Questions, Decisions & Compromises
Recently I distilled my beliefs about design and process into three short maxims. I can't claim they are wholly original, but they are my own.
- Strategy is the art of asking tough questions.
- Design is the art of making tough decisions.
- Implementation is the art of making tough compromises.
I’ve seen these truths either honored or avoided. You probably have too. For better or worse, the difference always shows up in the end product.
Strategy: Questions Are the Work
Strategy begins with asking questions because it’s an act of learning, not of declaring. The questions are how we uncover constraints, clarify goals, expose trade-offs, and surface the shape of the problem we’re actually solving. In strategy, premature certainty is the enemy; curiosity is the engine.
An agency leader I once worked with didn’t see it that way. He pushed us to limit the number of questions we asked clients in discovery and throughout design. “We’re not trying to boil the ocean,” he’d say. On the surface, that’s a fair caution against scope creep. But it left me confused. Each question we wanted to ask was not about expanding scope, it was about narrowing ambiguity. We weren’t boiling the ocean; we were trying to find the coastline.
Are there questions that should be avoided? Sure:
- Avoid questions that are performative rather than clarifying.
- Avoid questions whose answer won’t change a decision or direction.
- Avoid questions that disrupt momentum without improving fidelity.
Otherwise, fewer questions often means slower projects later: misaligned expectations, surprise constraints, rework, and erosion of trust. Strategy saves time by spending it well early, on the right questions.
Design: Decisions Are the Craft
Design is where the uncertainties of strategy start collapsing into form. Here, decisions are not an interruption of design. They are the substance of design. To design is to choose: hierarchy over noise, clarity over options, defaults over ambiguity.
Another catchphrase from the same leader: “No decisions. We want to move fast! Remember, NO decisions.” I still don’t know what that meant. How does one design without making decisions? Even a wireframe is a stack of decisions. Decisions about flow, emphasis, interaction, and what not to show.
Speed comes from sequencing decisions, not avoiding them.
- Make high-leverage decisions early (information architecture, interaction patterns, design principles).
- Time-box exploratory decisions (mood, direction, metaphors).
- Defer reversible, low-impact decisions without blocking momentum (icon choices, microcopy variations).
- Codify decisions as standards so future choices become defaults, not debates.
The fastest teams I’ve worked with were decisive—not reckless. They decided with intent, documented rationale, and revisited assumptions when data or business requirements demanded, not when opinions wandered.
Implementation: Compromises Are the Bridge
If questions are the fuel of strategy and decisions are the craft of design, compromises are the craft of implementation. This is where ideas meet reality: budgets, backlogs, legacy systems, security, performance, compliance, timelines, and the very human limits of attention and energy.
Here, I agreed with that same agency leader: development requires compromise. The goal is not to avoid compromise but to make the right compromises, consciously and transparently. Good development turns trade-offs into progress.
A practical hierarchy helps:
- Compromise on polish, not principles.
- Compromise on scope, not integrity.
- Compromise on timeline, not truth.
Compromise is not capitulation; it’s the art of conserving what matters most while making something real.
How These Fit Together
When teams stumble, it’s often because these three modes get swapped or suppressed:
- Strategy without questions becomes theater -- assumptions, instead of listening.
- Design without decisions becomes drift -- endless exploration, little coherence.
- Implementation without compromise becomes fantasy -- beautiful plans, brittle systems.
When teams thrive, each mode empowers the next:
- Strategy asks great questions → Design knows what to decide.
- Design makes crisp decisions → Implementation knows where to compromise.
- Implementation feeds back constraints → Strategy asks better questions next time.
This loop (questions -> decisions -> compromises) creates momentum you can trust.
A Note on Speed
Speed doesn’t come from fewer questions or fewer decisions. It comes from:
- Asking the right questions at the right time.
- Making decisions at the right level of fidelity.
- Compromising in ways that preserve future options.
Speed is a byproduct of clarity. Clarity is a byproduct of questions and decisions.
Closing
I still think about that “No decisions” mantra. If anything, it clarified my own stance: to proceed with intention and build things that last, we need more disciplined questions, more deliberate decisions, and more honorable compromises. That is not bureaucracy. That is craft.
