A unique way to organize projects for your startup
A problem-solving framework from the 1970s reimagined for startup goal and project planning
The how might we (HMW) methodology originated from Procter & Gamble (P&G) in the 1970s as part of their innovation practices but was later popularized by IDEO, the global design and consulting firm known for its work in design thinking. The approach was formalized in the context of design thinking, a human-centered problem-solving process. The HMW format at P&G emerged as part of a collaborative problem-solving technique used internally to stimulate creative thinking by framing challenges in a positive, open-ended manner. IDEO built on this approach as a key part of brainstorming and problem definition, encouraging teams to frame challenges as opportunities for creative solutions.
The core idea of How Might We is that it frames challenges as actionable questions, inviting possibility and exploration. For example, instead of asking "Why don’t we have enough customers?", the question would be reframed as "How might we attract more customers to our product?"
Startups are constantly changing, and in the age of AI, the change is getting fast and faster. OKRs get stale quickly, and goalposts seem to change no longer weekly or monthly but on the daily.
Responding to this, this summer at oAT, we experimented with a new way of organizing our work using the HMW method. Instead of focusing on specific numeric goals, we're reframing challenges as questions to open up the realm of solutions. The idea is simple: instead of asking "What do we need to accomplish to grow and hit this goal?" we ask "What problems are we trying to solve?"
We identified key "how Might We" (hMW) initiatives (oAT branded), framing each one around a core challenge we want to tackle. For example, a few are included below:
→ how Might We gain clarity and cohesion as a company?
→ how Might We become a company of doers, learners, and achievers?
From there, we brainstormed as a team - async - to identify a range of projects and tasks that will help us find clarity and drive experimentation. We’re a team of generalists with overlapping skills, so throwing projects into functional silos just didn’t work (which happens often with many of the early-stage startups we serve as well).
The process allowed us to start from a white space mindset, harnessing the diverse perspectives, expertise, and areas of interest of our team.
how DO you appropriately plan project work in an organization and ecosystem that’s constantly changing?
Turn stagnant goals into problems to be solved through the how Might We method.
Why This Works
This problem-first approach moves away from rigid, siloed objectives and allows for dynamic, cross-functional collaboration. Rather than assigning tasks based on job descriptions or departmental silos, we empower team members to contribute in areas where they can make the most impact.
It’s not just about solving problems—it’s about asking the right questions. By framing challenges as "how Might We" opportunities, we open up space for creative solutions that leverage the diverse skills of our team. This method encourages a more adaptive and flexible workflow, which is critical for startups, where innovation and rapid problem-solving are key.
Why Do This Now
Startups thrive on agility and innovation. A problem-first, question-driven approach helps us stay flexible and responsive. It encourages team members to take ownership and collaborate more fluidly, much like our most successful startup partners. By focusing on the "why" behind our work—clarifying the core problem—we enable smarter, more aligned decision-making.
This is also a proactive way to reduce siloed thinking, which can stifle creativity and limit impact. Now, more than ever, companies need to work cohesively to tackle big challenges. This approach creates a shared understanding of what we’re solving for, enabling the entire team to align around a common mission.
how We Do: Adopt a how Might We approach to project planning
Tools 🛠️
Manage tasks visually by using tools such as Notion or Asana to allow team members to "pull" tasks related to the key "how Might We" questions.
Collaborate on brainstorming and solution-mapping by using tools like Miro or Lucidchart, helping teams think through big challenges together.
Facilitate a regular cadence of real-time communication by using platforms like Slack or Zoom to encourage ongoing discussions around the challenges.
Document evolving initiatives and track progress by using knowledge management tools such as Confluence or Notion, ensuring lessons are captured and shared.
Rules (Process) 📝
Frame key challenges by identifying 3-5 “how Might We” questions that target the most critical problems your organization faces.
Appoint team leads to ensure ownership and accountability for each “how Might We” question, driving progress and solutions.
Allow task pulling by empowering team members to select responsibilities based on their interests and expertise, aligning with core problem areas.
Hold regular check-ins to evaluate progress, refine the questions, and iterate solutions based on feedback and team learning.
Refine and finalize solutions by adjusting approaches continuously, ensuring they address the core problems effectively and generate the best outcomes.
People 🫶
Include curious generalists who are adaptable and excited to learn across functions, alongside passionate specialists who bring deep expertise to problem-solving.
Foster collaboration by involving problem solvers who thrive in cross-functional environments and are comfortable challenging assumptions constructively.
Empower decision-makers by creating a culture where team members feel confident taking ownership and making decisions that move solutions forward.
Ensure leadership support by building a trusting environment where ideas, questions, and calculated risks are encouraged, allowing for innovation and growth.
Actually Actionable
Define your "how Might We" questions: Think about the big challenges your company faces. Frame them as open-ended questions to inspire creative thinking.
Let your team pull tasks: Empower team members to identify the projects they want to contribute to in support of the core problems, rather than assigning them specific tasks first.
Encourage cross-functional collaboration: Create opportunities for people to work across traditional boundaries, blending expertise to solve bigger challenges.
Continually refine: As you work on these questions, revisit them regularly. The more you drill down, the better your solutions will be.
Before you go
This shift toward problem-first thinking isn’t just a structural change—it’s a mindset shift. By moving away from tactics and toward the bigger “how Might We” questions, we’re seeing a few key benefits already.
Team members are more invested because they can work on what excites them, aligning with their strengths and passions. The flexibility in choosing tasks allows for more creative and collaborative solutions, leading to better outcomes. In fast-moving environments like startups, being able to pivot and solve new challenges quickly is critical. This approach fosters agility by keeping the team focused on the core problems rather than getting stuck in rigid tactical planning.
The best part? This is just the beginning. While we’re still iterating and learning, the results are clear: starting with the right questions has already sparked better conversations, stronger collaboration, and solutions we might not have thought of if we’d stayed in a tactics-first mindset.
As you think about your next project or initiative, take a moment to consider: what’s the bigger problem you’re trying to solve? What are your “how Might We” questions? The answers might lead you to even more impactful solutions.
Writer: Britt