Problem
Many new employees and contractors will start looking for another job shortly after starting one and the rationale for this often being that the job is not aligning with what they were expecting, priorities are unrealistic, or they don’t feel like they have the skill set or abilities to successfully meet expectations. While some companies and managers are effective interviewers in the sense that they provide an accurate overview of what the role will truly entail, many are not.
Solution
Job seekers need to be skilled at position “requirements gathering” during the interview process so they can determine a strong understanding of what the job will truly be and require, and as a result, if they would be both a fit for, and happy in that role.
Here are five themes/questions around what you should be asking during the interview process to help with role clarification.
What are the current organizational, group and/or team business needs and pain points you’re hoping this role will contribute to? This helps you understand the “why” behind the position and its overall purpose.
How will you measure success? What are you expecting this individual to accomplish within the first three months, six months and one year? This will provide insight into the true priorities and the success criteria.
Will you break down your complete technical landscape for me? What are all the tools, technologies, third party controls, methodologies, processes, etc. that your group/team uses and follows? What is on the docket to implement and/or upgrade to in the next 6-24 months? This helps you determine a clearer picture of full technology stacks and their tech strategy/roadmap.
What challenges do you foresee this role facing? This will help set your expectations on “the good, the bad and the ugly” of the role.
What skill sets and technical competencies do you view as an absolute requirement for being successful in this role? Managers often list a lot of requirements/plusses, but there are always a handful that stand out amongst the rest.
Next Steps
However you want to tweak the verbiage/line of questioning, ensure you’re asking questions that will help accurately gauge:
- The purpose of the role (i.e. how is it supporting team/organizational objectives or challenges)
- Key priorities and expectations
- Current technology landscape as well as future technology roadmap
- Expected challenges
- Primary requirements vs. what’s a preferred qualification

Erica Woods is the Director of Contractor Programs and Philanthropy at Apex Systems. Her focus is on overseeing programs, teams, communication channels, and other resources that support their IT Consultant Community of 16,000+. Erica also oversees corporate philanthropy efforts and acts as a technical community evangelist for various STEM programs/nonprofits. She has 18 years of experience in the IT staffing and solutions world and an MBA from Loyola University. She is a Professional and Career Development Author for the MSSQLTips.com online technical community, presents Career Development sessions for various communities, including SQL Saturdays, Code Camps, PMI chapters, IIBA chapters, BA World conferences, and provides internal and external Leadership and Hiring Coaching. Erica is a Co-Founder of the ‘Baltimore Techies for Good’ Meetup group, and Co-Founder/Co-Organizer of the Tampa Tech4Good Meetup group, which are monthly events that bring together technical and marketing folks looking for skills-based volunteering opportunities with nonprofits in need of technology help/guidance. She is also one of the three Founders of the ‘100 Techies Who Care’ group in Tampa, which launched in 2023.
- MSSQLTips Awards: Rising Star (50+ tips) – 2022 | Author Contender – 2016 | Rookie Contender – 2014