January 15, 2026

Identifying Need is Achieved Through Asking Questions

Most businesses do not actively recognize or articulate their IT problems because those issues have gradually blended into “business as usual.” Effective discovery is therefore not about pitching solutions, but about asking strategic, open-ended questions that help decision makers surface hidden friction, reflect on operational weaknesses, and acknowledge the cost of the status quo. By guiding prospects through thoughtful discussion rather than direct persuasion, reps simultaneously uncover genuine need, build trust, and create openness to a future solution.

Identifying Need is Achieved Through Asking Questions

Clients rarely come forward with their problems. Our job is to establish a context in which clients discuss their IT infrastructure and reveal or realize shortcomings. We establish this context by asking strategic questions, which unearth and then accentuate pain points in the current IT environment.

Why Ask Questions?

Most decision makers do not understand their IT environment in detail. If you ask someone the question:

“Do you have any IT related problems we could help you solve?”

  • 10% will be in desperate need and know it (“Yeah, this is actually perfect timing.”)
  • 10% will confidently know that they have no problems. Their system is great.
  • The remaining 80% will say “We’re good” and hurry off the call, not because they do not have problems, but because they have not consciously acknowledged them. The problems have diffused into the background as friction and become part of “business as usual.”

“It’s not the consumers’ job to know what they want.”
— Steve Jobs

Our job is to:

  1. Understand if there are any problems by asking open-ended questions
    • These questions are not designed to elicit a straight answer, but rather to invite the prospect to describe their situation, both the good and the bad.
  2. Probe whether they would like to have these problems solved
    • Once a problem has been acknowledged, we seek to emphasize the cost. How big of a problem is this really? What is the worst-case scenario being ignored?

“I have found people willing to tolerate any level of chronic pain in order to avoid acute pain.”
— Marc Andreessen

The acute pain of identifying, acknowledging, and then soliciting services to solve IT problems outweighs the chronic pain of the status quo.

Slow networks, inconsistent help desk support, questionable cybersecurity, and occasional downtime become normalized over time.

We change the balance by making it easy to identify and acknowledge problems, and then setting up a curated discussion to help solve them.

Unearth Real Need Through Questions

✅ Surfaces friction that has been normalized

✅ Makes it easy to say “yes” to a solution

Example of Effective Questions

Different types of decision makers and contexts require different questions. Here are a subset of the questions our reps are trained on.

In-House

  • When was the last time you outsourced for additional support?
  • What kind of IT issues have you had in the past?
  • How big is your internal team?
  • What does your day-to-day typically look like?
  • What do you wish you could spend more time on?
  • What is the number one thing you would improve?
  • What is on your tech roadmap?
  • If you ever had to outsource in the future, what would you look for in a provider?

Outsourced / Hybrid

  • Is that more of a “call him when something breaks” setup, or does he proactively monitor everything in the background?
  • What services are they providing for you?
  • How long have you been with them?
  • How would you rate them on a scale of 1 to 10?
  • What kind of issues have you had to call them for in the past?
  • If you started having issues with them, who would be the next company you would call?
  • When do you typically review providers?
  • What do you look for in a provider?

Security

  • If you were hacked tomorrow, are you sure your insurance would cover it?
  • How are you currently prioritizing security for your business?
  • What is your biggest consistent issue when it comes to security?
  • What would take your organization’s security to the next level?

Day-to-Day IT Support (Help Desk)

  • What is your biggest consistent issue when it comes to your employees’ IT needs?
  • What is your biggest consistent issue when it comes to day-to-day IT support?

Business Productivity

  • How are you currently leveraging technology to make your business more productive?
  • What is the most consistent productivity issue you are experiencing?
  • What plans do you have in place to continue evaluating opportunities to enhance productivity?

BDR (Backup and Disaster Recovery)

  • What is your organization’s backup and disaster recovery plan?
  • What is the most consistent issue you run into when dealing with your BDR plan?
  • What would take your BDR plan to the next level?

Cloud Computing

  • How are you currently utilizing cloud computing in your business?
  • What is the most consistent issue you run into when transitioning to or managing cloud infrastructure?
  • How do you plan to further enhance cloud computing within your business?

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