Transcript of a conversation with ChatGPT — with the same questions I was asked during a podcast in 2022

One thing is for sure. I definitely speak much less than ChatGPT. It’s indeed a chatterbox. Who gave better answers? That’s for you to decide. Let me know.

Hrishikesh Karekar
16 min readJan 15, 2023

Last year in November, I did a podcast with Bill Raymond of the Agile in Action podcast on the critical role of leadership and change management with agile. You can hear the full podcast at link below or read the text transcript.

During the podcast, I was asked questions by Bill about my personal experiences and opinions on various topics, especially around leading large-scale agile transformations.

I literally used the exact sentences that Bill had used in our podcast and let ChatGPT respond in my place. The conversation did provide some interesting answers.

What did I learn?

While AI bots like ChatGPT can provide quick, consistent and detailed responses, they might lack the ability to empathize, understand context, and generate truly original and creative ideas humans possess.

Though ChatGPT can certainly be a valuable tool for agile coaches, it cannot replace the role of a human agile coach who brings a unique combination of technical and facilitation skills, rich experience, and empathy to help teams and organizations succeed with agile methodologies.

It will, though, replace those coaches that are purely information broadcasters and rely on textbook and framework-based answers. A bot is going to do that much better and faster than them. However, it still is a long way from replacing an agile coach who has skills far that leverage their unique human abilities.

Some detailed thoughts are available in the medium posts, links provided at end of the transcript.

Happy Reading!!

Start of transcript

Hrishikesh Karekar: What in your mind, is a good agile transformation? What does that do for an organization?

CHATGPT: A good agile transformation is one in which an organization successfully adopts and implements the principles and practices of agile methodology. This can lead to a number of benefits for the organization, such as increased flexibility and adaptability, improved communication and collaboration among team members, and the ability to deliver products and projects more quickly and efficiently. Additionally, an agile transformation can help an organization become more responsive to customer needs and more competitive in the marketplace.

Hrishikesh Karekar: Now of course, we were talking about the fact that if you just implement the framework, you’re not really getting value and you’re not doing agile transformation. There’s a lot more that comes along with that. From what you just said, that there is going to be quite a bit of change management involved. So what are some of the challenges with the change management process as you’re going through these agile transformations?

CHATGPT: Some common challenges with change management during an agile transformation include:

  1. Resistance to change: Some team members may be resistant to the idea of changing the way they work, and may be resistant to the new processes and practices being implemented.
  2. Lack of understanding: Team members may not fully understand the benefits of agile and how it will improve their work processes, which can make it difficult to get buy-in and engagement.
  3. Limited resources: Organizations may not have the resources (time, money, personnel) to fully implement an agile transformation, which can make it difficult to achieve the desired results.
  4. Lack of leadership support: Without strong leadership support, it can be difficult to drive the change process and ensure that the organization is fully committed to the agile transformation.
  5. Difficulty in measuring success: Agile is a continuous improvement process and it may be difficult to measure the success of the transformation, especially in the short-term
  6. Difficulty in change culture: Agile is not only about tools and frameworks but also about the culture and mindset change. Changing the culture of an organization is difficult and time-consuming.

To overcome these challenges, organizations should have a clear plan for the change management process, communicate the benefits of agile clearly, provide training and support for team members, and have strong leadership support for the transformation. Additionally, measuring progress and success can be done through key performance indicators, and by fostering the agile culture change through practices like Scrum, retrospectives, and team building activities.

Hrishikesh Karekar: Your focus is on providing executive leadership in agile transformation. So how do you successfully navigate this change from the perspective of a leader driving the transformation?

Hrishikesh Karekar: As a leader driving an agile transformation, there are several key steps that can be taken to successfully navigate the change:

  1. Clearly communicate the vision and goals of the transformation: It is important to clearly communicate to all team members what the goals of the transformation are and how they align with the overall vision and strategy of the organization.
  2. Involve all stakeholders in the planning process: Engage all stakeholders in the planning process, including team members, managers, and other key stakeholders. This will help to ensure that everyone is on board with the change and understands how it will impact them.
  3. Provide training and support: Provide training and support to team members to help them understand the new processes and practices being implemented, and to help them adapt to the changes.
  4. Lead by example: As a leader, it is important to lead by example and demonstrate the desired behavior and mindset. This will help to create a culture of trust and respect among team members.
  5. Measure progress and success: Establish key performance indicators (KPIs) to measure progress and success, and use them to track the progress of the transformation and identify areas that need improvement.
  6. Embrace a change culture: As mentioned before, Agile is not only about tools and frameworks but also about the culture and mindset change. Embrace change culture, foster transparency, collaboration, and continuous improvement.
  7. Foster a strong and empowered team: Agile methodologies are team-based, and the success of an agile transformation is heavily dependent on the strength and empowerment of the team. Encourage team building activities and make sure that the team is self-organizing and has the autonomy to make decisions.
  8. Be patient: Agile transformation takes time and cannot be rushed. Be patient and focus on continuous improvement over time.

By taking these steps, leaders can help to ensure that the agile transformation is successful, and that the organization is able to fully realize the benefits of agile methodology.

Hrishikesh Karekar: Now, when we talk about this agile transformation team, I think I’d like to go through each one of these a little bit with you, the transformation team, the roadmap and the KPIs. And I also want to talk a little bit about your statement about being bold there in just a moment as well. But back to the transformation team, are there many of these in an organization? Because very often, we will see a business unit or a department within an organization saying, we’re going to do agile. But if we get up to the senior leadership role in an organization, this is usually coming from the CEO, the CFO, the COO, and they’re looking to transform the entire organization. So do we see multiple transformation teams focusing on each of the different areas of the business, or is this sort of a executive-level team at the top, kind of managing the status?

CHATGPT: When it comes to an agile transformation, there can be multiple teams involved, depending on the size and structure of the organization.

For large organizations, it is common to have multiple transformation teams, each focused on a specific area of the business or a specific business unit. These teams may be responsible for leading the change within their specific area and working closely with their respective teams to implement the new processes and practices. This can help to ensure that the agile transformation is tailored to the specific needs of each business unit and that it is more easily adopted by the team members.

However, it is also common to have a centralized transformation team that is responsible for leading the change across the entire organization. This team would typically be composed of senior leaders from different areas of the business and would be responsible for developing the overall strategy and roadmap for the agile transformation. They would also be responsible for communicating the vision and goals of the transformation, providing training and support, and measuring progress and success.

In either case, it is important for the transformation teams to have strong leadership support and to be empowered to drive the change process. The team should be self-organizing, and have the autonomy to make decisions and drive the change across the organization.

Additionally, having clear communication channels, and a governance structure that allows the different teams to align and work together is essential for the success of the transformation. Clear roles and responsibilities and a strong project management discipline is also needed to ensure the success of the transformation.

Hrishikesh Karekar: Yeah, and I agree with you there. I’ve actually seen this happen a few different ways myself. I had one particular company in mind that I used to work with that had a team that was considered, they called themselves, I don’t think this is the exact title, but it was a “center of excellence” for agile. And they were kind of considered “the corporate team,” and what they shared was a lot of the best practices that you’d see in industry, they provided training and things like that. But what we saw was that there weren’t any coordinated agile transformation teams in the business units. They just said, well, we’ll just take what that other team is saying and try to do it. And what they end up doing is taking some of the things that are standard, like, we’ll do sprints that are two to four weeks, we’ll do iterative design and development, even if we’re in HR or Marketing. But they kind of take these ideas and roll with it. But what we get lost there is the trying to figure out what’s the new value you’re going to provide? What are some of the things that we need to streamline? How do we change in this ever changing world? And a lot of those conversations get lost in the background. And that’s where I see your point of having these individual transformation teams at a lower level in the organization, where they’re really focusing on what are the changes that we’re going to make? And the corporate level entity, changed actually in this company, and they provided the funding, if people needed coaches, they could help find some coaches that worked for them. And they also provided some just general base training along the way, but they stop going from, here’s the best practices to, how can we help your transformation team?

CHATGPT: Yes, that’s a common scenario. Having a centralized team that provides guidance, training, and best practices can be helpful for organizations that are new to agile. However, it’s important for that team to be aware of the unique needs and challenges of each business unit and to be flexible in their approach. They should be able to provide support and guidance, but also empower the individual teams to drive the change and adapt the agile methodology to their specific needs.

It is also important for the centralized team to recognize that the agile transformation is an ongoing process, and that the organization will continue to evolve and change over time. The centralized team should be able to adapt and adjust their approach as needed, and be able to provide support and guidance to the individual teams as they continue to implement the changes.

Additionally, having individual transformation teams at the lower level in the organization is crucial in order to ensure that the changes being implemented are tailored to the specific needs of each business unit and that they align with the overall vision and strategy of the organization. It allows them to focus on the changes that they need to make, and how they can provide value to the customers while streamlining their operations.

In summary, having a centralized team that provides guidance, training and best practices is important, but it should work closely with the individual teams to ensure that the agile transformation is tailored to the specific needs of each business unit and that it is aligned with the overall vision and strategy of the organization.

Interviewer: When we’re talking about agile transformation, we’re really thinking holistically about how we are going to change our organization, change the way we work, change the way we think, and also have this much more focused team approach, that it is sometimes hard to get your arms around all of that. And so the immediate, and we talked about this earlier with building a project plan, the immediate thought is, well, we need to have some sort of beginning and end to all of this. When you say roadmap, that’s kind of what the picture looks like in my head. Could you maybe share what that roadmap might look like and how it differs from a project plan? I’ll give you an example of, um, uh, of a agile transformation in the IT department of a large enterprise that I was helping. So this department almost had more than 2000 people, and they have been doing traditional practices for a long time. Of course, given the popularity of agile in pockets, some of the teams are doing what they thought was SCRUM and so on. But more or less, the organization’s central processes, policies, et cetera, revolved around waterfall or traditional approaches. Now, the CIO of that particular organization wanted to transform and said, okay, let’s start with the transformation and what will be achieved at the end of a year?

CHATGPT: A roadmap for an agile transformation is a high-level plan that outlines the overall strategy and objectives for the transformation, as well as the key milestones and deliverables that need to be achieved along the way. A roadmap is typically more strategic in nature and focuses on the big picture, rather than the specific details of how the work will be done.

A project plan, on the other hand, is a more detailed plan that outlines the specific tasks, timelines, and resources that will be required to implement the changes. A project plan will typically include more detailed information about the specific activities that need to be completed, as well as the resources that will be required to complete them.

When creating a roadmap for an agile transformation, it’s important to keep in mind the overall vision and goals for the transformation, and to align the roadmap with the organization’s overall strategy and objectives. The roadmap should also take into account the unique needs and challenges of the organization, and should be flexible enough to adapt as the transformation progresses.

For example, in the case of the IT department of a large enterprise, the CIO could create a roadmap that outlines the overall strategy and objectives for the agile transformation, such as:

  • Developing a clear vision and goals for the transformation
  • Identifying the key business areas that will be impacted by the transformation
  • Assessing the current state of the organization and identifying areas that need improvement
  • Developing a plan to implement the changes, including timelines and milestones
  • Providing training and support to team members as they adapt to the new processes and practices
  • Measuring progress and success along the way, and making adjustments as needed
  • Having a governance structure that allows the different teams to align and work together
  • Foster a culture of continuous improvement and encourage the team to adapt to changes

It’s important to keep in mind that an agile transformation is a continuous process, and the roadmap should be flexible enough to adapt as the organization’s needs change. It’s also important to keep in mind that the roadmap is not only about the tools and frameworks, but also the culture and mindset change.

Additionally, it’s important to involve all stakeholders in the development of the roadmap, and to ensure that the roadmap is communicated clearly to all team members. This will help to ensure that everyone is on board with the change and understands how it will impact them.

Hrishikesh Karekar: Wow. That’s a really good example there. I mean, you shifted quite a bit, but you’re still meeting the objectives. And I’m sure by then, as the more excited teams learn, then there’s some kind of lead by example that happens, and other teams will start to see the value in it as it moves forward. Let’s talk a little bit about these KPIs and objectives as well. when it’s coming from a corporate level and you’re talking about doing agile at scale in an organization, what are some of the ways that you drive KPIs and objectives, so that everyone gets a view into what it is they need to be doing in their business? Or do you just say, every business unit builds their own KPIs and their own objectives for their transformation?

CHATGPT: When it comes to driving KPIs and objectives for an agile transformation, it is important to have a balance between top-down and bottom-up approaches.

From a top-down perspective, the centralized transformation team should establish overall key performance indicators (KPIs) that align with the organization’s overall vision and strategy. These KPIs should be used to measure the progress and success of the transformation across the entire organization. Examples of such KPIs could be:

  • Number of teams successfully implementing agile practices
  • Increase in productivity and efficiency
  • Reduction in time to market
  • Increase in customer satisfaction
  • Increase in employee engagement

From a bottom-up perspective, individual teams should also establish their own KPIs and objectives that align with the overall KPIs, but that are specific to their own business unit. This will help to ensure that the changes being implemented are tailored to the specific needs of each business unit and that they are aligned with the overall vision and strategy of the organization. Additionally, the teams should be able to track the progress and success of the transformation, and make adjustments as needed.

It’s important for both top-down and bottom-up KPIs and objectives to be aligned and communicated clearly, so that everyone understands how the changes will impact them and how they can contribute to the success of the transformation.

Additionally, it’s important for the teams to have the autonomy and ownership to decide how to measure and track their progress, and to have the support and guidance of the centralized team to ensure that the KPIs align with the overall goals of the transformation.

It’s also important to have a governance structure that allows the different teams to align and work together. Having a shared vision, clear roles and responsibilities, and a strong project management discipline is essential for the success of the transformation.

Hrishikesh Karekar: Yeah, that makes complete sense. And I’m guessing that is also part of just how you keep executives aligned with the transformation effort. Would that be right?

CHATGPT: Yes, that is correct. Keeping executives aligned with the transformation effort is an important aspect of the change management process.

One way to do this is by involving executives in the planning and implementation process from the beginning. This can be done by involving them in the development of the roadmap and the establishment of the overall KPIs and objectives for the transformation. This will help to ensure that the goals and objectives of the transformation align with the overall vision and strategy of the organization, and that the executives are aware of the progress and success of the transformation.

Additionally, it’s important for the centralized transformation team to provide regular updates and progress reports to the executives, highlighting the progress of the transformation and any challenges or successes that have been encountered along the way. This will help to ensure that the executives are aware of the progress and success of the transformation, and that they are able to make informed decisions.

Another way to keep the executives aligned is by involving them in the process of reviewing and adjusting the KPIs and objectives as the transformation progresses. This will help to ensure that the goals of the transformation remain aligned with the overall vision and strategy of the organization, and that the transformation is able to adapt and change as needed.

Overall, involving executives in the planning, implementation, and review process can help to ensure that the goals and objectives of the transformation align with the overall vision and strategy of the organization, and that the executives are aware of the progress and success of the transformation.

Hrishikesh Karekar: I’m curious, as we get towards the end of the podcast here,we’ve been talking about corporate executive-level, leadership-level changes across an organization. What advice might you give to an executive that’s thinking about going through this agile transformation effort?

Here are some key pieces of advice for an executive who is thinking about going through an agile transformation effort:

  1. Clearly communicate the vision and goals of the transformation: Clearly communicate to all team members what the goals of the transformation are, and how they align with the overall vision and strategy of the organization. This will help to ensure that everyone is on board with the change and understands how it will impact them.
  2. Involve all stakeholders in the planning process: Engage all stakeholders in the planning process, including team members, managers, and other key stakeholders. This will help to ensure that everyone is on board with the change and understands how it will impact them.
  3. Provide training and support: Provide training and support to team members to help them understand the new processes and practices being implemented, and to help them adapt to the changes.
  4. Lead by example: As a leader, it is important to lead by example and demonstrate the desired behavior and mindset. This will help to create a culture of trust and respect among team members.
  5. Measure progress and success: Establish key performance indicators (KPIs) to measure progress and success, and use them to track the progress of the transformation and identify areas that need improvement.
  6. Embrace a change culture: Agile is not only about tools and frameworks but also about the culture and mindset change. Embrace change culture, foster transparency, collaboration, and continuous improvement.
  7. Foster a strong and empowered team: Agile methodologies are team-based, and the success of an agile transformation is heavily dependent on the strength and empowerment of the team. Encourage team building activities and make sure that the team is self-organizing and has the autonomy to make decisions.
  8. Be patient: Agile transformation takes time and cannot be rushed. Be patient and focus on continuous improvement over time.
  9. Align with overall vision and strategy: Ensure that the goals and objectives of the transformation align with the overall vision and strategy of the organization, and that the executives are aware of the progress and success of the transformation.
  10. Adapt and change as needed: Agile is an ongoing process, and the transformation should be flexible enough to adapt and change as the organization’s needs change.

By following these steps, executives can help to ensure that the agile transformation is successful, and that the

End of transcript

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