Conversational AI
4 min read
January 23, 2023

2023 is the year we solve the challenge of interview scheduling for good.

2023 is here and interview scheduling is still a major pain point for hiring managers and recruiters around the world. Let's change that.

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It’s 2023, and somehow one of the most consistently nagging challenges with hiring remains the scheduling of interviews. 

Applicant tracking systems, which have been around for decades, have failed to solve for the complexity of interview scheduling, leaving it largely to be done manually, even after significant automation gains in other areas of the process. Sure, most (but not all!) have something to help with a simple 1:1 interview, but many still struggle with panels, room booking, round robin, code tests, and many other complexities.

What's complicating interview scheduling?

For outsiders, it’s easy to think: Why is this so hard? But those in the know understand that interview scheduling is one of the least structured parts of the hiring process, and that’s led to them requiring lots of people to be involved. Here are a few examples:


There’s tons of variability about who is involved in the process for each job. Complex scenarios such as “do a code test with a peer software engineer” are challenging to handle in traditional software.

Things change pretty fast — someone calls in sick or has an emergency meeting and needs to move around the entire schedule in real time, communicating lots of things to lots of people all at once.


Poor calendar hygiene — from the notorious “time blockers” to the “never accepts”, bad behavior makes automation tricky.

Yet, technology breakthroughs in things like automated negotiation are helping to clear some of the longstanding hurdles. If conversational AI can negotiate smartly in complex games, it can negotiate calendar availability as well. That’s a big deal in overcoming bad calendar hygiene of hiring managers and other interviews where communication at scale with potential interviewers can be done through conversational AI.

Similarly, the use of messaging platforms to displace email is helping with velocity of communication in real time to navigate time sensitive reschedules. Where email was once the primary method of communication, most companies are using messaging tools like Teams, Slack, SMS, and others where velocity of communication is much faster to respond to real time needs.  

And in combination, those things help deal with bad calendar hygiene. If “Dennis” won't keep his calendar up to date and wants his conversational assistant to send out messages for every single interview to negotiate times, there’s now a scalable way to make it happen without a room full of coordinators catering to Dennis.  

How to uncomplicate interview scheduling.

There’s also more that conversational assistants can do to drive good, useful interview processes. 

First, being sure that everyone is prepared going in. That includes the candidate, of course — but more importantly, it includes the interviewer's understanding of what questions to ask, what to listen for and what actions or decisions they should be making in the interview. Candidates tell lots of horror stories about multiple interviewers asking the exact same questions or being completely unprepared. 


Now, being prepared is essential for a good interview, but their interview session itself is an important point of experience. One after-effect of the pandemic and resulting remote work movement is that many more interviews are done via video conferencing for at least one participant. That’s a challenge, of course, and integrations with Zoom, Teams, and other popular video providers are important to avoid frustrations and logistical letdowns. But it also provides an opportunity to give managers a “heads up display” with the resume, notes, and interview questions all easily accessible to them. Features like recording and transcription also can lead to a better experience for video interviews to avoid some traditional pitfalls.

There’s also a growing body of software for interview intelligence that includes attempting to glean insights from the transcript of an interview. While this area holds some promise, we also find that most companies aren’t yet doing the basics of interviewing right in order to fully capitalize on any insights that can be gained there.  

Organizing interview feedback is another area where conversational software powered by assistants can continue to drive companies forward. Today, there’s not enough structured feedback and decision-making debriefs are flawed with a number of tricky problems. For all the time invested in interviews, we still make decisions with debriefs that start with “how did you like the candidate?” or waiting for the most senior person in the room to talk first.  

While technology shouldn’t make the decision about who gets hired, in 2023 it can help drive people to collaboration and action to improve all parts of the interviewing process — coordination, experience, and debrief — to make the process better for everyone. 

Written by
Adam Godson
Chief Executive Officer
Adam Godson
Written by

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