Early Stage Startup Sales Maturity Health Check Checklist

Who’s ready for their health check!?

TL;DR: This is a “Sales Maturity Checklist” I evolved to help me be more efficient and helpful with my interactions with early stage organizations figuring out their go to market. Maybe it can help you with yours!

I end up getting a pretty consistent flow of early stage founders showing up on my doorstep (either themselves, or referred by investors) who want to “pick my brain” on topics of sales, product marketing, go to market, etc.

I’ve found these “brain picking” exercises can often be less than efficient, in that they typically happen synchronously, over coffee or a beer (or maybe a Google Hangout), without a helluva lot of structure, and thus end up ranging all over the map.

Moreover, by waiting until the actual meetings to get the most basic of context, you can end up in a situation where it becomes apparent, mid-meeting, that you actually can’t be helpful - they don’t have the problem that you can solve. And now you’ve wasted their time and yours. Ugh.

But even if it turns out that in the course of a brain picking episode, you can sniff out that they do have the problem you can help address, you’re now trying to provide feedback in real time, without the benefit of more holistic understanding of what’s going on.

It’s not optimal.

Qualification criteria and discovery questions to the rescue

To make these meetings more efficient, I’ve pulled together a set of qualification criteria and a “discovery” question checklist that I can deliver, ahead of time. A Google Doc that I can flip to someone, giving them edit rights, which they can fill out that gives me fantastic, rich context ahead of our meeting.

In my case, this happens to be focused on go to market maturity, so this is in the form of a “sales maturity health check” checklist. But you can imagine making one for other topics, as well.

This turns out to be extraordinarily helpful for:

  1. Characterizing to me that, yes, indeed, they do have the problem I can help solve. (Or, not! And then I can say “I’m not the droid you’re looking for. Sorry.”)

  2. Providing me context to use in the meeting. I now show up extremely well informed. Moreover, I can actually start the “meeting” ahead of time via Google Docs comments, asking for incremental context, providing feedback, etc. It’s awesome, and makes for insanely productive, targeted face to faces. Not to mention I can skim it again 15 minutes before the meeting to load it all back into my brain.

  3. Screening out tourists. People who aren’t willing to spend 15 minutes doing some homework ahead of time, but who apparently are more than happy to consume more than 15 minutes in back and forth email scheduling, and then 30 - 60 minutes of actual meeting time. Yeah, maybe #3 should actually be #1.

Anyway, the maturity health check is embedded below (such that if I update it, it’ll automatically be reflected here).

I realize that my use case (for making “do my buddy a favor”, potential advisory, and investment meetings more efficient) may not by the commonest case. But, turns out this health check can be used for other stuff too!

So far I’ve seen it be used:

  1. By founders / sales leadership to evaluate their existing go to market and look for soft spots and what they should be looking to fix next.
  2. By investors to audit / backcheck the sales maturity of their existing investments.
  3. By investors to do diligence on deals. Rather than relying on what information is in a pitch deck, this is a more holistic checklist.

There might be other use cases, but honestly, #1 is reason enough to push this out for folks. Enjoy!

Google Doc version here.


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