Mike O'Sullivan

Crossing the UX Maturity Chasm I talk about “crossing the chasm” between low-maturity and high-maturity UX teams a lot, because it’s becoming one of the defining challenges of today’s job market. By my estimate, roughly 70% of designers are working in the long tail of low-maturity, feature-factory environments. This is where the lonely “design team of one” often lives. And that ratio is only growing, leaving more designers stranded on the wrong side of the market. The result is predictable: frustration and burnout for designers, and short-term thinking that quietly erodes long-term business value for companies. The problem shows up immediately when designers start applying for higher-maturity roles. You’re often competing with 1,000 applicants today. Even if only 30% of them come from high-maturity organizations, that’s still 300 designers who can easily demonstrate discovery work, research, metrics, and influence, simply because those practices were part of their day job. So I get asked all the time: “How do I explain my experience without sounding incompetent?” As a hiring manager, this is where I start probing: Did you run quick hallway tests? Did you sanity-check designs with friends or family? Did you use data or secondary research to influence decisions? Those answers matter. But in this market, they’re often still not enough on their own. What separates candidates is not how well they explain the system they were stuck in, but how clearly they show that they outgrew it. That usually means picking a real project and running a mature UX process anyway. Treating it as a proof of concept. Demonstrating better outcomes for the business. Showing the influence you earned as a result. That’s a story about grit, leadership, and changing the trajectory of work. And that's how you leapfrog those high-maturity Designers who often can’t tell these stories. They’re used to having research, discovery, and support built in. They’ve never had to fight for it. Cross that chasm!

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Smart design leaders do one thing before buying AI enterprise tools. The rest waste millions on digital dust. This week I spoke to a switched-on design leader from a traditional organization. Instead of jumping into vendor demos, they said: "I want to understand what's possible before we commit to enterprise tooling." That's when I knew they got it. All smart design leaders understand: An AI workshop helps them make better long-term decisions. Here's what strategic leaders do before any supplier relationship: 1. Frame the real problem first. Get your team in one room. Use AI workshops to extract all their thoughts, opinions, biases and challenges in one focused session. Most orgs skip this step and wonder why their expensive AI tools sit unused. 2. Experience AI live, don't just talk about it. I regularly use AI during my AI workshops. Clients get hands-on with live models. The moment they see AI analyze their actual challenges in real-time? Game over. They finally understand what's possible. 3. Independent research beats vendor pitches. Suppliers will sell you their hammer for every nail. Independent consultants who know their stuff? We run deep research with 3 different AI models (Perplexity, ChatGPT, Claude) to see what they recommend for your specific challenges. Usually it's a mix of buying off-the-shelf and custom tooling. 4. Custom vs. off-the-shelf reality check. Building custom tooling is easier than people think. Maintaining and scaling it for 1000+ concurrent users? That's where teams die. If someone's telling you not to buy Dovetail, Indeemo, TheyDo, or Mural and instead build everything in-house... run. Enterprise SaaS is a different beast than "vibe coding" a v1. 5. Look inwards before you look outwards. 9/10 of your colleagues are already using some shadow AI setup with unsanctioned solutions. They're getting results. Ask them: "What have you heard works/doesn't work for our challenges?" No reprimands for shadow AI use while you figure out your strategy - just make sure no private data gets inputted. 6. Controlled trials beat vendor demos. Don't race to install AI everywhere. Whittle down your favorite tooling contenders and pit them against each other in a 30-day controlled experiment. Real data beats sales presentations. The result? The smart leaders get clarity fast through AI Innovation Sprints. They don't just avoid costly mistakes - they get a strategic roadmap with actions and owners that puts them ahead of their competitors. The bottom line: The cautious leaders who do their homework first? They're the ones who end up with AI strategies that actually work. While others are stuck with expensive tools that collect digital dust, the smart ones are using AI to transform how their teams work. Be the strategic one. Do the research first. What's your approach to evaluating AI before committing to enterprise tooling?

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Great article on the Wizard of OZ research method and how it can be a great resource for product design teams. https://lnkd.in/g2mRPWvs #design #productdesign #ux #research #designthinking #technology #innovation #ai #uxdesign

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Are IC enterprise designers unintentionally sabotaging their portfolios in this AI-obsessed market? If you’re a Product Designer updating your case studies… you’ll probably want to read this... I’m actively hiring two Sr-to-Lead Product Designers, and after reviewing a lot of portfolios recently, a pattern keeps repeating: 👉 Too many portfolios are leading with AI chatbot projects. Not sprinkled in… leading with them. Often multiple ones in the same portfolio as Case Study #1 and #2. Here’s the problem👇 AI chatbots are important, but they’re not the center of gravity for most enterprise / SaaS product teams. In the last six-nine months, many of these patterns are already shipped and commoditized. And now with agentic flows, the UI work becomes more about reviewing, validating, and confirming work AI has already completed behind the scenes. Which means… “Old school” multi-step, end-to-end product flows are still valid – with a twist. Because every IC job post right now is calling for “high craft” or “consumer-grade design” – it’s no longer acceptable for flows to simply “get the job done.” Hiring panels want to see refinement and polish in the final output.  Otherwise you’ll get the feedback we give far too often: “The design thinking is great… but the visual design is just… [sigh/meh]… not quite there.” Visual craft always matters. Everywhere. At every company. Whether D2C or B2B or Enterprise. So if you’re refreshing your portfolio, here’s my ask as someone hiring in this tough market: Don’t over-index on AI chatbots just because they’re hot right now. Show me your complex, nuanced, multi-stage flows—the kind that prove you can handle the real product work most teams need. Just make sure they’re polished (ie. That “high craft” buzzword again), intentional, and tight. Because that’s what will actually differentiate you in 2025 and into 2026. And now the proverbial 🔌: If you’re a high-performing Sr. or Lead looking to innovate in the HR and Comp tech space, holler at me in my DMs or Comments. Thanks! 🙏

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