I still remember the day I traded my design toolkit for a seat at the hiring table. I’d been working in product design for years, immersed in creating user flows and crafting pixel-perfect interfaces. But every time I heard a frustrated executive ask, “Where can I find a true design leader?” I realized there was a bigger challenge lurking beneath the prototypes and user stories. Over time, I transformed my role from a designer into someone dedicated to finding and placing exceptional design leaders.
I’ve had a front-row seat to executives wrestling with the complexities of building a top-tier design organization. My perspective might be a bit unique—because I’ve spent countless hours on both sides of the coin. I’ve experienced the thrill of designing a new feature and the anxiety of filling a critical design leader role. This dual vantage point taught me that nothing matters more than bringing in extraordinary people. Below, you’ll find the insights I’ve collected along this journey: from why we need a fresh way to define job opportunities, to how we handle interviews, to the art of onboarding. My hope is that these thoughts resonate with every CXO tackling the ever-tough question: “How do we hire the best design leaders and help them flourish?”
Why Traditional Hiring Methods Hold Us Back
Let’s start with a blunt truth: making a hiring process more efficient doesn’t help if the process itself is flawed. When companies write unimaginative job postings that list cookie-cutter requirements, they’re less likely to attract the cream of the crop. And when they force talented people through clunky applications and robotic assessments, they risk losing the very ones who could drive meaningful transformation.
In many organizations, the system is designed to weed out weaker applicants rather than lure in standout individuals. All kinds of bias—plus manager desperation and uneven skill among those involved—end up determining who gets hired, instead of focusing on real achievements and future potential. It’s no surprise we’ve seen limited improvement in hiring over the past few decades when the process is still about ticking boxes rather than discovering brilliance.
The Scarcity vs. Surplus Dilemma
A core reason behind these mediocre outcomes is the mismatch between strategy and reality. If your company is swimming in applicants, a “weed out the unqualified” approach might squeak by. But if top design leaders are scarce—and they usually are—those same tactics won’t cut it. You’ll need a more personal, high-touch approach that draws in the most sought-after candidates, shows them the career leap you’re offering, and respects their time and expertise.
A Different Lens on Hiring: Focusing on Outcomes, Not Just Skills
My journey taught me that focusing purely on a laundry list of technical or soft-skill requirements isn’t enough to guarantee success over the long haul. What truly matters is what the person will accomplish in the first year and beyond. Does the role empower them to solve large-scale business issues? Are they going to lead pivotal initiatives, foster innovation, or coach future design stars? If they have done similar work in similar contexts—and delivered strong results—they’re far more likely to excel in your organization.
This mindset shift opens the door for diverse or nontraditional candidates who might not match every standard bullet point but have proven they can rise to the challenge when tackling related problems. Once you start defining roles by the impact you expect, you’ll discover people with varied backgrounds who can help you out-innovate your competition.
Bringing in Top Talent for the Long Haul
I’m a believer in hiring for the anniversary date—meaning you aim for success at the one-year mark, not just the day they sign an offer. By defining a small handful of big objectives for that first year, you’re setting the stage for a genuine partnership. It also changes how you source, interview, negotiate offers, and manage people post-hire because you’re all focused on longer-term gains.
Three Main Hiring Hurdles
1. High-Volume Positions
Organizations that need to fill large numbers of roles often default to an overly automated screening process. This is where technology can be useful, but it’s not a magic wand. If you blend automated workflows with clear, compelling job posts, you’ll still reach a wide pool—yet do it in a way that emphasizes quality over mere efficiency.
2. Bringing in Stronger Mid-Level Talent
When you’re seeking professional staff and middle managers, you want to raise the bar and hire people with room to grow. These folks typically have multiple options or aren’t actively hunting for a new role. Their interest comes from seeing a true career step forward, not just a bigger title or paycheck. Skilled recruiters can help connect with these individuals and show them why your role represents a genuinely meaningful advancement.
3. Strategic Leadership Appointments
Crucial leadership and technical roles can alter a company’s trajectory. If you need a design executive or an engineering visionary who will shape your future, you can’t rely on a cookie-cutter pipeline. You’ll need proactive networking and deeper conversations long before a formal offer goes out. The goal is to engage people who aren’t looking—and won’t be easily swayed—by demonstrating the influence they’ll have in your organization.
Outcome-Focused Recruiting: Making It Real
When I talk with executives about clarifying the job to be done, I encourage them to outline six to eight specific objectives they expect a new hire to achieve in their first year. This approach—often called an outcomes-driven or results-based approach—becomes the bedrock of your sourcing, interviewing, and onboarding. If you can describe the real hurdles a candidate will face and highlight the growth potential of solving them, you’re far more likely to get someone who’s not just qualified, but truly excited.
Defining these objectives should also address the managerial fit. If a design leader’s working style complements the hiring manager’s style, you get better results and stronger engagement. Once the team is aligned around how success will be measured, you’ll never have to scramble asking, “Who else can you send me?” after an interview. You’ll know precisely what ‘great’ looks like—and so will the candidate.
Concrete Hiring Practices That Raise the Talent Bar
- Write Job Descriptions That Inspire
Avoid dreary lists of “must-have” traits. Instead, highlight the challenges the person will solve and the broader vision they’ll be shaping. Show them the strides they’ll be making for the business—this is how you transform a lateral move into a genuine step up in their career. - Use Behavioral Interviews That Dig into Real Work
Structured behavioral questions are powerful for reducing bias, but make sure you’re asking about the candidate’s major achievements—especially those related to the objectives you’ve set. Doing so tells you if they can handle the actual work, not just talk about it. - Tie Strategy to Tactics
If you’re operating in a space where talent is scarce, invest in more personal outreach and deeper interview conversations. Strong referral networks, consultative recruiters, and genuine relationship-building matter in these cases. - Attract, Don’t Just Filter
When you post roles or reach out, stop using a “weed out the weak” mentality. Instead, think about how you’ll catch the eye of the best in the field. This might include more compelling messaging, talking about long-term career growth, or highlighting how design sits at the center of your corporate strategy. - Offer Clarity on the Non-Monetary Upside
I often advise telling candidates early on that their decision shouldn’t hinge solely on salary. Outline the “30% growth factor” that includes increased responsibility, more stimulating projects, better work-life balance, and faster multi-year advancement. Before extending a formal offer, ask them to articulate why they truly want the job beyond just pay. If they can’t, you probably haven’t fully explained the upside—or they’re not as invested as you’d like. - Onboarding and Early Success
Once your new design leader arrives, spend real time (in the first weeks, not months) clarifying the major objectives and how you’ll prioritize them together. This includes building a plan to tackle them in a sensible order. I believe setting clear expectations is the greatest strength any manager can have.
What Makes a Great Design Manager (and Why It Matters to You)
Over my years working with design teams, I’ve spotted three traits that set top design leaders apart. These insights come from my own past as a designer, as well as from coaching others through tough situations and big projects.
- They Tackle Problems Head-On
The best design leaders volunteer to fix broken critique processes or revamp inefficient workflows. They think about how they can have a “multiplier effect,” whether it’s smoothing out collaboration between teams or pushing the product roadmap to new horizons. They also excel at bridging silos—often spending more time with cross-functional peers (like product, sales, or engineering) than with designers alone. - They Think Horizontally Across the Organization
Exceptional managers see beyond the boundaries of their own team or function. They’re curious about what the sales director is up to and how pricing initiatives might reshape user interaction. They strive to connect dots in ways that benefit the entire company, not just their corner of the org chart. - They Create High-Trust Environments
For most designers, honest feedback is essential. Great managers build a climate where it’s okay to speak up, share vulnerability, or even break down in a moment of stress. They also have a reputation for drawing talent in—people outside the team often say, “I’d love to work for them.” They address performance concerns by first reflecting on their own management approach: are they setting realistic expectations, providing the right resources, or inadvertently creating churn with too many project pivots?
I’ve seen folks new to leadership (myself included) swing too far from micromanaging to under-managing. The fear of controlling everything can result in not giving enough guidance at all. If a design lead consistently delivers subpar visuals, it’s better to set up regular critique sessions or peer feedback loops instead of diving in yourself during every check-in. A few well-structured systems—like weekly design office hours—can help you strike the right balance between hand-holding and autonomy.
Interviewing for Design Excellence
When I’m helping organizations land a design leader, I like to break down the interview process into a few stages:
- Initial Chat with the Hiring Manager
This is where you confirm the candidate’s interests line up with your organization’s goals. If you’re making business software and they’re passionate about entertainment apps, that can be a tough mismatch. Be protective of your team’s time: only move forward those you genuinely believe are strong fits. - Portfolio Review
Pay attention not only to the visual polish or the usability but also to how the candidate tackled each problem. Did they describe their collaborators in product or engineering? Did they measure the success of their work? Did they face organizational constraints that forced them to pivot? If so, how did they manage those challenges? - Process & Collaboration Simulation
I often recommend a 45-minute whiteboard or brainstorming session with a product manager and a researcher. Watch how the candidate structures their approach, from identifying user needs to proposing quick prototypes. Strong candidates can lay out their process logically, collaborate with cross-functional peers, and handle unexpected twists.
Onboarding Your New Design Leader
I’ve found that onboarding has changed drastically with remote and hybrid work. New hires face complexity in learning not just your product but also your corporate culture—especially if they’re in a newly merged or rapidly expanding organization.
- Recorded Introductions & Knowledge Sessions: To help new folks get up to speed, record short videos on how each function operates, along with an introduction to key players.
- 30, 60, 90-Day Goals: Spell out what success looks like in the first quarter. Is the goal to revamp the design critique routine, or to improve the user interface for a high-revenue feature? Keep these objectives measurable.
- Encourage Personalized Exploration: Some new hires may map out the entire product flow to deepen their technical understanding. Others might hold interviews across various teams to build internal alliances. Give them the freedom to choose what suits their strengths and learning preferences.
- Letters from the Team: One practice I love is having each designer write a note to the newcomer—sharing tips they wish they’d known on day one. This personal touch helps build camaraderie and gives the new hire a sense of belonging right away.
Putting It All Together
As someone who’s lived and breathed design—from crafting wireframes to guiding top-level design hires—I’ve seen firsthand the transformative power of aligning the right person with the right role. When you define clear objectives, respect the candidate’s long-term growth, and build your hiring process around fostering genuine partnerships, you’ll bring on board not just employees, but catalysts for growth.
These ideas might seem like a big shift from how hiring usually unfolds, but in a world where design is becoming a competitive edge for so many industries, finding design leaders who can truly steer the ship is worth every ounce of effort. By centering on tangible outcomes, forging a high-trust interview experience, and onboarding carefully, you set up everyone—executives, teams, and the new leader—for shared success far beyond that pivotal first year.
If you’re a CXO struggling to fill a pivotal design seat, I hope this perspective helps spark fresh ideas. Hiring great design leaders isn’t simple or quick, but when done thoughtfully, it shapes the trajectory of your organization in ways no single prototype or sprint ever could. After all, the best decisions you’ll ever make often start with choosing the right people to help you build the future.rs is not simply a transaction. It is the strategic move that creates the foundation for enduring success.
