Navigating "The Last Mile" of the Interview Process with John Tincoff

Intro: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with John Tincoff. John is a partner at Remus Capital, which is an early- stage technology investor in Boston. John, it's good to see you.

John Tincoff: Yeah, great to see you too, Matt.

Matt Blumberg: I'm excited about our topic for today, which is the last mile of the interview process. You and I have both been involved in hiring lots of senior executives, board members over the years. Interview processes can be extremely drawn out and lengthy, and yet there is still an important last mile. So you coined the phrase, not me. Tell me what the last mile is in your view.

John Tincoff: Thank you. I need to make sure to trademark it. I think when I describe it that way, it's partly because of the sensation that you get, especially when you're working with maybe first- time founders who are kind of going through an arduous key hire process. And you get to that moment where you've got maybe three outstanding candidates that have all made it there for good reasons, right? They're on paper, excellent. They may interview really well for the role, have certain things that are very impressive about what they've done. But oftentimes we've seen, with our first- time founders especially, that there can almost be a rush at the end of such a long process where you've invested all this time, you've kind of calibrated profiles, you've had to figure out what you want, and I'm sure this is all very familiar to you, Matt, from both ends. And they get to the end and they kind of want to rush through a couple pro forma references. And so that last mile, in particular, the reference checking and doing back channel references that are kind of well thought through and considered, I think, can really make or break what ends up being a really successful process and successful outcome versus one that kind of takes that maybe wrong turn at the last minute. And we've seen this kind of go both ways, and both from the receiving end and the giving of references, where it was kind of crystallized for me in one case not too long ago where I was actually the person called for the reference at the very end of a pretty important process for a pre- IPO company, C- suite level hire. And all of a sudden, while I'm walking down the streets of Manhattan, I get this one kind of unexpected phone call from a number I don't recognize, and it's someone asking about, " What would you recommend? This person's up for a CXO gig."

Matt Blumberg: And it sounds like it's a perfunctory call, right, like, " Hey, don't want to bother you too long, just checking out."

John Tincoff: Exactly.

Matt Blumberg: Yeah, I've gotten those before.

John Tincoff: You know, as far as the clock in the process, it's at 11: 55, and they're making sure they're checking the boxes. And my immediate reaction is, " Well, I don't want to speak too soon, but effectively, if you talk to any member of the board of this company, they would tell you not to hire this person." And realizing it had gotten to that point was such a moment for me being on that end. And then I think on the flip side, it doesn't always have to be a pure reference call. You can think about how in certain cases where we've been trying to figure out who between two phenomenal candidates is the right person. An unconventional way of doing that last mile has been to have what I think you might call an audition, but with one of our other kind of VPs of product in the portfolio, someone who we know and have worked with very closely, who was willing to step in and effectively double as an interviewer in a different way inaudible

Matt Blumberg: Yeah, I love doing that. That's one of the things we do in a Bolster search is you bring a CXO, bring an operator into the process, and we find that that's really helpful for first- time founders. If they've never hired a CFO before, they don't know what good looks like.

John Tincoff: Sure.

Matt Blumberg: If it's a non- technical founder hiring a technologist, they don't even know what to ask them, so I think that's a great way of covering that last mile.

John Tincoff: Yeah, and as a CEO, I think it's obviously, we all know how hard of a job it is. But hiring is such a key component, and yet it's not like you've had the opportunity to have that many reps, particularly when you're hiring as a series A, post- series A company or post- series B company. You haven't probably had that many reps in hiring of each of these disciplines.

Matt Blumberg: Yeah, that's right.

John Tincoff: And so, it makes sense that you could end up falling into that trap.

Matt Blumberg: Yeah, so I want to back up for a second, because you just gave me an interesting thought, which is, so you're calling it the last mile, and it's a reference check at the last mile, how important it is. But the example you just gave of someone calling you, your reaction was like, " Really? You're just calling me now? It's 11:55." So the question I have for the sort of follow- up question here is, should it be the last mile? Or the minute you realize you're serious about a candidate, before you have them do 27 more interviews, should you start the back channel reference process in parallel?

John Tincoff: It's an interesting question. I don't know what best practice might be considered, kind of from a recruiting standpoint, particularly for someone like you, I'm sure, sees so many examples of this. But I will say from my personal experience, I've moved towards trying to push the references to kind of move up in the process, move up the stack in priority, because I've just seen them be so telling and instructive about... Ultimately, I think we all know that if you get the right person in the right seat, everyone's going to be happier. And figuring out what really allows you to distinguish between the right fitted candidate and what maybe questions to push on or probe more deeply in with another candidate, the sooner you can get to those, usually, the better, I think. But yeah, I think-

Matt Blumberg: At least one, right? Pull one of them up early in the process and make sure that you're not off track.

John Tincoff: If I think about the last process I did, Matt, that is something I did try and do. And in fact I did do, I should say. And effectively it was... I don't know if in some of these cases it produced kind of like what I might call a yellow light as opposed to a red light? But usually it was something that I was doing instinctively. Haven't necessarily made it a practice that I mandate, but I do think you're right that probably most founders would be better served by doing them at some stage, some milestone that's like two- thirds of the way through the process, as opposed to waiting until the very end when you're just picking between people.

Matt Blumberg: Till the end. And well, look, a yellow light, all that means is you should do another one.

John Tincoff: That's right. That's exactly right.

Matt Blumberg: So, this is great inaudible

John Tincoff: And it allows you to maybe better inform the deeper references that you might pull for further on. And sometimes it's just about making sure you're asking the right questions, and that's true, I think, of so much interviewing. You might be able to speak to that, but I think that that's the thing I would think about.

Matt Blumberg: Well, this was a fun conversation. I think you and I just may have co- created a new best practice for interviewing, but all keyed off of your framing of the last mile. So, John Tincoff from Remus Capital, thank you for being here today.

John Tincoff: A pleasure, Matt, and I really appreciate what you're doing here with Bolster.