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Four Boxes Discovery Framework

When we outline the qualification-led sales process with founders, the first question we get is, “I understand what information we need to pass each gate and why it’s important, but how do we get that information from the prospect?” 

We want to introduce the concept of the four boxes for performing discovery and taking notes throughout the sales process. The four areas you’ll do discovery around are: 

  • The current state of the business 
  • The desired future state 
  • The required capabilities to get them from the current state to the future state 
  • The success metrics they’ll measure to know they’ve achieved this goal 

By following this framework, you won’t forget to cover a specific area and all your notes can be contextualized based on the box they occupy. It’s also easy to continually update this during the sales process and review it with the prospect to make sure you’re aligned. 

Here is what a blank version looks like going into a conversation.

You’ll ask your discovery and qualification questions going left to right, top to bottom. This flow should also align nicely with the discovery deck you walk the prospect through. 

At a high level, these are examples of the questions you want to ask/answer for each box as you progress through the sales process.


Even though it's listed as a unique stage in the sales process, discovery never stops when working with prospects. Your goal should be to always leave every interaction with them (live or async) having added value and having learned new information about their problems, their ideal outcomes, their process, etc. If you leave a conversation with a prospect and after 45min-1 hour you barely learned anything about their current state, you’re probably pitching. 

The key to great discovery, aside from preparation, is genuine curiosity about the prospect/company's current state, why they do things the way they do, what could be better, where they want to go, what would it take for them to get there, and how will they measure success to know they’ve achieved their goals. 

Below is a quick overview of what you’re looking to uncover in each of the four boxes. 

Current State

The current state is all about understanding how things are today for the business, the team, and the individual prospect and what negative consequences (problems) have arisen as a result. Negative consequences should always be quantifiable (money, time, customer count, market share, etc). 

You’ll start by learning about the person or team you’re speaking with. You want to understand what they were brought on to achieve and how that’s going. Reference the questions we’ve outlined in the section on Interviewing Innovators to get the most value here. Then, you’ll want to hunt for instances where there is pain around a process or outcome that your product solves, and how the negative consequences are impacting them, their team, and the business as a whole. 

The best outcome for the current state is discovering that the prospect agrees with your paradigm on how their workflow could be improved, has a pain which is causing quantifiable negative consequences, and they have a compelling reason and timeline to solve it.

Design partners probably agree with your paradigm on how their workflow could be improved or they wouldn’t be design partners so you’re likely focused on the last two criteria. For example, you’ll want to uncover if any of the following are true.

Example Quantifiable Negative Consequences:

  • Missed revenue opportunities of $X
  • X% of customer churn, resulting in loss of market share 
  • Capital/operating expenditures over budget by $X 
  • Lost productivity resulting in estimated loss of $X potential revenue
  • Time-to-release taking an average of X, which is Y hours/weeks/days delayed

Sample Questions

  • Walk me through the current process for X. How long does that take? What would you be able to achieve if that time was cut in half or reduced altogether?
  • What’s keeping you from achieving that? 
  • Help me understand the importance of X? Who else in the business cares about this? How do they measure it? 
  • Given the choice, would you rather your team spend their time on X or Y? What higher value tasks could they tackle if they had that time back? Why those? 
  • Which tools do you rely on to complete your workflow? What’s the hardest part about using them? Is this your ideal workflow, or are you actively trying to enhance it?

Current State Goals:
  1. Where does the person/team sit in the org chart?
  2. What is their focus for the next 6-12 months?
  3. What does their workflow look like?
  4. How are they measured?
  5. Are they experiencing quantifiable negative consequences that we solve?
  6. Is there a compelling reason to solve these problems now?

Future State

Now that you’ve got an understanding of the current state and what's broken, it's time to transition your discovery to what an ideal scenario would be. 

The future state allows the prospect to step into the hypothetical where their current problems and the negative consequences they cause have been solved. These potential positive business outcomes also need to be quantifiable, and you’ll need to press for those numbers to make sure it’s something the business actually cares about. What gets measured gets managed! 

Sample Questions:

  • Describe the impact to the business if you were able to achieve X. How would you measure that?  
  • How could your team enable your company to get an advantage on the competition?  
  • How would you like to spend your time if X wasn’t an issue any more? What gains could you recognize as a result? 
  • How might you reinvest the budget currently spent on operational overhead (infrastructure, FTE’s, redundant platforms) if those tasks could be delivered as a service?  

When talking to prospects about their ideal workflow, process, and outcomes make sure to always ask second and third-level questions to verify that these aren’t just pipe dreams or nice to haves. Again, you’re trying to get to quantifiable business outcomes such as the following.

Example Positive Business Outcomes: 

  • Reduce time to market by Y, resulting in estimated $X gain in net new revenue 
  • Reduce time to decision making by Y% 
  • Increase revenue growth rate of X%
  • Spend $X less on infrastructure 
  • $X increase in revenue stream from new product launch 
  • Team gained Y% of their time back, dedicating it to X project that resulted in Z% quicker time to deploy
  • Reduce budgeted FTE headcount by X

Future State Goals:
  1. What would the ideal workflow look like for the prospect, the team, the company?
  2. How would the line of business owners measure the impact of moving to this ideal workflow?

Required Capabilities

The bridge between a prospect's current state and their future state can be found in the required capabilities. These features allow them to solve their negative consequences and unlock positive business outcomes. The majority of required capabilities should tie back to paid features of your product and are, ideally, unique to your solution. 

It's okay for 1-2 of the required capabilities to be product aspects that aren’t behind a paywall, or that your competition (including internal tooling) can do. However, if the majority of the required capabilities don’t tie back to features the prospect would pay for, they are likely not qualified and don’t warrant spending time with until that changes. 

Sample Questions:

  • What capabilities would allow you to solve your current pain around X? 
  • What would the workflow look like in order to achieve those positive business outcomes? 
  • If you could have 1-2 product capabilities to get a 10x increase in your team’s output, what would they be?  
  • In the workflow you described, if you could offload 2-3 of those tasks to a product which ones would they be? Why?  

Required Capabilities Goals:
  1. Do your paid features allow them to get from their current state to the desired future state?
  2. Are these features currently available in the product?

Success Metrics

Success metrics measure how the prospect’s business will know when they have achieved their ideal future state and positive business outcomes. These are usually technical in nature, since they are how you measure required capabilities. 

If positive business outcomes speak to the line of business buyers (CEO, CRO, CFO, etc.) then the success metrics usually speak to the technical users/buyers (VPE, CTO, CIO ,CISO, etc.) 

Example Success Metrics:

  • Increase release cadence by X%
  • Reduce time to production by X days/weeks/months 
  • Consolidate workloads from X platforms into one instance 
  • Reduce the amount of time team spends on non-strategic manual tasks by X%
  • Meet deployment date of Y 
  • # of FTEs required to complete release decreased by X 

Success Metrics Goals:
  1. What will they measure in order to know if they’ve achieved the desired future state?
  2. What are the technical success metrics that would enable the positive business outcomes?

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