Gut Check Questions for Strategy

On the way back from Miami last week, I rode to the airport with an executive in the Open division of American Express. We started talking business and I could tell in about two minutes that he was pretty sharp. He told me about some bad decisions he has made (which usually tips you off that people are smart, because smart people learn from mistakes, they don't hide them) and about a list of questions he has built over the years to review before presentations or major decision-making "moments of truth." I was intrigued and asked if he would send them to me to share, so here are my favorites from the list. Feel free to add to it in the comments section with your own gut check questions.

  • What are the guiding principles which are helping inform or drive your recommendation? If we agree on the principles, we'll problemably agree ultimately on the specific recommendation; if we disagree on the principles, the recommendation is likely going nowhere.
  • What are the success metrics? What's our rollout strategy if we hit them?
    What's our exit strategy if we don't?
  • What are the go/no-go points? sort of like an exit strategy question, it's a
    critical one to think through in the case of multi-phase projects
  • What does "disaster" look like in this situation? How would we handle it? In
    some situations, disaster can actually mean a wildly successful initiative
    — for instance, if we drastically underestimate the number of customers who
    call in to take advantage of a promotional offer, could we handle the call
    volume? I love the counterintuive aspect here… people miss that too often

  • What are the non-negotiables of an initiative vs. the nice-to-haves?
  • Does this initiative provide a large-scale solution or is it a
  • How's this look vs. what the competition is doing?
  • Can we take advantage of this initiative across other business units? Another one I love because I think people miss this too often
  • When talking in ratios or percentages — what's the numerator and what's the
    denominator? It's easy for a low number to have a huge % increase
  • What would you say the effort has been on this initiative, scale of 1-10? If
    less than 10, why? If 10 and we haven't been successful yet, what do we need
    to do differently to be successful?
  • What are the key units/metrics we should be looking at? As an example, at a
    certain point in a product's lifecycle do we need to keep our eyes more on
    new customer growth or on growth of the existing customer base? And what are
    the drivers of each of these?
  • If we only give you 50% of the funds you're asking for, will you only give
    us 50% of the results you're promising or can you use the funds more
    efficiently? frequently asked to get at the "biggest bang for the buck"
  • How does this initiative drive desired outcomes? Going back to question #1,
    if we're highly focused on bringing in new customers, how does this
    initiative help us do that?
  • How is what you're proposing differentiated from the competition? From our
    other existing products/services?
  • How assailable is your source of differentiation — that is, how
    easily/quickly can competition copy it?
  • Does the story "hang together?" That is, do the key metrics all move in the
    same direction? Do initiatives proposed all seem to be prioritized
    appropriately and match up well to strategy/identified needs?
  • So there you have it, a nice chunk of wisdom accumulated from American Express executives over the years. When evaluating a project or making a presentation, ask yourself these tough questions. Make sure it "feels right" before moving forward. It's better to find out for early (and privately) that something is wrong with your strategy instead of waiting until you have poured significant resources into it and your competition can watch you fail.