goals?
• What’s new in our company’s strategic priorities that you feel I should know about?

Seek growth opportunities and career advancement:

• What can I do to prepare myself for greater opportunities or to pursue X interest of mine?
• What should I be targeting as my next career move and why?

Get feedback on your performance:

• Am I meeting your expectations? I really value your perspective on my performance.
• What should I start, stop, or continue doing?

Read the full article: "28 Questions to Ask Your Boss in Your One-on-Ones," by Steven G. Rogelberg et al.

We can ask the following question when exploring to understand organization culture: 

• What values and beliefs are important within the organization?
• What is the leadership style within the organization?
• What does people do without giving instructions —the established “rules” under which the organization generally operates? 
• How are decisions made within the organization?
• How  do people behave toward customer, stakeholders and each other? 
• How is resource allocation within the organization?
• What is the approach to handling and learning from failures and mistakes?
• How does the organization recognize and reward contributions?
• What areas does the organization devote to both time and resources?  

Consider the answers to the following questions when communicating the organization's vision and eventually helps bring the vision to life.: 

• What are we doing today?
• Why are we doing the work we’re doing? Why now?
• What does my team care most about? How is the vision relevant, and how would anyone challenge the vision?
• What does success look like for our team?
• What could we do to achieve more, better, faster?
• What are specific, measurable goals and deadlines? How can we help, including solving problems so my team can achieve more?
• How will the team benefit in the end? ​

The goal is to facilitate meaningful discussions to ensure stakeholders' clarity, understanding, and alignment.

We can understand the organization's strategy by asking the following questions: 

• What are the organization's major strategic objectives right now?
• What is our organization already great at? What to improve? 
• What is our organization's weakness? We plan to do and not do? 
• What are the major needs, challenges, and opportunities we face over the next six months? Year? In the long term?
• How does my team fit into this picture? 
• What are my group's role and top priorities in carrying out this strategy? 
• How can I communicate the strategy to my team?

When listening to leaders explain their vision and objectives, we can use these answers to gain deep insights.  Additionally, you would use your own observation to spotting the strategic changes. 

After leaders present the new organizational vision, they are likely to pause and ask if there are any questions. In this situation, you don't want to keep silent. It's a great opportunity to interact and engage in the conversation. Let me give you a few questions you can ask in this situation:

• What are the changes from our previous vision? Why do we need to change? Do we have any specific challenges we'd like to address now? Any suggestions or plans on how to adapt to change? 
  These safety questions allow leaders to elaborate on the decisions and talk about changes. From the follow-up with the question, we can also find out why changes are needed and what each individual needs to adapt to align with the organization's goals.
• Are there any risks associated with our vision?
  Any decision has risks. Listening to leadership's risk assessment can determine the execution process. For example, the leader's vision is to build strong customer relationships, learning, innovation, and operational efficiency. Risks may exist in conflicting priorities between innovation and customer needs. If this is a projected risk, we can create a steering committee to prioritize requests.
• What does our team's success look like?
  ​This is another way of interpreting vision. This question allows leaders to connect their idea to the team's expectations.

Asking the right questions is crucial for success. Prepare to gain insights, build relationships, and advance your career by asking questions.​

Preparation

• Please be polite and show respect to void defensive emotion from those you disagree with.
• Be open-minded because you could be wrong.
• Don't say, "It's a good idea, but...? " The"but" trigger defensive, use "and" instead to extend the discussion to the area that you are doubt about.

Questions

• Can you elaborate more on ....? We ask for more information. The more we understand, the more we can make objections.
• Do you have an example? Can you show an example? Asking for examples that can allow us to get more details.
• How do you address ... issue? Or Have you considered ...(scenario)? Asking for a solution that we also question if the idea works and hear what the speaker says.
• How do you compare your viewpoint with ....? Bring in contradictory opinions and ask the speaker to differentiate. We can then figure out the pro and cons.

Stakeholder analysis is the foundation of political handling for a project. In this analysis, we need to identify the players, their commitments, power plays, interests, and relationships. We start the analysis with stakeholder influence and impact on the project execution. 
 The following questions can narrow down our list of stakeholders.

• Who has a fundamental impact on the organization’s performance? Can they be replaced? We would look for more than 2 but less than 6 key stakeholders for effectiveness. 
• What do we want from the stakeholder, and if we want the relationship to grow? ​

The analysis result allows us to decide on the engagement plan. On the other hand, we still need to communicate with each stakeholder to learn more about their expectations and adjust the plan. 

Seeking advice is an excellent way to connect with senior leaders and build relationships, but it's crucial to avoid taking action without proper preparation. Keep in mind that your actions can either strengthen or damage the relationship.Here are some suggestions to make the most out of the opportunity: 

1. Do your research and ensure that you have a complete understanding of the topic at hand. 
2. Work on it and experiment with different approaches. 
3. Find at least one to three potential solutions to the problem.
   
4. Plan the conversation by starting with your understanding of the topic , why the topic matters, and presenting solutions that the leader can choose from, rather than asking what you should do about it.

It's important to showcase your independent problem-solving skills and knowledge and provide insights that leaders may not have considered. If they perceive you as a valuable resource who can contribute to the discussion, it's a sign of success. Remember, it's a conversation of give and take, rather than simply seeking advice.