In a 1997 letter to his shareholders, Jeff Bezos describes decisions as either two-way doors or one-way doors: they’re either reversible or irreversible. He says one-way decisions must be made “methodically, carefully, slowly, and with great deliberation. If you walk through… you can’t get back to where you were before.”
Hiring employees, though not irreversible, is a big responsibility. You invest time, energy, and money into finding the right person. However, if hiring decisions take too long, they come at a cost to your business.
At Optemization, a tech consultancy that helps companies adopt modern productivity and collaboration tools, we’ve faced this challenge firsthand. Instead of handling client projects myself, I needed to prioritize efforts to grow the company, such as taking discovery calls and creating our newsletter. Hiring my first full-time employee shifted the trajectory of how fast our company could grow and deliver services.
Interviewing candidates can feel overwhelming, but if you develop a good process for interviewing and assessing them, you can find the right fit.
Below are some common interview questions you can ask during each phase of the process. I’ve also shared how we think about hiring at Optemization and what’s worked well for our small team.
The first phase: Initial screening interview
The first interview is your first line of defense. A trusted team member can vet candidates and determine which should move forward and which aren’t a good fit. This delegation is crucial: you, as the owner of the company, can’t conduct every initial interview. It’s not sustainable or scalable. Having someone you trust to conduct the first interview saves your time for later stages in the hiring process.
At Optemization, a candidate’s first interview is with our Chief of Staff, Natalie Pottie. She makes sure the interview aligns with the job description (covering the basics of what we need from the new hire) and transparently discusses what we’re like as a company.
Questions for the first interview should prompt the candidate to provide information that can help you determine if they should move on to the next phase. Here are five types of questions to ask in the first interview:
1. Introduction and background
You’ll have some information about the candidate’s background from their resume or LinkedIn profile, but you’ll want to hear them describe — in their own words — their work experiences. It’s more than a rehashing of their past work: you’re getting a feel for the candidate and their communication skills.
I also bookmark potential highly qualified candidates when I see someone’s profile on Twitter and think they might have the right skills. When we need to hire, I reach out to people in that talent pool and encourage them to apply. This proactive recruitment gives us initial insights about job applicants, making the interview process more informed and efficient.
Sample questions:
- Tell me about your background beyond what’s on your resume.
- How do you think your prior work experience has prepared you for this role?
2. Work experience
A candidate will probably give you a broad overview of their work history: where they’ve worked and what they’ve accomplished. You’ll want to dig a bit more to understand what was involved in each role — or, at least, the roles that are most relevant to the role you’re hiring for. You want to get a sense of how they get work done.
Sample questions:
- Can you describe a challenging project you worked on and how you handled it?
- How do you prioritize tasks and manage your time?
3. Company fit
Natalie lets candidates know that we’re a remote-first company and every role has a high degree of autonomy. It’s important for people to understand what it’s like to work at Optemization.
At the same time, because we don’t micromanage and need people to deliver projects on time and as expected, Natalie is looking for people who can take ownership of their work and have a self-starter mindset.
You’ll want to ask the right questions to determine whether the candidate’s work style matches your company’s.
Sample questions, though these will vary a lot:
- How do you approach learning new skills on the job?
- How do you approach building relationships with colleagues?
- Can you describe your ideal work environment and how you stay productive in it?
4. Job-specific questions
You likely have a specific skill set in mind for the role. Even if the candidate lists those skills on their resume, you’ll need to determine their competency, at least enough to move them to the next interviewing phase. As one of the first Notion Solutions Partners, we specialize in helping companies implement Notion. Our baseline requirement for moving forward is that someone is an expert in the platform.
Sample questions:
- Can you give an example of how you’ve used [specific skill] in a previous role?
- How do you stay current with trends and changes in the industry?
5. Logistics and salary
Remote first, in-office, hybrid, synchronous, asynchronous… these different ways of working matter to a candidate. You need to confirm that your company’s work environment matches what the potential employee wants (including work-life balance, paid time off, and other company benefits).
Sample questions:
- Are you comfortable with the work expectations? (hybrid, on-site, working hours, etc.)
- What are your salary expectations?
The second phase: Test assignment
While you can get some good signals by asking people about their experience during the first interview, a trial assignment can give you a clear understanding of a person’s skills (and creativity, if the job requires it).
With my first hire, Val, I put him on a paid client project right away. I’d received a work sample from him, so I was pretty confident he could do the work. In the worst-case scenario, I knew I could take over and wrap up the client work myself. But his first project was outstanding, and it was the foundation for giving him more work and, later, inviting him to join me full-time.
For a test assignment, you can have the candidates do an assignment that mirrors actual projects, prepare a mock-up, or have them take a stab at actual client work. What they produce will tell you a lot about the quality of work they can do, their attention to detail, and whether the result aligns with what you expect from the role.
The third phase: Final interview and checking for alignment
The final job interview happens once you’ve gotten the green light from the first interview, plus a solid test assignment. The person’s hard skills have been assessed; now it’s time to look at their soft skills.
As the founder and CEO, you’re trying to determine if the person’s attitude and values would be a good fit for your organization. As your organization grows, the second interview may also happen with the hiring manager for a specific department.
I talk about what I envision for the company over the next few years and check out the interviewee’s reaction. Do they seem excited by the vision, even though it’s in the future? I’ll also talk about some current projects for the same reason. If everything aligns, including compensation expectations, then we move forward with a job offer.
While you should take an approach that makes you feel comfortable, for me, this is a “vibe check,” and I try to keep the conversation casual. You should have your questions prepared and ask follow-up questions to get the interviewee to share as much as possible.
Here are five types of questions to ask in the final interview:
1. Company alignment
By our second year in business, we had a team of 10 people. We decided it was time to take a step back and clearly outline our values and mission.
We have an acronym for this: COAST. Conscientiousness, openness, autonomy, systems thinking, and trustworthiness.
When interviewing job candidates, I want to see how well they align with COAST.
Sample questions:
- What motivated you to apply for this role?
- Do you feel aligned with the company’s mission and values?
- What are your key strengths, and how will they benefit the company?
2. Behavioral and situational assessment
While the first interview digs into the mechanics of how the candidate gets work done, now you’re looking for how the candidate might respond to various scenarios on the job.
Behavioral interview questions can tell you a lot about whether or not the candidate will be a good culture fit.
Sample questions:
- Describe a situation where you had to work under pressure.
- How do you handle stressful situations or tight deadlines?
- Describe an instance when you had to adapt to a significant change at work.
3. Team collaboration and leadership
If you have an existing team, you want to make sure the candidate will gel with others. Even if you work remotely or asynchronously, the person will need to communicate and collaborate with other team members.
Sample questions:
- Can you give an example of a successful project you were part of? How did the team work together?
- How do you handle conflicts within a team?
- How do you motivate your team / direct reports? (for leadership or manager roles)
4. Problem-solving and critical thinking
The test project will give you a glimpse into how the candidate thinks, but you can ask pointed questions so the candidate can articulate their thinking. You’ll also want to understand their decision-making process, which can be crucial for a small business.
Sample questions:
- Describe a complex problem you faced and how you solved it.
- If you have multiple issues to address, how do you prioritize them?
- How do you approach decision-making when there is no clear right answer?
5. Career goals
One of the reasons I talk about my vision for Optemization during interviews is to see if the company’s future state aligns with the candidate’s career goals.
You want the person to stay and grow with your organization, so you need to understand their aspirations. You’ll also want to make sure you can support the potential employee’s professional development.
Sample questions:
- Can you describe your ideal career path?
- What steps are you taking to achieve your career goals?
Preparing for the interview
When I was in the process of hiring Val, I had a whiteboard to help guide my thinking. I thought about everything I valued or held to be true and wrote those things down on the whiteboard. After a few days, I had a whole board full of my ideas and notes. (And then, of course, moved everything into Notion.)
It was an interesting exercise because writing everything down was like a commitment. It helped guide what I was looking for in an employee. Later, we firmed up these ideas with COAST, but those notes from the whiteboard were the basis for many early hires.
During the interview, try to stay laser-focused on what the interviewee is saying and really engage in the conversation. Call transcription software allows you to be fully present — plus, you can review the transcript later and compare the responses to your company values.
As a small business, you need to understand your ideal candidate as you approach hiring. The right person can set you up for future success. The more prep and reflection you do before the interviews, the more clarity you’ll have about what you’re looking for in a candidate.
3 key takeaways
- Hiring is a significant commitment that requires careful consideration during the interview process.
- Implementing a phased interview process of an initial screening, test project, and final interview ensures a thorough evaluation of a candidate.
- Proper preparation and a clear understanding of company values and specific role requirements are essential to identify the right candidate.
Ready to secure your top candidate? Learn the best practices for extending a job offer that gets accepted. From timing and communication to crafting the perfect offer letter, this guide covers all the essentials to make sure your best candidate says “yes”! Check out the full guide here: How to Extend a Job Offer.
