back to indexCareer Lessons: Overcoming Mistakes, Navigating Challenges, and Triumph
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1:52 Sending a nasty email and leaving person on cc
10:0 Misspeaking to execs while intoxicated
19:7 Mistakes in mass emails to prospects
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You're listening to Let's Talk Jobs, where we give you practical insights into jobs and 00:00:13.420 |
Today, we're talking about horror stories from our careers and what we've learned from 00:00:18.480 |
Joining us is Troy Peterson and Jesse Ratner. 00:00:24.160 |
Now, naturally, you guys have both had your own episodes, and make sure you guys click 00:00:31.400 |
But between all of us, not to age us, we've got a fair amount of years of experience between 00:00:36.400 |
I think I've been doing, I think, 24 years in industry. 00:00:40.040 |
Yeah, I'm at 25 years in tech, and then before that, I was in media for about four years 00:00:49.560 |
And I'm in about the same space, actually, as you would know, when I first, almost, first 00:01:02.000 |
Actually, that was one of my first jobs in tech, and I think you were my manager for 00:01:06.680 |
And yes, I'm really excited to talk, and we certainly have decades of experience between 00:01:14.960 |
Lots of horror stories, and looking forward to talking about it. 00:01:19.120 |
Yeah, you know, the funny thing about horror stories is we've all got them, right? 00:01:22.760 |
And it can range from small or big, and it's all relative to who we are as people and how 00:01:30.920 |
I think what we do with it and how we respond to it is really important. 00:01:35.080 |
And I think early in our careers, mid and late, there's always something to take away 00:01:40.680 |
And so our goal is to share that with you guys who's listening and watching this podcast, 00:01:44.040 |
and hopefully you can get something out of that. 00:01:46.040 |
So I'm going to kick us off, you guys, and you're probably going to laugh at me, because 00:01:52.960 |
Have you guys ever sent a nasty email to someone and you forgot to take them off CC? 00:02:00.600 |
I've never done that one, no, unfortunately, but I've definitely received mistake emails 00:02:09.720 |
When you hit submit, you see the participants in the email quickly, and you feel this rush 00:02:18.440 |
of heat and blood coming up the back of your neck, and that freakout starts to happen, 00:02:27.400 |
The first one was younger, maybe like, I think, two or three years into my job experience. 00:02:32.720 |
And then the other one happened like, I think, within the past three years. 00:02:35.700 |
And I think how I dealt with it and how I process it was very different based on just 00:02:49.240 |
So my whole job is to build relationships with customers and hopefully build credibility, 00:02:56.360 |
I had this one particular client who was really, really difficult, both verbally abusive to 00:03:01.640 |
my team and typically, you give an inch, take a mile type of stuff, right? 00:03:17.680 |
And so they had sent an email to the team, which was not a nice email. 00:03:23.400 |
So I hit, so I did a reply all and I deleted them from the first draft of the email. 00:03:31.600 |
But then I didn't like the email, I closed it and I came back to it. 00:03:34.520 |
The problem is when I came back to it and I redrafted it, I didn't take them off the 00:03:40.000 |
And I was literally, my choice of verbiage was like, "They're terrible," like, "I can't 00:03:45.240 |
believe I have clients like this," and it was really bad and I hit send on that. 00:03:53.840 |
And my response to that besides, "Oh, crap," was sending an immediate follow-up email to 00:04:03.720 |
I sent another email to the client and in some cases, almost overreacting on my part 00:04:11.600 |
What I didn't do was pause, breathe, reread the email because I have more context around 00:04:22.400 |
why I said that, but the reader does not and they may not read it the same way I read it. 00:04:28.000 |
And what ended up happening was my manager told me, "Hey, look, if you didn't respond, 00:04:35.820 |
But because you overly focused on it, now it's a thing and you've drawn all this attention 00:04:43.220 |
And it ended up taking me off the account because it damaged reputation of our – with 00:04:52.240 |
Three years ago, I did another one and this one was about an individual. 00:04:57.440 |
And similar things, we have gripes about people and they're annoying. 00:05:02.040 |
And so I sent out an email and this time, similarly, accidentally CC'd them. 00:05:07.520 |
My response this time around being older and having more gray hairs on my head was a lot 00:05:14.760 |
I drafted an email and then I – actually, before I hit the email, first, I erased everyone 00:05:24.140 |
And whenever I send emails like that, I first remove everybody so there's no chance of 00:05:30.420 |
So I remove them all and I allowed myself about an hour or two to go back and forth 00:05:34.460 |
and read it, put in draft mode, come back, shorten it, right, shorten, shorten it. 00:05:43.820 |
And this time what I did was I went back to the individual and gave them context. 00:05:51.460 |
I was like, "Hey, man, that was embarrassing for me but here's what I meant to say." 00:05:59.420 |
I said, "Hey, look, if you don't have a conversation, here's what it is. 00:06:01.600 |
Here's what I truly meant and some of the truth behind what I'm trying to say." 00:06:08.160 |
So they came back saying, "Oh," they kind of laughed and like, "Thank you for calling 00:06:13.420 |
But then we got right to the heart of the issue of the concern, right? 00:06:19.100 |
I'm glad I haven't had too many of those but I had another similar one through chat 00:06:25.060 |
where I was talking about someone to somebody else and I was on the wrong window. 00:06:34.420 |
And so the message I meant to send to someone else, I sent to them directly. 00:06:45.980 |
And actually, that was the midpoint of my career. 00:06:48.300 |
And the way I dealt with that one is kind of like the medium of the two. 00:06:53.580 |
I was like, "Hey, man," oh, actually, first of all, he responded, "WTF," right? 00:07:01.300 |
And I said, "Hey, man, I just want to share with you what I sent to someone else because 00:07:08.780 |
I want you to know what I said because I'm trying to hold myself accountable." 00:07:14.060 |
But ironically enough, I was able to build upon that and use make lemonade out of the 00:07:19.100 |
lemons and allowed me to start having more frank conversations with this person. 00:07:25.500 |
I don't think they're that dumb, but that was my horrible mistake. 00:07:31.740 |
I feel like if we were younger, Tim, you would respond with a meme this thin age, right? 00:07:40.780 |
I don't think us old fogeys have those skills to respond in that way today, but what about 00:07:53.140 |
And, you know, I was thinking when you were telling the story, the second one, Tim, that 00:08:05.180 |
Some of it is sort of like a biological response. 00:08:10.420 |
You hear a loud noise and you're on the street and there's a backfire or something, you jump 00:08:19.660 |
Like the fear of public speaking, I think is maybe it's a little bit of both, but you 00:08:23.220 |
can unlearn it and become a good, confident public speaker, even though it's probably 00:08:28.900 |
one of the scariest things for most people to do. 00:08:31.620 |
And some things are cultural because of the culture you're in. 00:08:35.220 |
And, you know, in some cases, I think I've been on team cultures and corporate cultures 00:08:40.380 |
even where I might have said to somebody, you know, in error, "Oh, you're so annoying." 00:08:46.580 |
But the culture is a culture of forgiveness, of kindness, of understanding, and you could 00:08:51.660 |
And I actually was on the receiving end of one of those texts from a designer. 00:08:56.700 |
He actually, I sat, I had a standing desk and I sat or I stood on one side and he stood 00:09:03.980 |
And I think he didn't mean to send a text that basically said, "That guy, Jesse, is 00:09:08.660 |
And I looked over at him and I'm like, "I don't think you meant that for me." 00:09:13.580 |
And I didn't take it that badly, I just, he's a young guy. 00:09:17.940 |
He was also a guy who had been, he was very junior, but sort of like this was his first 00:09:27.340 |
And after about a year, he started asking to get promoted. 00:09:30.300 |
He started getting asked to be promoted to creative director every week. 00:09:34.300 |
Every week he'd come in and talk about how he needed to be, I was managing him and he 00:09:38.220 |
said, "I need to be promoted or I'm going to leave." 00:09:40.620 |
And then after a little while he left, so good for him, but I've been on a, not so much, 00:09:50.140 |
I've sent a few nasty grams and had to clean up things afterwards. 00:09:55.420 |
But I think in terms of biggest mistakes or big mistakes, certainly I have one that really 00:10:01.220 |
stands out and I was working at an agency where I had been in a sort of a managerial 00:10:08.460 |
role, a lead role, but I was sort of under somebody that I couldn't move up. 00:10:14.380 |
And I was on this same account for a long time, it was a big account, we had Google 00:10:24.940 |
I had done a two-year stint with one agency under the same manager and then another two-year 00:10:29.980 |
stint with another agency under the same manager. 00:10:34.140 |
And we were very successful together, we worked pretty well together, we ended up starting 00:10:40.060 |
But at some point, and the agency had grown from like a very small size to many hundreds 00:10:44.700 |
of people, we had weekly happy hours at this restaurant in San Francisco on the Embarcadero 00:10:54.900 |
right under the Bay Bridge, it was beautiful. 00:10:57.660 |
And so we'd go over there with the Googlers and hang out and talk about business, talk 00:11:01.500 |
about other stuff, it was very casual, we'd drink quite often, as you might imagine. 00:11:07.940 |
And one night I was really chafing under this, there's a lot of things going on in my life, 00:11:12.820 |
I was trying to buy a house, I had a young child, my wife and I have, still do, but our 00:11:20.060 |
And I had a couple drinks, let's say three or four, dark and stormies, and I went up 00:11:28.220 |
to the boss above my manager, oh, and by the way, I had been moonlighting for a client 00:11:38.340 |
that the agency subsequently gained as their client, which I then dropped. 00:11:44.580 |
But I felt like, well, once the agency gained this client and I learned that they had been 00:11:49.340 |
struggling a bit with the creative, and I thought to myself, well, this is a great opportunity 00:11:53.660 |
for me, I could say, hey, I actually know this brand, in and out, I can help you, blah, 00:11:58.580 |
You know, and I've been thinking about it for months, like, how do I make my move, when's 00:12:02.260 |
the right time, what's the right way to do it? 00:12:05.780 |
Anyway, so this Friday happened, and like I said, I had a couple drinks, and I pulled 00:12:12.500 |
the boss's boss aside, and I said, I can help you, here's why, I actually know this client 00:12:18.660 |
and I've been working for them on the side, and he was like, wait a second, timeout, timeout, 00:12:23.180 |
that's probably a conflict of interest, I need to talk to the partners, and soon after 00:12:30.780 |
You know, I was on a really good path, I was on a good path, had a strong, well, at least, 00:12:36.900 |
I would have probably continued in that sort of corporate agency path, and it completely 00:12:43.100 |
changed the trajectory of my career, and I've been a consultant ever since, and in some 00:12:48.140 |
ways it's been really good, you know, I took a risk, but it wasn't well thought out, and 00:12:54.260 |
I think I was going to be stuck in a role that I didn't feel satisfied with, if I didn't 00:12:59.420 |
somehow make a move, and I might have made the wrong move at the wrong time, but the 00:13:03.420 |
result was it opened a bunch of doors, because I had to, then I had to hustle, I lost my 00:13:07.700 |
job, I got another job right away, I had a good, you know, good resume, having worked 00:13:13.540 |
at a big brand, or at an agency for a big brand, and some of the things, and, you know, 00:13:18.740 |
other doors open, and I, you know, I can, some of the other things I think we'll talk 00:13:22.220 |
about in terms of fear of, you know, fear of fear itself, fear of failure, those kind 00:13:27.060 |
of things, came to the forefront as I then moved down the road in my journey, but yeah, 00:13:31.460 |
it wasn't a mistake, probably, you know, the timing, not so good, the inebriation part 00:13:37.540 |
probably not so helpful in my decision-making at the time, and I think I, you know, I held 00:13:44.140 |
that inside for a long time, and I saw the guy at the boss's boss, I hadn't seen him, 00:13:50.020 |
yeah, I hadn't talked to him, like, I was somewhat of a friend, I mean, he'd kind of 00:13:53.140 |
been to my house, and I'd been to his house, and, you know, we knew each other quite well, 00:13:57.860 |
worked close together, the boss's boss, that is, and then I didn't see him for like seven 00:14:03.220 |
years, you know, I got pushed out, I remember that last day, he walked me to the door and 00:14:09.460 |
like that was it, and I saw him like about six months ago, it had been like seven years, 00:14:17.940 |
and I was getting a test for CPAP machine, I took a sleep disorder test, and I go to 00:14:25.100 |
leave from the from picking up the instructions, and the elevator door opens, this is a hospital, 00:14:31.340 |
you know, upstairs, and the door opens, and there he is, and he walks out, and we shake 00:14:36.540 |
hands and sit, I sit down for him, with him for a few minutes, and it was weird, because 00:14:41.060 |
I still was kind of looking for him to acknowledge what had happened, and he didn't, and he texted 00:14:48.460 |
me or I texted him or something, we had like a very short text communication, and then 00:14:52.900 |
nothing really, you know, we're not really friends anymore, but yeah, really, it really 00:14:57.820 |
was a probably not such a good move on my part, sorry about that, but it happens, right, 00:15:05.300 |
and then you move on, because you have to, and I'm gonna put myself on mute for a second, 00:15:11.780 |
so Troy can maybe share about a couple of things, but that's probably the biggest mistake 00:15:16.320 |
that wasn't a mistake, but was a mistake type experience. 00:15:20.220 |
Yeah, I kind of actually wonder, you know, we always have stuff to bring to the table, 00:15:26.220 |
and I wonder if you hadn't brought up the fact that you're moonlighting, and you're 00:15:31.700 |
just like, hey, I have some insights, or maybe I know this company, and maybe this nugget 00:15:38.140 |
would help you, do you think that would change it, because now you're, again, you're trying 00:15:42.220 |
to position yourself in a company, and I think this happens all the time, right, like we 00:15:45.900 |
have connections, relationships, and some stuff might better position us, right, is 00:15:50.340 |
there a way that could have played out differently, do you think, or just in general, just having 00:15:53.940 |
a relationship was gonna doom you by whatever information you're about to disclose? 00:15:59.540 |
I think I definitely could have positioned it better, I didn't need to, you know, talk 00:16:03.900 |
about how I came by that experience, I just could convey that I had a, you know, a deep 00:16:08.660 |
appreciation, it actually was LinkedIn, oddly enough, that was the client that I knew about, 00:16:13.660 |
that had worked for, on the side, and yeah, I could have positioned it as I had this experience, 00:16:18.660 |
I understand the brand, I know their voice, I know their goals, I know their, you know, 00:16:23.820 |
the core value props, and I think I could help, and leave it at that, I didn't necessarily 00:16:29.380 |
need to go on how I came by that information, experience, and the problem was that I was 00:16:35.060 |
a little bit drunk, and you don't think straight, and if there's any lesson I could take away 00:16:40.820 |
from that is, you know, don't get drunk and ask questions that could change the trajectory 00:16:46.140 |
of your career, you might not, you might not know where you're going the next day, and 00:16:51.100 |
it's risky, it's highly risky, and it's probably one reason why, especially in agency life, 00:16:55.180 |
and you're probably familiar with this, Tim, it's often the case that you're smoothing 00:16:58.540 |
with clients, and there's alcohol involved, or other things, and you know, sometimes it 00:17:04.980 |
doesn't always go in a straight line, and I think that's life, right, and in some ways 00:17:09.700 |
fear is that accelerant, you know, it can accelerate us down a path that maybe we are 00:17:18.380 |
trying not to face, and so maybe this was a point in my life where I was sort of admitted 00:17:23.180 |
at crossroads for a long time, and I was sort of stuck in a role, I had all this experience, 00:17:27.900 |
I had led large teams, like the designer who told me I was a jerk, and things like that, 00:17:33.940 |
and had a bunch of success, and when then I was later able to go out on my own, just, 00:17:40.420 |
just enumerating the things that I had done often got me into the door when I started 00:17:44.820 |
my agency for conversations with potential clients, and even now I think, I still, you 00:17:50.140 |
know, I didn't lose all that experience, it just, I don't necessarily lead with that story 00:17:54.420 |
when I'm in an interview, but yeah, but to your point, I think, I think framing it certainly 00:18:01.860 |
is important, when you're in a situation where you're about to make a mistake, maybe step 00:18:06.740 |
back and write down a script for yourself, this is what I think I ought to communicate, 00:18:11.220 |
you know, and maybe sleep on it, you know, or show it to a trusted person, your spouse 00:18:24.000 |
That's interesting to hear you guys tell these stories, I feel like there's almost like two 00:18:30.580 |
layers of learning, there's the sort of short-term, and I think it's really important to short-term 00:18:37.000 |
sort of react in a way that is productive, but then there's also like the longer term, 00:18:44.220 |
like in terms of, you know, how do you deal with mistakes, you, whether you realize it 00:18:49.480 |
or not, when you make mistakes, you're learning, and even if you can't articulate what the 00:18:54.860 |
learning is, the next time I think you're faced with a situation that rings familiar, 00:19:00.820 |
I think you're going to be better suited to respond to it appropriately. 00:19:05.100 |
So like, you know, my example is much more tactical, but it was an important thing for 00:19:15.980 |
me to learn about how to take responsibility for it. 00:19:21.840 |
In the short term, I had started working for a software as a service company, my first 00:19:27.180 |
job that was like fully digital related is sort of around the 2000 time, 2010 timeframe, 00:19:35.740 |
and I was in charge of the CRM or slash email marketing at the time, and in one of the first 00:19:42.460 |
big email sends that we were, that I was responsible for, went out with the big call to action, 00:19:55.940 |
So it was like, I don't remember exactly what it was, but it was like, you know, sign up 00:20:03.980 |
And dead for the context that it was kind of a nightmare job for me in a lot of ways. 00:20:08.780 |
We might get into this later, but my boss was the temporary CEO because my other boss 00:20:24.060 |
He like just didn't like the whole practice of it. 00:20:26.660 |
But we also knew that email marketing and a lot of marketers know this, like it's one 00:20:29.980 |
of the, to your own, owned lists are one of the most high ROI tactics going and that still 00:20:39.220 |
So, you know, we weren't going to stop doing email, but the fact that this went out on 00:20:44.340 |
my watch and I was reporting to a CEO that hated email. 00:20:49.300 |
And I was, I was devastated because like, you know, the very concept that I could make 00:20:54.140 |
a mistake in front of, you know, thousands of people, you know, it was, it was, it was 00:21:02.180 |
But in the moment, I also, I was able to at least like quickly take responsibility. 00:21:08.900 |
And I knew that this, the news, the acting CEO was sort of a very matter of fact guy. 00:21:15.980 |
So like we quickly built sort of the mitigation plan, which was, you know, we're going to 00:21:20.340 |
re we're going to send another email, apologize and, and include the link. 00:21:25.380 |
Which it was very embarrassing, but you know, we, I approached him, I said, I'm really sorry 00:21:31.140 |
we made this mistake and had a verbal conversation with him. 00:21:33.660 |
I think it was the other thing that, you know, I think we've all had moments in our careers 00:21:38.820 |
where we follow up with a, with an email, we maybe send another follow up email. 00:21:44.380 |
It's like this is it swingers, the movie where the guy keeps, you know, leaving voicemails 00:21:48.340 |
for the girl he likes, and it just makes makes things worse, right? 00:21:51.420 |
It's like, it's better if you can just have like a quick conversation and attack the problem 00:21:58.380 |
Yeah, I think having a mitigation plan, or immediately building one as response to it 00:22:06.380 |
You know, I think in that moment, especially with stakeholders who are watching your response 00:22:13.980 |
to that, and how you're going to fix it in the plan, that's important to maintaining 00:22:19.180 |
and building on credibility, because your point, mistakes happen. 00:22:23.060 |
The difference is the person who is proactive and takes initiative. 00:22:28.580 |
The brand you're building for yourself is one of responsibility, right? 00:22:32.720 |
As opposed to, oh, you know what, I can't trust this person anymore, because they make 00:22:37.460 |
a mistake, they just go off the rails, and they just lose their marbles. 00:22:41.860 |
And I think you're, I've had a few emails go out as well, from like a nurture blast 00:22:48.180 |
or whatnot that had broken links or a website, since that's my domain, and we published wrong 00:22:54.620 |
information and analysts are seeing it right away. 00:22:58.300 |
And there's varying degrees of how apologetic you should be, right? 00:23:03.260 |
Because again, if you're too apologetic, sometimes you're going to blow something out of proportion. 00:23:08.640 |
And so being like, as we think about this way, like we've also received stuff before 00:23:16.220 |
And under construction, or hey, here's an updated link or whatever, that doesn't scream, 00:23:23.460 |
It just tactically tells me as a consumer, oh, here's another link, I'll just do this 00:23:31.540 |
There's sometimes where you just need to call it out. 00:23:33.620 |
And sometimes that actually helps build credibility and relationships with your customers. 00:23:40.800 |
I have a sort of related, I wasn't responsible necessarily for this, but I worked on a team 00:23:47.020 |
that sent out an email that had a broken link. 00:23:50.640 |
And we followed up with the email with just a very short subject line, oops, and it was 00:23:56.020 |
the best performing email of the whole year, just an engaging subject line. 00:24:03.140 |
I hate the fact that people actually, I think we've all received now purposeful mistakes 00:24:11.740 |
It's the digital marketing sometimes, marketing in general, I think we often end up doing 00:24:21.160 |
some things that feels a little uncomfortable, right? 00:24:27.140 |
I mean, I wouldn't necessarily call it clickbait because it was going to a friendly list, but 00:24:35.580 |
No, I mean, I'm saying that what's cringy to me is the people that do it on purpose 00:24:41.220 |
Oops, we made a mistake and then draws attention to it. 00:24:45.300 |
I think responding to a genuine mistake is authentic, right? 00:24:48.660 |
And then there's a difference, although sometimes the reader can't tell the difference. 00:24:56.000 |
But things like emails, your internal stakeholders, they think in terms of metrics, right? 00:25:03.000 |
And so having a mitigation plan and then doing something like, "Hey, here are the total amount 00:25:07.800 |
of sends and here's the amount of opens," because maybe the open rate, because you caught 00:25:16.440 |
And so the impact of the mistake may not be that huge, right? 00:25:20.080 |
If you don't provide context to people, then they just assume the worst. 00:25:23.160 |
So I think control the narrative as often as you can, and data is your best friend. 00:25:31.880 |
Our CEO at the time was huge into data, so I remember him showing him the, we showed 00:25:35.920 |
him the open rate, the click rate, and also the, yeah, I think even more important, the 00:25:41.560 |
And it was definitely within the normal range for any email. 00:25:44.640 |
It wasn't like a, yeah, it didn't, we didn't spur a huge loss in subscribers to the newsletter. 00:25:54.540 |
And I think for digital, it's an easy, well, not easy, but you can clean up a mistake. 00:25:59.760 |
If you put out something that has bad message, typo, whatever, missing link, you can update 00:26:05.560 |
it, send out a note, or if it's a webpage, you just update it. 00:26:09.760 |
I recently took a picture, this is a sort of a humorous aside, but I think it's relevant. 00:26:15.240 |
So this is a, in downtown, in North Beach, in San Francisco, there's an area of town 00:26:21.280 |
that has a number of strip clubs, and these strip clubs often have these big neon signs 00:26:28.880 |
I took a picture of next to each other that used the apostrophe, and one used it correctly, 00:26:35.800 |
One was Big Al's, A-L apostrophe S. The other was Roaring 20's, two, zero, apostrophe S. 00:26:44.600 |
Well, you know which business went out of, which strip club went out of business, Roaring 00:26:51.140 |
Now they met, I mean, it's sort of a humorous example, and they were around for decades, 00:26:57.160 |
but you know, and they didn't feel the need to change it, I guess, or didn't know. 00:27:01.360 |
They just made this giant sign with the grocer's apostrophe and left it up there for decades. 00:27:06.280 |
And yeah, the beauty of digital, so quite different than brick and mortar. 00:27:13.040 |
Hey guys, thanks again for watching and listening. 00:27:16.840 |
Next week, we'll be talking about dealing with difficult managers. 00:27:19.980 |
So make sure you hit like, subscribe and the notification bell so you don't miss an episode.