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How To Mentor Someone Without Ruining Their Career
24:55 with Steve HickeyIn just three years Steve Hickey went from being a failed product design apprentice to mentoring his own successful apprentices at Boston-based UX agency Fresh Tilled Soil. How did he do it and how can you avoid some of the common pitfalls that come up when mentoring young designers and developers? Use Steve's experiences to start your own apprenticeship program and spread your influence in the field through the people you mentor.
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[MUSIC]
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Hi everybody, welcome.
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Welcome to day three, second to last talk.
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You are all still awake so that works for me.
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Thank you for coming.
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My name is Steve Hickey, I work at Fresh Tilled Soil, which is just outside of
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Boston, Massachusetts, where I am UX strategist, whatever that means.
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And I also run a program we call AUX, that's our apprenticeship program.
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So today I'm gonna share with you a little bit about what we've learned from running
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this program for the last 3 years.
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So good place for us to start is with the boring dictionary definition
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of what an apprentice is, just in case you really like Webster.
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That's what he had to say on the matter.
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We have a few different thoughts on it.
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But, this is as far as we thought when we started the program originally.
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We really didn't figure out what we were trying to do.
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In fact the conversation went kind of like this, you can see my boss and
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I are trapped in Jony I'ves' white room,
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the one that Apple won't let him out of in every video.
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And he walks up to me in his suit and says, we should have apprentices.
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And I act very confident and say, yes, yes we can do that.
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And then once he walks away, there's dramatically shifting light source in this
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room by the way, and make sure nobody can see me, and here's my actual reaction.
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What do I do now?
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So it took us a while to actually figure out the answer to that question, so
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you can imagine me walking around with that confused look for about a year and
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a half maybe.
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One way we figured it out early on though,
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was that we think an apprentice is not an intern, very different from an intern.
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Usual view of that position is somebody who fetches coffee.
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They'll do grunt work.
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They probably don't get paid.
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They are just happy to be in the game, just to be around a bunch of people who
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are doing really good work and learning what they can.
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Hopefully they do learn a lot.
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But we think an apprentice is a little bit different.
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So, first of all, we select people because they've already demonstrated a level of
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experience and skill in this field.
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They might not be 100% sure what they want to do with their career yet, but
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they have a pretty good idea that they wanna do something with the web.
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They're just not sure what.
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Maybe they don't actually understand what the different positions are because,
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frankly none of us do no matter how long we've been doing this.
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The experience is important to us because we expect
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them to contribute a bit to the bottom of the line.
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The bottom line is they progress.
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Usually not something you expect out of interns, and
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we're also very, very insistent that we pay these people.
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It's an apprentice program, we don't pay a lot, but
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we know these people have obligations, they have bills.
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We can't just ask them to walk away from the people they have to pay.
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So in order to get the right people into our program we do have to offer money.
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And we also believe it's the right thing to do.
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So our first lesson today, we have to define what we're trying to create.
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And that was the biggest problem we had at first, as I mentioned.
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We had no understanding of what an apprentice should be.
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We didn't even know what a UX designer was.
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I'm not entirely confident we still know what that is now.
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And that meant we didn't have a goal for teaching.
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So we ran for a while this way.
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Just about, I think I said a year and a half, two years.
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We completely revamped our program recently, and to us it was very important
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this time around to actually define what we were taking in and
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what we were trying to put out.
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And so we settled on this idea for who we were taking in.
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An apprentice candidate is someone who has some sort of background in web design or
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development.
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No matter how brief it is.
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We usually think of around a year as the sweet spot,
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as long as they've done something on the web.
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And that they have to have done this work in a professional capacity.
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That it can't just be like, oh, I did four years of school.
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Because we think that first year of employment
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with other people is incredibly important.
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Their background is a great way for us to start and
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we can use a standard portfolio evaluation to figure that out.
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We'll just take a look at their work, talk to them a little bit.
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That gets us part of the way there.
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But it's very important on the experience side to us, that they have worked for
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somebody else and not by themselves.
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We don't have a problem with freelancers, but we know there's a lot of people who
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come out of design school and they go straight into freelance and so
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you miss out on some of that really vital working with other people experience.
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So we're trying to get candidates that have that.
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The difference between the candidates we've met that
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have these qualities versus the ones that don't has been very stark to us.
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And we know that with these requirements, we're probably missing out on some really
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great people, but it works more often than it doesn't.
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And so, that's how we do it for now, but we're always tweaking.
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This also meant defining what a UX designer is.
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I mentioned earlier that I don't think that anybody knows what that is.
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So, we have a very lengthy list.
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It's very opinionated.
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I'm happy to share it with people later if you want.
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I'm sure we could have a great rousing argument about it.
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But I'll spare you from that for now.
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But if you do want to start your own apprenticeship program,
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you are gonna have to figure out the answers to these questions.
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What type of people do you want to take in, and what are you trying to turn out?
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So, when we run our program, from the applicant pool that we get,
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we usually pick maybe 10 to 15.
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And we put them through a process that we call bootcamp.
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It's a day long workshop in how to run a design sprint.
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And we're also able to schedule really short informal interviews with each of
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them so we get an idea of who they are and how they communicate.
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And we're looking specifically for those soft skills.
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Communication with us, interaction with the other candidates,
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just how people are getting along.
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Whether or not leadership emerges in some of the group dynamic from some of
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the activities we have them do.
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And then after we've given them this workshop they spend the entire next week
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prototyping a simple application.
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Just working through the design sprint process.
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We do it this way because we know they have jobs and
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we cannot expect them to quit a job to come in and hopefully be the right person.
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We sort of did that at first and then what we found out was,
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we just never felt like we were big enough jerks to
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get rid of people who had quit their jobs to come to us.
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So, our original boot camp was not a good boot camp.
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This worked a lot better for us.
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They'll go through this process, it's a bit rushed because we just give them
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a week outside of their working hours.
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And we want them though to get to running at least one user test and then they come
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back on the following Saturday and they'll present their work to us in the group.
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And so we wanna take a look at their process, we wanna see how they got through
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this, but we also want to see how they present to the other candidates and
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how their interaction with them affected the work they're doing.
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So this was a real turning point for us.
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Our track record with just doing standard intake interviews before
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had been a little bit spotty.
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This gave us such a better picture of the individual qualities of
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the candidates we were looking at, that I think that we're gonna keep doing this for
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the indefinite amount of time that we continue running this program.
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It really gives us a chance to see their skills under pressure,
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which is not quite what we get out of an interview.
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I mean, there's little tasks you can do in interviews, but
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I don't think that forcing somebody into a box with a whiteboard and
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a marker is really the best way to see what they do.
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Whereas watching them talk to the people they might end up working with and
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seeing how the produce individually and
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as a group, has been a really good indicator of how well they'll do.
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Then after people start the program, we usually invite about four or
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five people in, which is a good group size.
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We assign everyone a mentor,
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this doesn't happen untl after the first couple weeks of the program are over.
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They get a chance to interact with the different people in the company to see who
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they're comfortable with,
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to start seeking out people that have similar backgrounds to them.
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And in fact, we make our mentor pairings very specifically around the idea of, does
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this person have a similar background and can they help this person grow further?
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We have much better results with this than with people who come in and
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say, I'm already a good designer, I wanna learn more about development, okay,
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we'll pair you with a developer.
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It's actually very common for that to happen, at least it was in the early days.
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Designers would come in and think they know enough about design,
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which thinking you know enough in this industry is always a funny little concept
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to me to begin with.
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But, they wanna work with a developer because they wanna get better at
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development and it was not working out great.
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And we figured out that the reason, is that a mentor's job is really to amplify
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their apprentice's abilities more than anything else.
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So, we pair them with people with similar strengths and backgrounds.
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The only difference is that the mentor has the advantage of experience at this point.
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So, they need to be the kind of person who understands what they've done wrong and
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what they've done right and how they've gotten where they are today.
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And then they need to teach their apprentice how to do that.
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Hopefully making less mistakes along the way.
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We're trying to build better versions of the mentors, really.
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And again with the whole designers wanting to do more with dev stuff,
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we think it's great when they want to improve their dev skills and
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with the way they run the program, they definitely would get that chance.
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We work really hard to facilitate that.
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But we stopped pairing based on that desire and
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I think that's worked out a lot better for us so far.
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The first couple of times we did it the other way, we let devs mentor designers or
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vice versa, after a few weeks, they realized they didn't want to do that.
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And it's not because dev was too difficult for them, or too hard.
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It's a vital part of their skill set.
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It's just not the thing they fell in love with necessarily and
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by the time we figured that out and repaired them with somebody else,
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they had missed a few weeks of growth and so we wanted to stop having that problem.
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So, we think that pairing people with their mentors and
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the way we do it now, for strengths and
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similar backgrounds, makes it easier for
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them to help develop, their apprentices further.
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If they don't get that sort of contact that really helps nurture
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the things they're good at, they actually risk stagnation.
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Again I said I don't like the idea that you know enough about design.
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That's never gonna happen especially if the majority of the people were dealing
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with they're maybe three to eight years of their career at most.
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I'm seven years into my career and
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I finally learned about four years ago that I don't know everything.
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That was a wakeup call.
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We want to avoid having people who come in like I did when I started my career and
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thought I knew everything.
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It's important to us because sometimes
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a mentor will have to deliver a harsh message to their apprentice.
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And so when the mentor is somebody who's been through the same things as them,
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it's a little easier to deliver that.
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So sometimes your apprentice is not going to like you, but
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I actually think that's okay.
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We want the people in our program to be happy, we want them to get along well.
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But in the end we're there to train them to be effective at their jobs.
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We're not there to be their best friends,
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we're there to make them effective in their chosen career path.
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Sometimes you're gonna have to show
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an apprentice that they're not as good at something as they thought they were.
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You might have to actually tell them that they really screwed something up.
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Or you could give them a really silly and arbitrary constraint
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on a project that they're not going to be happy with because you recognize that
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that's going to be something that's going to help them progress their skills.
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These are all things we've done for our apprentices in the past.
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They've all made them unhappy, and
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they're all things that we were thanked for later on.
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I think a mentor really needs to be able to have
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those uncomfortable conversations with their apprentices.
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If you're not willing to do that you're not gonna be able to help them grow as
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much as they could.
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So I had one apprentice a few years ago.
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She was a really great visual designer.
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We actually met her the day before the application deadline, and
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she hadn't known about the program.
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And after talking to her for about ten minutes,
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we were just like, you need to be in this.
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So she just made the cutoff, great visual design skills.
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But she shied very strongly away from any bold or dominant use of color in her work.
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She would cover up for this perceived weakness in her abilities by making things
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that relied on a lot of white space or monochromatic color schemes.
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Just things that kept her from having to sort out whether or
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not these colors were gonna work nicely with each other.
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She did ask me to help her get better at this.
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She recognized on her own that she had a problem, but
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she didn't know how to solve it.
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So, I gave her a very simple constraint.
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You are not allowed to use the colors white or black for two weeks, and
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you can not do anything monochromatic and, do not try to take like 99% transparent
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green, and tell me that's green and not white.
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And she knew what I meant to not use super dark or super light colors, you have
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to use stuff that's gonna force you to figure out relationships with each other.
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She was pissed, but she also knew I had probably settled on the right
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way to get her through this because she had been using white space as a crutch.
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So for two weeks, she worked very hard to actually figure out these color schemes,
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figure out how these things related to each other,
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figure out how to avoid clashes.
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And she came out the other side of it with a much better understanding of color.
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She's great at it now.
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She was, like I said, pissed at me first, but it worked out because I was
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able to tell her to do something that was probably not gonna make her happy
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because with the benefit of experience, I knew that it was gonna help her improve.
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So that was a pretty silly example, but I have a more serious one.
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So one time,
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we agreed to hire an apprentice before she had actually come into the program.
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We agreed to actually hire her as a full-time hire.
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The end of it, this did not turn out to be a good idea for us.
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Halfway through the program, she just really wasn't doing very good work, and we
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were beginning to think we had seriously misjudged her capabilities at first.
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So we had to figure out what to do about that.
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And I think for a lot of companies the answer would have been easy.
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It's like, okay, didn't work out, cut the asset loose.
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That's not how we run our company.
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That's not how I wanted to run this program.
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Coming into an apprenticeship program is taking a risk often.
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You're accepting lower pay and
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a lower position to shift your career in different direction, and
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it needs to be a good understanding between both parties what's being offered.
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So I was not prepared to just cut her loose.
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So instead what we did was we sat her down and told her the truth.
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We told her what we thought was happening, we wanted to know how we could help her,
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but we were very open and honest and up front about it.
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We told her that we wanna help your work get better, but if it continues the way
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we've been seeing it, we just, we're not gonna be able to hire you.
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It's not gonna work out.
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It was not a fun conversation.
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It was the second worst conversation I've had with an apprentice.
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I'll get to the first one later.
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But, it had a good effect, because she understood where we were coming from and
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what she needed to improve at.
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And she got her act together after that.
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We were able to hire her in the end.
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And, she does amazing work.
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I'm so glad that we chose to have an uncomfortable conversation,
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to make the moment a little bit more awkward for everyone involved, so
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that we could help her long term growth.
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And, she has contributed back into the company in an amazing way.
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So, that's my fourth lesson.
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Don't plan to hire your apprentices.
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This mistake repeated itself once more,
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despite the fact that we thought we had learned that lesson.
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That was the worst conversation, which I'll get to in a minute, but
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it took us both of those to really fully internalize that.
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I think that when you plan to use your apprenticeship program as a hiring program
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you're actually creating the wrong set of incentives.
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So when it goes well, of course you're going to stay involved.
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It's great, people are happy, they're doing good work, you think
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you've found a good employee, you've got a good, cheap trial run out of them.
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Fantastic, you stay involved.
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But when it goes poorly, it's very different.
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I should know this better than most people because prior to being at my current
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company and starting this program, I fell victim to this problem.
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So I was an apprentice at a different company.
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At the time they had just started hiring designers as apprentices.
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They had a very well developed, developer apprenticeship program and
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I was gonna be one of the first two designers they tried this on.
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And it was really exciting at first.
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I hated the job I had prior to that.
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This was the way I saw to shifting my career around.
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I thought it was gonna be great, but it didn't go well.
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That first job was a very high pressure job,
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and it forced me to unlearn all of the good habits I had learned in school.
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Over the three and a half years I had that job,
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my entire process just fell completely to shreds.
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I was not a great designer when I came out the other side of that.
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So, these habits followed me into the apprenticeship.
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My first mentor decided really quickly that they
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werent interested in helping me anymore.
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I was going to be a negative return on investment I was not worth the time.
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So they abandoned me.
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I sensed this abandonment, it was not really hard to figure out and
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this just caused my shame and my self doubt to grow.
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And it created this horrible spiral where I wasn't doing good work and
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I knew it, and I felt worse about it, and the work got even worse after that,
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and that just all fed back into each other.
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So I got farther and farther away from any chance of landing that job.
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So the lesson I learned from that was this.
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Because their program was structured for hiring, they didn't feel any incentive to
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help me once they had decided they weren't going to hire me.
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I didn't wanna run our program this way.
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I see it primarily as an educational program.
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We have hired people from it before.
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We will hire people if they're in the right place at the right time.
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But we don't run it with the intention of hiring people.
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We run it because we wanna put good people into the community.
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The lesson I learned from all of that is that you are responsible for
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your apprentice.
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You are responsible for what happens to them and
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if they fail it is because you failed them.
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So now I'm gonna tell a story about the worst conversation I had.
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Second apprentice we agreed to hire after the program was over,
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didn't learn our lesson the first time.
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We had interviewed him for
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a job initially and we thought he had some really great work.
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But we knew he was really inexperienced and we thought, well we have
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an apprenticeship program coming up, why don't we put him through that so we
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can give him some experience and then we can hire him right away when that is over.
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Based on the work that he presented to us, we didn't see any problems with that.
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We really messed up.
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He presented very well, in fact he had filtered his portfolio really well too.
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He understood better than a lot of the young designers that you don't wanna show
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thirty projects where two are great and twenty eight are mediocre.
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You wanna show four projects if those are the good one, so
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the people get the right impression of your work.
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But because he had never had a job as a designer before,
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because these were all personal projects that he was using for his own education.
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20:00
He didn't really understand what it was like to work in the type of
-
20:04
environment that most design agencies have.
-
20:07
And he just couldn't keep up with the pace, the quality of the work began to
-
20:11
falter, he started to sense it much like I had when I was in his position.
-
20:16
And gradually we decided we could not hire him.
-
20:19
Three months was not enough time for us to get him up to speed.
-
20:23
So, I had to tell him.
-
20:27
He's my apprentice, he's my responsibility at that point.
-
20:32
It was a terrible conversation.
-
20:33
It's the closest I've ever come to having to fire somebody.
-
20:38
I wasn't firing him.
-
20:40
I was telling him how it was.
-
20:41
But it felt like there was no real difference between the two.
-
20:45
I didn't want it to end there, so I made him an offer.
-
20:50
We can't hire you, but we're not gonna let you go because we brought you into this.
-
20:55
We're responsible for you.
-
20:57
We wanna work together for a positive outcome for everyone here.
-
21:00
We're gonna give you an extra three months with us.
-
21:02
We're gonna spend more time teaching you.
-
21:04
We're gonna get you up to speed so you can work in an environment like this.
-
21:08
You're gonna be a junior member of a team, wherever you end up, but you need that for
-
21:12
a few years.
-
21:13
But, we're gonna get you there, we're not gonna let you go.
-
21:19
He was, expectedly, gutted by this conversation.
-
21:24
He had had an inkling that things were not going well, but
-
21:27
nobody had really talked to him yet.
-
21:29
And I'm afraid that it might have gone further if I hadn't insisted we
-
21:34
talk to him.
-
21:35
But the conversation had an amazing effect on him.
-
21:38
He came back after the next weekend, he had had a chance to
-
21:42
think about what we talked about to figure out how this could benefit him.
-
21:46
To think about what his goals were and what he needed, and he was ready to work.
-
21:51
We talked about the conversation a bit, we both agreed it was not enjoyable and
-
21:56
that we didn't want to have to repeat it, but it was the right thing to do.
-
22:00
So we worked together to get him a job.
-
22:03
We spent the next three months getting him a portfolio,
-
22:06
making sure that he was the kind of person that was going to be able to contribute to
-
22:09
a team as a junior member.
-
22:10
Gradually ramping up the pressure on him so
-
22:12
he understood what the actual expectations were gonna be at most places.
-
22:17
And we helped him find a job.
-
22:18
He's at a fairly large local agency in Cambridge just outside of Boston,
-
22:23
and he's a junior member of the team.
-
22:25
He's got people around him with a lot of experience who are gonna keep helping him
-
22:28
grow over the next couple of years.
-
22:30
It worked out in the end for him.
-
22:32
I have no doubt that he's gonna be ready for bigger things soon.
-
22:36
But I don't think that if we had
-
22:41
refused to have that conversation that he would have kept developing.
-
22:45
I think that considering his newness to the field that might have been the final
-
22:49
nail in the coffin for him.
-
22:50
And I think that based on the rate of growth we witnessed with him at
-
22:55
times he's a valuable asset that he will be Incredibly valuable to somebody and
-
23:00
that he's gonna do amazing work.
-
23:01
He just he didn't fit the role we had open at the time.
-
23:06
I told you how I had failed my apprenticeship.
-
23:10
I told you about my first mentor, the one who had abandoned me.
-
23:14
I didn't tell you about my second mentor.
-
23:16
They swapped me onto somebody else after it was clear the first guy and
-
23:20
I were not gonna be able to work together.
-
23:22
And he was very different.
-
23:25
He felt responsible for me, he made that very clear.
-
23:29
And when I started working with him, we determined what wasn't working for
-
23:33
me, and we made some goals and we figured out how to improve my skills.
-
23:39
They'd already told me they weren't going to be hiring me so
-
23:41
I knew that I was gonna have to find my own thing.
-
23:43
And he made it his personal mission to make sure that I was employable,
-
23:46
to make sure that I was gonna find somebody who I could learn and grow with.
-
23:51
And he helped me find the job I have now.
-
23:55
I am where I am today because he refused to cut me loose.
-
23:59
And, that is the most important lesson that I've carried forward into how we run
-
24:04
our apprenticeship.
-
24:05
That this isn't some sort of back door hiring program that's entirely about
-
24:09
advantages to us, monetary benefits, etc.
-
24:13
We are educating people.
-
24:15
We are attempting to create value by spreading good knowledge and
-
24:18
good people throughout the community.
-
24:20
And then we need to treat our program and our apprentices and our mentors that way.
-
24:25
And make sure everyone understands the massive amount of responsibility they have
-
24:28
to each other to make this successful.
-
24:31
So far, I think we're doing a good job.
-
24:34
We graduated almost 30 apprentices, they are all gainfully
-
24:38
employed in a career that I love and I can't wait to meet the next 30.
-
24:44
Thank you.
-
24:44
[MUSIC]
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24:45
>> [APPLAUSE]
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