Minisode 3: Work Fails with Special Guest Merit Kahn

In this episode of The Leadership Habit Podcast, we continue our newest minisode series, Work Fails. We’ve all had experiences when things did not go as planned in the workplace, but people don’t talk about it. Great leaders know that failure is a part of life, and eventual success depends on how we handle the situations and learn from them. So we decided to talk to people about real-life examples of when things didn’t go quite right, how they felt it, and what they learned from the experience. Today we are talking to Merit Kahn, founder of Merit-Based Business and author of Myth Shift: Challenging The Truths That Sabotage Success. Merit is also the creator of The Merit Method: Sales Mastery for Life program. Listen in for Merit’s, fails, and learn how she recovered- so you can too.


Full Transcript Below:


Jenn Dewall:  Hi everyone, it’s Jenn DeWall, and I am interviewing Merit Kahn. Today, we are welcoming her as a guest for our minisode on work fails because we want to be sure to share with everyone that failure is a commonality, and it’s something that you cannot escape. It’s not a matter of whether you’re going to fail, but it’s about how you’re going to deal with it. And Merit is actually one of my favorite people to interview because she has shared with us that she actually has not failed in 25 years. We’re just kidding. We’re kidding. But you know, sometimes that’s kind of the way that people come on, right? They pretend that they haven’t had a failure or I can’t believe you’ve done that. Like I have never made a failure. Whereas failure is a part of life. No one’s escaping without failing in some way. And as a matter of fact, if they won’t admit that they’re failing, they’re failing by not having the self-awareness that they’re failing.

Merit Kahn: That is true. But I am going to tell you an old work fail story that I tell others because it actually plays into exactly what you just said. And it’s something that I learned a great lesson from, and it’s helped me throughout my career. This was, this goes back to when I was working in radio advertising sales, and I was brand new. It was my friend who was working in a big downtown Chicago radio station.

Jenn Dewall: Oh my gosh, so exciting!

Merit Kahn: JMK, we play the oldies. It was! I was over the moon. I was really young, and I’m super excited, and I really wanted people to think that I knew what I was doing. So there was a salesperson who left, and I got their account, and it was my first advertising agency- that’s a big deal to have an advertising agency. Because then they would just, you know, call you and say, can I book this time on the radio station?

Merit Kahn: So it was very little sales effort. So the agency called and said I’m checking available times for like a River Boat Casino and I’m, so I’m checking avails over the next 30 days. And I checked what was available on the radio station, terms of the commercial time that we could sell. And I wrote up an order for $30,000, and I faxed it. So this is a long time ago. I faxed it and the old fashioned machine to my client, and I had a note, thanks for the order. Now, by the time the fax got to my client, I had already done the victory lap around the office.

Jenn Dewall: You’re like look at this! I closed it!

Merit Kahn: Woo. Right. And I’m the general manager who is not a man known for his personal warmth. He comes out of his office all the way down the hall to the sales pit. Hi-fives, me, hugs me. Back in those days, you could hug people in the office and, and we are just celebrating. Like, they’re ringing the bell. And it was, and then my phone rang, and my agency client said, I’m sorry, I’m confused. Why did you send thanks for the order? I was checking avails, and I thought, so you weren’t checking to see how much time you could buy, and you wanted to buy all of the available time? And she said, no, no, no. I was just seeing what you had available. And then I was going to select the time that I want. And I learned a very important lesson that instead of acting as if I knew what that meant, I should have asked as if I really wanted to understand a term I didn’t know.

Merit Kahn: So I had to hang up the phone with her, walk through the walk of shame back to my General Manager’s, and then I go, “So Harvey you remember that $30,000 order I just put in like eight minutes ago?” He’s like, “yeah, rockstar salesperson, what can I do for you?” And I’m like, “yeah, that’s not gonna happen.” Like, that’s not going to go through. And he’s like, “well, what happened?” And I, yeah, that was a very expensive, difficult failure to overcome. I am pretty sure I felt sick for the rest of the afternoon. I couldn’t go into the office the next day. But you know, I think to your point, you always learn something from your failures. I sure have, I have multiple stories. I could tell you about more recent failures, but that one I learned that day in a big, big way. And now I share with everybody- never ever act as if you are the success you want to be. If there’s something you don’t know about it, ask as if you really want to understand everything you need to know about the problem you’re trying to solve.

Jenn Dewall:  Gosh, I feel like so much of that also comes down to, you know, assumptions. And that we talked about this and the other podcast episode, the optimism, wanting to see things in this kind of grandiose, positive rose-colored glasses way. And that’s totally natural, but sometimes it can lead us down the wrong path to making assumptions, which are not necessarily valid data points. Exactly. How did you recover from that? Because I know that to be able to go from high-fiving your GM to say, yeah, I got that sale to then walking into Harvey’s office and saying, I didn’t do that. That must have been hard.

Merit Kahn: It was really hard. Mostly because I had built up this identity. Like, I really, I was young and enthusiastic, and I really wanted to be liked, and I wanted to be respected, and I wanted to do a good job. And I think, I don’t remember exactly all the details, but I know I set up a meeting, I went into the office the next morning early, and I sat outside of Harvey’s office, the General Manager, and I sat down with him, and I just said, this is what I learned. I won’t do that again, and here’s what you can count on me for in the future. Like I won’t make that assumption. And, and obviously, I have a lot more to learn about some of the terms that an agency might use that I wasn’t prepared for because all the other business I had done was direct.

Merit Kahn: Like I would go to the mom and pop shop that wanted to get people in their store, and I would tell them about radio advertising, but I wasn’t dealing with a more sophisticated buyer. And so I asked him for better training, and I asked him if I could shadow people who had worked with agencies more. So I think what I had going for me, and that experience was I wasn’t afraid. I mean, I ate crow. I was like, I messed up. My bad. And here’s what I think I need to develop myself further, so I don’t make that kind of mistake again. I will make other mistakes, that’s guaranteed, but I don’t want to make that one again. So I have some gaps in my learning, and I just took responsibility for it. I think that’s, you know, the people that recover from any work fail are the ones that are going to as quickly as possible take responsibility for their role in that failure. And what can they learn and move on?

Jenn Dewall: Well, and I think that it’s- you went a step beyond responsibility because you took responsibility for it. But it sounds like you also thought, what are some other things that I can learn to set myself up for success in the future, so I don’t make this mistake again. Or what else did I not realize that I didn’t know that would have been helpful in that instance. And so you went, you went above and beyond just assuming responsibility. You said, okay, here are the ways that I want to develop, to even make a greater impact for the organization. And that’s a big deal because I think sometimes it’s easy to live in your shame of it and you can take responsibility, but then secretly be shaming yourself and kind of kicking yourself for maybe making that mistake. And I don’t think everyone crosses over to say, throw themselves into learning.

Merit Kahn: Well, yeah, I actually hadn’t thought about it until you said it like that. But I think because I was new and in the very early stages of my career, it might’ve been easier for me at that stage too, to acknowledge that I had a lot to learn. I think if that situation had happened and I had been at the radio station for a year or two years, and I legitimately should have known better. And I should have known what that term is, and it probably would have been a lot harder to admit that I didn’t have it all figured out. So I wonder, you know if I would’ve had that same opportunity to take full responsibility had I not recognized that I was in a learning phase. But I think that that’s one of my favorite books, business books, life books on the planet is Carol Dweck’s book, Mindset.

Merit Kahn: And she talks about the distinction between a fixed mindset and a growth mindset. And I think, you know, like you said, I mean, we’re all going to have work fails, and anybody who tells you otherwise is completely lying to you and themselves. I think something I don’t know, I probably just had it young. And I probably, my parents beat it into me or something that I kind of have a mindset of, you know, I may not be the best at something, and immediately I might make mistakes, but I believe in my ability to figure it out. You know, I, and I think that has helped me in a lot of situations, kind of be okay with the fact that I’m not going to be excellent at something right away.

Jenn Dewall: Yeah. You have to give yourself permission to just be a beginner.

Merit Kahn: Yes. That beginner mindset.

Jenn Dewall: Yeah. And it’s such a common thing. I think as we get older, we just assume that we should know everything. We put this pressure to have the answers, to know what you’re supposed to do when and where. And that’s when I think we stop learning because we think that we’ve already had the mastery, right. And it’s actually the opposite. That learning and growth are never done. And if you stop in a business sense, you can consider your business done because you’ll be out-performed.

Merit Kahn: Yeah – things around you change. I mean, you know, I just look at my personal life, right? My personal life has changed. And after 20 years of being in a marriage, like all of a sudden, I’m dating again. Like that’s weird. And I had to acknowledge that yeah, I knew how to date when I was 25, but I am not 25, and I had to relearn all that. And it’s different now. Back, you know, when I was dating the first time around you just met a guy like at Blockbuster, you know?

Jenn Dewall: People are like what is Blockbuster, and how do we use that?

Merit Kahn: This place where we look at movie titles on a box and then take it home and hoped it was rewound! And yes it was,

Jenn Dewall: You know, it’s, it’s reminding ourselves like we have to crawl before we can walk and there is nothing wrong with learning how to crawl.

Merit Kahn: Exactly. Exactly.

Jenn Dewall: Thank you so much for sharing your work fails. I just, I love talking to you! Thank you so much.

Merit Kahnl: Thanks, Jenn.

Thank you for listening to today’s Work Fails Minisode. If you enjoyed the episode, please share it with your friends and family, and don’t forget to leave us a review on your favorite podcast streaming service. If you want to learn more about Merit, head on over to or find it in our show notes there. You can find out more about Merit’s two-day sales intensives and find valuable resources to elevate your sales success.