Asking the Right Questions

One way to approach positioning is to ask the right questions

I know exactly how my ideal client will answer the 16 questions below. When they answer them the right way, I can guarantee them a successful engagement with me as a consultant.

I’d like you to design your own questions, as a future-positioning exercise. More on that below. But first, take a look and if you know this person, send them my way (:

  1. Do you pretty much always work from home?
  2. Do you tend to prefer video conferencing on initial calls, or after it’s been a while, but are you flexible other than that? IOW, do you just dial in from your cellphone sometimes?
  3. When someone asks you what you do, do you say entrepreneur?
  4. Do you understand how software and other technology works without being a technical person yourself?
  5. Have you created a venture leveraging some kind of emergent technology, such as AI, VR, cloud computing, or blockchain?
  6. Does the business model package this technology into a succinct product that you sell to businesses or HNW individuals?
  7. Is it at least your second business?
  8. Are you based on one of the 3 coasts of the US? (Texas/Chicago count as #3).
  9. Are you enthusiastic, engaging, laid-back, informal, fun-loving, and intrigued by your business?
  10. Do those qualities define you beyond work?
  11. Do you enjoy building valuable relationships with experts, whether as consultants, contractors, employees, partners, or just people?
  12. Have you assembled a small core team of 2 to 4 people?
  13. Do you completely delegate the work you do with consultants, partners, and clients – or are you hands-on with the ones that matter? 
  14. Does your new business need to say what it does better, to make it easier to sell?
  15. Do you want to invest 5-10k to make that happen?
  16. Do you make decisions quickly and with your gut? Or through analysis?

That’s my question set to them. Maybe you guessed the answers.

Now here’s my question to you: what 16 (or 15, or 20, or 10, or whatever?) questions will let you identify your absolutely perfect client?

Because your ideal client IS your future positioning. You want to position yourself as the solution best suited to work with your perfect clients.

Of course, these aren’t the questions I ask to help me understand a client’s strategic priorities.

And actually, I don’t ask them at all, most of the time. Because the most important things about a person, they can’t reveal to you, as I discussed last week in talking to/about black swans. You can ask a few questions, but you have to infer the rest.

In hindsight, these questions are easy to answer because you got to know someone when you worked with them.

But these questions are for someone you don’t know. Asking them is a matter of divination.

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First things first – how do you know what questions to ask?

I’ll share my exact process. I analyzed the 50 or so clients I’ve worked with over the past 2 or 3 years by transforming them from memories into a spreadsheet.

The columns of the spreadsheet look like this:

[client name]
My Profits
My Happiness
Client’s Happiness 
Company Maturity
Technical Founder
AI or Blockchain
Product or Service
Client Type [kind of like industry and/or business model]
Work Directly With Owner
Core Team Size
Client Personality
Top 5 Personality Traits
Client Score

I used the first three metrics – my profits, my happiness, client happiness – to calculate a client score. This is pretty common advice, often expressed with a Venn diagram. But those “choose your career” Venn diagrams only scratch the surface.

So then I added new metrics to look for patterns – and found plenty of interesting ones. Mostly they confirmed what I suspected, but some were entirely new realizations.

Some columns (“Technical Founder”) I added after a few days of reflection. And each time I did so, I was asking a new question of my memory of the client engagement. I simply asked the questions I really wanted to know or think about. I do better working with non-technical founders, despite the fact that I myself have a technical background.

If you do this positioning exercise, it should look completely different. There are different questions you need and want to ask. Ask whatever you want, let me know how it goes.