You were an apprentice in the company you now run. How did you make that work?
It's kind of two parts. The apprentice has to bring a lot of interest with them. They want to do the work, though they may not know a lot about it, and everything they know is kind of third person.
Second, the mentor has to have a desire to share and to let someone basically be their shadow. Especially in professional services, mentees have to be in the meetings and listening to the phone calls. You’ve gotta slow down. Prepping your apprentice means you almost have every meeting twice. You've got to be patient with someone's knowledge base that is growing, but not where yours is.
However, I won't say it’s a lot of work if work implies a ton of effort. The apprentice wants to learn, and the mentor wants to teach, so they’re both doing the thing they want to do.
You’ll have people with all different backgrounds and needs on an apprenticeship path. How do you meet a particular apprentice’s needs?
That's a good question. I think you learn that by being around them, and just asking, what do you need?
But there's more of a burden of adaptation on the mentee. The mentor is basically doing things the way that they do it, and they’ve proven that their way makes money. I think what might be one of these little fairy tales that's out there in Less Experienced Land is that the mentor has to be the more plastic of the two.
That's incorrect. The person who's learning has got to be a lot more willing to adapt themselves to get what they need.
It's kind of a big gamble, right? How do you know when it’s not going to work out long-term?
I think the mentee actually knows that first. They don't have the experience or a lot of good day/bad day comparisons. So, something being hard or difficult is probably not the true measure. It still comes down to interest: Do you still love it? Do you still want to be where your mentor is?
You must have some conversations up front about how you’re going to communicate.
Absolutely. For instance, Serena Concepcion, an associate advisor, is in that apprenticeship process. She did a great job for a couple of years in a different role, but eventually I could tell that maybe some things were wearing thin. And based on me watching her work and how she carried herself, there was more to offer.
So, we just had a series of conversations about, not whether she was happy or unhappy, but more about fulfillment. You know, where do you see yourself in two years? Doing what you’re doing now? You’re very well paid, but is that gonna cut it for you for the next 10 years?
Do you know if there’s a higher retention rate for apprentices?
Boy, I hope so.
[laughter]
I don’t have any data on whether mentees and mentors stay together. But I do think sometimes you learn enough from a person, or they’ve given you all that they can. The mentee has to decide where that off ramp is, because I think the mentors will just keep going because they're committed.
Is this a long-term process?
Depending on the level the mentee is trying to reach, it could definitely be a multi-year commitment.
A simple skill transfer could probably be shorter. But at the end of the day, in our world, it’s how much of a student of human nature are you? Financial planning is a practice just like medicine, and 80% of the job is understanding the person in front of you—that's a multi-year thing.
How do you know when that person has evolved from mentee to colleague?
Where the mentor has to back off a little bit is when the mentee begins delivering things themselves, in their own way, with their own voice. Mentors sometimes want to make carbon copies; that doesn't work.
At first, it shows up with fewer questions that start with the word how. How do I do this? How do I say this? They want to mimic closely or at least just get some rails to run on so that they can figure out how they wanna do it.
Then you start getting more “what” questions. The less experienced person is able to not just see what's in front of 'em, but they're able to start looking around the corner. It doesn't take five years before you're able to do that.
But again, it depends on the eagerness and the fire coming from the mentee: they’ve gotta supply 100% of that.
So how do you know when they're ready for show time with clients?
No one ever feels ready. It's kinda like, when are you ready to get married? When are you ready to start a family? You just have to do it.
I asked Serena to figure out one client’s quarterly commentary on salient financial happenings, and then present it to me as her mentor.
I picked a clientele where I knew she could do well, and she did a really, really good job. But she wasn’t yet sure how to present that to the client, so I gave her three days to figure it out, and then we role-played it. Again, she did well, and I said she was ready. But she was like, “No I’m not.”
What did that feel like when you saw that she was so good at it?
I am a parent and not to patronize, but, I mean, you feel proud. You care about this person’s success, and you're watching them be successful.
Did you tell her how well she knocked it out of the park?
Yes, but also, it's like, hey, you're gonna have to do that a thousand more times. If you get your first one right, you’re batting a thousand. That said, a lot of times people say, “My very first one was a disaster. My very first one sucked. My very first one failed. You get all this trauma—I know it’s an overused word—if you will.
My approach is to put the cookies on the bottom shelf. Let’s understand what it's like to win. It’ll progressively get tougher.
How do you make your clients comfortable with a mentee?
I started bringing Serena to meetings and telling the clients she was apprenticing to be an advisor, and that she’d be mostly quiet at first, but that would quickly change.
That kind of gives that client peace of mind when you hand off the account.
I asked Serena to figure out one client’s quarterly commentary on salient financial happenings, and then present it to me as her mentor.
Now, you probably shouldn't be paired up with a mentee that is diametrically opposite to you in manner and background. So, there's also a little bit of chemistry and sort of matchmaking, if I could use that word.
We do Enneagram and DISC Profile personality assessments around here. So, I gave Serena both of my personal reports—like, 50 pages each. And then I pulled out hers and showed her all the notes I’d written on it. This helps us understand how we need to work together, and how she might need to manage up a little.
Candidly, Serena and I couldn’t come from any more different backgrounds. So, we have to do some work to understand each other’s outlooks on work and especially money. The first question we ask a new client is, “What's your first memory of money? When did money become real to you?”
What’s your first memory of money?
My parents arguing about it. My dad was an accountant, CFO for a school system, and super skilled. So, it wasn’t due to a lack of financial literacy. As a mentor, I’m showing how to learn that kind of background stuff and how it might color someone’s view when they're talking to clients. You can’t advise people to do something you wouldn’t with your own money. You’ve got to have integrity.