How to Interview for an IT Position at a Startup

How to Identify a Startup

  1. Operate with few resources.
  2. Environment has little or no documentation, policies, or procedures.
  3. Everyone “pitches in” to make the dream work.
  • Runway: The amount of money your company has left before it no longer has any money.
  • Equity: Private shares in the company.
  • Social Committee: A volunteer body that governs social activities and distributes funds for game nights and dodgeball leagues.
  • Talent Team: Recruitment Department
  • People Team: HR Department
  • Town Hall/All Hands: Company-wide meeting providing transparency at a high level.
  • IT Administrator = Individual Contributor managing IT.
  • IT Lead = IT Manager, sometimes with one direct report.
  • Head of IT = IT Director

Know the Types of IT Roles in a Startup

  1. The Neo.
  • Hiring manager is not in IT and has no experience in IT. They’ve accepted the burden to date and recognize the need for an IT professional.
  • Duties in the job description are wide ranging and require a ‘generalist’ or ‘jack of all trades’ where she will be required to ‘wear many hats’.
  • 2–5 years experience in IT
  • 2nd round interviews will include an Engineer asking how many IP addresses are in a /24 subnet.
  • Reports into Operations side of business
  • The company is likely in the middle of an Office Relocation or Build-out of a New Space. This is often the point at which the facilities administrator loses their mind and needs to hire you.
  • Standardize hardware, assume procurement efforts, and create inventory
  • Create an Onboarding Process for New Hires and Training for all
  • Setup 2FA in gSuite, Slack, etc
  • Stablize the environment (videoconference likely drops out, WiFi has dead zones, former employees still have active accounts)
  • Implement a Device Management System (BYOD, EMM, MOM, etc.) JAMF, InTune, Meraki Systems Manager.
  • Implement Single Sign-On (Okta, OneLogin)
  • Take over all the IT for the New Office
  • Reports into Engineering side of business, no longer the Operations side of the business.
  • Optimism that one person will save them has been replaced with the harsh realism that they’ll need an IT team. Desperation from the first hire has turned into wariness and you may be asked how you would structure a team.
  • Many interview questions will be prefaced by, “The person who we originally hired for this role was trying to do X, or did X. Do you think we should do X?”
  • Trying to figure out the password to many services.
  • Trying to figure out why things were setup the way they were.
  • Creating network documentation and maps
  • Replacing Single Sign-On
  • Creating an IT Roadmap
  • Primary duty will be “handling the day to day”.
  • 1–3 years experience in a Helpdesk role.
  • Reports directly to the IT Administrator or IT Lead or IT Manager.
  • Fix the printer.
  • Setup laptops for new employees. Likely figure out how to mass deploy through imaging.
  • Further configure the Helpdesk or implement one.
  • Become point of contact for all staff concerning all IT issues.

Reading between the Job Description’s lines

How to Apply

Interview Format

  • 15 minutes with a recruiter to primarily determine ability to communicate. May also validate claims on your resume.
  • Provide availability in the late morning or mid-afternoon when they’ve had lunch.
  • Recruiter likely has very little experience with IT. This isn’t the time to get technical.
  • Use a few buzzwords and be very concise. They have twenty more 15 minute interviews to do today.
  • Be respectful of their time. They can end your application here.
  • Is often a second call or video with hiring manager and one or two other team members.
  • Will include elements of a technical interview, if not specifically that. You will be required to speak to the technical elements of the role with clarity.
  • 60–120 minutes
  • On-site or video, 120–240 minutes.
  • Often intended to determine cultural fit and achieve clarity regarding outstanding questions from second round interviews.
  • Will meet with potential colleagues across organization and tour the office.
  • Usually yours to lose at this point, or you’re one of a few remaining candidates from which they will choose.

Do/Do Not Do

Qualities of a ‘Strong Hire’

  1. A ‘do what it takes’ attitude

Red Flags

  1. Do not take the call on the street or in your car. If you must, I recommend acknowledging it up front.
  2. Do not act surprised when they call — instead, signal that you were expecting it.
  3. Do not take the call when other priorities will create a distraction, please schedule the call around them.
  4. Do not ask stock questions that you Googled because every other applicant is also asking them. Instead come up with 2 questions you legimately have about the organization, role, or department. This may have come out of your research for the cover letter.
  5. Do not Google answers to questions while in the interview. It’s all too obvious that a candidate is frantically googling the question.

Star Candidates/Strong Hires often do this.

Reference Check



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Dave Bour

Dave Bour

Building IT infrastructure and teams where there was none before. Fitness, wellness, and adventure enthusiast. Engagements at