Design mapping with Post-it notes

Strategic Thinking for Designers

Kazden Cattapan
Mar 19 · 5 min read


The first step toward becoming a more strategic-thinking designer is to learn how to anticipate. Great strategic designers are vigilant, honing their ability to anticipate design trends by scanning the environment for signals of change.

  • Conduct market research and analyze competing products to gauge your users’ likely reactions to new initiatives or products, and predict potential disruptive offerings
  • Use scenario planning to imagine various futures and prepare for the unexpected
  • Look at fast-growing rivals to examine any puzzling actions they’ve taken
  • Try to identify users you’ve recently lost and try to figure out why
  • Attend conferences and events in other industries or functions to widen your perspective


Once you’ve refined your ability to anticipate, it’s time to put the forward-thinking ideas you have to the test. Strategic designers aren’t afraid to challenge the status quo. They challenge their own and others’ assumptions and encourage divergent points of view.

  • List long-standing assumptions about an aspect of your product (e.g. “high switching costs prevent users from choosing an alternative product”) and ask a diverse group if they hold true
  • Encourage debate by holding “safe zone” meetings where open dialogue and conflict are expected and welcomed
  • Include stakeholders in the decision process to surface challenges early
  • Capture input from people not directly affected by design decisions who may have a good perspective on the repercussions
Two people brainstorm at a whiteboard. Photo by Kaleidico on Unsplash


Once you’ve brought ideas to light and given them a chance to be put through the paces, your next step is to synthesize the information (something designers have a leg up on, thankfully). Instead of reflexively seeing or hearing what you expect, you should synthesize all the input you have. You’ll need to recognize patterns, push through ambiguity, and seek new insights.

  • Force yourself to zoom in on the details and out to see the big picture.
  • Actively look for missing information and evidence that disconfirms your hypothesis.
  • Supplement observation with quantitative analysis.
  • Step away — do something else to promote an open mind


In uncertain times, we may have to make tough calls with incomplete information, and often we must do so quickly. Strategic designers insist on multiple options at the outset and don’t get prematurely locked into simplistic go/no-go choices. They follow a disciplined process that balances rigor with speed, considers trade-offs involved, and takes both short- and long-term goals into account. And then they make a decision.

  • Divide big decisions into smaller pieces to better understand component parts and see unintended consequences
  • Tailor your decision criteria to long-term vs short-term projects
  • Let others know where you are at in your decision process (are you still seeking divergent ideas and debate, or are you moving towards closure and choice?)
  • Determine who needs to be directly involved and who can influence the success of your decision
  • Consider experiments instead of big bets and make multi-staged commitments


The penultimate step in the strategic design process is to ensure everyone is on the same page. Strategic designers must be adept at finding common ground and achieving buy-in from stakeholders who have disparate views and agendas. This requires active outreach. Success depends on proactive communication, trust building, and frequent engagement.

  • Identify key internal and external stakeholders, mapping their positions on your initiative and pinpointing any misalignment of interests. Look for hidden agendas and coalitions.
  • Use structured and facilitated conversations to uncover areas of misunderstanding or resistance
  • Reach out to resisters directly to understand their concerns and address them
  • Be vigilant in monitoring stakeholders’ positions during the rollout of your initiative or strategy
  • Recognize and otherwise reward colleagues who support team alignment


Finally, open yourself up to continuous learning. Promote a culture of inquiry, and search for lessons in both successful and unsuccessful projects. Study failures — your own and your team’s — in an open, constructive way to find hidden lessons.

  • Encourage experimentation and failure
  • Conduct frequent learning audits to see where decisions and team interactions have fallen short
  • Identify initiatives that are not producing as expected and examine the root causes
  • Create a culture in which inquiry is valued and mistakes are viewed as learning opportunities

Myplanet Musings

Thoughts, ideas, insights, and more from the Myplanet team.

Kazden Cattapan

Written by

Product Designer @shopify

Myplanet Musings

Thoughts, ideas, insights, and more from the Myplanet team.