For the last century, we’ve been learning about the best ways to hire and work in an office setting. Now the clock has reset and we’re racing to find the new best practices for the remote era. This sudden cultural shift to remote work presents an opportunity for startups. Startups that adapt will have the advantage and they will become magnets for the best talent.
Like with technology shifts such as web-to-mobile, rapid cultural shifts can also provide a ledge on which to build iconic companies.
Long-term increase in search interest for “remote jobs”. Source: Google Trends
Adapting to remote work requires relearning how to recruit the best talent. There are two sides to this. Half the equation is about learning to discern talent within the structures of a remote hiring process: figuring out which qualities to look for and what questions to ask. The other half is relearning how to attract the right people.
Today we’ll walk you through what we’ve learned so far about attracting and discerning remote talent, including a list of remote interview questions that we’ve collected through surveying top Founders. Some of it is common sense, and some of it is counterintuitive.
We surveyed 100s of top Founders to get their #1 favorite interview question based on the qualities we’ve identified as most important for a remote hire. Below are the 34 best to help you build your remote interview process.
A short list of qualities and characteristics to particularly look for in a remote job candidate would include speed, initiative, adaptability, and intrinsic motivation. And of course, you should be asking questions to figure out if they can help you attract more remote talent.
1. Is it more important to move fast and get it done, or to take your time and do it right?
2. Can you describe an example of when you helped your team move faster?
3. Describe a time when the organization you were working for went too fast and it was a problem. How did you feel about this? (They should say they loved going fast even when things went wrong.)
4. How do you prioritize building processes and systems versus shipping against your goals and deadlines?
5. Describe a time when you over-delivered against what was expected of you. Why did you want it so badly?
6. What are some projects you’ve done in the past that you came up with yourself? If it didn’t get implemented, why could you not convince your boss at the time?
7. What do you consider to be your best idea at work, and what obstacles did you overcome to make it happen?
8. Three years from now, what new things will you have learned, who do you want to have added to your network? How will this job help you achieve this?
9. If you were to get this role, what would be your biggest challenge and how would you approach it?
10. We are resource-constrained and things are really ambiguous here, is that what you want for yourself?
11. Describe a time when your boss changed plans really quickly. How did that make you feel?
12. Describe a time when things were changing really quickly. What was the environment like for you? (Notice if they use negative words or positive words.)
13. Describe a time when you had to change your plans suddenly. How did you communicate this with other people?
14. Who’s the most difficult person you’ve worked with?
15. Tell me about a time when you loved your work. What did you enjoy about it?
16. Describe a time when you became consumed with what you were working on. How did you deal with it?
17. Describe something you created, either in work or outside of work, that you are proud of.
18. When was the last time you were working on something and looked up at the clock only to be shocked at how much time had passed? What were you working on, and why were you so absorbed by it?
19. Tell me about a niche product or something for your hobbies or passions that you’re extremely opinionated about and why.
20. What’s the most recent thing you learned about yourself at work? How did you learn it? Why?
21. Walk me through your last few jobs. What did you learn and why did you leave each?
22. What do you want out of your next job that you aren’t getting now?
23. How long can you see yourself being here? What’s next for you?
24. What was the highest performing team you’ve ever worked on? Why was it so high performing? What was your role?
25. What is your superpower? What is the one thing you do better than most others in your profession?
26. What do your coworkers tend to respect and admire most about your work?
27. What do you consider your natural gifts, and what are the things you’ve worked hardest to get good at?
28. Who have you learned the most from in your career? What did you learn?
29. How do you push the boundaries and limits of what you do?
30. What advice would you give to someone starting new in your profession? What are the best things to spend time learning and doing, and what’s a waste of time?
31. What are you most proud of in your career so far?
32. If we hired you today, who would immediately want to join us?
33. Can you name a time when you recruited someone to a company you were working on?
34. Who are the three most exceptional people you’ve ever worked with and what made them so exceptional? Do you think you could convince them to join you here if we hired you?
Beyond the interview questions, more of your hiring process needs to adjust for a world of more remote.
There’s an opportunity there. The current systems for hiring aren’t that great, so now is a chance for us to improve how we hire overall.
One advantage of remote hiring is access to volume. The number of people you can interview remotely is more than what you could do in person. In theory, this means you’ll have a greater chance to meet the perfect candidate.
Secondly, doing interviews remotely is also going to allow us to digitize and coordinate questions between interviews more easily. It’s a good opportunity to overhaul old analog hiring processes. Redundancies between interviews can be lessened and wait times eliminated. Inconsistencies between different interviewers can be removed. Remote gives us the opportunity to be more systematic and coordinated.
Third, there are biases that may not come into place remotely, which may help us to make better decisions in who we hire.
Fourth, some people who would be poor office mates may be great remote workers and vice versa. Remote work will change who we consider the top performers.
Fifth, vetting becomes more important. References are even more critical if you’re never going to meet the people you hire in person.
Remote candidates should also expect the vetting process to be longer and more rigorous and should be willing to put in more work during the interview process — even potentially working with your company in a “try before you buy” scenario.
Adjusting your hiring process for remote includes changing how you make your company an attractive destination for the best talent. Showing people that you have the best place to work is no longer about having a fancy office like the Googleplex with 3-star chefs and nap pods. Now you have to compete by offering people:
Having a sense of community and belonging is a big and underrated reason why people work where they do. “Belonging” is not as tangible and obvious as compensation, so belonging is often overlooked. But the unseen hand of network force is just as powerful in our work lives as it is anywhere else. The people you work with are a big part of your life.
Building a strong remote culture doesn’t happen organically as it might in an office with daily, unplanned interactions. Remote work means you have to put more effort into fostering a culture.
What stage is your startup, and how do you expect it to evolve over time?
Self-knowledge here is important. Be really clear where you land on this grid, both now and in the future. Are you building a remote culture and community from scratch, or are you transferring a culture you built in an office online? Will you become more or less remote as your company grows? Having a clear answer now will allow you to build for the future.
Some Founders are adamant about being fully remote. Some want to be fully in-office. It’s safe to say we are going to see more fully and partially remote companies than we did before, and there are going to be successful companies in every box on the grid above. Success will depend on implementing the right culture and processes for the box you’re in.
One thing to consider is, how iterative and creative does your product need to be? Highly creative products have typically been done better in person. If you’re changing significant business and product attributes more than once or twice a day — language, onboarding flows, your go-to-market, channels, product features, etc. — it’s possible that being in the same room still produces the most iteration speed and the least friction.
For instance, can you build a consumer-facing social product with a fully remote team? Yes, of course. Can it be done as quickly or as well as your competitors if they are in person? The jury’s out.
What type of company you are or what stage you’re at should come first in deciding your long-term mixture of remote work.
We wrote the Company Culture Manual as a guide to building culture in person. While many of the same principles apply in a remote context, there are adjustments that need to be made.
Remote work is a skill in itself. People who make good office workers may not necessarily be the best remote workers. Some of us need to be in an office to perform at our best. We perform better with an audience. We need to know that others are right there watching what we do. We like periodic eye contact and coaching.
Some other personalities do better when remote. More independent work, fewer interruptions, not as much social time.
Thus, a big part of building a strong remote culture is therefore to discern the right talent for remote vs in office. Hiring people with the right qualities and motivations to succeed remotely will seed the culture.
The other part of creating a good remote culture is to iterate through elements to see what sticks. We’ve seen some positive results simply by taking synchronous experiences from office environments and moving them to remote — experiences like birthday celebrations, happy hours, yoga, meditations, stand-ups, all hands, etc. They have been adapted for remote and they work to some extent.
Asynchronous experiences take it to the next level, with nicknames, employee awards, competitions, trivia games, meme sharing, volunteer work on shared values, donation programs, structured mentoring, etc. As time goes on, we expect new types of remote-only rituals and activities to develop and stick. Create them, test them. They are important. [You can download our comprehensive list of company rituals here.]
There are companies that have been 100% remote for many years. Some of the most discussed ones are Automattic, GitHub, 37Signals, InVision, Zapier, and TopTal. Automattic, for instance, started as an open-source project, with people remote all over the world contributing to the code base. They slowly picked up their best contributors as full-time employees. These were folks who were attracted to remote work from the beginning and it created a unique company DNA.
If you can show prospective employees that you’re building a strong remote culture, it will be a magnet for top talent who are looking for companies that have adapted for the future.
Founders should take care that they don’t lose the energy and camaraderie that in-person work creates in the transition to remote. Remote work may be lifestyle-friendly, but in the startup world competition is fierce. You have to take care to retain a competitive level of energy and camaraderie to operate, whether remote or not.
In the end, winning startups are made of people who are 100% switched on 100% of the time and operating at a world-class level.
If remote work is part of the playbook for operating at that level, then it makes sense. But if it’s implemented for some other reason, then it may make it harder for you to compete. Choose carefully in deciding what makes sense for your company. If you do embrace remote for the long term, put your full effort into adapting your hiring practices and culture building to succeed as a remote or partially remote organization.
The percentage of work that is done remotely will certainly increase. Companies that thrive in the new era will learn to turn the challenges of remote work and remote hiring into an advantage.
Thank you to the fantastic group of Founders who participated in the creation of this essay.
As Founders ourselves, we respect your time. That’s why we built BriefLink, a new software tool that minimizes the upfront time of getting the VC meeting. Simply tell us about your company in 9 easy questions, and you’ll hear from us if it’s a fit.