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Mastering the Art of Storytelling in Business


Chapters

0:0 Introduction
1:20 The importance of making a connection with your audience
5:45 Kent's journey from religious science minister to corporate storyteller
12:30 Using anecdotes to captivate senior leadership
20:10 Real-life examples of storytelling successes and failures
30:50 Tips for young professionals on leveraging storytelling in their careers
35:40 Final thoughts and wrap-up

Whisper Transcript | Transcript Only Page

00:00:00.000 | [MUSIC]
00:00:06.520 | >> You're listening to Let's Talk Jobs,
00:00:08.320 | where we give you practical insights into jobs and careers.
00:00:11.360 | I'm Tim Chen and I'm joined by Kent Young. Kent, how are you doing?
00:00:15.200 | >> Hey, Tim. I'm doing great.
00:00:17.560 | >> Kent, you and I were talking about the art of
00:00:20.520 | storytelling and how to capture someone's attention.
00:00:24.840 | I wanted you to share with the listeners
00:00:27.500 | your example because I thought it was really fascinating.
00:00:30.040 | >> The example about my history, learning how to be a minister?
00:00:34.440 | >> Yeah, that and you went into the whole like
00:00:36.400 | the preacher analogy and how
00:00:39.500 | they capture attentions and that just really fascinated me.
00:00:43.000 | >> Well, I think with any style of communication,
00:00:49.560 | you have to make some connection with your audience.
00:00:53.040 | I think the best way that that's done,
00:00:55.960 | and we see it all the time like comedians,
00:00:58.640 | what do comedians do?
00:01:00.060 | They basically through a process
00:01:03.640 | of telling their own personal story
00:01:07.240 | because people really want to hear about someone else.
00:01:10.640 | Then they immediately pull themselves into that experience
00:01:16.400 | and through that filter begin to feel how that might feel for them.
00:01:21.480 | That's how we create empathy as human beings.
00:01:25.880 | It's funny. Yes, I did study
00:01:29.480 | four or five years to be a religious science minister.
00:01:33.600 | Now, religious science in and of itself is a little bit different,
00:01:36.440 | little new thought, but the reality was learning all the concepts was great.
00:01:42.400 | But then at the end,
00:01:43.880 | they go, "Okay, now you get to stand up and talk about it."
00:01:47.000 | >> Yeah.
00:01:47.920 | >> You can actually talk about what you learned and why somebody else should care.
00:01:53.680 | I think that's the point.
00:01:55.440 | The point is that in storytelling specifically,
00:01:59.800 | what we start out with is,
00:02:01.960 | we start out with ourselves and we talk about,
00:02:05.680 | we'll present the concept,
00:02:07.800 | but then we'll backtrack and we'll say,
00:02:09.840 | "Hey, this means a lot to me because,"
00:02:14.240 | and we begin to explain how in our own personal lives,
00:02:19.480 | how that topic, that concept,
00:02:21.560 | that view of the world applies to me personally.
00:02:27.120 | The goal is that if we are paying attention to our audience,
00:02:34.720 | we explain that in a way that the majority of people will get it.
00:02:40.240 | We'll appreciate that and they get pulled into it.
00:02:43.960 | Then at that point, you can pretty much start dropping
00:02:47.600 | other topics in that they then begin to be even more engaged about.
00:02:53.520 | >> Yeah. I totally agree.
00:02:55.040 | I think, yeah, you're right.
00:02:56.640 | There's some formulas out there that allow you to do a better presentation,
00:03:02.440 | and they usually say,
00:03:03.680 | start with a personal anecdote or a grip or a hook that's interesting,
00:03:08.280 | and then you lead into what you want to talk about,
00:03:09.920 | and you come full circle back to the hook.
00:03:11.760 | >> It reminds me of this one preacher I had once.
00:03:14.080 | Yeah, this is when we started off this conversation while preaching.
00:03:16.320 | He started off with this hilarious anecdote or story.
00:03:19.880 | The story goes, there's a man in a boat in the middle of the ocean,
00:03:24.040 | and the boat springs a leak.
00:03:27.080 | The water is going up,
00:03:29.000 | and so this preacher, he says,
00:03:31.000 | he prays to God, say, "God, help me."
00:03:34.280 | For a while, nothing happens.
00:03:36.840 | An individual on a canoe rose by,
00:03:40.120 | and the guy's like, "Hey, you need some help over there?"
00:03:42.320 | He's like, "No, no, don't worry. I got this.
00:03:43.600 | God's going to help me." He's like, "All right, cool, cool, cool."
00:03:45.880 | Then now the water's up to his waist,
00:03:47.720 | and now the boat's about to capsize.
00:03:49.640 | He's like, "God, where are you? Come help me."
00:03:52.240 | A guy comes by in the motorboat and comes by and say, "Hey, man,
00:03:55.720 | it looks like you're taking on some water there, buddy. You okay?"
00:03:58.120 | He's like, "No, no. I'm good, man.
00:04:00.400 | God's going to take care of me."
00:04:01.880 | Now the water's totally capsizing the boat.
00:04:04.440 | The boat's no longer visible.
00:04:05.560 | He's just treading water.
00:04:06.520 | He's like, "God, where are you? Help me."
00:04:08.400 | Then this carnival ship, a cruise ship comes by.
00:04:11.040 | He's like, "Yo, you okay out there? Do you need a life vest?"
00:04:15.320 | He's like, "No, man, I'm okay.
00:04:16.880 | God's going to help me," and he goes away.
00:04:18.520 | Then he drowns.
00:04:20.640 | He goes to heaven. He's like, "God, where were you?
00:04:23.920 | Why didn't you help me?" God's like, "I tried.
00:04:25.560 | I sent you a canoe, a boat, and a cruise."
00:04:28.680 | That led into his whole point around like,
00:04:31.040 | "Hey, are you listening?
00:04:32.080 | Are you paying attention? Are you being aware?"
00:04:33.880 | But that intro totally took me by surprise
00:04:38.280 | because normally I'm sitting there in a pew
00:04:40.080 | kind of falling asleep or daydreaming,
00:04:42.440 | and that totally pulled me in.
00:04:44.480 | I utilize a very similar skill set at work, too,
00:04:47.840 | where you mentioned earlier about captivating your audience
00:04:51.480 | and knowing your audience,
00:04:52.320 | and it differs by seniority level.
00:04:54.920 | And with senior leadership, I do the very same thing.
00:04:57.920 | Give a little anecdote,
00:04:59.720 | something that's top of mind for them,
00:05:01.640 | and I'll bring an illustration
00:05:04.800 | of something I'm trying to solve, for example,
00:05:07.280 | to kind of illustrate what I'm trying to do,
00:05:09.080 | and I'll lead very quickly into it.
00:05:10.640 | So like, given that, here's what we're trying to do today.
00:05:13.840 | We're going to do these three things as an outcome,
00:05:16.000 | and we'll lead right into it.
00:05:17.480 | But again, it's grabbing their attention,
00:05:19.240 | and you know it's working
00:05:20.360 | because they'll close their laptops
00:05:22.320 | or they'll stop scribbling on their notebooks.
00:05:25.400 | So the body language is also a tell.
00:05:28.040 | - Totally, and it's interesting, too,
00:05:31.560 | because if it's something that you've done in the past
00:05:37.400 | and it's something you haven't tried at this new company,
00:05:40.960 | one of the things that I'll do is I'll say,
00:05:43.400 | you know, in my last engagement with this sort of setup,
00:05:47.360 | I did these three specific things
00:05:50.280 | and saw a net increase of X, right?
00:05:54.760 | I find that, especially with senior leadership
00:05:57.760 | and to a certain degree, people that are peers,
00:06:01.280 | if you show up with not just an example,
00:06:04.880 | but you show metrics where you've hit the ball
00:06:08.880 | out of the park or at least, you know, got a base hit,
00:06:12.840 | people listen to that
00:06:13.680 | because we tend to be very metrics-driven, right?
00:06:17.320 | - Yes.
00:06:18.160 | - Sometimes that's good, sometimes that's bad,
00:06:20.500 | but if you're metrics-driven and you give that anecdote
00:06:23.880 | and you say, I did this with this result,
00:06:27.280 | wow, it's an amazing level of engagement you get.
00:06:31.120 | - Yeah, you know, I'll give you an example
00:06:33.160 | of where it fails, you know,
00:06:34.960 | and it just happened in the last 30 minutes at work
00:06:38.400 | and I'm just trying to figure my way through it.
00:06:41.760 | So one of the senior leaders in the company,
00:06:45.000 | they're in the break room, I was in there as well,
00:06:47.800 | I don't have any opportunity to speak to this individual,
00:06:49.880 | so part of it is like, hey, I want to put my name out there
00:06:53.640 | and whatnot, didn't come to it totally prepared though,
00:06:56.640 | probably should have thought this through a little bit.
00:06:58.340 | So I went in there and just say, hey, you know,
00:06:59.720 | like, how are you doing?
00:07:01.240 | It's a Friday, right?
00:07:03.160 | And then they responded, they're really kind
00:07:06.080 | and they threw out a question at me, it's like,
00:07:07.440 | hey, how is this aspect of your business doing,
00:07:09.840 | like web traffic or whatnot?
00:07:11.440 | And I panicked and didn't have anything.
00:07:14.880 | And I threw out a number, which absolutely made no sense.
00:07:17.160 | As a matter of fact, I think the number I recalled
00:07:18.840 | was based on my last job, which is peanuts compared
00:07:21.000 | to the metric that I was supposed to give him.
00:07:24.720 | And then like, and I kind of stumbled my way through that.
00:07:28.520 | And then like, but then I said, hey, look,
00:07:31.200 | I do have data I do want to share with you.
00:07:33.480 | Like, if you want to have time, let's talk through it.
00:07:34.960 | He's like, cool, let's do that.
00:07:37.200 | Then I was thinking to myself, like, oh man,
00:07:39.080 | I did a really bad job of engaging my audience there.
00:07:41.360 | That was like a total fail.
00:07:43.240 | What I hoped would redeem myself and we'll follow,
00:07:47.480 | we'll figure out if this happened or not.
00:07:49.240 | I can talk offline, is I sent them a message afterwards.
00:07:52.680 | I was like, hey, you know, like, here's the answer.
00:07:56.080 | Here's the actual day that you're looking for.
00:07:58.760 | And here's how it performs against the quarterly,
00:08:02.080 | monthly average this year.
00:08:03.120 | So kind of immediately paint a good story.
00:08:05.560 | Like, here's how we're doing.
00:08:07.000 | Embrace my vulnerability a little bit.
00:08:09.800 | I was like, hey, look, by the way, like, you know, honestly,
00:08:11.800 | like in that moment, I don't get,
00:08:13.720 | I don't get many opportunities to talk to you.
00:08:15.280 | So you know what?
00:08:16.120 | I kind of panicked and my mind blanked, but you know what?
00:08:18.960 | I do have a lot of good data to share with you
00:08:20.680 | that I prepared for you.
00:08:21.760 | So looking forward to going through with you.
00:08:23.560 | Even that is my version of an anecdote where you,
00:08:26.840 | you take something,
00:08:27.680 | an element of your personal experience you're going through,
00:08:30.360 | kind of open that up a little bit to your audience
00:08:32.200 | and then have a different connection
00:08:33.760 | beyond just the data, right?
00:08:35.120 | So now like he knows, okay, Tim's human.
00:08:37.760 | That wasn't the best first impression probably,
00:08:39.880 | but hey, there's, he set some context.
00:08:42.680 | It's kind of funny, self-deprecating humor,
00:08:45.280 | but like we're still gonna get what's important.
00:08:47.000 | And so again, just even that example
00:08:49.640 | is like trying to use personal story to tell,
00:08:54.960 | maybe influence a conversation
00:08:57.240 | or a direction that you want to go
00:08:59.120 | is really, really important.
00:09:01.360 | - Well, and, but we're all fallible.
00:09:04.600 | And some executives, I'll be honest,
00:09:07.000 | some executives don't place a high value
00:09:10.000 | in someone's willingness to fail and admit to it.
00:09:14.120 | Yet others are like, oh, he totally saw his mistake
00:09:19.360 | and he corrected for it.
00:09:21.240 | And that's all they really care about.
00:09:22.680 | I mean, you're not always gonna have the answer
00:09:26.600 | in that moment, right?
00:09:28.920 | But more importantly, like, did you wait two weeks
00:09:32.800 | to get back to him?
00:09:33.640 | No, you did it within minutes.
00:09:35.480 | - Yeah, well, let's hope he sees it that way.
00:09:37.680 | I'll let you know how it goes.
00:09:39.720 | - Right, right, right.
00:09:41.240 | It's all about how we deliver on stuff.
00:09:43.480 | - So shifting gears a little bit,
00:09:47.040 | you and I were talking about the importance
00:09:49.720 | of project management.
00:09:52.280 | And that topic is really near and dear to my heart
00:09:56.280 | 'cause that's how my career started.
00:09:57.600 | Now, I don't know if I told you like,
00:09:59.000 | like I graduated during the dot-com bubble burst,
00:10:01.280 | like nobody was hiring.
00:10:02.440 | And what I, and then with a marketing degree,
00:10:06.200 | like first position game, like go during that time,
00:10:08.800 | that and effective sales.
00:10:11.360 | And so I took on all these random oddball jobs.
00:10:16.360 | One of them was at a startup
00:10:18.160 | and essentially it was project management.
00:10:20.960 | And I think the, I didn't have any hard skills to my name.
00:10:23.840 | Like I wasn't a developer, I wasn't whatever.
00:10:25.760 | As a matter of fact, when I graduated from college
00:10:28.000 | and it was like a business, you know, business major,
00:10:31.240 | the only skillset I had was like communication skills.
00:10:34.240 | And that doesn't read well on resumes at all.
00:10:37.240 | And so what it looked like to me was like taking,
00:10:40.960 | being able to communicate,
00:10:42.360 | knowing how to hold people accountable,
00:10:45.080 | and then just be organized.
00:10:47.000 | I kind of stumbled my way into project management.
00:10:50.000 | And so I kind of want to hear from you, you know,
00:10:51.640 | like obviously you have a really strong point of view
00:10:54.280 | on the value of the skills of project management.
00:10:57.240 | Can you just tell me a little bit,
00:10:58.160 | like what it means to you?
00:10:59.480 | - Oh, I can, I could spend a lot of time on that.
00:11:04.200 | (laughing)
00:11:05.040 | Oh, so we're clear.
00:11:06.400 | Well, so let's think about this for a second, right?
00:11:10.480 | The context in which we were originally talking about this
00:11:13.120 | was when I talk to people that are getting
00:11:17.400 | out of high school, new college grads,
00:11:19.880 | people that are looking for summer jobs,
00:11:23.320 | young people for the most part.
00:11:25.080 | And one of the things that I'll tell them,
00:11:26.560 | especially in the workplace,
00:11:28.440 | one of the first things I'll say is,
00:11:29.840 | hey, if you're going to do any continuing education,
00:11:32.920 | I would recommend that you take a project management course.
00:11:36.480 | And they look at me and I go,
00:11:38.040 | so let me tell you why that's important to me.
00:11:41.560 | And I tell them, hey, when I was new to my,
00:11:46.560 | when I first moved to Northern California,
00:11:48.840 | I had a little bit of experience doing marketing.
00:11:52.680 | I was a graphic designer slash with a college degree.
00:11:57.680 | So what I learned pretty early
00:12:01.440 | with that project management class was,
00:12:04.680 | oh crap, everything I do, right?
00:12:08.520 | Everything I do has an impact if I'm organized, right?
00:12:14.640 | If I'm not organized, it always looks like a yard sale.
00:12:19.120 | Right? - Yeah.
00:12:19.960 | - And the example is that,
00:12:22.080 | even when I was as a graphic designer, right?
00:12:26.040 | The old style of graphic designer,
00:12:28.160 | basically you had to take line art,
00:12:32.560 | go into a camera room, take a picture of it,
00:12:35.680 | create a negative.
00:12:37.040 | Then you took that negative, you manipulated it.
00:12:39.960 | You did, if there were photographs,
00:12:41.760 | you had to shoot what we called half tones,
00:12:46.640 | basically breaking it up into a bunch of dots.
00:12:49.240 | And then you would strip all that stuff together
00:12:51.080 | and make basically a platform
00:12:56.080 | that you would use to burn a printing plate.
00:12:59.600 | And then somebody could go
00:13:00.520 | and print that piece of artwork.
00:13:03.800 | Well, you have to understand
00:13:06.960 | every single piece of that process
00:13:09.280 | and do it in a certain process
00:13:11.880 | 'cause you don't end up with a finished product otherwise.
00:13:14.960 | Right? - Mm-hmm.
00:13:15.880 | - So one of the things that made me,
00:13:18.680 | I went from just being a graphic designer
00:13:21.480 | to actually being a salesman in the printing industry.
00:13:26.480 | And what made me a great salesperson
00:13:28.880 | was I understood what my audience, my prospect,
00:13:33.880 | I really understood well what they wanted to accomplish.
00:13:38.200 | 'Cause I understood all of the pieces of the puzzle
00:13:42.560 | and what they were actually trying to finish with
00:13:45.880 | and actually give to their audience.
00:13:48.920 | And often I would sit there and I would negotiate with them,
00:13:52.280 | hey, I can do this,
00:13:53.880 | but I can do it more efficiently and cheaper
00:13:56.600 | if we do it like this.
00:13:58.160 | And they'd look at me and they'd go, really?
00:13:59.960 | And of course, it made me a really great salesperson.
00:14:03.680 | So even in sales, having that background
00:14:08.640 | and understanding what the process was
00:14:11.360 | that was gonna be employed
00:14:13.000 | in order to get them a finished product
00:14:15.800 | made me an even better salesperson.
00:14:17.760 | - Yeah, I thought you were gonna go
00:14:20.600 | a different direction with this,
00:14:21.600 | but that makes a lot of sense.
00:14:23.920 | When I think of project management,
00:14:25.920 | especially in today's day and age,
00:14:29.240 | there's a few things.
00:14:30.080 | Like the skills you gain
00:14:31.840 | from knowing how to hold people accountable
00:14:34.240 | and driving a schedule forward.
00:14:35.920 | Rightfully, that skillset applies to many a job discipline
00:14:39.400 | as you're describing, right?
00:14:40.840 | Project management specifically is fascinating
00:14:44.800 | because you can actually shift across industries.
00:14:48.960 | You can go from consumer to enterprise
00:14:52.200 | to you can go from marketing to product management.
00:14:56.360 | Like it's truly the one transferable skill
00:15:00.360 | that can be like a leap off point to so many things.
00:15:02.760 | I think that's what's so important today,
00:15:05.240 | especially with the way the job market is right now.
00:15:08.880 | We're trying to figure out like how do I market myself
00:15:11.560 | and how do I maybe reinvent myself or whatnot,
00:15:14.160 | or you're maybe looking for a new starting point.
00:15:16.840 | There are a lot of developers I know
00:15:18.840 | who went from development to technical project management
00:15:23.120 | and from technical project management
00:15:24.720 | into product management, right?
00:15:27.000 | And then part of that is like they couldn't make
00:15:30.720 | or they weren't comfortable making the leap
00:15:31.960 | from development to product management
00:15:33.800 | 'cause they lacked at that point
00:15:35.480 | some of the soft skills needed to do that
00:15:37.240 | as well as like how to present.
00:15:39.160 | And so that was a good path for them.
00:15:42.200 | It's also a good entry point
00:15:43.760 | into things like program management as well.
00:15:45.720 | And program management is actually a whole,
00:15:47.520 | it's very distinctively different than project management,
00:15:50.440 | but lean on a similar skillsets.
00:15:52.520 | So I always tell people,
00:15:53.400 | it's like, hey, if you're very early career,
00:15:55.360 | like we started this conversation around like college grads
00:15:58.560 | and you're looking for that first entry point,
00:16:00.080 | like project management, I think is the way to go.
00:16:02.760 | And you also interact with so many disciplines
00:16:04.600 | that you can figure out like
00:16:06.240 | if there's something else you want to jump into
00:16:08.200 | or you start passively getting all the knowledge.
00:16:11.120 | So you kind of understand how the departments work.
00:16:13.360 | I think it's just, I think it's the most powerful,
00:16:15.320 | most overlooked role in any organization.
00:16:20.080 | - Oh, and I will tell you this,
00:16:22.560 | that in the companies where they had
00:16:25.000 | departments of project management,
00:16:27.360 | that stuff went so much better
00:16:29.280 | than the majority of other companies that I was at
00:16:31.560 | where we didn't have a dedicated project manager,
00:16:34.400 | because frankly, they'd assign you somebody
00:16:37.120 | and they would sit down
00:16:38.720 | and they would dig into all the dependencies.
00:16:41.360 | And a lot of people don't understand
00:16:42.480 | what a dependency is, right?
00:16:44.200 | - Yeah.
00:16:45.040 | - And that means that if that thing doesn't get done,
00:16:47.000 | that stuff that falls further downstream doesn't, right?
00:16:51.600 | So yes, it was critical to have that.
00:16:55.080 | And that stuff will often get missed
00:16:57.240 | for a couple of reasons.
00:16:58.600 | But most of the time, those dependencies get missed
00:17:02.240 | because people don't understand
00:17:04.200 | the roles and responsibilities
00:17:06.320 | and the work stream that actually has to happen
00:17:09.640 | in order to produce product.
00:17:11.040 | - Yeah, absolutely.
00:17:13.360 | You know, I think we think about the topic
00:17:16.280 | of all these skills being additive,
00:17:18.560 | you know, like life or work experience is experience.
00:17:22.680 | You know, and when I talk to people who are younger,
00:17:25.040 | they're like, "Oh, maybe they lacked experience
00:17:26.960 | "to bring into a job interview," for example.
00:17:30.480 | It's like, no, like you could be a star runner
00:17:33.680 | on a track team that has nothing to do with work,
00:17:36.240 | but telling a story, back to storytelling,
00:17:38.120 | around how your dedication to your craft
00:17:40.800 | and being a team player or excelling
00:17:45.200 | or going through the struggles and hardships
00:17:47.240 | to be the best runner you can be,
00:17:49.240 | like those skillsets are another way
00:17:51.800 | of helping people understand
00:17:53.800 | what you might bring to a work situation, right?
00:17:55.960 | So I think knowing, again, like knowing
00:17:59.760 | how to tell a story about who you are,
00:18:02.960 | wrapping your experiences is huge.
00:18:06.160 | I'm kind of curious, Kent, do you,
00:18:10.200 | like you and I are like, we're old hats,
00:18:12.040 | you know, we're not necessarily just hats,
00:18:14.000 | but like we got plenty of white hairs
00:18:15.400 | under these caps, and we've had cumulatively
00:18:18.760 | many tens of, 20s of years in the industry.
00:18:22.400 | Do you have any personal stories,
00:18:27.320 | whether it's work-related or could be a personal story
00:18:31.680 | of something that was really influential
00:18:35.960 | on how you handled yourself in the workplace
00:18:38.400 | or in your career?
00:18:40.320 | - As it relates to storytelling or--
00:18:44.600 | - Or just your life, just life experience.
00:18:46.400 | Maybe I'll lead you off with an example.
00:18:48.400 | I once, during a period of unemployment,
00:18:52.640 | this is during the time that .com bubble burst.
00:18:55.080 | And so one of my temp jobs was,
00:18:57.360 | I was a outbound sales at a call center for Wells Fargo.
00:19:02.360 | And it was every Saturday morning,
00:19:07.440 | you're on an automated dialer,
00:19:10.200 | meaning like a machine is calling someone for you,
00:19:12.880 | and you're measured by how long the conversation is.
00:19:16.080 | And so you're literally auto-dialing,
00:19:18.200 | calling people at like eight in the morning,
00:19:21.120 | telling them that they've overdrafted
00:19:22.520 | their checking account by $5, now they're able to make 20.
00:19:26.320 | Like no one likes that conversation.
00:19:28.360 | And the thing that really sucked was,
00:19:30.600 | sometimes you're still in the middle of a call
00:19:32.680 | and the dialer already initiates the next one.
00:19:35.120 | And so by the time you cut over,
00:19:36.600 | the person's already been there for like 20 seconds,
00:19:38.120 | like, "Hello, hello, who's there?"
00:19:41.160 | And in fact, when you pick up like,
00:19:42.920 | "Hi, this is Tim from Wells Fargo."
00:19:44.560 | Like they're pissed off immediately.
00:19:46.440 | And like that season was really, really tough.
00:19:49.440 | And I remember I learned how to deal with rejection.
00:19:52.960 | And I had a lot of crazy stories around people next to me,
00:19:56.160 | just like flaming out after a week or two weeks,
00:19:58.680 | 'cause it's a grueling job and it was just terrible.
00:20:02.120 | And I had my terrible weeks as well,
00:20:03.760 | but it was really formulative
00:20:05.480 | in terms of how I process information,
00:20:08.320 | how do I figure out how to take someone
00:20:10.360 | from like one end of the spectrum to like totally angry
00:20:14.880 | and somehow bringing them around to a happy place
00:20:17.080 | where they're willing to pay the big money
00:20:19.280 | in like three minutes flat?
00:20:21.040 | And how do you do that, right?
00:20:23.640 | So that was like a crazy experience that really shaped me.
00:20:26.520 | Like, is there anything that you've done
00:20:28.320 | that's kind of similar where it's like,
00:20:29.760 | you know what, this thing that happened to me,
00:20:31.600 | I just can't shake it.
00:20:32.440 | It just, for better or for worse,
00:20:34.240 | changed how I did anything at work?
00:20:36.240 | - Well, I'll use a real life experience
00:20:39.560 | where I talked about being a graphic designer
00:20:43.880 | and moving into sales for a printing company.
00:20:47.800 | So I was in Phoenix and I'm like,
00:20:50.960 | these guys are like, "Hey, do you know your stuff?
00:20:52.840 | You're really good with people.
00:20:54.800 | Do you want to hire you to be a salesperson?"
00:20:56.320 | I'm like, "Okay, great."
00:20:57.840 | And so what they did was the head sales guy,
00:21:00.960 | he was the older son of the two sons of the owner
00:21:05.640 | that owned this business.
00:21:07.080 | He would take me out for one day each week
00:21:11.720 | and we would cold call businesses
00:21:14.480 | in these, basically these industrial parks.
00:21:18.600 | And we'd go from door to door to door
00:21:20.640 | to find out A, what kind of business they were in,
00:21:23.160 | B, is printing something they actually do or use?
00:21:27.960 | And then if those two things are checked,
00:21:30.880 | then do they have somebody that they already use?
00:21:33.560 | Are they open to getting a quote for a project?
00:21:38.200 | So interesting where he would go in
00:21:42.480 | and he'd do the pitch and I'd just listen
00:21:44.560 | and we'd leave and I'd ask him questions about that.
00:21:47.120 | Then I would go in and I would do a pitch
00:21:49.800 | and he would critique my pitch
00:21:52.320 | because we didn't go into every business.
00:21:54.800 | I mean, some businesses don't need that, but very specific.
00:21:57.920 | And one of the things that I learned from that
00:22:01.640 | was it isn't the person who's the best at it, right?
00:22:06.640 | I got very good at it,
00:22:09.440 | but it isn't necessarily the person who's the best at it.
00:22:12.160 | It's the person who turns over the most rocks, right?
00:22:15.840 | So I, trust me, I got a lot of rejection.
00:22:19.600 | I would go in, if I didn't actually see the person who buys,
00:22:23.960 | I'd get their business card and I'd call them
00:22:25.920 | and I'd call them and I'd call them and I'd call them.
00:22:28.240 | Sometimes they would actually answer my phone call
00:22:30.560 | and give me an opportunity to bid on something.
00:22:33.120 | But probably 90% of the time it was either crickets
00:22:37.640 | or don't ever call me again, right?
00:22:40.120 | So it was a lot of rejection.
00:22:41.480 | But what I learned was, I'm in Phoenix, it's a big city.
00:22:45.640 | I figured when I was going out to deliver a print job
00:22:50.280 | or pick up a proof or whatever,
00:22:53.000 | along the way I would stop
00:22:54.920 | and I would just hit a bunch of businesses
00:22:58.720 | in these office parks.
00:23:00.600 | And it's not, like I said,
00:23:03.800 | it wasn't that I was any great salesperson.
00:23:08.120 | I was just diligent and I focused
00:23:10.800 | and I took every opportunity to make some cold calls
00:23:15.800 | and to drop off a business card.
00:23:17.600 | And let me tell you what the result was.
00:23:20.720 | The result was, after about a year of that,
00:23:26.080 | a little less than a year,
00:23:27.360 | but after about a year of that,
00:23:29.440 | they pulled me aside and said,
00:23:32.440 | we need you to dial back the selling.
00:23:34.280 | 'Cause we can't handle,
00:23:37.720 | I mean, you're finding the right businesses,
00:23:39.760 | you're finding the right projects,
00:23:41.760 | but we don't have enough people to support the production.
00:23:46.440 | So we have to hire more people,
00:23:49.800 | put on more shifts or get more equipment.
00:23:53.320 | And we don't wanna do that.
00:23:54.960 | So we dialed.
00:23:56.360 | And now the problem is that they tell you
00:23:58.680 | that you've gotta have the killer instinct
00:24:00.200 | to go out and find business, right?
00:24:01.720 | To be a salesman and do that cold calling.
00:24:04.640 | And I looked at him and I was like,
00:24:07.120 | that is not the right answer.
00:24:08.600 | Right answer is,
00:24:11.160 | we're gonna give you some house accounts to manage
00:24:13.560 | so that you can spend time doing that
00:24:15.280 | instead of cold calling
00:24:16.360 | because you're beating us up with too much work.
00:24:19.240 | That's one of those things where I learned,
00:24:23.920 | I listened and I executed.
00:24:26.480 | And I executed so well that they finally said,
00:24:30.040 | dude, dial it back.
00:24:31.120 | - Yeah.
00:24:32.960 | Do you have any examples of like advice you receive
00:24:39.040 | on the job that was really, really helpful?
00:24:43.640 | 'Cause your anecdote there reminded me
00:24:46.520 | of a situation I had where it was that previous company
00:24:50.200 | and I was a senior manager at the time.
00:24:53.760 | And I had just earlier in that,
00:24:56.440 | maybe like a year before that,
00:24:57.600 | I was like a project manager.
00:24:58.560 | So I was still trying to learn
00:25:00.600 | what the difference is between these roles.
00:25:02.800 | And I wasn't confident in how I presented myself
00:25:07.280 | or I didn't have confidence in my own ideas.
00:25:10.360 | Like I knew they were solid,
00:25:11.720 | but for some reason when I talked to people,
00:25:13.960 | it came out a lot less confident.
00:25:16.480 | I remember there was one individual I worked with
00:25:18.560 | and he was really intimidating to me.
00:25:21.560 | Like he was like physically intimidating
00:25:23.720 | and he had like, his demeanor was intimidating,
00:25:28.040 | but we get to know him.
00:25:28.880 | He was actually a real softy,
00:25:29.960 | but most people don't see that side,
00:25:32.280 | at least not immediately.
00:25:33.520 | And so I remember I had one conversation with him
00:25:35.640 | and he stopped me in mid speech.
00:25:37.960 | He was like, Tim, stop apologizing for stuff.
00:25:43.560 | Like, you know your shit.
00:25:46.440 | Like, don't apologize, speak confidently.
00:25:48.880 | 'Cause I was always doing these things like,
00:25:50.920 | hey, you know, I don't know what's cute with you,
00:25:52.320 | but answer blank.
00:25:53.520 | Or it's like, hi, I noticed this thing in the data.
00:25:56.440 | I'm not sure if it was relevant to you,
00:25:57.480 | but here's what I saw.
00:25:58.320 | Like all of that kind of apologetic framing of my thoughts
00:26:01.560 | was really prevalent in everything I said.
00:26:03.040 | And from that moment on,
00:26:03.880 | and I still continue to try to improve upon this,
00:26:06.400 | like exert myself with more confidence,
00:26:10.320 | and know it's coming from a place of experience.
00:26:13.240 | Do you have anything like that
00:26:14.440 | where like someone gave you on the job advice
00:26:17.800 | and it kind of just changed your mindset
00:26:19.360 | about how you carry yourself or how you do work?
00:26:21.760 | - Well, we all have, I think we all have examples of that.
00:26:26.480 | I will say this, that as I've gotten older
00:26:30.040 | and more comfortable with my skillset,
00:26:32.600 | my confidence, I mean, you know this, right?
00:26:35.840 | I don't mince words about what I do, right?
00:26:38.640 | Like, you know, if you're gonna play in my sandbox,
00:26:42.280 | dude, I'm gonna tell you exactly what I think
00:26:44.520 | and why I think that.
00:26:46.320 | That wasn't always the case.
00:26:48.320 | (both laughing)
00:26:49.880 | So I can appreciate, you know, I'm the go-along guy.
00:26:52.960 | So, you know, I would be like,
00:26:55.400 | hey, sorry to bother you, don't wanna interrupt, you know?
00:26:59.360 | But, so I played a lot of that soft peddling.
00:27:04.120 | I think one of the things
00:27:08.120 | that there's a big problem of in some marketplaces,
00:27:13.120 | and certainly with people that are getting newer roles
00:27:17.120 | is this concept of imposter syndrome, right?
00:27:22.120 | - Yeah.
00:27:23.820 | - 'Cause I think when I was at,
00:27:26.580 | I wasn't there very long, but I was a VP at GoDaddy.
00:27:32.640 | And it was very, very, very tumultuous time for them
00:27:38.040 | 'cause they'd just been acquired by a, you know,
00:27:40.260 | big private equity firm,
00:27:42.860 | I think two private equity firms for a lot of money.
00:27:45.240 | Anyway, so, but what was really interesting was
00:27:49.800 | that was one of those situations
00:27:52.080 | where I really did not know the landscape.
00:27:55.480 | And I got, I learned really fast that people who,
00:28:00.480 | people who you think you can trust,
00:28:05.920 | they may not have your best interest at heart, right?
00:28:10.560 | 'Cause everybody's looking out for themselves.
00:28:12.560 | So I think that was a challenging role for me,
00:28:15.880 | not because I didn't know what to do.
00:28:17.920 | I was very clear about what the role should do
00:28:21.040 | and what the work stream looked like.
00:28:24.000 | The problem was more how I saw myself in that role
00:28:28.240 | and how I interacted with folks was basically,
00:28:32.880 | I wasn't comfortable yet in that role and in that position.
00:28:37.880 | And so it affected how I came across.
00:28:42.080 | So I totally agree with you from that perspective.
00:28:45.320 | Absolutely.
00:28:46.640 | But I think one other concept, I think, you know,
00:28:49.680 | this whole concept of imposter syndrome,
00:28:52.080 | I think is really prevalent with people who get,
00:28:56.320 | who seek advancement, get it.
00:28:59.280 | And then when they're in it, they can't feel comfortable
00:29:02.480 | because they feel like somehow they didn't earn it.
00:29:05.400 | They didn't do enough to earn it.
00:29:07.560 | Even though all of the people around them
00:29:10.240 | have already given them credit for being capable
00:29:13.680 | and see them growing into the role and all of that,
00:29:16.640 | but yet they have a hard time, right?
00:29:20.600 | - Yeah.
00:29:21.440 | - In that role.
00:29:22.320 | And probably the best example of that,
00:29:24.800 | you're gonna love this
00:29:25.840 | 'cause it has nothing to do with work.
00:29:27.520 | Best example of that is people who win the lottery, right?
00:29:31.040 | 85% of people who win the lottery within five years
00:29:34.960 | are more broke than they were before they won.
00:29:38.000 | Did you know that?
00:29:39.280 | - No, that's a fascinating stat.
00:29:41.800 | - And it's because they can't see in their mind, right?
00:29:46.800 | They can't see in their mind them being rich.
00:29:51.880 | And so what they do is they end up spending all that money
00:29:55.280 | and end up spending too much of it
00:29:57.400 | and end up worse off than when they'd gotten it.
00:30:01.320 | And so there's a whole industry of lawyers and counselors
00:30:07.360 | and financial analysts and stuff
00:30:09.760 | that just deal with sudden wealth syndrome, right?
00:30:13.580 | People that are suddenly wealthy
00:30:15.880 | and they can't figure out how the hell to be in that,
00:30:20.680 | have it be a comfortable place for them.
00:30:23.920 | And so it's a really interesting situation
00:30:27.720 | where people don't get it and because they don't get it
00:30:31.360 | and they don't get the help they need
00:30:33.280 | to really understand what that means.
00:30:35.800 | - Yeah.
00:30:37.560 | - They end up squandering all of it.
00:30:39.360 | - Yeah, it's funny.
00:30:41.920 | I've had a few conversations with folks
00:30:43.920 | in some of these videos as well
00:30:45.560 | and imposter syndrome comes up in almost all of them, right?
00:30:49.360 | And especially folks who are living in the Bay Area
00:30:51.320 | where I had a conversation with someone yesterday.
00:30:54.080 | They're like, "Hey Tim, in a world where cost of living
00:30:59.080 | "keeps going up higher and higher and higher
00:31:00.920 | "and you got kids and you gotta deal with all these things,
00:31:03.100 | "but then at the same time, you accumulate wealth
00:31:06.120 | "and then you're looking around to other people
00:31:07.880 | "and you're seeing what things that they're doing
00:31:09.960 | "and kind of fighting the keeping of the Joneses.
00:31:13.760 | "How do you do that?"
00:31:16.000 | And I told him, I was like,
00:31:17.680 | "Quite frankly, it's a persistent thing."
00:31:20.560 | Part of it is being able to shut it off.
00:31:22.960 | Some of it's kind of coming to grips
00:31:24.760 | with which aspects of it are true, right?
00:31:27.280 | And then the true areas of weakness.
00:31:29.280 | And then some of it is just turning off the noise
00:31:31.120 | 'cause an example that's not work-related is,
00:31:34.520 | I look down a street in my neighborhood,
00:31:36.160 | I've got like a 60-year-old house now, right?
00:31:39.240 | Which by California standards, like that's new.
00:31:42.560 | You're not gonna rebuild, that's new.
00:31:45.000 | But everyone on my street, well, not everyone,
00:31:47.160 | but quite a significant number of people
00:31:49.240 | are rebuilding and remodeling, right?
00:31:53.320 | And it's like, you know the cost of materials is going up
00:31:56.920 | and I'm looking at these people, I'm like,
00:31:58.940 | "You know what, how are you affording this?"
00:32:02.040 | I know the tear down of one property, for example,
00:32:04.500 | in itself and rebuild that in itself
00:32:07.240 | was like a 1.2, $1.3 million venture,
00:32:11.640 | but they had to buy the property first, right?
00:32:14.600 | And so it's like, how does that math work?
00:32:17.120 | You know, and then there's other ones
00:32:19.080 | with like their single income earners
00:32:20.400 | and they're doing remodel.
00:32:21.240 | I'm like, "How are you doing that?"
00:32:22.840 | 'Cause I'm comparing their output with my output,
00:32:27.840 | which is like zero, it's not connected in dots.
00:32:30.920 | And what I had to remind myself is like,
00:32:33.320 | A, I don't know the context
00:32:36.420 | of where their wealth is coming from, right?
00:32:40.100 | Zoom just put that thumbs up on the screen.
00:32:43.300 | I don't have any context.
00:32:44.480 | I don't know, like they could have been a lottery winner.
00:32:46.540 | They could have been a really good job investing.
00:32:49.700 | Maybe they had parents and they all pulled in.
00:32:51.740 | Like you just don't know, all you see is the output
00:32:54.920 | and to measure yourself against that
00:32:56.820 | is just unrealistic, right?
00:32:58.380 | And the same thing goes into work.
00:33:00.300 | Like you don't know what took someone to get there
00:33:03.100 | and like, there might be a reason
00:33:05.860 | why they're just being really awesome
00:33:07.900 | and making you feel inadequate.
00:33:08.940 | 'Cause maybe they just busted their butt and they got there.
00:33:11.820 | But some of it could just be like,
00:33:12.960 | you're only seeing like the veneer of it.
00:33:16.280 | But underneath the water, like ducks,
00:33:17.940 | their feet are doing like, right?
00:33:19.740 | 'Cause they're struggling just like you are.
00:33:21.220 | And like, maybe that hard work
00:33:22.780 | is because they're also insecure as well.
00:33:24.400 | And so I think you're totally right.
00:33:25.540 | It's such a prevalent thing.
00:33:28.380 | I deal with it all the time to various degrees.
00:33:30.780 | And by the thing, as we get older, like you mentioned,
00:33:33.620 | like I think we start separating like what's fact
00:33:36.300 | from fiction, what's truly important versus not.
00:33:38.780 | And I think over time you develop a sense of your worth.
00:33:42.300 | And so I think you're right.
00:33:43.500 | As you get older, you have less appetite for the fluff.
00:33:47.160 | Just shoot from the hip.
00:33:48.400 | Here's what it is.
00:33:49.240 | You know what you put to the table
00:33:51.300 | and let's just get right down to it.
00:33:52.740 | Let's forget about the packaging.
00:33:54.660 | Let's just get right to business.
00:33:56.360 | - Well, and I think with young people,
00:33:59.800 | you find that, well, some people middle-aged,
00:34:02.260 | but sometimes you see it with young people
00:34:04.700 | where they will hop from job to job.
00:34:06.980 | - Yeah.
00:34:08.100 | - The money isn't right, or this isn't right,
00:34:11.180 | or the management isn't right,
00:34:12.660 | or they'll have an excuse.
00:34:14.940 | - Yeah.
00:34:15.820 | - 'Cause they're looking for the perfect scenario.
00:34:19.180 | Well, dude, sometimes you have to make the perfect scenario
00:34:22.620 | in the place that you're at, right?
00:34:25.240 | And so that lack of patience,
00:34:27.820 | that lack of willing to pay your dues is concerning.
00:34:32.820 | - Yeah.
00:34:34.220 | - And you see that happen where,
00:34:35.900 | like, dude, you're not gonna learn the hard lessons
00:34:38.260 | if you keep jumping from job to job.
00:34:40.300 | You're gonna learn hard lessons
00:34:41.500 | about people not wanting to hire you
00:34:43.400 | because you jump jobs, right?
00:34:45.300 | That's a pain by itself.
00:34:47.160 | But just the fact that sometimes toughing it out, right?
00:34:52.160 | Just being in the role long enough
00:34:56.120 | to learn the lay of the land,
00:34:58.500 | to learn how to manage people's expectations
00:35:01.740 | and how to work with everybody at every level.
00:35:05.340 | So whether it's executives, peers, or subordinates,
00:35:08.420 | or people that are somehow,
00:35:11.540 | just how you treat the receptionist.
00:35:14.260 | I mean, just sometimes those soft skills,
00:35:17.860 | they don't show up.
00:35:20.740 | You actually have to practice them to be good at them.
00:35:24.820 | - Yeah, I love that.
00:35:26.240 | I like making your own environment.
00:35:28.520 | I'm gonna make that a t-shirt.
00:35:31.160 | Well, hey, Kent, I just wanna thank you for your time.
00:35:34.140 | This is really fun.
00:35:34.980 | You've just gotta come back and we gotta do this again.
00:35:36.880 | There's so many things that I wanna talk to you about
00:35:38.880 | and pick your brain about.
00:35:39.900 | Some of it serious, some of it not.
00:35:42.760 | But yes, thank you for spending your time with me here.
00:35:45.940 | - Oh, my pleasure.
00:35:46.780 | Thank you for inviting me.
00:35:48.080 | - All right, thanks, Kent.
00:35:49.320 | - Yeah, bye.
00:35:50.160 | (gentle music)
00:35:54.800 | [BLANK_AUDIO]