Interview the interviewer
with Pat Reilly // @PRPatReilly
Favorite ice cream: Salted caramel ice cream
First job: Bakery assistant
Current job: Principal at PR and Company
& with Tod Hill
Favorite ice cream: Coffee ice cream
First job: Watering lawns in Hillsborough
Current job: Partner at PR and Company
What is strangest thing a candidate has ever said in an interview?
[Tod] I was interviewing sales reps for a company I was working for and this guy came in and it turns out that he was Peggy Lee (the jazz singer’s) former assistant… and without prompting he let me know some rather intimate details of Peggy Lee’s personal habits, shall we say—um, not sure how relevant they were to his position as a sales rep but I learned about her toilet behavior; it was really interesting. I think the lesson on that is: Keep it relevant. He didn’t get the job
[Pat] Over the years I’ve had a lot of strange questions asked of me over the years, but one of them that comes to mind is where a person who was applying for a senior level position was asking me questions about how often I had dinner out with prospective clients and whether she’d be able to go along on those dinners. What it demonstrated to me was that she didn’t really understand our business nor what her role would be. And I guess the takeaway on that would be: Stay focused on getting the job before asking what the benefits would be.
Looking back on some of the hiring decisions you’ve made, what is a mistake that stands out to you now?
[Tod] Unfortunately I think it’s a mistake I’ve made more than once and it’s something I am always having to relearn. And that is never hire from a place of desperation of trying to fill a role because you have a capacity restraint you’re trying to fill. Whenever I’ve been in a situation where I’ve done that, I’ve ended up regretting it. And not just because the person was a bad fit. It’s a bad way to come on board, it’s a bad way to set someone up for success when you’re just wanting to fill a chair out of a desperate need. I haven’t done it all that often, but I’m surprised when I do it again even if there’s a 5-10 year interval in the time between when again I’m doing this thing I said I wouldn’t do. But i think it’s common because we have a need, and then find someone who may fit and go with them; in this instance the mistake is not trusting my gut. When there’s a little voice saying this is not the right time or person but settling for it.
[Pat] I think my mistake that I think other people do often is hoping that someone you like will change. Another way of saying that is rather than really focusing on their ability and their skill to do the job, falling in love with who they potentially are as a person: “Well they have a nice smile, they kind of remind me of my sister, they didn’t really answer that question that’s key to how we work the right way but gee, I really like them; maybe if they stay here a little while they’ll get better…” And invariably it’s focusing on the wrong thing in an interview and setting that person up for that failure and from the get-go going to be disappointed. You have friends outside of the office and there’s a reason you have friends outside of the office. And there’s a reason you need to hire the person who can do the job.
How about some great advice you’ve gotten before about interviewing or hiring?
[Tod] It’s actually advice that my father gave me a long time ago. My father was high school history teacher and had a steady stream of student teachers he had every year so he interviewed a lot of people over the years. And he said: Take a curiosity shot before you go into an interview. Whether you’re interviewing someone or you’re being interviewed. Curiosity is so key. And I find that when I’m on the interviewer side when someone doesn’t come in with that high level energy on the curiosity side it can be a deal breaker for me. Because it is such a great demonstration of their interest. It’s a great way to develop rapport—which is key in an interview. And from an interviewer side, actually being curious opens the door for the interviewee to actually be on common ground where you’re trying to figure out things as opposed to an examination where you’re merely trying to see someone jump over hurdles; not to help people over the hurdles, but to approach it with a sense of curiosity get better answers and a clearer sense of who someone is.
[Pat] I love podcasts like this; I’m a big student of reading how successful executives who have run successful enterprises have found and cultivated the right talent. SO one of my new favorite questions that I’ve picked up—not that I apply to every candidate but one who gets close to joining the team which is: Ask them about what they learned, and specifically what they learned from their mother. And it sounds kind of like a gotcha question, and it may be in the context of when you’re talking about the currency of what you do every day and then you ask “What did you learn from your mother” what you’re doing is piercing that professional competency and getting to in my mind—and why it’s a successful question in my mind is—I only want to hire people who have always learned something, and walked away from any experience or relationship saying: Here’s what I learned. I also because I am the woman founder of a company need to be sure that whoever I’m working with enjoys working with strong women! So if you walked away from a relationship with that primal female figure in your life and you go in and almost all the time when I ask that question, the responses I’ve gotten from candidates who I want to keep working with, the responses I’ve gotten is “I couldn’t even tell you all the things I learned from my mom,” and it’s usually something about their character. It’s like, “my mom taught me never to give up,” or “my mom taught me to always do your best,” and because it’s outside of a professional setting, they usually answer in a really honest way—and that gives me a window into who they are outside of the office, and that is important to our work at PR and company because having a passion—having a passion for social impact and change is important; so being sure that whomever we’re bringing on board is stirred by those things is important to me.
[Tod] I think someone who is not bringing their full self to their job, especially our line of work, is going to be limiting. For example, when we ask somebody: what issues do you care about? Given that we focus on social impact, they don’t have to check a list of issues that our clients work on or that we’re currently working on; but knowing that they actually care about something and knowing why. Sometimes in an interview setting we’ll hear, “I really care about access to education because I grew up in a poor family in a rural area, and it was my education that enabled me to pull out of that and to achieve what I have and that is a value that I hold;” hearing that you’re not just hearing that they care about education. You’re hearing the arc of their personal story, a greater understanding of what their values are and where their passions lie, and in our line of work that’s important, and on some levels, in all kinds of work. You want people who are capable of demonstrating passion towards something.
Imagine it’s 2026 and you can change anything about the hiring process? How would you improve how we hire today?
[Tod] Okay this may just be me venting my pet peeves about hiring rather than transformational vision! But one of the pet peeves I have is when you’re filtering through resumes and cover letters that people don’t apply a sense of creativity and depth to how they present themselves. I’m not necessarily looking for somebody who’s done exactly this job before, but I want you to have the creativity and analytical ability to present yourself in a way that’s connected to the job. Instead we get very cookie cutter responses, very cookie cutter communications, very much like they are checking boxes and just sort of letting you know. That greater depth of analysis, I’d love to have a product like Unitive or something that actually filters for that. So you’re not having to engage with applicants and applications that are just generic. You know—dive in. Prove to me why you’re good for the job. Align with the qualifications and competencies we’re looking for in the job, but also takes it to the next level. And gives specifics—not stretching into something you’re not qualified for, but give specifics and make your case. Don’t make your case in a way that’s merely robotic.
[Pat] I imagine that in 10 or 20 years, hiring will be completely different. And I imagine it will be completely different in the context of tools like Unitive being embraced. But I also hope that it’s different in the context of more deeply connecting the experience of work with the pathway of getting a job. I’m a big believer in trial. So at PR and Company for example, almost everyone who works at PR and Company has a three month trial where we work on something together because I think getting that experience really helps you understand all the things that are difficult to understand from paper or a series of meetings or lunches. Instead what is a collaborative process that will allow college students and people just entering the workforce a better flavor of who they are as people and what kind of setting their going to be best working in, on one side in terms of people coming into the workforce; and then also it will become customary for people to have either some determined trial period where you can see what it’s like to work together (where they’re compensated for their work) but they’re coming in with a sense of ownership of their own destiny. And I think increasingly, as people become multiple jobs, their responsibility to own who they want to be in the world and what path they want to take has gone back to the individual. Flipping that dynamic a little bit so that you as an employer can search for that quality by having people work with you in that real setting. And there’d be a greater assumption of responsibility for the applicant in recognizing that it’s up to them to make decisions about how their career path is moving forward, what setting they work best in. What I mean by setting is some people are well suited to very large organizations with a lot of structure and infrastructure to them. Some people (I’m one of them!) work better in a smaller dynamic setting. And a lot of people I think get side tracked in their careers because they don’t understand what kind of setting they’ll be successful in. Having an opportunity to experience that setting and then having the ability to make that call about who they want to be in that setting to me would be a really beneficial shift. You’re getting right to the work.
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