Diagnosing & Trouble shooting sales as an early stage founder

by Whitney Sales

As a startup mentor, I’m introduced to a number of companies with ‘sales’ problems. To get to the root of these problems, I always ask the same three questions:

  1. What’s working?
  2. What’s not?
  3. What would you like to see more of?

I call this process diagnosing the problem. While these questions may sound basic, they allow me to get past the surface level issues and dissect what’s actually going on. Too many founders come to me with assumptions about what their problem is and the solutions they’ve come up with that aren’t working, rather than identifying the real problems and solving for those. I’ve found that companies almost always know how to find their real problems, but you have to start by asking the right series of questions. Then you have to take each answer and ask the same 3 questions above again and again until you get to the root of the issue.

Almost always, the sales ‘problem’ that the founder thinks they have is a byproduct of a problem earlier in the sales funnel that they haven’t yet identified. Think of a sales problem like joint pain, it’s rarely the joint itself that is the issue.  Generally, it’s the joint above where it’s connected to the body that you’re actually having the issue, causing pain to migrate down. Always look one to two steps in the sales funnel ahead of the problem for the solution.


  • iagoIssue in the Sales Cycle: Trouble driving customer urgency when it comes time to close an account. There’s clearly a need, but the customer sees it as a nice to have vs. a need to have.
  • The Real Problem: You’re pitching your product too soon without understanding what the customer’s problem actually is. You’ve profiled the customer using a customer profile to understand their problem without actually asking the customer themselves.
  • Solution: Make sure the customer explains their core problems before ever presenting as solution. This ensures the customer feels heard and is feeling the pain they’re describing before ever presenting your solutions

90% of problems in a sales conversation occur because salespeople make assumptions about a customer’s problems without letting the customer tell the salesperson themselves.


In order to properly diagnose your sales problem, you need to look at all the components that go into a particular result and figure out what’s working and what’s not for each piece. The best way to do this is to work backwards. It forces you to compartmentalize each step of your process and see where things went wrong in flow of the sales cycle

Diagnosing a sales problem is like trying to figure out why a tree in’t flowering. If the tree isn’t producing fruit, it’s unlikely that simply watering it more will make it do so. You need to look at all the factors that contribute to the tree’s wellbeing. A tree has a roots, a trunk, branches, etc.  It’s placement in the sun or shade, the health of its root system, the soil it’s growing in, and the surrounding environment. All of these things are factors of and contribute to the health of the tree and it’s ability to bear fruit.

Just like with trees, sales diagnosis and troubleshooting requires a step by step approach. You must ask the right questions to get to the right answers and drill down, test and repeat until you get the results you want.

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