Locking in Success: The Wisdom of Talking to the Curmudgeons


So, feeling my oats, and being a hotshot 30-something in a Fortune 100 firm, I was running around with my hair on fire, with three major product programs, and doing my best to make sure they all “made it.”  I had just come back from a meeting when I received a message from someone I had seen around, but hadn’t taken the time to talk to.

I picked up the phone and called this person back…and am I glad I did.

It turns out that one of the components in our product would have been unusable as specified, and might have cost us months.  The surprise was that the part conformed to all the current best practices and looked for all the world to be solid.  Once “Nicole” had given me the hard won insight, I realized that she had just saved the program from a major setback.

Such is the contribution of the curmudgeon.  (I use the term endearingly)  

When you are leading a growth program in the strategy and testing phase (see my post here), one of the major sources of overlooked information is the team members or industry leaders that participated in the last hero’s journey. Particularly in tech, but other industries as well, teams form and disperse so quickly that very little learning is passed on to the next product or service team in the pipeline. With the current trends of short tenures and using highly-specialized contractors, this problem is going to get worse.

That makes their wisdom all that much more important and high leverage.

I got lucky that day, and received the information even though I hadn’t sought it out. The thing I can take credit for is that I never missed the chance again to seek out a thought leader as part of the planning process.

The surprising truth is they are usually more than happy to have a virtual cup of coffee with you if you take the time to be well prepared for the discussion.

How do I find them?

It turns out that most times they are hidden in plain sight – you just need to be looking for them.  There is a predictable career progression in most organizations, and looking one layer up, or one function over, you can often find those who led the last wave. If  you are in a small firm, you are going to have to work a little harder – but LinkedIn makes it much easier than it used to be. By carefully using search terms, you can find alumni of your firm or of the product.  Many times they have moved on to new firms in adjacent industries, or industry groups roles, and can be found via older records or notes.  If there have been patents or public presentations, check out who the inventors and presenters were.  Uncle Google is your friend.

What do I ask them?  Isn’t it a new time and challenge?

There are a couple of key lines of questions that will yield lots of information, and one that will not.  First the productive ones:

  • What were the toughest or most persistent problems in bringing the current favorite product or service to market?
  • Can you share how you were able to solve them?  (What you are looking for is transferable algorithms)
  • What piece of product or process know-how was critical?

Now for the unproductive one:

  • Don’t ask them to comment about the feasibility of what you are doing – ever.  You are in a far better position to apply the current tools to the solution than they are, even though they might want to help.  Things do change, and quickly, so you want to be curator of the hard-won wisdom, not testing your current solution.

How do I make use of the information?

  • If you gain critical insight, take time to triangulate before making a directional change.  Ask for two other people that were close to the action that you can “check in with.”  By the time you finish three conversations, you will have validated independent research to work with.
  • Build better testing vectors for phase II.  By knowing what the hard spots were, you will be in a much better position to design good tests to gain the knowledge you need.  Remember that NASA spent half its budget on testing – and good testing is the key to a successful launch in new space
  • Use these insights as one piece of your phase I due diligence.  It’s really important to gather as much as you can about the known unknowns, and by opening your aperture, you are reducing your blind spots in the reality discovery phase.

Asking those pioneers who have gone in front of your group is a key way to avoid getting blindsided unnecessarily on your way to developing your growth product or service. If you’d like to explore other ways to lock in success, drop me an email or give me a call at 847-651-1014.

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