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
Phase 2
(Re)discover your customers' goals.
Move from technical intake to strategic business discovery.
Strategic partnerships are not built on assumptions. Discovery helps your team understand the business goals, risks, and priorities behind the technology work.
Run Discovery or rediscovery calls with clients ready for strategic guidance.
Use assessments to validate gaps and risks inside the environment.
Sort what you learn into goals, initiatives, action items, and follow-ups.
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 format that allows key decision-makers or stakeholders to be there.
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.
Group
Goals
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.
- What are your biggest business priorities this year?
- Are there any big changes coming - new products, leadership shifts, market expansions?
- Are there any risks or concerns on your radar right now?
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.
- Are there tools that feel outdated or underused?
- Are there recurring technical issues we should be aware of?
- How confident are you in your cybersecurity and IT support?
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.
- Where do your teams feel slowed down or frustrated?
- Are there any manual processes you'd love to automate?
- Is it easy for departments to share data or work together?
Listen and record ideas.
During the call, your goal is to listen and take notes. When clients describe business pain points, write them down so you can trace them back to a technical solution later.
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
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.
Think of Discovery as the wide-angle view that helps you understand the client's big goals and challenges. Assessments are like zooming in to see what systems are working, what is at risk, and how serious the issues are.
Categories
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. Example: Do all devices have up-to-date antivirus installed?
Stick to a 1-5 scale or yes/no answers to keep scoring simple.
Leave space to write quick notes about anything that should become a project, compliance item, or Roadmap entry.
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.
- Goals and Initiatives become anchors for your strategic Roadmap and proposals.
- Action Items should be routed to your service team for immediate handling.
- Follow-ups should be validated in a future client meeting 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.
- Opening a new location
- Achieving cybersecurity compliance, such as SOC 2 or HIPAA
- Improving employee onboarding experience
Initiatives
Opportunities for improvement or strategic growth that aren't urgent but could add value. These may need planning or budget approval.
- Rolling out MFA across the org
- Migrating legacy systems to Microsoft 365
- Creating an IT security awareness program
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.
- Unpatched critical systems
- Backup jobs failing
- Expired endpoint protection license
- Staff unable to access a key system
Follow-ups
Unclear or incomplete areas where more information is needed. These often show up as vague answers or cross-team dependencies.
- Vague reference to a big project next quarter
- Client unsure if a process is documented
- Leadership turnover without clear IT direction
How This Applies to Your Segments
High
Maturity
Low
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.
Maturity: high to low. Appetite: low to high.
Lifecycle Manager
Make annual assessments a Customer Success advantage.
Standardized assessments support more strategic planning and better client conversations.