Tech Sales Discovery Questions

Strategic Questions are an important part of the sales process.

Asking Strategic Questions during a sales call provides the salesperson the information needed to shorten the sales cycle and optimally close the sale through understanding the client’s specific needs and pain points. Understanding how one’s products and services can solve their client’s problems, reduce costs, increase performance and all of those fuzzy warm things, is critical to making their life easier.

Understanding the personality types of those a salesperson speaks with can also come in handy, such as with Dr. Taylor Hartman’s Personality Color Theory, where he describes how people with certain behavioral patterns communicate in different ways, and matching that can help in engaging people according to how they communicate best.

Know what I’m talkin’ ’bout?

Ya heard?


The following is my session with openAI’s ChatGPT, where I asked what questions would be good for a tech sales person to ask different contacts during a sales call. I will fine tune these lists over time, and I imagine ChatGPT can come in handy.

You are an expert in providing advice to tech sales job seekers like me. I need you to help me by creating a list of questions a tech sales person such as myself would ask different people I may come into contact while cold calling different companies. My goal is build rapport while asking strategic questions in order to learn more about the company, including who the decision makers are, information about their current tech stack and situation, who I should speak to about these things so I can help with my company’s resources. Some people will be more resistant to talking and giving information depending on their roles and personalities. For the customer roles below, I need a list of 15 questions for each the people I come into contact with on the phone, ranked by the most important and useful questions listed first. Gatekeeper (often a receptionist) Office Manager IT Manager IT Administrator CTO CIO CFO CEO Department managers End users ChatGPT

Creating effective questions for different roles within a company is crucial for a tech sales professional. Each role has unique concerns, priorities, and levels of authority, which means tailoring your questions is key to gathering the right information and building rapport. Here’s a set of questions for each role you mentioned, ranked in order of importance and usefulness.

Gatekeeper (often a receptionist)

Can you guide me to the person responsible for decisions regarding [specific technology or service]?

I’m looking to understand who manages your IT infrastructure; could you direct me to the right contact?

What’s the best way and time to reach the decision-maker for tech-related queries?

Could you tell me more about your process for evaluating new technology vendors?

Who is currently in charge of [specific project or tech area] in your company?

Are there any ongoing tech projects I should be aware of when I speak to [relevant decision-maker]?

How does your company usually handle inquiries or proposals for new technology solutions?

Can I leave my contact information for the person responsible for tech purchases?

Is there a specific department or individual that deals with tech upgrades and improvements?

What’s the best method to follow up on a proposal with your company?

Could you share the company directory or the relevant department’s contact information?

Who would be the best person to discuss company-wide technology challenges with?

How can I make it easier for the decision-makers to review what we offer?

What are the normal business hours when decision-makers are most available?

Can you tell me about any upcoming events or meetings where decision-makers will discuss technology needs?

Office Manager

Can you describe some of the key technology challenges your office is currently facing?

Who in your team usually takes the lead on deciding technological improvements or purchases?

How do you currently manage [specific tech need] in your office?

What’s your role in the decision-making process for new technology adoption?

How does the company evaluate new tech vendors and solutions?

Are there any specific technology goals or projects your office is focusing on this year?

What are the main considerations or constraints (like budget, compatibility) you face with tech upgrades?

How do you prioritize technology investments in your office?

Who are the key stakeholders in technology decision-making in your organization?

Can you tell me about the current tech stack your office uses?

How has your experience been with your current technology solutions?

What improvements would you like to see in your existing tech tools?

Who should I talk to for detailed technical discussions about your infrastructure?

Can you guide me on how to propose a technology solution that aligns with your office’s goals?

What’s the process for a vendor like us to get included in your bidding or evaluation process?

IT Manager

What are the main priorities and challenges you’re currently facing in your IT infrastructure?

How do you typically evaluate and select new technology solutions?

Can you describe your current tech stack and any planned upgrades?

What are your key criteria when choosing a technology vendor?

Are there any specific technology pain points that you’re looking to solve in the near future?

How do you see your technology needs evolving over the next few years?

What’s your process for testing and implementing new technology?

Who are the decision-makers when it comes to investing in new technology?

Can you tell me about your budgeting process for IT investments?

What security, scalability, and compliance factors do you consider when adopting new tech?

How do you measure the ROI on your technology investments?

What’s your timeline for making decisions on technology purchases?

Are there any upcoming projects or initiatives where our solutions might fit?

How do you prefer to be approached by vendors with new technology solutions?

What’s the best way for me to provide you with more information or a demo of our product?

IT Administrator

Can you share insights into your daily challenges managing the IT infrastructure?

What kind of tools or solutions would make your job easier?

How do you currently handle [specific task or technology area]?

What improvements would you like to see in your existing technology stack?

Who should I talk to for strategic technology decisions in your company?

Are there any gaps in your current tech setup that you’re looking to fill?

How do you stay informed about the latest technology trends and products?

What’s the process for adopting new technology in your organization?

Can you describe any recent technology changes or upgrades you’ve undertaken?

What are the main performance and reliability issues you face with your current systems?

How do you assess the success of a new technology implementation?

What kind of support do you look for from technology vendors?

What security measures are you most focused on in your current setup?

Are there any specific technology areas where you feel your organization is behind?

How can I help you with information or solutions that could address your current IT challenges?

I’ll continue with the remaining roles in the next part.

Continuing with the questions for the remaining roles:


What are your key strategic goals for technology in the organization?

How do you envision the future of your tech stack evolving to support business growth?

What are the biggest technology challenges you face in achieving your long-term goals?

How do you evaluate the impact of new technologies on your business processes?

Can you share some insights into the upcoming tech projects or initiatives in your pipeline?

How does new technology adoption fit into your overall business strategy?

What criteria do you use for selecting technology partners and vendors?

Are there any specific technology trends or innovations you’re particularly interested in?

How do you balance innovation with maintaining existing infrastructure?

What’s your approach to data security and compliance in your tech strategy?

What is your process for testing and implementing new technology solutions?

How do you prioritize technology investments in your organization?

Who else in your team should I speak with to understand your technology needs better?

What are the key performance indicators you use for your technology infrastructure?

How can I best align our solutions with your strategic technology objectives?


How do you align the organization’s technology strategy with its overall business objectives?

What are the main challenges you face in digital transformation and IT management?

Can you describe your strategic priorities for IT investments over the next few years?

How do you assess and manage the risks associated with new technology adoption?

What’s your vision for the future IT landscape of your organization?

How do you ensure data security, privacy, and compliance within your IT infrastructure?

What are the critical success factors you look for in a technology partnership?

How do you manage the balance between cost, efficiency, and innovation in IT?

What methodologies do you prefer for project management and implementation in IT?

How do you measure the ROI and effectiveness of your technology investments?

What are your key considerations when modernizing legacy systems?

What’s your approach to cloud computing and its integration into your IT strategy?

Who are the key stakeholders in technology decision-making in your organization?

Can you share any insights into upcoming IT projects or areas needing attention?

How can I tailor our solutions to better meet your strategic IT objectives?


How do you evaluate the financial impact of technology investments on the organization?

What are your top priorities when it comes to allocating budget for IT?

How do you assess the ROI of technology initiatives?

What financial strategies are you employing to support digital transformation?

Can you describe the budgeting process for technology investments?

What are the main cost-related challenges you face with your current IT setup?

How do you balance cost control with the need for innovation in technology?

What metrics do you use to measure the success of IT spending?

Are there any specific financial or budgetary constraints impacting IT decisions currently?

How do you prioritize funding for different technology projects?

What’s your approach to technology spending in relation to overall business growth?

How do you ensure financial compliance and governance in IT investments?

Who else in the organization should I talk to regarding technology budget and spending?

How do you view the role of technology in driving operational efficiencies and cost savings?

Are there upcoming fiscal cycles or review periods that I should be aware of when discussing potential IT projects?


What role does technology play in your overall business strategy?

How do you see your industry evolving, and what technological advancements are you focusing on to stay ahead?

What are your long-term goals for the company, and how does technology support these?

How do you prioritize technology investments to support your business growth?

Can you share your vision of the ideal technology landscape for your company?

What challenges do you face in aligning technology with your business objectives?

What are the key outcomes you expect from your technology investments?

How do you see emerging technologies impacting your business model?

What’s your approach to innovation and staying competitive through technology?

How do you balance the need for operational efficiency with technology adoption?

What’s your perspective on digital transformation within your industry?

How involved are you in decisions regarding major technology changes or investments?

Who are the key people in your team driving technology strategy and implementation?

How do you foresee your company’s technology needs evolving in the next few years?

How can we best align our technology solutions with your vision and business goals?

Department Managers

How does technology impact the daily operations and goals of your department?

What specific technology tools or solutions are you currently using, and what are their limitations?

Are there any technology-related challenges that hinder your department’s performance?

How do you prioritize technology needs within your department?

What’s your role in the decision-making process for technology investments?

Can you describe any upcoming projects or initiatives that might require new technology solutions?

How do you collaborate with the IT team to address technology needs?

What are the main objectives you’re trying to achieve with technology in your department?

What kind of technology training and support does your team require?

How do you evaluate the success of a technology implementation within your department?

Are there any specific technology trends you think could benefit your department?

What budget constraints do you face when considering technology upgrades or new tools?

Who else in your department should I speak with to understand your technology requirements better?

How often do you review or update the technology used in your department?

What’s the best way for me to present a technology solution that could address your department’s needs?

End Users

What technology tools do you use most in your daily work, and what do you like about them?

Are there any challenges or frustrations you face with your current technology tools?

What features or improvements would you like to see in the technology you use?

How does technology help you achieve your work goals or tasks?

What’s your process for providing feedback on technology tools or requesting new ones?

How user-friendly do you find the current technology solutions you work with?

Can you describe any recent technology changes that have impacted your work, positively or negatively?

What training or support do you receive when new technology is implemented?

How do you stay updated on new technology tools or trends relevant to your role?

What’s your role in the decision-making process for new technology tools?

Are there any specific types of technology or tools that you think would enhance your productivity?

How does technology influence collaboration and communication in your work?

What are the key factors you consider when adopting a new technology tool?

How often do you encounter technical issues, and how are they addressed?

What’s the best way for a technology provider like us to understand and meet your needs?

These questions are designed to elicit valuable information while building rapport and understanding each role’s unique perspective on technology. Tailor them as needed based on your product, service, and the specifics of the conversation.

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