Conducting Comprehensive Interviews

While scaling Asana and Dropbox from <$25M past IPO, I saw one big mistake over and over: hiring smooth-talking execs who crashed & burned in the weeds. The disconnect? Never actually testing for hands-on depth in interviews. As a leader who relishes being in the weeds of thorny issues, I've developed an interview technique to probe for other leader-executors: the Depth Method. I adapted this approach from NASA's Science Directorate launch readiness assessments. If it can prevent rockets from exploding, it’s got the power to help spot a BS artist in a suit. I wrote up the full technique in incredible detail for my good friend Adam Fishman’s weekly newsletter (link in comments), but here's the framework overview: 🗺️ Phase 1: Map the Territory Pre-interview prep. Start with universal exec skills (communication, culture, management). Talk to people who've graduated from the role. Create a checklist mapping what excellence looks like. ⚒️ Phase 2: Drill Down Relentlessly Each question builds deeper. Hiring for growth? Start broad: "Tell me about building a growth model." Then deeper: "How'd you get the data?" Deeper still: "What broke?" Keep drilling until they hit bedrock or BS. Do this in 3-5 areas. 🏄♂️ Phase 3: Surface and Assess Look for Knowledge Boundaries (where they max out) and Expertise Signals (where they shine). You're not looking for someone who knows everything, you're identifying if they know their limits and where they'll need support. Beware the Common Pitfalls: - Overconfident delivery: executives are trained for smooth delivery. Don't confuse polish with depth. - Conversation redirects: press-trained pros know how to pivot when they hit limits. Stay on target. - Time: give yourself 45-60 minutes or you won't reach the depths. - Preparation: without a thoughtful checklist, you'll chase SQUIRRELS! (see the newsletter for this reference 🐿️) The full method, with actual interview scripts and depth-testing questions, is in Adam's newsletter below. Drop any thoughts or adds to this approach below: I’m always looking to hone the tools used to build and lead…

Most interviews stay surface-level. You get polite answers. You get user stories. But you don’t get the kind of thinking that changes roadmaps. Here’s what most researchers miss: Every question triggers a type of thinking. If your question is basic, the answer will be too. Bloom’s Taxonomy breaks cognitive effort into 6 levels and the best UXRs shape their questions around them. Here’s how to spot which one you’re aiming for (and what to ask instead): 𝗪𝗮𝗻𝘁 𝗿𝗲𝗰𝗮𝗹𝗹? 𝗔𝘀𝗸 𝗳𝗼𝗿 𝗸𝗻𝗼𝘄𝗹𝗲𝗱𝗴𝗲. Great for timelines and habits. Not insight. ↳ “When did you last use it?” ↳ “Who was involved?” ↳ “Where were you?” Use when you’re mapping the what, not the why. 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆? 𝗔𝘀𝗸 𝗳𝗼𝗿 𝗰𝗼𝗺𝗽𝗿𝗲𝗵𝗲𝗻𝘀𝗶𝗼𝗻. Perfect for mental models, first-use tests, confusion points. ↳ “Walk me through how you would explain this to a teammate” ↳ “Explain what you think this does.” Use when you want to catch mismatched expectations. 𝗪𝗮𝗻𝘁 𝘁𝗼 𝘁𝗲𝘀𝘁 𝘂𝘀𝗮𝗯𝗶𝗹𝗶𝘁𝘆? 𝗔𝘀𝗸 𝗳𝗼𝗿 𝗮𝗽𝗽𝗹𝗶𝗰𝗮𝘁𝗶𝗼𝗻. This is real-world behavior, not theory. ↳ “Show me how you’d complete this.” ↳ “Tell me about what you did the last time X happened.” Use when you need to see the friction. 𝗪𝗮𝗻𝘁 𝗶𝗻𝘀𝗶𝗴𝗵𝘁 𝗶𝗻𝘁𝗼 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻-𝗺𝗮𝗸𝗶𝗻𝗴? 𝗔𝘀𝗸 𝗳𝗼𝗿 𝗮𝗻𝗮𝗹𝘆𝘀𝗶𝘀. This is where users break things down. ↳ “Describe what matters most when deciding.” ↳ “Explain where you get stuck.” Use when you’re mapping criteria and tradeoffs. 𝗪𝗮𝗻𝘁 𝘁𝗼 𝘀𝗽𝗮𝗿𝗸 𝗰𝗿𝗲𝗮𝘁𝗶𝘃𝗶𝘁𝘆? 𝗔𝘀𝗸 𝗳𝗼𝗿 𝘀𝘆𝗻𝘁𝗵𝗲𝘀𝗶𝘀. (my fave!!!) Co-creation starts here. ↳ "Tell me about a time when a tool or product really impressed you. Describe what made it stand out.” ↳ “If you’ve ever hacked together your own version of this, walk me through what you did.” Use when you’re in the generative zone. 𝗪𝗮𝗻𝘁 𝘁𝗼 𝘂𝗻𝗰𝗼𝘃𝗲𝗿 𝘃𝗮𝗹𝘂𝗲𝘀? 𝗔𝘀𝗸 𝗳𝗼𝗿 𝗲𝘃𝗮𝗹𝘂𝗮𝘁𝗶𝗼𝗻. This is judgment, reasoning, preference. ↳ “Talk me through what you would recommend.” ↳ “Explain why you chose that one?” Use when you’re surfacing what matters most. If your research isn’t getting deep enough, it’s not the user, it’s the question. Want to rewrite your interview guide using Bloom’s? I’ve made a cheat sheet with prompts for every domain: https://lnkd.in/eSuNdv_V

The key to designing powerful interview questions is to focus on cognitive patterns rather than past accomplishments. Research shows strong connections between certain thinking patterns and job success. For example: • Original thinking strongly predicts innovation ability • Intellectual independence correlates with leadership effectiveness • Perseverance consistently outperforms raw intelligence in predicting achievement These research findings demonstrate why carefully crafted questions matter. To develop your high-impact questions, focus on five cognitive domains that predict exceptional performance. Follow this formula to create questions that uncover thinking patterns, not just experience: 💡 Design questions targeting original thinking: Ask about problems candidates see that others miss. Format: "What [challenge/opportunity/trend] do you notice that seems overlooked by most people in [relevant context]?" This reveals pattern recognition and the capacity for novel insights. 💡 Craft questions probing intellectual independence: Encourage candidates to articulate contrarian but thoughtful positions. Format: "Where do you find yourself disagreeing with conventional wisdom about [relevant domain]?" This assesses courage and independent analysis. 💡 Develop questions that examine perseverance: Structure questions around specific obstacles that have been overcome. Format: "Tell me about a time when you pursued [relevant goal] despite [specific type of setback]." Focus on process over outcome. 💡 Create questions measuring intellectual flexibility: Ask candidates to describe evolution in their thinking. Format: "What important belief about [relevant domain] have you revised recently and what prompted this change?" This evaluates adaptability and learning orientation. 💡 Formulate questions exploring intrinsic motivation: Probe self-directed development activities. Format: "How do you invest in developing [relevant skill/knowledge] when it's not required by your role?" This reveals a proactive growth mindset. The most effective questions avoid hypotheticals and instead target specific behavioral patterns that reveal how candidates actually think and operate. That's how you can develop interview questions that identify true potential—uncovering the cognitive patterns that transcend resume qualifications. Coaching can help; let's chat.  Follow Joshua Miller #executivecoaching #interviewing #careeradvice

I've conducted interviews with hundreds of artists, entrepreneurs, and leaders throughout my career in music-tech research and education, and have had the opportunity to mentor several of my peers in the craft. What I've found is that the best interviews aren't just a series of questions and answers; they create a dynamic space for dialogue, debate, and discovery. They can spark new ideas, inspire new actions, and even change the way people think. After nearly a decade in the field, I've decided to do a public breakdown of my own four-part framework for conducting great interviews. The piece below — approx. 2,500 words! — covers everything from doing background research and preparing the right questions, to steering the conversational flow and following up. I pour my heart and soul into preparing for every interview. In line with my systems-thinking approach, around 50% of the work takes place before the interview even happens — i.e. deep background research on my subject, my target audience, and the wider landscape in which my subject is operating. It's more academic, and certainly more time-intensive, but has always served me well. The remaining 50% of the work is mastered only with time and experience: Framing the most salient questions as directly as possible, while leaving ample room for serendipitous insights and ideas to emerge in the moment. This is part of a series I'll be publishing on my website that gives a window into my process as a researcher and educator, in the hopes of paying it forward to peers, professional acquaintances, and present/future students (!). Especially in today's increasingly polarized and divided world, I feel that the deep, empathetic listening associated with great interviews is more important than ever. It can help us build bridges across differences, expand our own understanding of the world, and, ultimately, tell stories that matter. I'm curious if these tips line up with your own experiences as interviewers, and/or if there is any other advice I might be missing! #interviews #musictech #musicbiz #musicindustry #conversation #journalism #reporting

Turn interviews into two-way dialogues where you’re evaluating them just as much as they’re evaluating you—while naturally showcasing your strengths and encouraging the company to show you why the role is worth your time. 1. Shift Your Mindset: You’re Interviewing Them Too • Frame it like a collaboration, not a test. You’re both here to assess fit. • Remind yourself: “I bring value. I’m here to solve problems, not to beg for a job.” 2. Lead With Confidence, Not Just Compliance • Instead of passively answering questions, match each response with curiosity or a strategic question: • Q: “Tell me about a time you handled risk.” • A: “Here’s how I handled a vendor risk incident… How do you currently identify or escalate similar risks here?” 3. Prepare High-Impact Questions That Flip the Script Ask questions that: • Show your expertise • Make them reflect • Encourage them to pitch the role Examples: • “What challenges are top of mind for your GRC team this quarter?” • “What does success look like in the first 90 days—and how do you support that ramp-up?” • “What’s something you wish candidates asked, but rarely do?” 4. Highlight Value Without Overselling • Share relevant experiences as solutions, not stories. • Keep it short, confident, and focused on outcomes. • “In my last role, I built a scalable compliance program from scratch. I’m curious—do you see a need for that level of structure here?” 5. Use Strategic Curiosity to Get Them Talking After a solid answer, toss the ball back: • “Would love to know how that compares to your current approach.” • “Is that something you’re looking to improve here?” 6. Close with Confidence End the interview like a top-tier candidate: • “Thanks for your time—this conversation only confirmed that this could be a great match. What are the next steps?” • Or: “What’s something you’re hoping to find in your ideal candidate that we haven’t covered yet?”

----A COMPANY'S INTERVIEW PROCESS IS A WINDOW INTO IT'S SOUL ---- Are you respectful of confirmed interview dates/times, and the fact that the individuals have made accommodations in their schedule to discuss opportunities within your organization? Does your team take the time to prepare for the interviews, much the same as they would an internal leadership meeting? Have you invested in ensuring leaders are appropriately trained on how to conduct an effective interview? Are hiring leaders fully engaged during the interview, avoiding distractions (phone calls, texts, email, etc) whenever possible? If there is a potential unavoidable interruption that is foreseeable, it is important to provide the individual a heads up on the onset, and to apologize in advance if the meeting does get interrupted. Is the organization committed to selling itself to candidates in the process, much the same as it expects the individuals to sell themselves to it? Who might this individual become if they were join the company, that they cannot become in their current role, or at another organization? Are the leaders involved in the process aligned on the mission, vision & values of the company? Are the expectations of this role clearly established and consistently communicated throughout the process? What are the three most important problems this person will be tasked with solving? Has the expectation been set that the interviewers will provide prompt, and whenever possible constructive feedback? Have you eliminated any unnecessary stakeholders from the process? Consensus building with a bloated stakeholder committee is extremely difficult. Can you conduct a thorough process < 60 days, w/out compromising diligence? Great candidates seldom come on the market, and are scooped up immediately. Be prepared to act deliberately once the process has commenced. Is your offer process dynamic? Candidates have drastically different value centers. There are usually 7-8 different levers a company can pull in an offer. Talking to the individual about which ones they most highly value, and crafting an offer accordingly can really endear a company to the candidate, and signal a collaborative working environment lies ahead. There is a reason Steven Hankin of Mckinsey & Company coined the term "war for talent" back in 1997. Companies are engaged in a never ending, extremely expensive battle to acquire their most valuable and presumably prized strategic resource. Putting it's best foot forward in the interview process is vital to the engagement, attraction, and retainment of the industry's best and brightest. If you are not taking into consideration the issues above, you are not maximizing the firms opportunity to win this war.

How do you avoid hiring someone who interviews well but performs poorly? Most companies have the same hiring process: Review resumes. Conduct interviews. Check references. Make an offer. Then six months later, they realize the person isn't working out. The problem: interviews test presentation skills, not job performance. Here are three ways to hire for actual performance, not just interview skills: 1. Give them real work before you hire them. The best predictor of future performance is past performance (but in your context). Create a paid project or work sample that mimics what they'd actually do in the role. Need a strategist? Give them a real client scenario and ask for their approach. Need an operations person? Have them map a process and identify bottlenecks. Need a salesperson? Have them research your market and pitch a prospect strategy. This reveals how they think, work, and deliver under real conditions. Not how they answer hypothetical questions. 2. Ask about failure, not just success. Everyone has rehearsed stories about their biggest wins. But how someone handles failure reveals character and judgment. Ask: "Tell me about a time you made a significant mistake. What happened? What did you learn? What would you do differently?" Great performers own their mistakes and learn from them. Weak performers deflect blame or minimize the problem. 3. Assess cultural fit through scenarios, not questions. Don't ask "Do you work well in ambiguity?" Ask "Walk me through a time you had to make a major decision without complete information." Don't ask "Are you a team player?" Ask "Tell me about a time you disagreed with your team. How did you handle it?" Scenarios reveal actual behavior. Direct questions just test whether someone knows the "right" answer. Companies that hire A-players don't rely on interviews alone. They test real work, probe real failures, and assess real behavior. They make hiring harder upfront to avoid expensive mistakes later. *** What's your process for testing actual performance before you hire someone?

Director-level clinical development roles require a unique blend of expertise, leadership, and strategic thinking. As you prepare for interviews, it's important to be ready for questions that test your experience across these areas. Here’s how you can confidently approach some of the most common ones: 1. Tell me about a time when you led a clinical program through different phases of development. How to approach it: Reflect on specific programs you’ve led and walk the interviewer through the stages—from early-phase studies to late-phase trials. Highlight the challenges you faced at each phase, such as regulatory hurdles, patient recruitment, or timeline shifts. Don’t forget to mention your cross-functional team collaboration and how you balanced competing priorities like budgets and timelines. 2. What’s your experience with protocol development and clinical trial design? How to approach it: Talk through your hands-on experience designing trials. Discuss your role in protocol development, particularly how you navigated scientific, regulatory, and patient-centered considerations. Emphasize the key elements of trial design, like patient selection, endpoints, and safety measures, and showcase your ability to align scientific rigor with regulatory expectations. 3. How do you foster collaboration across different functions like medical, regulatory, and safety teams? How to approach it: Explain how you manage cross-functional relationships. Highlight examples where you facilitated communication, coordinated different teams, and ensured alignment across departments. Be sure to mention specific tools, strategies, or regular meetings you’ve used to ensure seamless collaboration and resolve conflicts when they arise. 4. Describe a time when you made a critical decision based on clinical trial data. How to approach it: Share a detailed example where clinical data led to a pivotal decision. Whether it was halting or advancing a trial or pivoting the approach, explain how you analyzed the data, assessed the risks, and communicated your decision effectively to stakeholders. This demonstrates your ability to make data-driven decisions with strategic foresight. 5. How do you build and maintain relationships with key opinion leaders (KOLs) and external partners? How to approach it: Focus on how you’ve built trust and long-term partnerships with KOLs and external collaborators. Talk about the importance of mutual respect and alignment on goals. Highlight your ability to listen, adapt, and leverage their expertise for mutual benefit, emphasizing your commitment to fostering ongoing collaboration. What interview questions have you faced in your clinical development career? Let’s hear about the ones that tested your skills the most!

Over the past year, I have designed and conducted interviews and focus groups with over 100 stakeholders across four client engagements at Angeles Impact Advising. Whether informing an organizational strategic plan or a specific initiative, these discussions provide insights that drive key decisions. Next week, three of my graduate student teams will present their final deliverables to their clients, leveraging these very same qualitative research methods. Gathering meaningful insights requires an intentional approach that deeply respects people's time. I have found that success comes down to a few critical steps: 1️⃣ Designing a thoughtful and rigorous interview or focus group protocol: This is a crucial early deliverable used to align on how to frame the need, the purpose, and the exact questions that are critical to ask. 2️⃣ Creating clarity upfront: The most important element of intentionality happens before the first question is even asked. I always start by clearly framing my role, exactly what I am seeking to learn, and how the participant's specific insights connect to the broader context of the project. Before beginning, it is also important to let the participant know how their comments will or will not be attributed, and allow them to ask any questions about the process. 3️⃣ Designing for tension and vision: Creating this clarity upfront removes the guesswork. It opens up a targeted, trusting space for stakeholders to dive right into two critical things: what they are currently wrestling with, and their vision or recommendations for the future. I am looking forward to seeing my students elevate their stakeholder and research findings and recommendations next week and continuing to do the same for my clients!

After interviewing hundreds of candidates, here’s what I’ve found truly works: Respect their resume. I read their resume beforehand and come in with a working understanding of it. I tell the candidate up front that I’m not going to walk through it line by line—I assume it’s truthful. That frees us up for a more valuable conversation. Set the tone early. Right after the greeting, I let them know: “If you see me looking down, I’m just taking notes—please feel free to do the same.” It immediately lowers the tension and encourages real conversation. Make it human. I start with them as a person. Not just their work history, but who they are, what motivates them, how they think. I weave in role-specific questions naturally throughout. It creates a conversation—not an interrogation. Skip the fluff. I don’t ask why they want the job—it’s obvious. I don’t ask about their “greatest challenge”—it’s subjective and unverifiable. And I definitely don’t ask what kind of tree they’d be—because, really, who cares? I’ve found that by approaching interviews this way, I can tell within the first two minutes whether someone is a fit. I get a sense of whether they’re a personality match—which is often the most important factor—and whether they have a solid enough foundation to succeed in the role.