Strategy workshops done right:⭕Loop Framework for Product Leaders

Written on 11/12/2023
Bandan Jot Singh

Over last many months, Productify seemed to have been finding its niche through high percentage of deep dives on product strategy. We started with All the strategy frameworks you need (April,2022) but then backed it up with many more: Advanced Strategy Frameworks (Oct,2023), What Stanford Teaches about Product Strategy (Sept,2023), Complete guide to product moats (July,2023), Spotify’s product strategy pivot (June,2023) and more.

But we are yet to touch upon a very important aspect of product strategy i.e how does the process or methodology to arrive at strategy (outcome) look like?

You might be happy about how strategy is arrived at in your company, or you might be completely bonkers hating it, but if you’re in the second camp, you’re not alone. Let us be honest, have we (as product community) ever been able to align on what is the scope and intent of product strategy? Sometimes it takes a shape of roadmap, other times it takes shape of bets without the how, and most other times it is something in between.

As Professor Burgerlman (Stanford) describes it: Strategy is the thinking that drives action to be successful in competition and collaboration.

But you can also learn a lot about strategy from actions of past historic figures:

As Napolean put it: "On s'engage et puis ... on voit," i.e First we engage, and then we shall see

and hence in today’s edition of Productify we focus on three important sections to make product strategy discussions and workshops better:

📖1.What’s wrong about how we run product strategy workshops today

🔒2.Loop framework: The iterative workshop approach to strategy discussion

🔒3.How to manage internal organizational resistance to Loop framework

Note that 📖 is for free subscribers, 🔒 is exclusively for paid subscribers. You can upgrade here:

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What’s wrong about how we run product strategy workshops today?

  1. 10 commandments approach: One of the biggest problems in the way strategy discussions are run inside companies are that they are thought off as a one-time process that is deep, intensive and the team is expected to come out with 10 commandments of what we need to do next X years.

    Most of the times this process runs at the end of the year, with an ambition to grow and improve on certain aspects next year. The problem with this approach is that it creates a perception in the organization that there is a document now (sealed and locked for eternity) that is to be executed upon next year, while the market continues to do what it does - act uncertain.

    How much of your strategy workshop process allows for flexibility when it comes to down to change of strategy or certain aspects of it later in time? Do you build this mindset during strategy sessions that the strategy being decided will be reviewed and re-visited and hence it is a living document?

  2. Too vague to make sense or too narrow to allow for sense: Depending on the participants in a strategy exercise, your strategy can take multiple flight levels - in some cases it could be too vague and visionary (mostly run by vision-led individuals) that it allows your team to act in many possible ways or it could be too narrow that it allows your team to not apply their own brains at all (led by execution led individual)


    Have you been ensuring that your workshops on strategy lead to right level of detail? i.e leave enough for teams to figure out and at the same time ensure your problems are well-defined and specific.

    Confused-lady GIFs - Get the best GIF on GIPHY
  3. Rigor and market focus lacking: By rigor, I mean the required attention to details and analytics behind ideas and bets. This can be derived from internal dynamics and data insights or this could be a result of external factors, which brings me to second aspect. Is your strategy addressing your internal ideas that you believe should work, or is it addressing market movements and ideas needed to address that market and needs.

    Economy GIFs - Get the best GIF on GIPHY


    Often, market is hard to measure and you go for macro factors and hearsay one-off anecdotes - which is often not enough to know the market well enough.

    Have you been including market insights, market movements, competitor aspects and more in your strategy workshop sessions? If yes, how rigorous are you? and how much of that rigour is needed in workshops?

  4. Missing red seal of buy-in: If you have a good strategy in place and you believe this is what gets you to collaborate and win in the market, it would still not be effective if you fail to get organizational buy-in. Have you been including the right stakeholders in your strategy setting sessions? Have you been iterating during your strategy sessions to make sure all views internal and external are considered?

    𝚜𝚎𝚗𝚜♡𝚛𝚢 — sensory

Have you and the management had an agreement on which big problems to solve? Do you also agree with other teams that these problems or bets make sense? Without a buy-in from others on your strategy, you will struggle when it comes to execution because every team will continue to execute on their own strategy. How many strategy outcomes do you end up with when doing workshops across your organization?

⭕Loop framework: The iterative workshop approach to strategy discussion

What I am about to introduce is not rocket-science, but it is another way and mindset to look at how you run strategy process in your company. Many strategy processes in companies are linear i.e that they have a start date (let us look at our strategy again!) and an end date (this is our strategy, let us communicate) and then the next many months go into bridging the strategy and execution gap without revisiting strategic aspects again.

Linear strategy processes have a big disadvantage. They reduce the impact and importance of strategy outcome and makes it rather a checklist in the huge list of corporate to-dos. Also, it makes the team think ‘strategy is done’ now it is all about execution - we need resources, we need people, we need tools and more.

In the loop framework of establishing strategy, setting the outcome and reviewing becomes a second nature to the organization, driven by an iterative looped approach rather than a linear process. Also, to make sure we don’t get lost in fancy jargons, I have tried to keep the steps in loop framework easy to follow. Here’s what it looks like:

  1. Right Questions

    This step aims to reach a consensus on which type of customer and business problems need to be solved. Problems should be defined specifically and precise, rather than too open-ended.

  2. Decide: Current and Future State

    This step aims to find the current state and future state for each of those questions.

  3. The Path to Future State

    This step aims to figure out the how to reach the target state. Hence, the focus is defining broad actions, tactics and success metrics.

  4. Competency Check and Commit

    This step aims to check for organizational competency gaps that might lead to non-achievement of future state. This could be related to cultural aspects, skillsets, tool sets, resources and people - without which executing on the how (path to future state) will be tough.

  5. Adapt and Evolve
    This step aims to revisit the questions, future state, the path to future state and competency check and modify/change one or more of them as needed. If there is a change in one or more of them, you go back to the original strategy outcome, and add/edit/remove certain aspects to reflect the new reality.

How to run strategy workshop for steps 1 to 4 above

Pre-Work (Before the Workshop):

  • Distribute relevant materials, articles, or case studies for pre-reading to ensure participants are familiar with the market and business context.

  • Ask participants to brainstorm potential questions related to customer and business problems and share them in advance, before day 1 of workshop.

  • Ensure that participants are defining problems in a specific manner (Ex. How to protect drop in B2B enterprise transactions against increasing threat of player B’s X feature) and not generic (Ex. How to create new revenue streams). Here are some more tips:

Day 1: Setting the Foundation (180 - 240 minutes)

  • Introduction (15 minutes):

    • Welcome and agenda overview.

    • Brief explanation of the importance of the strategy exercise.

  • Review Pre-Read Material (45 minutes):

    • Participants share their insights from the pre-reading.

    • Facilitator highlights key concepts and challenges.

  • Icebreaker and Group Formation (30 minutes):

    • Icebreaker activity to create a comfortable atmosphere.

    • Form small groups for breakout sessions.

  • Step 1: Right Questions - Part 1 (90 to 150 minutes):

    • Brief presentation on the importance of asking the right questions.

    • Look at the whole set of customer and business problems input from pre-workshop homework but also add any questions that might be missed out.

    • Groom and clarify all questions and align on whether we believe these questions are really the right ones and can tackle both customer and business aspects

Day 2: Deep Dive into Right Questions (4-6 hours)

  • Step 1: Right Questions - Part 2 (4 hours):

    • Now club similar questions under a theme, so as to create some pattern of kind of problem areas being tackled.

    • Divide participants into groups as per number of themes

    • Breakout sessions (theme wise) for groups to further refine and prioritize questions.

    • Facilitator circulates among groups to provide guidance.

    • Each group presents their finalized questions and the group agress on the final set of problem statements on which the strategy is to be based.

Day 3: Current and Future State, The Path to Future State (6 hours)

  • Step 2: Decide - Current and Future State (3 hours):

    • Presentation on the concept of current and future state.

    • Breakout groups to identify the current and future state for each problem. This can be done for each problem statement allocated to one group. Or it could be group of problem statements allocated to each group.

    • Then allow each group to present the current and future state for their problem statement almost like a pitch deck emphasizing on why they believe the future world of their problem statement will be much better than current world.

    • Allow other groups to critique, ask questions and make the target state better.

  • Step 3: The Path to Future State (3 hours):

    • Keeping the groups as the same. Now you can ask each group to come back with the approach they would recommend for reaching the target state related to their problem statement.

    • Group activity is to define broad actions and tactics, and not precise steps. The right level of detail is important.

    • Always important to emphasize the need to define success metrics to know if the approach is succeeding or not in the future.

Here is an example of current state and future state narrative for a chosen problem statement:

Day 4: Competency Check and Commit (3 hours)

  • Step 4: Competency Check and Commit

    • Overview of the importance of competency checks.

    • Breakout sessions to assess organizational competency gaps that exist to address the problem statements and target states to be accomplished

    • Reconvene for group discussion and commitment to bring up those gaps to the right stakeholders or management in the company


    Here are some examples:

Logistics and Tools:

  • Pre-Work:

    • Ensure participants have access to and complete pre-reading.

  • In-person or Virtual:

    • Virtual workshops can be conducted using video conferencing tools.

  • Stakeholders and Tools:

    • Same as before, adjust based on the team's dynamics.

  • Creating a Safe Environment:

    • Emphasize the importance of open communication and active listening.

    • Use anonymous feedback tools if necessary.

  • Conclusion:

    • Summarize key takeaways.

    • Communicate next steps and ongoing support.

    • Express gratitude and encourage further collaboration.

Step 5 (Adapt and Evolve) sharpens your strategic stand

It is true that strategy (i.e set of bets or problems to be solved) is generally finalized for a period of 1 to 3 years, but I have often seen for industries in super dynamic space, market assumptions and competitive dynamics can change in matter of months.

Hence, Adapt and Evolve is key part of strategic exercise - the only difference is that this step is not part of strategy outcome exercise but part of strategy revisit exercise.

Just like product discovery and product delivery are dual side of product learning cycle, similarly strategic outcome exercise and strategic revisit exercise are part of strengthening the strategic understanding in your organization.

Adapt and Evolve Workshop should ideally happen once every 6 months and in some cases it could also be done once every 3 months to find answers to below questions:

  1. Do we still know and believe in strategy that it will make us win? (Problem, Target States, Approach to Target State, Metrics)

  1. Do we have what it takes to win? (Team, Culture, Skillsets, Infra)

  2. Are we doing what we’re saying? (Execution is in direction of strategy or not?)

It may happen that in such exercise you may agree with 1 as a team, but not with 2 or 3 - which is often the case if you did a good process of arriving at strategy - hopefully the problems and target state view should not change.

However, you may also come to a conclusion that we no more believe in the problem statement and target states because a regulation changed, competition did an M&A or something disruptive happened (like it was when corona crisis happened) - in that case, you could also sharpen or modify your problem statements and target states..

Hence, what was initially a linear strategy process, now becomes a strategy process with an inbuilt feedback loop.

Big advantage of this approach is that, by the time, 12 months are over and you’re about to re-do strategy process, you will cut down your time to arrive at strategy outcome by a lot since you’ve been doing the ‘Adapt and Evolve’ exercise every 3 months or 6 months.

Organizational resistance to the Loop framework strategic planning process can take various forms

Here are three common types of resistance and ways to overcome them:

  1. Change Aversion:

    • Resistance Type: Some individuals or teams may resist the strategic planning process due to a fear of change. They may be comfortable with the current state and are reluctant to embrace new approaches or feedback loops to revisit strategy.

    • Overcoming Resistance: Communicate the benefits of the strategic planning process clearly. Highlight how it will lead to improved outcomes, efficiencies, and long-term success for the organization. Engage employees in the process, get their buy-in and make them feel a sense of ownership and involvement in shaping the future.

  2. Lack of Understanding:

    • Resistance Type: Resistance may arise if team members do not fully understand the purpose, goals, or methodology of the strategic planning process. This lack of understanding can lead to skepticism and pushback.

    • Overcoming Resistance: Provide comprehensive training and communication sessions to ensure everyone understands the importance of each step in the strategic planning process. Create a culture of transparency where employees feel comfortable asking questions and seeking clarification. Foster an environment that encourages learning and development.

  3. Resource Constraints:

    • Resistance Type: Teams may resist strategic planning if they perceive it as a resource-intensive process that takes time away from their regular duties. This could be due to concerns about additional workload or a lack of available resources.

    • Overcoming Resistance: Clearly communicate the efficiency gains and long-term benefits of strategic planning. Emphasize that the process is an investment in the organization's future success. Provide adequate resources and support to ensure that the strategic planning process does not unduly burden teams. Streamline the process to make it as efficient as possible without compromising its effectiveness.