Ask an Expert
In Brief
Ask an expert is a generative research method where you consult someone with deep domain experience to uncover blind spots, identify industry-specific risks, and generate options you had not considered. You interview the expert, collect their recommendations, and use those insights to formulate testable hypotheses. The output is qualitative direction-setting, not validation — expert opinions still need to be tested against real customer data.
Common Use Case
You are entering an unfamiliar industry and need to understand the regulatory landscape, common pitfalls, and standard practices before designing your product. Rather than spending weeks reading, you want to have a focused conversation with someone who has years of direct experience in the space.
Helps Answer
- What is the standard approach or common assumption in this market?
- Am I missing an important part of the overall picture?
- What mistakes do newcomers typically make in this industry?
- Which areas should I investigate further before building?
Description
Experts provide deep insights into a particular problem domain, and provide useful input for problem types that are complicated according to the Cynefin decision making framework. These are problems with predictable but many factors, components, or pieces. There are many “known unknowns” that can be analyzed using cause-effect analysis to uncover a range of appropriate answers. Ultimately, founders need to be able to execute quickly, so piggybacking on others’ knowledge can serve as a useful shortcut.
Certain industries require significant expertise to compete effectively (FinTech is a good example). Finance itself is highly regulated and highly dependent on detailed models used for valuation, risk assessment, or accounting. Each of these are context-sensitive. While it’s possible to learn some of this from books, seeing how these play out in a competitive environment gives us extra insight. Some areas of finance have high degrees of product innovation, such as derivative markets. On top of that, technology itself has been changing rapidly over the past few decades. Founders entering this market would be wise to consult with experts in areas where they feel it will help generate additional options that they hadn’t considered.
Even in other contexts, quite often an expert will be able to view a founder’s situation in the context of many companies facing a similar problem. For example, if you are considering channel-testing around Facebook, consulting with a Facebook marketing expert can be a good use of resources.
As a general rule, though, using third-party expertise to evaluate existing options is an anti-pattern. Experts will view the situation through assumptions that may not hold up in the data.
LLMs like Claude, ChatGPT, and Perplexity have become a useful starting point for preliminary domain research. For complicated problems in the Cynefin sense — those with many known unknowns — AI can help you formulate sharper questions before you engage a real human expert, saving both your time and theirs. However, LLMs are not a substitute for genuine domain expertise. AI models can confidently present outdated information, miss critical nuances that only come from lived experience, and lack the ability to evaluate your specific competitive context. A real FinTech expert knows which regulations are actually enforced versus technically on the books, which investors are currently active, and which approaches have been quietly tried and failed — an LLM only knows what has been published about these topics, which is a different and often inferior form of knowledge. Use AI to orient yourself in a domain and find the right expert faster; do not use it to replace the expert.
How to
Prep
- Find an expert via free channels:
- Google or Bing: Enter specific terms or questions and look at who is publishing useful content on the topic.
- LinkedIn: Search by keyword, current title, or company to locate working specialists.
- Meetup: Tap local experts who present or organize on your topic.
- Academia.edu: Find researchers who specialize in a narrow topic and have published in it.
- Quora, Medium, Substack, or YouTube: Long-form public writing or video reveals depth and point of view before you commit a meeting.
- Your own sales team: Salespeople talk to customers daily and accumulate insight into objections, feature requests, competitive landscape, and lost-deal reasons. Treat this as secondary market research — one degree removed from a direct customer interview.
- Your own customer support team: Support staff hear directly about pain points, frustrations, and unmet needs. Their qualitative assessment of recurring themes can surface problems that don’t show up in quantitative data. For quantitative analysis of support ticket data, see Customer Support Analysis.
- Partners and suppliers: Key partners and suppliers can verify the feasibility of your approach, reveal hidden dependencies, surface logistics and scalability constraints, and provide cost estimates before you invest fully.
- Consider paid sources for vetted access:
- Clarity.fm — pay-per-minute calls with named experts.
- Intro.co — booked sessions with vetted operators and creators.
- GLG, AlphaSights, GrowthMentor — expert-network platforms ranging from enterprise to founder-priced.
- Industry-specific forums and trade associations.
- Reach out and arrange a call, video meeting, or in-person session. Be specific about the time you need and the topic you want to cover — vague requests get vague responses.
- Prepare a written brief before the meeting:
- Questions you want answered, ranked by priority. Lead with the highest-stakes one in case the call runs short.
- Areas where you want critical feedback on a draft, decision, or assumption.
- Topics you want to brainstorm, where you’re looking for options rather than answers.
Where the problem space is complicated rather than truly novel, an LLM can sharpen your brief before you spend an expert’s hour: it can surface terminology you should know, common failure modes in the domain, and the kinds of questions a working expert would expect a serious founder to ask. Tom Wujec’s “How to make toast” exercise is a useful reminder that even routine processes contain hidden complexity — drafting your own naive model of the domain first makes the expert’s corrections far more valuable.
Execution
- Conduct the meeting. Open with the highest-priority question. Take notes verbatim where you can — paraphrase loses nuance.
- Capture key ideas, recommendations, and any sources, frameworks, or numbers the expert cites. Distinguish what the expert claims from first-hand experience versus what they have read or heard.
- Ask for a referral to another expert in the same or an adjacent area. The second conversation is where you start to triangulate.
- Translate the learnings into a falsifiable hypothesis you can test with customers, not another expert. Expert input sets direction; customer behavior settles it.
Analysis
In general, it is best to limit yourself to experts who either
- Have personal experience (success or failure) in the topic area.
- Have gained significant insight through academic or journalistic research.
Keep in mind that all advice is context-dependent. Even if an expert was successful before, the situation and competitive landscape changes over time. And despite their best intentions, an expert’s advice might not be relevant to your specific case.
- If you take advice from anyone, make sure their interests are genuinely aligned with your own. Confirm there are no conflicts of interest that would affect the expert’s advice. It’s best to pay for impartial advice if you’re unsure.
- Free advice may or may not be useful. You often get what you pay for. Time spent executing bad advice is still wasted time.
- Some topics naturally invite strong opinions. Try to get access to data that the expert used to formulate their recommendations or advice, so you can evaluate its relevance.
- Independent judgment No matter how much advice you have collected, always think for yourself.
- Apply, don’t accumulate Information is plentiful; wisdom is rare. Ask experts to figure out what to test in your business, not just what to know (@LaunchTomorrow).
Learn more
Case Studies
Lemonade Insurance
Co-founders with zero insurance experience recruited Ty Sagalow (25 years at AIG) and deliberately sought “insurance insiders who were simultaneously outsiders.” Expert consultation shaped their regulatory approach, actuarial models, and product structure for what became a publicly traded insurtech.
Peloton
Before launching, Peloton consulted extensively with fitness industry experts and content licensing specialists. Failure to consult music licensing experts early led to a lawsuit from music publishers that grew to $300M in 2019 — a cautionary tale about the cost of skipping expert consultation.
Further reading
- Expert Financial Advice Neurobiologically “Offloads” Financial Decision-Making under Risk
- Find the Right Expert for Any Problem
- Got a wicked problem? First, tell me how you make toast
- Croll, A., & Yoskovitz, B. (2013). Lean Analytics. O’Reilly. ISBN 978-1449335670. — Frames expert input as a way to identify the right metric to test, not the answer itself.
- Alvarez, C. (2014). Lean Customer Development. O’Reilly. ISBN 978-1449356354. — Treats experts as one input among many; emphasizes testing expert claims against customer behavior.
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