Every rep talks about "current state" in discovery.

But if you’ve never seen the process with your own eyes — you're guessing.

‍Shadow discovery fixes that.

It’s simple: ask the prospect to share their screen and walk you through their actual workflow, step-by-step.

By doing it live, you uncover pain in real-time, pinpoint where your product stands out, and build a business case that doesn’t rely on assumptions.

So today, we’re gonna break down exactly how to use shadow discovery in your sales cycle:

1. What You Should Cover In Shadow Discovery
2. My 5-Step Shadow Discovery Call Framework
3. How to Turn Shadows Into a Business Case

1. What You Should Cover in Shadow Discovery

There are three high-level factors I use to dictate where to focus shadow time:

1. Where Is The Pain? When you’re doing the initial discovery, it should become clear where their current-state pain lies. Shadow the process where the pain lies.
2. Where Can You Differentiate? If there are systems, workflows or personas that align to your product’s technical differentiators, guide the conversation in that direction and use the shadow to emphasize the pain within these processes.
3. Who Do I Need To Meet? If you’re pigeonholed with a certain persona and can’t gain access to technical contacts, use the shadow to have a concrete reason to meet these parties. During the shadows, find ways you can align to their pain.

For example, if I was selling Outreach to someone using Excel, Email, and their cell phone, I would probably ask my prospect to show me:

1. How do they manage their prospects’ emails and organization’s phone number
2. How do they make a cold call and send a cold email
3. How are they tracking activity metrics and prospect coverage
4. What is their CRM tracking at the account level

Send a list like that a few days prior to the shadow to give the prospect time to prepare and organize what they’re going to show.

Oftentimes, they’ll realize that they need to pull in a report or someone from an adjacent team to execute on all of the items, so giving them specificity and time to prep is crucial.

2. My 5-Step Shadow Discovery Call Framework

Once you’ve identified a process to shadow, I follow these five steps to guide them through each workflow:

Step 1: Set the stage and recap the workflows you want them to walk you through:

“These shadows help us lift and shift what’s working, understand exactly what’s not working, and take those learnings straight into implementation. We’ll start with [insert workflows for shadowing].”

Step 2: Ask them to share their screen and begin the first shadow:

“So Sue, if you could get started in the place where you store all of your contacts that you plan on reaching out to…”

Step 3: Guide them into the zones of pain, your differentiators, and key stakeholders:

“Thanks for walking through the contact spreadsheets, Sue. Typically we see folks move from this contact spreadsheet into another spreadsheet where they’re actually tracking email activity. Is that how it works for you too? Let’s walk into that.”

Step 4: Run discovery on those zones to illuminate the gap in their current solution:

“You said the marketing team looks at these dashboards as well? Why is it important to them? Do you think your CMO would be interested in this outbound email automation?”

Step 5: Set clear next steps based upon the result of the shadow:

“This shadow was extremely helpful in understanding where we’ll integrate & how we’ll enable your teams to drive more targeted volume. Based upon what I’ve seen today, I think we should start out with a custom demo to team X to validate our approach. Once you guys love what you see it probably makes sense for us to pull in Team Y and go from there.”

3. How to Turn Shadows Into a Business Case

Now that you have the exact process mapped out, you can use their data to present a real business case to the decision makers instead of hypotheticals.

For example, that shadow discovery selling outreach might allow us to show the exact reasons their team has been seeing a pipeline generation gap:

SDR Time Wasted: $2M Pipeline Potential

• Before: When we followed your SDR team’s workflow, we found they waste XX time with manual activity tracking and correcting bad data in downmarket accounts.

• After: If we implemented basic automation and targeting, your team would be able to cover 2x the accounts in the same prospecting time, which your team has calculated should lead to $2M in additional pipeline in the next 6 months.

Cross-Functional Overhead: $100k Cost Savings (And Faster Decisions)

• Before: We also found that the marketing team and revenue executive orgs can’t report on email attribution and make decisions on where they should double down.
• After: By giving these teams real-time access to inbound and outbound email data, we believe we can reduce $100K in operational overhead and speed executive decision making by 2 weeks / 100 executive hours.”

That's a Wrap!

When you shadow, you see the problems completely unfiltered.

When you show the problems completely unfiltered in a business case, it’s actually believable.

Give this shadow discovery framework a try, and you’ll find that it makes their problems, your solution, and your overall business case land with the toughest CFO.

Watch Max's Episode on YouTube