It’s not simply in-person interviewing done over video chat.

Liana Dumitru

Sep 10, 2020·10 min read

Earlier this year, I left my previous job at Dropbox to do a month-long silent meditation retreat. When I came back a month later, ready to start the job search, the world had turned upside down. I found myself interviewing for a new job during a global pandemic, reading racial injustice books and infectious disease articles, alongside job postings and recruiter emails.

As I started video conversations with tech companies that had just moved to remote work, one thing I kept an eye on was their interview process. Having run dozens of interviews as a manager at Dropbox and as a founder before, I knew good interview process is rare. Now, having just gone through remote interviewing as a candidate, I realized something else. Good remote interview process is so rare it’s almost impossible to find.

Good remote interviewing is not simply in-person interviewing done over VC. Good remote interviewing means deliberately investigating, understanding, and altering processes to shift interviewing practices to a remote-first mindset.

If your company is up to the challenge, here are three areas to look into as you’re adapting your interviewing processes to remote-first: (I) Developing a remote interviewing philosophy, (II) Putting together remote-first interviewing processes, and (III) A relentless focus on the remote candidate experience.

I. Remote interviewing philosophy

“Let chaos reign…”

When I started conversations with companies, one of the questions I asked recruiters was: How does remote interviewing look like for your company? The response was usually an overview of the normal interview process, with the added detail that everything would be run on Zoom.

More often than not, the ensuing experience reminded me of Andy Grove’s words: “Let chaos reign, then rein in chaos.” With onsite interviewing simply transplanted to VC, it was the first part of that quote that really resonated with the experience of remote interviewing. Not even recognizing that their interview processes had broken in the transition to remote, companies were simply reacting to the endless stream of problems that inevitably showed up.

Once you acknowledge that the way you’re interviewing remotely is broken, you can move on to actually fixing it. And you can start by developing a philosophy for remote-first interviewing. Here are some questions that can help your company kickstart a conversation about remote interviewing:

• What are the problems we’re solving with interviewing in general? What are the problems we’re solving with remote interviewing?
• What does success look like for us when it comes to remote interviewing?
• What does success look like for our candidates in remote interviews?
• Where does our current interview process fall short for remote interviewing? Why is it falling short?
• What are they key areas to fix in our remote interview process?

Answering these questions can help come up with a more principled approach to remote interviewing. Once you have a high-level philosophy on what that means for your company, you can move on to shifting your processes to be remote-first.

II. Remote interviewing process

“… then rein in chaos.”

As I started interviewing, almost each conversation I had began with “Hey, can you hear me?” and continued with “Hello? Hello! I can hear you!”. That, among other things, made it difficult to feel like I was in control. If your expectations as candidate, or as interviewer, are only calibrated to in-person interviews, you’re in for a big, chaotic surprise. In-person interviews never start with people in the room furiously shouting at each other, unable to clearly hear or see each other.

In the best interview experiences I had, the people I was talking to were ridiculously well prepared to handle the chaos of remote interviews.

So, for companies adapting their interviewing processes to remote, training interviewers is important. But so is training candidates. And, if need be, changing interviews altogether. So let’s look closer at each of these.

1. Train interviewers

… and everyone else involved in the interview loop

Your company most likely has some training in place for hiring managers, recruiters, recruiting coordinators, interviewers, and everyone else involved in interviews. Similarly, you need to train everyone on remote interviewing, by explaining your new interviewing philosophy, and how processes are changing.

Coming out of that training, ideally, everyone feels informed and empowered to adapt their part of the process to work for remote conversations. Here are some examples of best practices I’ve experienced in different parts of the interview process:

• Recruiting coordinators scheduling large breaks in-between chunks of interviews. This gives candidates space to rest, given how tiring VC interviews can be.
• At the beginning of the conversation, each interviewer giving the candidate 3–5 minutes to stretch and drink water. This helps people move their bodies and keep hydrated.
• All interviewers knowing how to handle spotty internet connections. Each interviewer has the candidate’s phone number, in case VC no longer works.

2. Modify interviews

No matter how well people are trained, some interviews simply don’t work on VC. When the candidate has to draw on a piece of paper, point to things on their phone, or write on a whiteboard, the interview is likely to break. It’s almost unbelievable how much time my interviewers and I wasted, thinking of creative ways to make whiteboard interviews work on VC. We tried it all, from drawing in Zoom, to attempting in vain to find the right position for my laptop to show both my face and my paper drawings.

Ultimately, the question companies should be asking is not what’s the perfect angle for the candidate’s computer to capture what they’re drawing. The real question is: what’s the signal we’re looking to get in this interview, and how might we get it remotely?

That can mean fundamentally changing some interviews to fit the VC format. You might need to experiment with different interviews, and try various ways to get the signal you’re looking for.

For example, here are some ideas you could experiment with in remote design interviews:

• For a whiteboard exercise could you use an online tool, like Figma, to think through the problem?
• If that doesn’t work, is there a way to get the signal you’re looking for through a conversational interview?
• Could app critique interviews be limited to desktop apps where the candidate could share their screen?

Role play within your company and experiment with different ideas, until you find something that works for you and your interviewees.

3. Train candidates

Once interviewers are trained, and your interview format works for remote conversations, there’s one more thing you need to do: train your candidates.

In my interviews, companies offered different levels of detail about the interview process, and what each interview entailed. In most cases, simply asking was enough to get more information. But I’m convinced that not all candidates ask.

When I interviewed people in the past, I’ve seen a fair number of qualified candidates be unsuccessful, not because they weren’t skilled or knowledgeable, but because they weren’t prepared for specific interviews that different companies do.

When you don’t share details about interviews, you’re biasing your loop to select for candidates with a specific skill set: those who can improvise on the spot, and who can project confidence in uncertain situations. Those are good skills to have, but most times that’s not what matters most in knowledge work.

This is especially important on VC, when candidates cannot take social cues in their interviews, and when they have conversations in new formats and environments.

So, as a company moving to remote interviewing, it’s good to share as much as possible about each interview. Here are some ideas for things you can do to give all your remote candidates a fair chance:

• Take time to explain what you’ll focus on with each interview.
• Share what interviewers are looking to get signal on.
• Explain in practical terms what the interview will look like.

And some questions you might want to cover with candidates:

• Is the conversation very structured or more informal?
  → If more structured, is the candidate expected to solve a problem? Will they write things down, draw, or code?
  → If more informal, is it a conversational interview, with questions and answers? Or is it an open-ended chat?
• Should the candidate prepare in any way? Should they have paper and pen nearby? Do you expect them to have their phone on hand?
• Do you expect folks to give you specific examples from their past work experience? Or rather to speak more to abstract principles that they use to guide how they work?

III. Remote candidate experience

Remember that the people you’re interviewing are job hunting during a global pandemic, social upheavals, and economic uncertainty.

As I wrapped up my interviews, I realized that I was fairly lucky in my job search. Remote interviewing had its challenges along the way, but, for the most part, I steered clear of major problems. One of poorest interview experiences I heard of was from one of my mentees. A company she was interviewing with unexpectedly instituted a hiring freeze, right in the middle of her loop.

As a company, running interviews remotely during a global pandemic is hard. But, as a candidate, interviewing during this time is even harder. With that in mind, for companies shifting to remote operations, it’s important to place a strong focus on remote candidate experience.

Three important areas to think about are: transparency with candidates, sending strong signal on culture, and, finally, being kind.

1. Be transparent with candidates

Given the current economic uncertainty, it’s understandable that companies shift their hiring strategy, or freeze hiring. Even if it’s expected that might happen, it can be demoralizing for a candidate to have their interviews canceled mid-way through.

If there’s reason to believe your company will slow down hiring or that a specific role might be cut out, mention that to candidates at the beginning of their loop. It can feel difficult for recruiters or hiring managers to risk losing promising candidates by sharing this information. But it’s the ethical thing to do. And, in the long term, people will respect the companies who are honest about this more — it’s a strong signal on your culture and the things you value.

2. Give signal on culture

Speaking of company culture — having finished my job search, it dawned on me that remote interviewing made it much harder to get a good sense of different companies’ culture, to see their values in action.

In successful interview loops, companies get the signal they need on a candidate. But also, the candidate gets the signal they need on the company. Hiring someone to join your company is two-way street, the start of a relationship — and both parties need to feel convinced that the fit is right. So think about ways to give candidates signal on your company when they cannot meet people in-person or be in your office.

You can start thinking about this by asking yourself these two questions:

• How might we embody our company’s values in our remote interview process?
• How can candidates get a sense of our culture when they’re interviewing remotely?

3. Be kind

When I was finally ready to make the decision as to what company to join next, I looked back on my interviewing experiences, and something dawned on me.

The companies I interviewed with were in various stages of progress with their transition to remote interviewing — some more advanced, others less so. And not having clear, trustworthy processes was challenging for interviewers, candidates, and everyone else involved in the interview loop.

But in the midst of this transition to remote interviewing, what made a huge difference for me between good and bad interviewing experiences, was kindness. The kindness to set aside some time to breathe in between interviews, bringing lightheartedness in the conversation by saying a joke, or creating moments of delight in the interview loop, with small, thoughtful gestures.

For companies moving to remote work, here are three things folks on interviewing panels can start doing right away:

• Be kind to candidates. There’s a lot going on in the world, and interviewing during this time is intense. So offer kindness whenever possible.
• Bring joy and humor in interviews. Some of my most productive conversations started with me and the interviewer talking about the most awkward VC hiccups we’ve had at work in the past.
• Bring delight in the interview process. Surprise the candidate with a nice gesture. For example, you can send them lunch on the day of the interview, or a give them card signed by folks on the team.

When making the final call as to what company to join, there were many factors I considered. Industry, team, company culture and values, mission, compensation, role, interview process, and so on.

Among many other things I appreciated, one of the companies I interviewed with had a super kind and delightful approach to interviewing. I still remember getting an email from them the day before my “onsite”, letting me know they made a donation on my behalf to a Covid-19 Solidarity Response Fund. And that was Plaid — the company I ended up signing with. I chose them for many reasons, but not in small part because they were the kind of company who would make a donation to Covid-19 Fund on behalf of candidates.

Remote interviewing was challenging, but also a great learning opportunity. If you’re about to start interviewing, or transitioning your company to interviewing via VC, hopefully the tips above help make things easier. And if you have ideas about how to make remote interviews better, reach out! I would love to hear about it!