Constructive Devil’s Advocate: Rude Q&A

Nothing clarifies things quite like a hyperactive, all-knowing, all-seeing, real asshole of a devil’s advocate beating the living crap out of you.

(Cartoon by Andertoons)

Baseball players swing heavy bats before going up to the plate; acclimating to difficult working conditions makes it easier to hit the ball out of the park.

What’s the equivalent of the heavy bat for honing your skills at pitching your product and raising money for your company?

For years I’ve been a fan of Scott Berkun’s concept of Rude Q&A:

What would the meanest, nastiest, but smartest people in the world grill you on when you show your work?

A Rude Q&A is a list of questions [about your work that] you don’t want to hear.

When you’re contemplating an exciting new idea, you don’t want to hear questions that might contradict your concept.

And of course, that’s exactly when you need the biggest, baddest, smartest, devil’s advocate to challenge all your assumptions.

It’s not just about testing the mettle of your ideas, it also forces you to refine and clarify your marketing messages, your target customer profile, and your feature set. When you’re being grilled there’s no room for being generic about how you’re different from the competition, no leniency for not knowing exactly what customer pain you solve, and no clemency for wavering on your company values and what compromises you’re willing to make.

Scott goes on to explain just how unfair the questions need to be:

Make sure to include questions that are unfair or based on erroneous information. Reporters, clients, and the public all have their share of unfair questions and erroneous information, and you want to be ready for them.

These answers take more time as the responses need to be more polite and mature than the questions. They also need to carefully refute assumptions in the questions without being dismissive.

I love it; now we’re deep into “heavy bat” territory.

So how do you go about writing your Rude Q&A? Oddly, the hardest part can be coming up with the questions.

To get you started, I’ve assembled a laundry list of questions common to many startups:

  • Your biggest competitor just dropped their price to $0. How do you continue to justify your price point?
  • If your idea is any good, you’ll have competition from multiple players, both funded and bootstrapped, both smart and stupid, both large and small. How will you persevere?
  • If the economy stays bad for two more years, how will you survive?
  • The last thing anyone needs is another damn tool. What’s the overwhelming reason I should even bother looking at you?
  • Technorati reports one million new blog posts appear every day. Why should I read yours?
  • What are the top three features your competitor has that you lack? How do you address that today, and what are you doing about it in the next six months?
  • How can you call yourself an expert when you’ve only been at this for a year?
  • What are three tangible, undeniable ways in which your product/company saves more money than you cost and saves more time than you consume?
  • Truly great products and companies are rare, even when smart people are at the helm. What makes you think you have what it takes?
  • There are thousands of consultants who make the same basic claims you make: high-quality, on-time, on-budget, good service, happy customers. What makes you any different?

These are generic; you’ll need to come up with more specific attacks. For example, if I were defending this blog and answering the question about why anyone should read it, I would make the question more specific:

There are already too many blogs about startups, especially high-tech startups. Those blogs are far more popular than yours, their authors far more famous, and their advice is excellent. Smart Bear is a success but it’s nothing like the success earned by someone like Steve Blank. Why should anyone listen to you?

And here’s my answer:

I read those blogs; they’re great! But the world needs more perspectives, not fewer.

For every Jason Fried who says “simple design is better than complex features,” someone else needs to point out that they’ve (I’ve!) made millions with poor graphic design and too many features. For every Seth Godin who says a tribe of 1,000 followers is all you need, someone else needs to point out that it’s not true in practice.

The biggest reason to read is that my advice and perspective, while not a massive thought-revolution in the universe, is “unique enough” that I constantly meet intelligent, capable, thoughtful entrepreneurs who haven’t heard it before, haven’t thought of it themselves, and whose lives and companies are improved after they’ve heard it, even when they disagree with my point of view.

I know this because of the comments and wonderful emails I receive. As long as people keep saying that I’ve lifted a burden off their chest or produced invaluable customer feedback or prevented them from wasting time and money, or even if they just get a laugh, that’s my answer to why anyone should listen.

Don’t get discouraged if you’re not happy with all your answers. That’s a good sign — it means you’re being honest about the exercise and you’re not yet satisfied. Keep it in the back of your mind and look for answers while you forge ahead. Discuss the hard ones with other people to get more ideas.

This is all just another way of being introspective, but it’s a technique I’ve found to be particular useful.

Do you have more Q&A to contribute? Leave a comment!

17 responses to “Constructive Devil’s Advocate: Rude Q&A”

  1. Funny, in a sense we blogged about similar topics today although here you are definitely not backing down (which is fine). I guess my reaction to this is that you continue to demonstrate why you were (are) successful as an entrepeneur. You’re a good sales guy Jason, and I mean that in the most complimentary fashion. I understand you are very technically competent but so much of life is sales in an odd way and a lot of people struggle with this (you don’t seem to which means you are natural at it). You clearly show this in your last 2-3 paragraphs. And what is the ulimate trait of handling any situation like the one you outlined here: Be prepared. It is literally the hallmark of good sales and successful entrepeneurs. Excellent post, I continue to enjoy and benefit from your work.

    • You nailed it: Be prepared. Honestly beating yourself up is the best way to get there.

      I liked your post about conflict avoidance. Since you graciously didn’t promote it yourself, allow me:

  2. The one that really gives me heartburn is: What keeps you up at night?

    It’s such a loaded question that it sometimes throws people off. The right response is typically one and only one thing that you worry about that you are actively working on.

    Another one is: Tell me a time when you failed and what you learned.

    Answer this one with “I have never failed” is just a lie. We all fail and being honest about your failings will give you creditability as long as you have learned from it and are upbeat about it.
    .-= Jarie Bolander’s latest blog post: Both Sides of The Table: How to Not Suck at a Group Presentation =-.

    • So funny — yes I like the “When have you failed” question in interviews (or really, phone or email screens) and it’s amazing how many people will claim to never have failed, or their story of failure turns into how they did something right and it failed for external reasons.

      Agreed that “what keeps you up at night” is the right probe for customer development. Unfortunately phrasing it that way is strange and abstract enough that it often doesn’t extract the info you want. But yes, that’s what you’re trying to unearth.

      I’ve had some luck with: “Complete this sentence: I will lose my job if ….. Or: I might get a promotion if …..” If your tool/service can complete those sentences, you’re in a good position.

      • When I was asked a variation of this question, I answered:

        “Failure” is a charged word – it means many things to many people. For many, it means making the wrong decision. For me, failure comes from not learning from the decision one makes.

  3. I do this all the time – but it my head (yeah, I know it sounds weird)

    My devil’s advocate is really good – he knows exactly which questions I don’t want to hear.

  4. This is all great and I agree that really stretching your mind to come up with difficult and awkward questions is a fine preparation, but sometimes the best criticism comes from people who don’t understand what it is that you do – so, my advice on this would be to think about what your company does or the products it offers, and seek out the ignorant, the opinionated, the naive and the cynical amongst your friends and acquaintances – we all have ’em, so use ’em!
    .-= John Clark’s latest blog post: The iPad As Quorn =-.

    • I agree that those furthest from the project often make the best critics. They’re not caught up in the daily flow of your business or even your industry.

      However you also have to be careful about optimizing for the wrong audience. If your product is supposed to be wide-reaching customer-facing, then yes. But e.g. at Smart Bear one of the big features of our product is really tight version control integration. If you don’t know what version control is, I can’t explain why this is interesting briefly — and it doesn’t matter that I can’t because those people will never ever be customers.

  5. Jason –

    Thanks for this post. I’m not interesting in raising money, but this will be a good exercise for responding to objections by prospects. They’re more “well armed” with information than possibly anyone else. And — bonus — if you can respond appropriately to the questions, you win the sale!

    .-= Brian St. Pierre’s latest blog post: Data vs Code =-.

  6. Hi Jason, I found this post really useful, thanks. I’m off to attack myself with a big cricket bat :)


  7. Jason,
    Your post (and especially your answer) really inspired me. I will look at it from time to time during lower moments. Thanks for the morale booster.
    .-= E’s latest blog post: Puck In Sunny Beaches =-.

  8. What I would say is that there are a lot of popular blogs out there discussing the exact same things I am. This is true. Those blogs have much authority and that is excellent.

    What makes my blog or my stuff anything worth checking out is that I am not like them and come from a different perspective completely. I’m (compared to them) a nothing and have much else to offer on a completely different scale.

    I feel this is what you were going for. Either way, this is my answer.

    What do you think?
    .-= Eric’s latest blog post: Real Or Robot =-.

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