Discovery
(Re)Discover Your Customers’ Goals
Strategic partnerships aren’t built on assumptions. To deliver real results, you need to deeply know your client’s business — not just their tech. But most customer intake is generic and only scratches the surface. To uncover your customer’s bigger goals and priorities, you’ll need to shift the conversation from tools and systems to business strategy with a more intentional approach.
In this section, we’ll cover:
- How to run more strategic Discovery Calls
- Where Assessments fit into planning
- How to organize and store what you learn
3
Conduct a Discovery (Or Rediscovery) Call
What is a Discovery Call with an existing customer?
In this context, a Discovery Call is a meeting to dig into your customer’s larger business goals, team needs, and tech challenges. It’s not for selling — it’s about listening and learning. The goal is to learn what business success means to your customer and show them you’re thinking about more than just IT projects.
To start your Discovery, reach out to clients who may be ready for more strategic guidance (ideally, those in Segment A). If you’ve done a Discovery Call before, consider it a “rediscovery” call to dig into broader goals or changes to the business.
Here’s our recommended approach for having a successful call:
Set meeting expectations.
When pitching the call to your clients, describe what it’s for, what to expect during it, and why it matters. Tell them it’s a strategic conversation about their business — not a technical review. Find a time and/or format that allows key decision-makers or stakeholders to be there (otherwise you may miss vital information).
Template: Email Outreach for Strategic Discovery
Subject: Aligning on Your Business Goals
Hi [Client Name],
I’d love to schedule a strategic Discovery Call with you and/or your team. We want to better understand your business goals, challenges, and future plans so we can set you up for long-term success.
In the call, we’ll ask about:
Your team’s current challenges and priorities
Larger business goals you’re prioritizing
Your long-term vision for innovation and growth
This call is a chance for us to step back from the day-to-day. We want to focus on the bigger picture and explore how we can support your business in a more meaningful way.
Please let me know if you have any openings for a conversation in the next week or so.
Looking forward to chatting,
[Your Name]
[Your Title]
[Company Name]
Prepare your questions.
There are no presentations or decks needed. You only need a list of open-ended, layered questions that cover business, technical, and operational topics. By asking about a broad range of topics, it’ll be easier to uncover how you can bridge the gap between your client’s business struggles and your technical expertise.
| Group | Goals(s) | Sample Questions |
|---|---|---|
| 1. Business Questions | Understand customer goals, challenges, and what success looks like so your technical advice is aligned with what the business actually needs. |
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| 2. Technology Questions | Assess whether the client’s tools, systems, and infrastructure are supporting their business goals. You’ll also identify risks or inefficiencies that could impede success. |
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| 3. Operation Questions | Focused on how well the people, processes, and platforms are working together so you can connect business goals with tools and systems. |
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Listen and record ideas.
During the call, your goal is to listen and take notes. Clients may not know how to describe a technical problem clearly. But they may say “It takes too long to onboard new staff” or “We’re constantly chasing down approvals or data.” When you hear these pain points, write them down so you can trace them back to a technical solution later.
Discovery Do’s:
Ask open-ended questions
Tailor language to the client’s role, industry, and comfort level
Listen for signs of change (like new hires, shifting goals, or roadblocks)
Summarize what you hear back to the client to confirm accuracy
Discovery Don’ts:
Jump into solutions
Stick rigidly to a template without adapting to the client’s mood or responses
Ask only about services you already deliver, which limits the conversation
Forget to take notes, or you may forget details
4
Complete an Assessment
What do we mean by an “Assessment”?
An Assessment looks for technical gaps in a client’s IT environment. They’re needed to build effective plans (or Roadmaps) for improving your client’s systems. Assessments usually happen during onboarding, but they can be done at different points in the client journey to hone in on specific areas as needed.
Think of Discovery as the wide-angle view that helps you understand the client’s big goals and challenges (the “why”). Assessments are like zooming in to see what systems are working, what’s at risk, and how serious the issues are (the “what”).
Listen and record ideas.
During the call, your goal is to listen and take notes. Clients may not know how to describe a technical problem clearly. But they may say “It takes too long to onboard new staff” or “We’re constantly chasing down approvals or data.” When you hear these pain points, write them down so you can trace them back to a technical solution later.
| Categories (Pick 5-7) | Questions to Ask | Score | Notes |
|---|---|---|---|
| Hardware and devices | Ask a few clear questions per category to understand if the area is healthy or at risk. Bad: “Is your antivirus good?” Good: “Do all devices have up-to-date antivirus installed?” | Stick to a 1–5 scale or yes/no answers to keep scoring simple. Don’t overthink it — the goal here is consistency, not complexity. | Leave space to write quick notes about your scores. Highlight anything that needs to become a project, be linked to compliance, or added to your Roadmap later. |
| Software and licensing | |||
| Network and infrastructure | |||
| Cybersecurity | |||
| Backups and disaster recovery | |||
| Cloud services | |||
| User experience /training |
5
Categorize Your Findings
After your Discovery Call and Assessment, it’s time to organize your findings. This will help you focus on what matters to the client and plan your next steps. Sort notes into four categories: Goals, Initiatives, Action Items, and Follow-ups.
- Goals and Initiatives will become the anchors for your strategic Roadmap and proposals (which we’ll cover in the next section on Alignment).
- Action Items should be routed to your service team for immediate handling.
- Follow-ups should be validated in a future client meeting or touchpoint before becoming projects.
| Category | What to Look For | Examples |
|---|---|---|
| Goals | Clear, forward-looking business targets or changes the client is planning. Listen for statements about growth, strategy, or outcomes they want to achieve. |
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| Initiatives | Opportunities for improvement or strategic growth that aren’t urgent but could add value. These may need planning or budget approval. |
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| Action Items | Immediate, tactical items causing disruption or posing risk. These are part of your expected service delivery and usually don’t need client approvals. |
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| Follow-ups | Unclear or incomplete areas where more information is needed. These often show up as vague answers or cross-team dependencies. |
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How This Applies to Your Segments
Educate
(Segment C - High Maturity, Low Appetite)
Discovery should focus on education. Ask structured questions about departments and workflows to see if you can uncover business priorities or gaps. Keep stakeholder conversations light, as they may not be open to long-term planning. Use Assessments to highlight areas of improvement or misalignment with goals.
Transform
(Segment A - High Maturity, High Appetite)
Discovery should focus on transformation. Ask high-impact questions about innovation, OKRs, market positioning, and emerging technologies in structured, multi-stakeholder sessions. Assessments should validate plans and present budgets and Roadmaps that align with strategic goals.
Sustain
(Segment D - Low Maturity, Low Appetite)
You likely shouldn’t conduct Discovery with this group. Instead, focus on short-term, tactical support that’s needed to sustain their environments until their systems are more mature. Assessments should highlight foundational gaps in their operations and help determine immediate needs vs. long-term goal setting.
Modernize
(Segment B - Low Maturity, High Appetite)
Discovery should focus on modernization. They may benefit from shorter, focused conversations on increasing maturity and addressing foundational gaps. Assessments should help build a shared language about technology and systems so these clients prioritize the must-haves before getting to strategic impact.
