TBM 204: 40 (Roadmap Item) Questions

Midjourney: a neural network drawing, bayesian belief network, network, line art modern art drawing with charcoal and water color

Here’s a list of potentially helpful questions (and multiple-choice answers) to help you explore the ideas, strategies, opportunities, problems, bets, initiatives, and projects on your roadmap. Some notes:

• Embrace uncertainty. Saying “I don’t know” is a great outcome.

• Embrace different perspectives. If two people disagree, that is an excellent signal for a conversation.

• Embrace learning. As you progress as a product manager, you’ll learn how to 1) answer more of these questions, and more importantly 2) know what to do based on your answers.

• Don’t use this as a gate. Most product efforts attempt to answer these questions as a continuous, ongoing effort.

• Don’t feel like you need to answer all the questions. Jump around. There are correlations. You’ll notice patterns.

• Don’t turn this into a form. That would defeat the purpose.

• Don’t take this too seriously. It’s a fun product manager workout.

• Don’t make anyone’s life difficult with this post (including your own life). Thank you.

• Want to make comments? Try this Google Doc.

Finally, if you found this helpful (no pressure at all)…

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Where are we at in the life cycle of this problem/opportunity?

1. It's very difficult with lots of false starts—an exploratory phase.

2. It's a can't-miss opportunity with low-hanging fruit—things are on the up-and-up.

3. It's a bit tougher, but gains can still be made—a playground for disciplined optimizers.

4. Wins are hard to come by and just preventing a slide is an accomplishment.

5. We shouldn’t even try. Let’s do the bare minimum while we consider other opportunities.

How quickly can we make progress here?

1. Very quickly. We can make visible progress in a very short period of time.

2. Moderately quickly. There are some challenges to overcome, but progress should be achievable within a reasonable timeframe

3. Slowly. There are significant obstacles in the way that will take some time to address

4. Very slowly. Progress will be difficult and take a long time to achieve, if it's achievable at all

5. Uncertain. I'm not sure how quickly we can make progress on this problem

What is the risk profile of this proposed initiative?

1. Very risky with the potential for a big payoff

2. Somewhat risky with the potential for a moderate payoff

3. Moderately risky with a reasonably certain but smaller payoff

4. Not very risky with a fairly certain but small payoff

5. Very safe with a low but predictable payoff

What is the expected blast radius for trying to address this problem/opportunity?

1. The initiative is low-risk and can be implemented by a small team without any additional resources or coordination.

2. The initiative requires some coordination with other teams but can still be implemented by a relatively small team.

3. The initiative has moderate risk and requires significant involvement from multiple teams and resources.

4. The initiative has high risk and requires involvement from multiple teams, significant resources, and coordination with upper management.

5. The initiative has a very high risk and requires the involvement of the entire organization, including external partners and vendors.

In terms of differentiation, how critical is this proposed initiative for the company to be highly differentiated from its competitors?

1. Extremely critical; the company must be highly differentiated from its competitors to succeed.

2. Somewhat critical; some differentiation from competitors is important, but not essential.

3. Neutral; differentiation from competitors is not a significant factor in the success of this initiative.

4. Somewhat unimportant; the company can be slightly below average compared to its competitors and still succeed.

5. Extremely unimportant; the company does not need to differentiate from its competitors at all to succeed.

What is the current level of differentiation of the company when it comes to the proposed problem/opportunity?

1. Highly differentiated; the company has a significant advantage over its competitors.

2. Moderately differentiated; the company has some advantages over its competitors but also faces significant competition.

3. Neutral; the company is on par with its competitors in terms of differentiation.

4. Slightly undifferentiated; the company is at a slight disadvantage compared to its competitors.

5. Highly undifferentiated; the company has a significant disadvantage compared to its competitors.

What level of solution specificity do you have in mind for this initiative?

1. We are completely open to exploring a wide range of options and haven't settled on any particular solution yet.

2. We have some general guidelines for what we're looking for, but we're open to exploring a range of potential solutions within those parameters.

3. We have a general solution in mind, but we're still exploring different ways to execute it.

4. We have a specific solution in mind, but we're open to feedback and suggestions for potential improvements.

5. We have a specific solution in mind that we're confident will work for this initiative.

Would you describe the initiative as solution focused, problem focused, or opportunity focused?

1. Solution-focused

2. Problem-focused

3. Opportunity-focused

4. A mix of both problem and opportunity-focused

5. None of the above.

What is the potential "shape" of negative impact if we choose not to work on this initiative?

1. The negative impacts will be immediately evident and significant.

2. The negative impacts will accrue linearly over time.

3. There will be no immediate negative impacts, but negative effects will accumulate gradually over time.

4. The negative impacts will only be noticeable in the mid to long term and will increase non-linearly.

5. It is impossible to predict the potential shape of negative impact without further analysis and evaluation.

How would you rate the leverage of this proposed initiative?

1. Very high leverage: the initiative has the potential to produce an outsized and non-linear effect. We expect many positive 2nd and 3rd order effects.

2. High leverage: the initiative has potential for significant non-linear effects.

3. Moderate leverage: the initiative has potential flywheel effects, but they are more linear.

4. Low leverage: the initiative has a limited but still linear potential for impact. Effort in, results out.

5. Very low leverage: benefits will quickly level off and become flat. 

Describe the connection between the proposed initiative and sustainable business outcomes.

1. The initiative has a clear, well-defined causal relationship with sustainable business outcomes.

2. The initiative is expected to have a somewhat defined impact on sustainable business outcomes, but there may be some degree of uncertainty.

3. The initiative is expected to have a moderate impact on sustainable business outcomes, but it may be difficult to pinpoint the exact effects.

4. The impact of the initiative is expected to be dispersed and less defined, making it harder to immediately identify its effects on sustainable business outcomes.

5. It is unclear how the proposed initiative will impact sustainable business outcomes.

What is the level of significance of the proposed initiative?

1. It is a critical initiative addressing an existential threat to the organization.

2. It is an important initiative that addresses a significant problem but not an existential threat.

3. It is a moderate initiative that will provide some benefits to the organization.

4. It is a minor initiative that is a nice-to-have.

5. It is a trivial initiative that does not provide any significant value to the organization.

Describe the ideal funding approach for the initiative.

1. Incremental funding based on progress and achieving milestones

2. Funding based on hitting milestones, but with a requirement of a batch of funding before any progress is possible

3. Funding based on delivering a specific deliverable.

What reference data is available about how other companies with a shared context address the challenge of the proposed initiative?

1. None - this is a novel challenge

2. Limited - a few companies have attempted to address this challenge

3. Some - there are several companies that have faced similar challenges

4. Plenty - there is a wealth of data available on this challenge from a variety of companies

5. Extensive - this challenge has been extensively studied and many companies have published their approaches

How much research has been conducted to support the proposed initiative?

1. A great deal of research has been conducted already.

2. Some research has been conducted, but more is needed.

3. A moderate amount of research has been conducted.

4. No research has been conducted yet, but the team plans to learn as they go.

5. The team does not believe any research is necessary.

How operationally ready is the company to tackle this proposed initiative?

1. Extremely prepared and ready to take on the challenge

2. Moderately prepared, but may need some additional resources or planning

3. Somewhat prepared, but will require significant effort and resources to be allocated

4. Not very prepared, and will require a substantial amount of time and resources to prepare for the initiative

5. Not prepared at all and would require significant investment and time to become operationally ready.

Does this bet add a new capability or improve an existing capability? And is it a step change or an incremental improvement?

1. Adding a new capability with a step change

2. Adding a new capability with an incremental improvement

3. Improving an existing capability with a step change

4. Improving an existing capability with an incremental improvement

5. Not sure/Other.

How reversible or easy to pivot is this proposed initiative?

1. It can be easily stopped or pivoted with minimal negative impacts.

2. There are some risks involved, but it can be reversed or pivoted with moderate effort and some negative impacts.

3. It would require a significant effort to reverse or pivot with substantial negative impacts.

4. It would be extremely difficult, if not impossible, to reverse or pivot with severe negative impacts.

5. I'm not sure.

How comfortable is the company with failure in this area?

1. Completely comfortable - failures are seen as learning opportunities

2. Somewhat comfortable - failures are tolerated, but not celebrated

3. Neutral - the company has no strong opinion on failure in this area

4. Somewhat uncomfortable - failures are frowned upon and seen as a weakness

5. Completely uncomfortable - any setback or perceived weakness in this area is unacceptable

If we agree to this proposed initiative, how much do we need to shift priorities?

1. No deprioritization required, it fits right in.

2. Minor deprioritization of some initiatives, but overall, it won't significantly change our direction.

3. Some deprioritization of many initiatives, but we can still stay on course with our current strategy.

4. Major deprioritization of most initiatives, and significant changes to our current strategy are necessary.

5. Drastically changing direction is required, and most current initiatives will need to be deprioritized.

To what extent is the proposed initiative politically charged or threatening to certain people, agendas, or perspectives?

1. Not politically charged: No significant opposition or controversy is expected.

2. Minimally politically charged: Some minor opposition or controversy may arise.

3. Moderately politically charged: Some significant opposition or controversy may arise.

4. Highly politically charged: Strong opposition or controversy is expected.

5. Extremely politically charged: Intense opposition or controversy is expected.

How would you describe the level and strength of consensus within the organization regarding the proposed initiative?

1. Broad and deep consensus among a large number of stakeholders

2. Broad but not deep consensus among a large number of stakeholders

3. Deep consensus among a few stakeholders

4. Limited consensus (not broad or deep)

5. Unknown

How would you characterize the level of objectivity or subjectivity in measuring progress for this proposed initiative?

1. Completely objective - progress can be measured using quantifiable metrics that are provable and widely agreed upon.

2. Mostly objective - progress can be measured using quantifiable metrics, but there may be some subjectivity involved in interpreting the data.

3. Neutral - progress can be measured using both objective and subjective metrics.

4. Mostly subjective - progress cannot be easily quantified and will require subjective interpretation and analysis. (Note: this is not necessarily a bad thing, but may require a different approach to measuring progress.)

5. Completely subjective - progress is entirely open to interpretation and cannot be measured using objective criteria. (Note: this is not necessarily a bad thing, but may require a different approach to measuring progress.)

How does this proposed initiative relate to other opportunities within the organization?

1. This initiative is completely independent and standalone.

2. This initiative has some overlap with other initiatives, but is largely unique.

3. This initiative is one of several related initiatives that are being pursued, but there is no broader strategic effort that encompasses all of them.

4. This initiative is part of a broader strategic effort that encompasses multiple initiatives.

5. It is unclear how this initiative relates to other opportunities within the organization.

How would you characterize the problem area you hope to address?

1. Simple/Obvious: This domain is characterized by clear cause-and-effect relationships and predictable outcomes. Solutions are often straightforward and can be applied in a standardized way.

2. Complicated: This domain is characterized by multiple possible solutions to a problem, with various degrees of effectiveness. Experts are often needed to analyze the situation and identify the best solution.

3. Complex: This domain is characterized by unpredictability and emergent outcomes. The solution is not obvious and may require experimentation and iteration to find what works best.

4. Chaotic: This domain is characterized by a high degree of uncertainty and no clear cause-and-effect relationships. The focus is on stabilizing the situation as quickly as possible to prevent further harm.

5. Disorder/Unknown: This domain is characterized by a lack of clarity about which of the other four domains the situation falls into. It can be useful to take action to move the situation towards one of the other domains.

Credit: Cynefin Framework / Dave Snowden

What is the level of technical innovation and new opportunities in the area that the proposed initiative is addressing?

1. Highly innovative with many new technologies and opportunities emerging

2. Moderately innovative with some new technologies and opportunities emerging

3. Somewhat innovative with limited new technologies and opportunities emerging

4. Not very innovative with few new technologies and opportunities emerging

5. Static with no new technologies or opportunities emerging

Can you tell me about the data we have regarding prior efforts to address this opportunity?

1. We have a wealth of trustworthy data showing significant progress in addressing this opportunity.

2. We have some reliable data indicating moderate progress in addressing this opportunity.

3. We have a limited amount of data showing some progress in addressing this opportunity.

4. We have very little data indicating minimal progress in addressing this opportunity.

5. We have no data at all because this is a new effort or prior efforts yielded no data.

When it comes to feedback loops, which of the following options best describes the proposed initiative:

1. The feedback loops are extremely tight, making it easy to see if we're moving in the right direction

2. The feedback loops are mostly tight, but there are some areas where cause and effect may not be immediately apparent

3. The feedback loops are balanced, with a mix of tight and long loops, allowing for some noise but still giving clear direction

4. The feedback loops are mostly long and noisy, with little opportunity for clear cause and effect

5. The initiative does not have any feedback loops in place

What is the level of familiarity of your team and company with the proposed initiative?

1. This initiative is entirely familiar, and we have successfully addressed this type of challenge multiple times before.

2. This initiative is mostly familiar, and we have tackled similar challenges before.

3. This initiative is a mix of old and new elements, and we have some experience with some of the elements.

4. This initiative is mostly new, but we have some experience with similar challenges.

5. This initiative is completely new, and we have not tackled anything like this before.

What is the technological scope of the proposed initiative? Which of the following options best describes the level of technical overhaul it requires?

1. No changes to existing architecture and technologies are required

2. Minor tweaks to existing architecture and technologies

3. Moderate changes to existing architecture and technologies

4. Major modifications to existing architecture and technologies

5. Complete overhaul of existing architecture and technologies

If you were to describe this opportunity as a game, how would you describe it?

1. Candy Land. No agency. Do what the game tells you.

2. Rock Paper Scissors. Agency, but no strategy.

3. Tic Tac Toe. Some basic tactics.

4. Chess. High level strategies, but the situation is clear.

5. Poker. Many hidden unknowns. It is about people!

Credit: Andrew Cheung

What is the level of anticipation for the proposed initiative?

1. Very proactive, with an eye towards future trends and needs

2. Somewhat proactive, but not necessarily ahead of the curve

3. Neutral, addressing current needs but not particularly innovative

4. Somewhat reactive, addressing needs that have emerged recently

5. Very reactive, addressing needs that should have been addressed earlier

What level of constraints do you anticipate for this proposed initiative?

1. Completely non-constrained with many degrees of freedom

2. Somewhat constrained with moderate degrees of freedom

3. Moderately constrained with limited range of movement

4. Highly constrained with very limited range of movement

5. Completely constrained with no degrees of freedom

How long will we be working on this?

1. 1-3 weeks

2. 1-3 months

3. 1-3 years

4. For the lifetime of the company

5. Hard to tell

How disruptive do you anticipate this proposed initiative will be for customers?

1. It will not be disruptive at all

2. It will cause some minor disruption, but customers will adapt quickly

3. It could cause significant disruption initially, but customers will likely adjust over time

4. It has the potential to completely transform and disrupt the current product offering, but in a positive way

5. It has the potential to cause significant disruption and may negatively impact customers' experience with the product

How much of an improvement do you think this proposed initiative will provide for customers?

1. It will not provide any significant improvement

2. It may provide some minor improvements, but not a significant change

3. It has the potential to provide moderate improvements to customers' experience with the product

4. It has the potential to significantly enhance customers' experience with the product offering

5. It has the potential to completely transform and improve customers' current perception and usage of the product

What is the expected timeline for customers to notice the impact of the proposed initiative?

1. Almost immediately

2. Within a few weeks

3. Within a few months

4. Within a year

5. Barely perceptible in the near term, with an eye towards long term improvements

How broadly will this impact our customer base?

1. It will impact all customers

2. It will impact most, but not all customers

3. It will impact a significant portion of customers

4. It will impact a small but influential group of customers

5. Not sure yet

How similar is your new idea to what your competitors are doing?

1. We plan to basically copy and paste their approach.

2. We will mostly follow their direction, but with some minor deviations.

3. We aim to be on par with our competitors, but we also plan to explore some new ideas.

4. We intend to take a somewhat different path than our competitors, but with some common ground.

5. We plan to actively pursue paths that our competitors have not explored or are very different from theirs.

What is your level of emotional attachment to the proposed initiative?

1. Highly attached and emotionally invested in the initiative

2. Moderately attached and somewhat emotionally invested in the initiative

3. Neutral and objective about the initiative

4. Slightly detached and open to considering alternatives to the initiative

5. Very detached and willing to objectively evaluate the initiative from all angles

Got this far?

If you found this helpful (no pressure at all)…