Mentors 1/18: Be Socratic

Since today is the first day of the new Techstars Boulder program, I figured that it’s time to get rolling Deconstructing The Techstars Mentor Manifesto.

My goal with this series of posts is not to get the detail right, but to flesh things out and get your feedback. So please comment on anything and challenge everything to help me get it better.

First up (of the 18 items) is “Be Socratic.”

If you think “be socratic” means “ask questions”, you are partially correct. When David Cohen was crafting the mentor manifesto, it was obvious to start with “be socratic” since such a key part of the Techstars mentor process is to ask questions. But it’s not just the act of asking questions, it’s how you ask questions, what you try to accomplish with the questions, and what your responses to the answers are.

The “how” is important. As a mentor, it’s easy to establish a 1-up / 1-down relationship with the entrepreneurs you are talking to. In most cases, you start that way, especially with first time entrepreneurs. However, your goal should be to create a peer relationship, where the mentee learns from the mentor and the mentor learns from the mentee. As a result, tone matters. A lot.

The cliche “there are no stupid questions” applies. Body language matters. If you – as the mentor – don’t understand something, ask a question. You don’t have to show the mentee that you are smarter than her. You don’t have to establish your credibility – you already have it.

While one of your goals with these questions is to learn more about the company and the problem you are exploring, recognize that if your engagement with the mentee is a one-way Q&A session with no clear goal, your mentee will only be getting part of the value out of the experience. Use your questions to guide the discussion, presumably toward testing hypotheses you might be developing in real time. Be explicit about these hypotheses as you are testing them and try to show your thought process through the questioning. This can be subtle, where you just guide things along, or it can be explicit, where you state your hypothesis and then start asking questions.

Your goal should not be to come up with the answer and state it, but rather to help the mentee reach the answer or a set of new hypotheses she can test. This is a collaborative process, especially if you are trying to develop a peer relationship. It won’t happen comfortably in your first interaction, but after a lot of time together you’ll find you are learning from each other during the process and reaching a better set of answers, or at least new hypotheses to test.

In the same way that how you ask the question matters, how you respond to the answers matters just as much. The corollary to “there are no stupid questions” is “there are no stupid answers” and it’s just as important to realize that. For most people, answering questions in real time, especially when you are getting them from lots of different directions (as in multiple mentors over a short period of time) can be intimidating. When a person hasn’t thought deeply about the answer to a question, or hears a new question for the first time, the answer often doesn’t really address the question.

When this happens, just ask “Why?” If you’ve never heard of 5 Whys it’s one of the most brilliant things I ever learned about getting to the root cause of any issue. The example in Wikipedia is wonderful, since it reminds me of Zen and the Art of Motorcycle Maintenance.

The vehicle will not start. (the problem)
Why? – The battery is dead. (first why)
Why? – The alternator is not functioning. (second why)
Why? – The alternator belt has broken. (third why)
Why? – The alternator belt was well beyond its useful service life and not replaced. (fourth why)
Why? – The vehicle was not maintained according to the recommended service schedule. (fifth why, a root cause)

What matters here is the root cause. And that’s what you are trying to get to with your questions. So don’t dismiss the first answer – keep digging. And use the third answer to set up a few hypotheses because at this point you are actually getting into the meat of the discussion.

The goal is not to end up with the definitive answer to the questions. Rather, you are trying to use the questions to set up a new set of hypotheses to go test. You are at the beginning of a long arc of inquisition – use being socratic as a continuous process to try to find answers.

  • Paul Barrett

    Brad, you’ve hit the nail on the head, both in how to ask questions and how to listen. Often the entrepreneur will ask a question, but it ends up not being the one they really need an answer to. The 5 Why’s is a good start, and entrepreneurs with mentors who follow that course will often feel the inquisitive hypothesis forming approach is frustrating, but in the end, you are not only helping to determine what the right question was, but also teaching the rigor needed in the learning/discovery process. After several iterations of this type of interaction, it is rewarding to hear the mentee follow their own logical path as they search for answers, and begin to ask for your feedback on the answer they’ve already arrived at!


    I taught computer classes for years and I always think about it this way: “When I walk away will the person be able to get things done on their own?” The first thing most people think is I provide the steps needed to complete the work. But that’s not the case. I provide the steps needed to figure out the steps needed to complete the work.

  • “When a person hasn’t thought deeply about the answer to a question, or hears a new question for the first time, the answer often doesn’t really address the question.”

    This is a really good insight. Sometimes when you’re drinking from a firehose you don’t have time to catch your breath. When asking in-depth/brainstorming questions I always stress that they may not know the answer to them now and in any case the answers may even lead to a dead end. They don’t have to answer just for the sake of answering.

    • The answer, “I don’t know the answer” remains a really good answer!

  • Yep, why is google so quick to give you results, rather than asking why?

    • Hah – brilliant!

  • So…I was waiting for you to end by saying there are 2 possible outcomes resulting from a Socratic inquisition: a) you either help the entrepreneur find better hypotheses, or b) you help them identify and eliminate those that lead to contradictions. Right?

    • Yup.

    • There are 10 possible outcomes, which seems like a lot unless you know binary.

      • what are they? that’s a good follow-on post.
        Maybe a separate post topic for Brad – Outcomes of a mentoring session. What’s next.

        • Good suggestion to wrap into what I’m writing on this.

          • Great. I’ll email you about a couple of them on my mind, because I have been self-conscious about the outcome and follow-ons after each mentoring interaction I have recently had.

  • just saw this come over my twitter feed. Peter Drucker’s tips

  • Jeez, when I first read that your first point was “Be Socratic”, my heart leaped being an enthusiastic Plato fan. However as I continued to read, I started thinking, you’re telling them to be Socratic and all that means is ask questions? There’s a little more there that is probably even more useful…

    • Sometimes the beauty is in the simplicity.

  • David Cohen

    It amazes me how many people still don’t know about 5 whys. after i apply it to them, they are often amazed at the discovery of the root cause. strangely, it’s almost always on why #4 or #5, which shows just how far and non-obvious (to the person being questioned) the symptom of the problem is from the cause of the problem.

    • We should make sure we always teach it in the first week of Techstars.

    • David (Brad) –

      I am still struggling a bit with the 5 Whys for Fit4IT (see above). Getting fit is hard, sitting on the couch is easy (basic Anthony Robbins stuff 😉 The conclusion I come to through the 5 Whys is that you need to make it fun and easy for people to get fit while providing effective motivation and social support. Am I getting this right?

      • Use the 5 Whys for deeper stuff. It’s helpful at the high level concept (e.g. for the company) but it’s especially powerful when you are drilling into root cause on an issue.

        • OK. I am getting it:

          Why? social fitness
          Why? because people stick to diet / exercise with a support group
          Why? social support provides accountabilty
          Why? because your peer / support group knows when you are on/off-track?
          why? because you share your progress with your support group

          …. this probably could either use more granularity, or whys, but I am feeling the power.

  • Michael de la Maza, TS mentor

    A key to asking questions in a way that does not create a 1-up / 1-down relationship is to ask the questions from a place of non-judgment: “The major barrier to mutual interpersonal communication is our very natural tendency to judge, to evaluate, to approve or disapprove the statement of the other person or the other group.” – Carl Rogers

    • Yup. Well said. Also, instead of asserting what to do, you can say “from my experience” or “I’ve experienced …” Eliminated the judgement.

  • Brad –

    Thank you for sharing the ‘5 Whys’. This has taught me that when exploring problems I often may not go deep enough.

    Applied to my field:
    1/3 of the World’s Population is Obese or Overweight
    Why? dieting / exercise is harder than doing nothing
    Why? dieting / exercise takes work doing nothing requires no work
    Why? fattening foods taste good / exercise requires exerting energy
    why? people naturally tend to take the easy path
    why? they do not have enough motivation
    why? they do not have the enough support

    I am not sure I did this right – any suggestions?


    • Solid. That would lead you to exploring what kind of support they need, and why they need it. This is at the basis of what Retrofit ( does!

      • Thanx Brad. I like Retrofit. Retrofit is correct, getting fit means changing your lifestyle; diet and exercise habits. Having a personal diet coach and good tracking devices, like Fitbit, can provide the motivation, and accountability, it takes to get fit.

      • A recent Neilson study stated ‘Social interaction is a big motivator for consumers who want to get healthy — 49 percent of respondents said their family and friends were the most helpful for staying motivated.’ This is what Fit4IT does well. Fit4IT makes it fun and easy to get fit with friends and family while earning rewards. Fit4IT and Retrofit are very complimentary and both excellent tools to help people get and stay fit.

  • My rabbi opined years ago, “Answers are easy, it’s the questions that are hard!” The quality of the student is therefore revealed by the quality of their questions. 5-Why thinking leads to quality, actionable questions.

    In the Process Triaging protocol, before we apply the 5-Why’s we begin with a ‘Process Capability Goal” or PCG. The PCG translates the Executive Voice’s EBITDA+ objective into what a highly repeating process must be capable of performing. For example — using one of Brad’s favorite company’s products — the Sphero robotic ball-toy, the CPG for the ‘Point-of-Sale Ordering Process’ would be something like ‘Perform the Point-of-Sale transaction up to 1000 times/hour with zero payment method errors, shipping destination errors (etc., etc.) in one website visit, delivering anywhere in the world”

    “What is the CPG?” is a question that, tactically, sits between the firm’s financial objectives and what process performers must be able to deliver. IOW, a process point-of-pain is any measurement of a behavior that inhibits the CPG, such as ‘# (some number)% of Sphero POS transaction attempts fail” That observation matters because it clearly reveals the CPG is not being met. Crafting exquisite CPG’s gives business model implementers — ‘managers’ the handle they need to make financial (and other strategic goals) actionable.

    Now, one can ask the 5-Whys with confidence that solving the root cause matters to EBITDA (and all there wonderful other goals and values sufficient cash flow pays for).

    Extra credit: At the end of your 5-Why interrogation, what one does to remedy it root cause will begin with one of four verbs (or their synonyms): Analyze, Design, Train and/or Enforce ‘X’ — and that ‘X’ is expressed in another famous acronym, ‘SMART’ — something Specific, Measurable, Achievable, Relevant (made so because the point-of-pain hinders the CPG), and Time Bound.

    Love the blog, Brad!

  • Buffalo Entrepreneur

    I appreciate, and use, the 5-Whys method. It’s simplicity draws attention, and it is a very useful to get to root cause as it drives towards quantitative answers. And yet focusing on just one aspect of Socrates methods minimizes the true nature of a mentor. A mentor (as Socrates understood and practiced) must not only seek the truth (root cause) but he/she must seek the virtue that underlies that line of questions/answers. Put in less stilted language, a mentor seeks to understand what lies within their mentee, what drives their decisions, what causes them to ignore reality, or over emphasize a personal belief to the detriment of their efforts. Without understanding how the virtue explains the truth, the quantitative answers may satisfy for awhile, but eventually the mentee drifts back to where they operated before. A mentor is about the “care and feeding” of an entrepreneur, not just the person who asks the tough questions.

  • Saw an interview with Mitch Lasky once, where he said the only thing that makes him a good investor is that he likes to ask lots of questions.

    • Ironically, that also is what makes a bad investor. Specifically, Mr.Socrates, the investor who ONLY asks questions, especially when they are non-substantive, random, or off the point. I’ve met many of these investors who ask endless questions, but never guide the entrepreneur anywhere with them. And, most importantly, never express a clear opinion on the answers, or their own answers to the questions in the context of what is going on.
      So questions are good, but they aren’t the only thing necessary to be a great investor.

      • I’ve met Mr. Socrates many times. He is insufferable. Thanks, Brad, for pointing that out.



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  • I was waiting for you to end by saying there are 2 possible outcomes resulting from a Socratic inquisition: a) you either help the entrepreneur find better hypotheses jenis bisnis rumahan , or b) you help them identify and eliminate those that lead to contradictions. Right?

  • The first question must be put to the mentor by the mentor. Questions such as, what motivates me? What adjectives truly describe me – for better or for worse? What words or phrases do I use repeatedly? What triggers me? You get the idea. By becoming conscious of one’s preconceptions (a process known as ‘bracketing’ in qualitative research), a mentor is able to see and assess a mentee more accurately.

  • ilusifar

    We should make sure we always teach it in the first week of Techstars

  • villiampeater

    That would lead you to exploring what kind of support they need, and why they need it. This is at the basis of what Retrofit

  • nime76

    I’ve met Mr. Socrates many times. He is insufferable. Thanks, Brad, for pointing that out

  • nime76