Why Most Design Hiring Fails (and How to Fix It)

Hiring great designers is one of the hardest challenges in UX leadership. On paper, a candidate might check all the boxes—solid portfolio, impressive resume, glowing references—but once they’re in the seat, things don’t always work out. Why? Because most design hiring processes are broken in ways that set both the company and the candidate up for failure.

Here’s what’s going wrong—and how to fix it.

1. Prioritizing Portfolios Over Thinking

A stunning portfolio is great, but it doesn’t tell you how a designer thinks. Too many hiring teams over-index on polished visuals without understanding the problem-solving process behind the work.

Fix: Prioritize case studies that show a candidate’s reasoning, constraints, trade-offs, and impact. In interviews, have them walk through a past project and focus on why they made certain choices—not just what they made.

2. Ignoring Team Fit and Collaboration

A designer doesn’t work in a vacuum. If they can’t collaborate effectively with PMs, engineers, researchers, and stakeholders, their work won’t drive impact—no matter how good they are individually.

Fix: Assess collaboration and communication skills. Ask about past experiences working cross-functionally. Consider a time-boxed working session where they solve a problem with your team to see their real-world approach. This does not mean give them a take-home assignment.

3. Overvaluing “Culture Fit” (and Under-Valuing “Culture Add”)

Many hiring managers unconsciously look for designers who feel familiar—people who match the existing team’s style, background, or personality. This leads to homogeneity and missed opportunities to strengthen the team’s perspective.

Fix: Instead of “culture fit,” assess what a candidate adds to the team. Do they bring a different way of thinking? A new skill set? A perspective your team lacks? These are strengths, not risks.

4. Testing for the Wrong Skills

Whiteboard challenges and design exercises can be useful—but only if they reflect the actual work the designer will be doing. Too often, hiring processes rely on hypothetical exercises that reward speed and confidence over depth and critical thinking.

Fix: Design exercises should be relevant to the role. If the job involves deep systems thinking, test for that. If it’s about rapid iteration, structure the challenge accordingly. Avoid unnecessary stress tests that don’t map to real work.

5. Lack of Clear Expectations for the Role

If you ask five different people on the hiring panel what they’re looking for in a designer, you’ll often get five different answers. Without alignment, you end up with an inconsistent and unclear hiring process.

Fix: Define success before you start hiring. What problems will this designer be expected to solve? What skills matter most? What will they be measured on? Get clear internally before assessing candidates. Each interviewer should be assessing specific skills of the candidate.

6. Not Selling the Role and Team

Great designers have options. If your interview process is all about evaluating them but not showing them why your team is a great place to work, they’ll go elsewhere.

Fix: Hiring is a two-way street. Be intentional about showing what makes your team unique, the kind of work they’ll be doing, and the impact they can have. Make sure they leave excited about the opportunity.

7. Relying Too Much on Gut Feel

Hiring based on “I have a good feeling about this person” is a fast track to bias-driven hiring mistakes. Your gut might be useful, but it shouldn’t be the primary decision-making factor.

Fix: Use structured interviews with defined criteria. Make sure every interviewer evaluates candidates against the same key skills and qualities. Balance intuition with evidence.

8. Failing to Provide a Good Candidate Experience

A messy or disorganized hiring process can drive away top talent. Long delays, unclear expectations, or lack of feedback all create a negative impression—and the best candidates won’t wait around.

Fix: Make sure your hiring process is well-structured, timely, and respectful of candidates’ time. Even if they’re not the right fit, leave them with a positive experience of your company.

9. Neglecting Onboarding and Growth

Hiring a designer is just the beginning. If they’re left to sink or swim with no support, they won’t reach their full potential—or worse, they’ll leave.

Fix: Have a clear onboarding plan that sets them up for success. Assign mentors, set early goals, and provide growth opportunities. Great designers stay where they feel supported and challenged.

Final Thoughts

Hiring the right designers isn’t about luck—it’s about having a process that identifies not just great designers, but the right designers for your team. You design team makeup should reflect your user base to ensure the types of solutions delivered are the types of solutions needed. By focusing on problem-solving, collaboration, structured evaluation, and a great candidate experience, you’ll build a stronger, more effective design team.

What’s been the biggest challenge in your design hiring process? Let’s discuss.

Read, Adapt, but Don’t Copy: Avoiding the Pitfalls of Blind Implementation

Don’t blindly implement what you read in a book

Books, frameworks, and case studies are valuable—they distill years of experience into actionable insights. But context is everything—what worked for one company, team, or industry may completely fail in yours.

🚨 The pitfalls of blindly applying a book’s advice:

Ignoring your unique challenges – A startup can’t implement the same processes as a 10,000-person company. A UX team in fintech faces different constraints than one in gaming.

Forcing a framework that doesn’t fit – Not every team thrives with Agile. Not every company should “Move Fast and Break Things.” Context dictates success.

Overlooking culture and team dynamics – Leadership strategies that work in one environment may backfire in another. A process that fosters collaboration in one team might create bottlenecks in yours.

Wasting time and resources – Implementing a system just because it worked for someone else can lead to overcomplicated workflows, disengaged teams, and solutions that don’t solve your problems.

✅ How to assess if a book’s advice will work for your team:

Is it a one-way or two-way door decision? A irreversible or costly-to-reverse extensive can be thought of as a one-way door. These decisions require deeper scrutiny—restructuring a team or shifting core strategy isn’t easy to undo. Two-way doors (reversible decisions) are safer to experiment with—if a new design critique format or sprint cycle doesn’t work, you can revert.

Does it align with your team’s size, stage, and constraints? A process that works for a company of 10 designers might break when scaled to 100. Instead, look for snippets that can plug into existing processes or ways of working.

Have you pressure-tested it against your company culture? Does the advice assume decision-making power you don’t actually have? Or, will it build a culture that doesn’t align to your business values?

Can you run a small, low-risk experiment? Before overhauling a workflow, try a pilot version with a small team. Gather feedback, iterate, and only then consider scaling. When things do go well, shine the spotlight on that team as a bright-spot in the company. This will help with change management over time.

☠️ But what if you’ve already implemented something, and it didn’t work?

Reversing a bad decision isn’t easy, especially if it’s hurt morale or trust. But there are a few different approaches on how to walk back a bad decision and potentially help minimize the damage without losing your team’s confidence:

1️⃣ Own the mistake—transparently. Acknowledge that the change didn’t have the intended impact. Your team will respect honesty more than defensiveness.

2️⃣ Share the “why” behind the reversal. Explain what you learned. Was it a misalignment with team needs? An unforeseen bottleneck? A cultural mismatch?

3️⃣ Involve your team in the next steps. Instead of dictating the fix, ask for input. What would they keep? What should change? This shifts ownership back to the team and builds a more collaborative, iterative culture.

4️⃣ Rebuild trust through action. Demonstrate that you’re listening. If you say you’ll iterate, follow through. If you promise fewer top-down changes, commit to it and make it so.

5️⃣ Make “experimentation” part of your culture. If your team sees decisions as learning opportunities rather than rigid mandates, they’ll be more open to future changes.

The takeaway:

The best leaders and designers don’t just follow advice; they adapt it for their context.

Read widely. Learn deeply. But always test before you implement—and be willing to course-correct when needed.

What’s a book or framework you’ve had to walk back after realizing it didn’t fit your team?

Escape the Swoop-and-Poop Cycle: How to Manage Up Like a Pro

Is Your Boss a Swoop-and-Pooper? Here’s How to Fix It.

Does your boss fly in, dive deep into an area outside their expertise, challenge your direction, push ill-formed ideas, then disappear—only to repeat the cycle later? Do they constantly ask for updates or bombard you with new ideas when you’re already swamped?

Yeah, we’ve all had these bosses. `It’s frustrating and exhausting. So, how do you deal with it? Pack your bags and pull the ripcord? Maybe—if the entire job (culture, environment, team, the problem you're solving) is toxic. But if the job is otherwise good, quitting over a meddlesome boss may not be the best move.

The Hard Truth: It’s Probably You, Not Them

Two things are likely true:

Your boss is invested in the outcome of your work. It’s tied to their strategy and, ultimately, their success.

Your boss answers to someone—their own boss, the board, shareholders, or other stakeholders.

This means they need to be confident in your ability to deliver on key outcomes and that they can adequately represent the value to their stakeholders. If they’re constantly buzzing in your ear, it signals a lack of confidence in your execution.

Put simply: your boss doesn’t trust you—at least not entirely. That doesn’t mean you’re unqualified, but it does mean there’s a gap in trust, understanding, or communication.

So what do you do?

How to Stop the Swoop-and-Poop

Your goal is to proactively close the trust gap. Here’s how:

1. Identify What’s Missing

What aspect is unclear to your boss? Is it the vision (how your work aligns with company goals)? The execution (confidence that work is progressing well)? The strategy (whether the plan is sound)? Understanding this will help you communicate effectively.

2. Provide a High-Level Plan

If your boss struggles with the big picture, create a high-level plan with clear milestones. Walk them through it and establish a shared understanding. Then, keep it updated as you make progress. This ensures they know where you’re going, how you’re going to get there, and reassures them that you’re on track.

3. Offer Proactive Updates

If they’re micromanaging the execution, it’s because they feel out of the loop. Solve this by regularly sharing structured updates. If your boss is asking for updates, you’re already behind.

• Maintain a running document with weekly or biweekly summaries.

• Include bullet points, key decisions, blockers, and progress highlights.

• Provide links to artifacts (docs, mockups, dashboards) to minimize back-and-forth.

4. Manage Expectations

Set clear expectations for when and how you’ll communicate. If they know they’ll get a detailed update every Friday, they’ll be less likely to swoop in mid-week with random check-ins.

5. Engage Them on Their Terms

Some bosses are high-level thinkers, others love details. Pay attention to how they process information and tailor your updates accordingly. Do they prefer concise summaries? Visual dashboards? Data-heavy reports? Give them what they need in the way they prefer.

6. Make Them Look Good

Remember, your boss has their own pressures. The better you equip them to report up confidently, the less they’ll meddle. Give them the talking points they need to communicate your progress effectively.

The Payoff: Trust and Autonomy

Once your boss sees that you’re proactively managing your work, keeping them informed, and delivering results, they’ll begin to trust you more. Over time, their need to swoop in will decrease, and you’ll gain more autonomy.

If you’ve tried all this and they’re still interfering? Well, then it may be time to consider other options. But in most cases, better communication and proactive transparency can turn a swoop-and-pooper into a supportive, hands-off leader.

10 Rules

Zach Lieberman is the co-founder of the School for Poetic Computation. He and his students explore fine art and design principles, using code as the medium, rather than paints or charcoal. In Zach’s talk at Adobe’s 99U 2019 conference, he showcased some of the amazing things he and his students are doing around designing with code. Fascinating things, but certainly outside of my wheelhouse. However, he shared a list of the ‘10 Rules’ by Sister Corita Kent and popularized by John Cage. I can’t believe this is the first time I’ve ever seen this list.

This list serves as a great reminder of key principles that can be applied in school, design, and even business. These rules will help you not take yourself too seriously, and remind you that everyone is an expert in something and you always have something to learn. 

As a design leader, there is a lot to learn from this list as well.

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Image curtesy of ArtStandardTime

10 Rules

1. Find a place you trust, and then try trusting it for a while.

2. General duties of a student: Pull everything out of your teacher; pull everything out of your fellow students.

3. General duties of a teacher: Pull everything out of your students.

4. Consider everything an experiment.

5. Be self-disciplined: this means finding someone wise or smart and choosing to follow them. To be disciplined is to follow in a good way. To be self-disciplined is to follow in a better way.

6. Nothing is a mistake. There's no win and no fail, there's only make.

7. The only rule is work. If you work it will lead to something. It's the people who do all of the work all of the time who eventually catch on to things.

8. Don’t try to create and analyze at the same time. They're different processes.

9. Be happy whenever you can manage it. Enjoy yourself. It's lighter than you think.

10. We're breaking all the rules. Even our own rules. And how do we do that? By leaving plenty of room for “X” qualities.
    
    HINTS:
    Always be around.
    Come or go to everything.
    Always go to classes.
    Read anything you can get your hands on.
    Look at movies carefully, often.
    Save everything. It might come in handy later.

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You can read more from Ms Kint in her book Learning by Heart: Teachings to Free the Creative Spirit.

Schedule Time to Focus

I have a fairly busy job as a director at a Fortune 10 company. I have a 12 person team, 9 major projects, three massive initiates for the year, and teams in three states and two countries. It got to be where my job was managing me. Here’s a look at a typical day:

6:00 am – Wake up, shower, feed the dog.
6:45 am – Leave to catch the train
7:15 am – Board train. Quick planning call with my team or sort email
8:15 am – Arrive at the office. Make coffee and get settled.
8:30 am – Process email
9:00 am – Meeting
9:30 am – Process email. Team is arriving, so I’m starting to field questions here and there
10:30 am – Meeting
11:00 am – Impromptu feedback with some of the team
11:30 am – Brief firefighting call with someone on my team
12:00 pm – Lunch
12:45 pm – Email meeting minutes and do a few other small tasks I signed up for from past meetings
1:00 pm – No meeting, awesome. Now… what should I do….
1:15 pm – Quick status chat with someone on the team
1:50 pm – Right, back to email
2:00 pm – One-on-one with someone on the team
2:30 pm – Meeting
3:30 pm – Catch up on email, and answer a few questions and provide a bit of feedback
4:00 pm – Meeting
5:00 pm – Catch the train home, wrapping up email or small tasks

Looking at that schedule, you’d think email is a primary initiative, right? Of course it’s not.

With such a fragmented day, I had no time to focus. The only thing I could complete in the short 15 minutes of free time was one or two emails.

My productivity went down, night-time working went up, and overall job satisfaction went down. Time to inflict some changes

Make Time for Work

First change I made was blocking out time in the morning and evening to do actual work. For this, that means creating repeating ‘Work’ blocks on my calendar. One wonderful-yet-terrible feature of Outlook is that it allows people to see your calendar is free so they can schedule a meeting. Similar to Parkinson's Law where work expands to fill the time available, the number of meetings will expand to fill your day if you allow it.

High Priority Work First

Now that I had dedicated time to work, I made sure to working on the highest-priority tasks first when I’m fresh and thinking clearest. I’ll fit the low-priority tasks in the small windows of time between meetings or in my evening work block. I use Things to constantly track tasks that need doing.

Plan the Day

The last thing I do (normally on the train) is review my schedule and to-do list for the next day. I choose the high-priority items and assign time-slots in my morning work-blocks for the next day. Now I relax for the night, knowing what tomorrow holds.

First thing I do when I start my workday is block my calendar for the day. I don’t accept any day-of meetings, unless it’s with my team or mission critical. This keeps me proactive throughout the day and keeps my plan mostly on track.

New Schedule

6:00 am – Wake up, shower, dog, train, etc.
8:00 am – Work!
11:00 am – Meetings, ad-hoc team feedback, etc.
2:00 pm – Every day I have a 1 hour one-on-one with someone on my team. Everyone rotates on a two-week cycle.
2:30 pm – Meetings, ad-hoc team feedback, etc.
4:00 pm – Work!
5:00 pm – Catch the train home and plan tomorrow’s work

Ahhhh, that’s better, right? Well, so far so good. I’ve only been doing this a month or two, but it’s already feeling better.