Technology planning and provider comparison checklists.

Read practical checklists for provider comparisons, invoice reviews and technology planning. No download or email gate.

Reference binders and an open workbook beside a tablet checklist

Start with your next decision

Compare Technology Providers

Use the same requirements for every proposal so differences are visible before you choose a provider.

Read the checklist

Review Your Technology Invoices

Organize invoices and agreements before discussing a billing review. These questions help identify what needs closer examination.

Read the checklist

Prepare for a Security Conversation

A useful security discussion starts with business requirements and current responsibilities, before product names.

Read the checklist

Plan a Cloud Evaluation

Give each provider a consistent picture of your workloads, budget and migration constraints.

Read the checklist

Evaluate Business Communications

Start with how employees and customers communicate, then evaluate voice, collaboration and contact center options.

Read the checklist

Frame an AI Use Case

Define a practical problem and a way to measure improvement before comparing AI tools.

Read the checklist

Compare Technology Providers

Use the same requirements for every proposal so differences are visible before you choose a provider.

  1. Write down the business problem and the requirements that matter most.
  2. Separate essential capabilities from optional features.
  3. Ask each provider to identify included services, exclusions and assumptions.
  4. Compare recurring costs, nonrecurring costs and costs based on usage over the same period.
  5. Document implementation responsibilities and dependencies.
  6. Review service levels, escalation contacts and renewal terms.
  7. Record unanswered questions before you make a selection.

Review Your Technology Invoices

Organize invoices and agreements before discussing a billing review. These questions help identify what needs closer examination.

  1. Gather recent invoices and the agreements that apply to them.
  2. Match billed services to the locations, teams and equipment using them.
  3. Flag unfamiliar charges or services you no longer recognize.
  4. Compare billed rates and quantities with the agreement.
  5. Note renewal dates, minimum commitments and cancellation provisions.
  6. Document questions for the provider rather than assuming a charge is wrong.
  7. Use Billing Breakthrough if you want to request an invoice review.

Prepare for a Security Conversation

A useful security discussion starts with business requirements and current responsibilities, before product names.

  1. Identify the business systems and information that need protection.
  2. List existing security tools and the teams or providers responsible for them.
  3. Describe known concerns and the outcomes you want to improve.
  4. Record any contractual or regulatory requirements for your business.
  5. Ask how monitoring, response and escalation are divided between teams.
  6. Discuss integration, implementation and ongoing support expectations.

Plan a Cloud Evaluation

Give each provider a consistent picture of your workloads, budget and migration constraints.

  1. Inventory the workloads and dependencies being considered.
  2. Document capacity, performance and availability requirements.
  3. Consider public, private and hybrid options against the same needs.
  4. Compare operating costs, migration costs and required support.
  5. Identify who owns migration decisions, testing and ongoing operation.
  6. Discuss how data and workloads could be moved at the end of an agreement.

Evaluate Business Communications

Start with how employees and customers communicate, then evaluate voice, collaboration and contact center options.

  1. Map calling, messaging, collaboration and customer routing needs.
  2. Identify which teams, locations and customer channels are in scope.
  3. List existing numbers, systems and required integrations.
  4. Compare user licensing and contact center requirements separately.
  5. Ask about migration, number transfer and user training responsibilities.
  6. Agree on support contacts and a way to assess the new experience.

Frame an AI Use Case

Define a practical problem and a way to measure improvement before comparing AI tools.

  1. Describe the workflow you want to improve and its current cost or effort.
  2. Identify the data needed and who is allowed to access it.
  3. Define a measurable outcome and an acceptable level of review.
  4. Ask how proposed tools fit existing systems and governance.
  5. Compare implementation and ongoing operating costs.
  6. Discuss ownership, training and evaluation before extending a pilot.

Put the questions in context.

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