What Candidates Interviewing In Startups Really Want To Know (Actual Questions Asked By Our Team at ContactOut)

In 2022, ContactOut embarked on an ambitious journey, one that was deeply rooted in our CEO’s vision.

This vision, transformed into tangible hiring goals, set us on a path to create three pioneering cross-functional squads.

Each of these squads was tasked with a critical component of our product’s lifecycle: building, maintaining, and innovating.

This mission led us to invest countless hours in interviewing candidates across various domains – product, design, and engineering.

In this narrative, I’m going to pull back the curtain and share with you the most frequently asked questions for each role – caveat that these are initial questions, so they won’t be as in-depth.

This is particularly crucial if you’re navigating the waters of:

  • hiring in startups
  • tech roles
  • hiring in Asia
  • or any combination of the above

Then read on! I’ll be sharing the top FAQs for each role based on our initial conversations with them.

This insight will not only help you anticipate these questions but also understand what truly matters to candidates in different roles.

Moreover, it will guide you in positioning your role as an enticing opportunity.

Product Designer FAQs

“How can ContactOut grow 5M revenue and will be $100M by 2023?”

For context, we sent them slides to read in advance – these were our growth plans. The intention was to let them in on the vision. If it resonates, then there’s common ground and that’s always a good start. 

Candidates may ask this question in different forms, such as: 

  • What’s your projected growth YoY? 
  • What’s Company X’s ARR?

“What is the deliverable that you will expect from Product Designer?”

Other ways that candidates ask this question: 

  • What does  ‘good’ look like in a 3-6-12 month period? 
  • What projects/parts of the product will be working on?
  • What problem are we solving/who are we solving it for?
  • How do we connect with our customers?

“Will we work remotely or go to the office?”

Since we were working remotely, candidates often wondered whether we had an office or if there were opportunities to see each other in person. This is the part where I usually share all the meeting cadences we have to foster a sense of connection and transparency in teams (e.g. daily stand-ups, learning sessions, and All hands) 

“How do product designers, engineers, and product managers collaborate?”

Other ways that candidates ask this question: 

  • How is feedback shared and integrated among the design, engineering, and product teams?

The remote life, although desirable, was not without its set of challenges – communication and timezone differences being one of them. Out of all three roles, Product Designers asked this question the most. Understanding team dynamics was an important part of the early conversations. 


Software Engineer FAQs

“Is the work geared towards support or product development?”

Translation: Will I be building new features or sustaining an existing product? 

The best way I learned about the engineering ecosystem was through our Head of Engineering, Albert. Discussing candidates’ frequently asked questions helped these conversations evolve. 

“What is the direction of ContactOut moving forward? (E.g., Ongoing or upcoming project plans)”

Engineers are meticulous by nature. They want to get a clear picture of what they’ll be working on. 

“What skills are you searching for? (technical tools)”

Other ways that candidates ask this question:

  • What’s the tech stack? 
  • Are there any plans to change the tech stack in the near future?
  • Microservices or monolithic? 
  • Will there be training for new tech or areas of interest?

“How do product designers, engineers, and product managers collaborate?”

Or they may also ask: 

  • what systems or tools do you use to facilitate collaboration between designers, engineers, and product managers? 
  • How do we decide which feature to work on? 
  • How do we go about sprint planning?

Similar to product designers, this question does get asked a lot. I usually dive into the specifics and provide visuals when I explain how teams collaborate. 


Product Manager FAQs

“What strategy do you have for growth? Do you want to launch a new subsidiary product targeting a different audience or push the existing product to new users?”

This is usually a question that comes after: can you tell me more about the product and target audience? This leads to question #2

“What’s the product roadmap for the next x months?”

Alternative question: what are ContactOut’s long-term and short-term goals?

PMs want to know how they can add value to the grand scheme of things. Understanding what the company plans looked like in the next 6-12 months helped shape my conversations with candidates. Though I take them through relatively high-level roadmaps, this context helps to create more meaningful conversations with hiring managers 

“How do product designers, engineers, and product managers collaborate?”

Alternative question: how are decisions made when there are differing opinions among design, engineering, and product management?

I give PMs more or less a similar walkthrough as our engineers and designers. I even show them one of our PM’s calendars so they’ll see weekly cadences and the purpose of each.  

Detailed question about understanding ContactOut’s processes and limitations in data protection laws.

We aim to connect people, and that also means having access to tons of data. A lot of candidates are curious about this, and that is why we take them through our process in very early conversations. 


Key takeaways

  • Product Designers are primarily interested in the company’s growth prospects, role expectations, teamwork, and remote work possibilities. Their questions often revolve around how their role contributes to the company’s goals and the working dynamics within the design team.
  • Software Engineers tend to ask more about the nature of their work (support vs. product development), future projects, skill requirements, training opportunities, and logistical aspects like start dates. This reflects a focus on technical specifics, career development, and practical aspects of joining the company.
  • Product Managers inquire about growth strategies, operational logistics like remote work, team dynamics, and specifics about the role’s requirements. Their questions indicate a focus on strategic planning, operational efficiency, and understanding the broader impact of their role within the company.