My Toughest Assignment – Ever

No one goes through childhood saying, “What I want to be when I grow up is a mentor.” That’s like saying, “When I grow up, I want to be an actuary.” It just doesn’t happen that way. When given a Successchance, believe it or not, not everyone wants the awesome responsibility of carrying someone’s future career in their hands. That is, of course, if you take being a mentor seriously.

I first learned of Jamie Collins when she literally picked up the phone, called me and told me that I was going to be her mentor. I’m sure she has a different version of the story but to me, that’s how it happened. I hadn’t a clue why had been selected. It felt like I was Glenda, the good witch. I didn’t even know her.

In my mind, she was some kid somewhere in Indianapolis, a state I still can’t spell properly and she had absolutely no credits I could get my hands around other than a strong desire to “make good”. She didn’t know me, and she didn’t know my background. I think she knew I was Editor-in-Chief of KNOW Magazine for Paralegals but I don’t think she knew I founded, designed it, and had 15 years of writing behind me nor that I had written 10 books let alone any other credible actions behind me. I think she just read a column and said, “Yeah, I choose her.” 

Yet, there was something about her that wasn’t going to let me say no. Here is someone who you don’t know targets you, tells you that you’re going to spend a great deal of your very little precious and  practically zero free time helping them launch a wildly successful career, who may ultimately end up to be your competitor and for the life of you, something about her appeals to you.

To this day, you haven’t a clue why and have never in all the time spent with her, worrying about her, praising her, getting angry with her, pulling your hair out over her, wondering when she’s going to “get it”, dissuading her to stop sounding like you, begging her to adopt her own style, not yours not once having ever regretted the decision. The only people that even come close to experiencing that kind of feeling are your kids and ok, marrying the right guy which I just got lucky enough to do. And that’s saying a lot.

The first thing that I learned about being a real mentor, one where someone didn’t just call you a mentor so you and she looked good, was that it took a lot of real work. You also had to be right on point, each and every time. The second thing I learned was: are you a mentor or are you a coach? It turns out, in Jamie’s case, in the beginning, I was more of a coach than a mentor. What’s the difference? Tremendous. But, as I’ve explained to Jamie over and over (and over) again….well, let me digress (and use a cliché, my first no-no-no).

A mentor is someone you can go to for guidance. They’ll impart a little information here, a little information there……they are role models, They expect you to follow their lead. They give advice. A coach, on the other hand, rolls up their Neiman Marcus sleeves well above the elbow, sticks their hands in your mess, pulls out the good, the bad and the downright oh-my-god-you- -didn’t-really-say-that- did-you??? attitude and teaches you how to do it. 

With Jamie, I was definitely a coach. I don’t care what she tells you. Maybe she eventually wanted to write a column or 10 books or get interviewed in all the national publications I’ve been honored to be in but I’m telling you, unless she learned how to construct a sentence every cliche in the Ladies’ Guide to Cliches and Other Ordinary Writing Phrases, I swear, she didn’t stand a chance. Ok, so I was a tad hard on her but no one under my tutelage was going to say she was my mentee and embarrass me. That was my first rule I made to myself if I were to take this project on and swore to abide by.

Her first piece she turned in (expecting to get published) in KNOW was a disaster. I think, like most beginners, she sat down, dashed it off, and thought ,”Wow, this is some good writing.” It had a lot of possibilities but it was a weak attempt to sound like every other piece that was out there. .A desperate attempt to fit in – kind of like gliding into the world of sounds-like-every-one-else-no-original-thinking-no-strong-opinions-I’ll-be-just-the-same-as-everyone-else-is-at-the-fifth-grade-level. <sigh> I get dozens of those submitted on a regular basis. If I was going to do this mentoring thing, we’d better get to work immediately right from the opening.

I wasted no time. She even came close to using “pink polka dots” but if memory serves me, that actually came from someone else. But it had a spark. A tiny little spark that said, “C’mon, Estrin, read into me just a bit further. See what I can turn into.” OK, it didn’t really say that. But something about it kept me going. It had me hooked.

I remember being hard on her. She kept telling me things like, “I can take it. Pile it on.” That wasn’t my normal approach.

This was one time I chose to believe someone was telling me the truth and not egging me on hoping I would be soft on her and compliment her because I was giving in. Not here! I had her rework each and every sentence. This was beginning to be a lot of excessive work I hadn’t planned on. I asked her, “What is the purpose of each line? Why does is segue into the next paragraph? What is the beginning, the middle and why does it end the way it does? What is the purpose? If you’re going to say what you’re going to say, why are you going around the meaning?” I was relentless. She took it. She was a boxer who refused to go down. Her writing improved and improved. “And for the last time,"  I insisted, “Get rid of those damn clichés.” Everything she wrote was a cliché.

What she didn’t know was that I was trained by a fellow who taught me the same way. Writing a piece with him was torture. I had either the fortune or the misfortune to have face-to-face sessions with him. There was no Skyping in those days. He was a former AP reporter who went on to be a journalist for major newspapers and then wrote books with well-known attorneys such as Gerry Spence.

By the time I got out of a session with him, I was shaken up and in tears. They were those big tears that dripped makeup down onto my white blouses and wouldn’t come out no matter how many times you washed the dang thing. Was that the way it was supposed to be? Heck, no. But I learned more from him in one session than I would ever learn from one nicey-nice middle-aged Barbara Cartland wanna-be adjunct professor in some Podunk college with 45 students in a 10 week semester.

I felt, for some reason, to pass that learning on to this yes, very talented paralegal who insisted on writing just like everyone else with nothing to distinguish herself from all the hogwash I was reading in paralegal newsletters. The type of welcome articles that kept telling me how much fun the last meeting was, how the membership was growing and how great the last meeting was. I always am on the lookout for originality and after reading so many, they all begin to sound alike. 

I began to look forward to receiving her work. This paralegal was going to be a star if I was going to give up my only free time after 12 -14 hour days of my own work and dedicate another couple of hours to someone else’s career. Heck, it was the least I could do. Frankly, for myself, let alone her. Who was I kidding? I wanted her to be as successful as she wanted to be successful. I was as determined as she was.

So when she asked me to write this article, I had to sit down and really come to grips with what made a good mentor/coach? Ego? Drive? Determination to pay it forward? Maybe all of that. I had never really thought about it. However, I realized that maybe what I was doing was not mentoring. Maybe I was coaching. I looked up the difference. Here’s what I discovered:

Differentiator #1:

Mentoring is relationship oriented. 
It seeks to provide a safe environment where the mentee (or mentoree) shares whatever issues affect his or her professional and personal success. Although specific learning goals or competencies may be used as a basis for creating the relationship, its focus goes beyond these areas to include things, such as work/life balance, self-confidence, self-perception, and how the personal influences the professional.

Differentiator #2:

Coaching is short term. A coach can successfully be involved with a coachee (apparently, there is such a word) for a short period of time, maybe even just a few sessions. The coaching lasts for as long as is needed, depending on the purpose of the coaching relationship.

Mentoring is always long term. Mentoring, to be successful, requires time in which both partners can learn about one another and build a climate of trust that creates an environment in which the mentee can feel secure in sharing the real issues that impact his or her success. Successful mentoring relationships last nine months to a year.

Differentiator #3:

Coaching is performance driven. The purpose of coaching is to improve the individual's performance on the job. This involves either enhancing current skills or acquiring new skills. Once the coachee successfully acquires the skills, the coach is no longer needed.

Mentoring is development driven. Its purpose is to develop the individual not only for the current job, but also for the future. This distinction differentiates the role of the immediate manager and that of the mentor. It also reduces the possibility of creating conflict between the employee's manager and the mentor.

Differentiator #4:

Coaching is task oriented. The focus is on concrete issues, such as managing more effectively, speaking more articulately, and learning how to think strategically. This requires a content expert (coach) who is capable of teaching the coachee how to develop these skills.

I had a theatre background. That meant we rehearsed a lot. You know those movies where you see, “Again. From the top.” And the actors or singers take it again and again from the top – over and over – and they don’t think anything of it? That’s how Jamie and I drilled. We tweaked. We changed. We crossed out paragraphs. We debated words. We changed meanings. And finally, finally, real product started to come forward. Let me correct that. Not just real product. Good, solid writing. Thank, God! Frankly, I was beginning to run out of ways to teach. I found that I was learning. I was stretching. But I knew she had it in her. I just knew.

Here’s what I learned. When I say I learned, I actually mean, I learned from this experience the hard way (as usual): 

1.      Find out why this person wants a mentor.

Do they really need a course or even a degree? Are they expecting you to teach them the topic from the very beginning? Or, are their needs a little more pedantic? They need to enhance their learning; support areas they may already know but are afraid to take steps. Perhaps they are unfamiliar with the territory and don’t know which avenue to take. If it seems that they want to use you as a college course instead of actually taking the course, by all means,don’t take them on. You should be acting more of a guidance counselor.Are you willing to share your expertise, experience and knowledge?     

Some people are not. You’re too afraid this person may end up leaving you behind. Maybe they’ll end up, god forbid, better than you. You have to be secure in your skills, reputation, abilities and most of all, your ability to still learn new things and unafraid to pass those new things on. Mentors are in a position to illustrate how the field is growing and changing and there are always still new things to learn. If you fell stagnant in your current position, you will not make a good mentor. You have to still be enjoying the time and energy you are putting into your career.

 2.      Are you respected in the field?

If not, it would be a good thing if you found out now. There’s nothing worse than for your mentee’s to tell their colleagues you are their mentor and to have them be stared blankly into their face with no more than an “oh”. I’m telling you, this is no way to build an ego – yours or theirs.

 3.      Are you interested in mentoring or is it a chore?

The mentee is going pick up that their phone to call or email to you and realize immediately they are a nuisance if you let this relationship deteriorate. You need to be willing to tackle the responsibility from the moment you say yes. It’s a long-term relationship. It ends when it ends and not before. (Oh, dear. Did I honestly just use another one of those nasty clichés?)

 4.      Do you know the difference between mentoring and coaching?

 In a blog from the Association for Project Management, I found this explanation:





Ongoing relationship that can last for a long time. To be really successful, the mentor and mentee need to develop ‘rapport’.  They often become friends.


Relationship generally has a short duration. ‘Rapport’ is not so important, although the client needs to be comfortable with being ‘open and honest’.

Can be more informal and meetings can take place as and when the mentee needs some guidance and or support

Generally more structured in nature and meetings will be scheduled on a regular basis.

Agenda is set by the mentee with the mentor providing support and guidance to prepare them for future roles or specific skills development.

Agenda is set by the client and is focused on achieving specific, immediate goals.

Revolves more around developing the mentee professionally, particularly regarding their skills and their application to the specific work context.


Revolves more around specific personal development areas/issues, perhaps related to behavior, attitudes or self-awareness.

More long term and takes a broader view of the person. Often known as the 'mentee' but the term client or mentored person can be used.


Short-term (sometimes time bounded) and focused on specific current development areas/issues.

 Mentoring and coaching Jamie was a joy. I know she pulled her hair out. I heard the frustration. I also heard the victory when she knew she got it right and she saw the difference from the first piece to the final.

As I watched her develop, she emerged as a professional writer. Her blog (The Paralegal Society) thrived. I saw genuine experiences expressed in creative and original themes. She got rid of the clichés (well, most of them – we can’t get rid of all of them); she gave independent thought to her writing. She used her background; she wrote from the heart; she developed a genuine sense of humor; she wrote from what she saw around her but most of all, she wrote well. Sadly, I saw that she really no longer needed a coach. I felt a sense of real loss. It felt empty without her.

She allowed me, yes, allowed me, to remain a mentor. While not on a regular basis anymore – she no longer turns in her articles for approval or bounces every single idea off of me – she reaches out to me frequently. I give her my honest opinion. She fires back with educated, well-thought out ideas and now, instead of only developing her professionally, we can hold intelligent debates. It’s thrilling, exciting and I look forward to it as much as I did when I was not Glenda, the good witch but the wicked old witch, redlining every word, questioning every segue, wondering how the heck could she turn a piece into an ending that had nothing to do with her voice to right on point each and every time. A piece that left me smiling or crying because she touched me. Hard to do, believe me. How I got so lucky to have been chosen by Jamie Collins, I still don’t know. My guess is, The Writing Gods must have been looking down on me that day I received that phone call.

 Chere B. Estrin is CEO of the Paralegal Knowledge Institute providing continuing legal education for experienced paralegals. She is CEO of Legal Careers RX, a well-known legal careers job hunting coach and strategist. She’s written 10 career books in the legal field, has been an executive in a $5 billion corporation is President and Co-Founding member of the Organization of Legal Professionals (OLP). There’s a lot of other stuff but you can always Google her as well. That’s the beauty of the Internet today.

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