Getting That MBA Recommendation From Your Boss

So it happened today–THE conversation with the boss. While I will admit that I did not have nearly as much to be fearful of as some bloggers that I’ve read about (for reasons that I will get to in a moment), ANY conversation with your boss about how and/or when you plan to EXIT the company is a big enough deal to run your blood pressure up a few notches-even if said exit is about a year away.

How it Happened

After my employees left work to start their weekends this afternoon, I stole over to the break room for a few games of ping pong in preparation for my company’s annual tourney that begins next week. Its a pretty big deal and I am just one of about 100 people who will be in the week long competition. Ping pong tournaments (and regular play year round) are just one of MANY reasons why I love working for nerdy companies, but I digress.

At any rate, I tend to REALLY get into my ping pong matches and get pretty physical…like today I jumped onto the table—all 215lbs of me—and shoved it 3 feet to the right while trying to catch a trick ball that was hit just hard enough to barely make it over the net. Such antics, of course, make me sweat profusely. By the time I got back to my desk after virtually taking a shower in the men’s bathroom, my boss was getting back from a walk he typically takes in the afternoon after most everyone is gone. I figured that there was no time like the present and just launched into my short speech.

Misplaced Fear

One of the reasons why I felt I had a better chance at success than failure on this mission is because my boss comes from the whole bschool-ly world. Since he’s a graduate of Penn/Wharton undergrad and a McKinsey alum (I uncovered the latter fact while chugging back beers with him, our CTO and director of product while we were in San Francisco a few months ago for a conference), I doubted that I would need to do much explaining on why I wanted to make this step. In fact, my predecessor (who is several years younger than I) took a similar path and leveraged the position I have now as a springboard into the London School of Economics.

After I popped the question, my boss’ face immediately lit up as he agreed to write my recommendations. I think more than anything else I feared the possibility of an awkward moment if he really didn’t feel strongly about doing them. Again, I had NO real reason to think this would be the case, but you just never really know what someone is thinking until you ask them to make an actual commitment to something, you know?

The Right Place at the Right Time

At my old job in big corporate, I would have had much more to worry about in the same scenario. Its the kind of place where upper management becomes insulted if they catch wind that you aren’t planning to be carried out in a pine box after you’ve worked there until you’re old and gray. Insanity. At an internet company, no one expects anyone to stay in the same spot for more than a year or two without some sort of move, whether internal or external, unless they are already at or near the top–basically at least a director if not an executive like my boss (because why would you stay put otherwise?). See, THAT logic makes total sense to me; again confirming that I am where I am supposed to be.

Another thing about my old company is that you get treated like crap (and sometimes let go early) once they know you’re planning to leave–which is why I resigned while on my couch at home via email from my laptop with all of my friends (about 80 of whom were mentioned and thanked by name in my resignation letter) bcc’d–because I knew that I would not have been allowed to say goodbye with dignity had I done it any other way. And as I had anticipated, I was asked to leave on the spot, even though leaving was my choice and it was not done on bad terms. That’s just the way big corporate works. SMH.

Also, I would have had to do much more coaching on how to get my recommendation right if I had had to ask for it there because no one knows the game. All of the H/S/W/Tuck types are at corporate, thousands of miles away. Otherwise, everyone just does a part time program, largely since a part of the culture is that you only develop yourself to benefit that company–not to actually broaden your horizons–oh, NO; your retirement from “the big company” is considered to BE “your horizon”.

Additionally, most folks who are looking into MBAs at my old company are about my age and are generally tied down by families and mortgages at this point (neither of which is a bad thing; both are pretty awesome, actually). In that ecosystem, the MBA is a box to check for their next promotion, basically; but no one would ever think of actually leaving to never return; and the company would frown at anyone who let it be known that was their intention.

That reminds me of the other added benefit to my current work environment that hasn’t existed previously. Pedigree. Not so much the company itself because its not a household name like my last gig (although my current company is owned by a well-known PE firm and holds several #1 and #2 brands in its verticals); however, the top brass (who I get to work with personally–another benefit of a smaller company) are a veritable poo-poo platter of Stanford/Anderson/Wharton/Marshall etc. alums–and it shows. The whole environment and level and quality of ideas and conversation are worlds away from anything that I have experienced in YEARS (since college). The move was definitely worth the pay cut.

While I had not 100% decided that I even wanted an MBA when I joined the company nearly a year ago there could not have been a more perfect ecosystem for me to land in to round out and unify my pre-mba background under a banner that makes really good sense considering my ST and LT goals. I love being in environments where above average is actually average.

Being around so many incredibly bright people helped finalize my b-school plans. I decided that I wanted/needed to be around people like that all the time and would never again settle for any environment that offered less (says the person who lives in Los Angeles, but we won’t talk about that). Now, that’s not to say that my last job did not have smart people, because it had plenty. The problem is they aren’t the ones running the show; and thus, are not fully utilized (as I was not) because “it takes one to know one”–but again, I digress.

My Boss, the Back Seat Driver

I was pleasantly surprised (or was I surprised at all?) at how upbeat, knowledgeable and helpful my boss was once I let the proverbial cat out of the bag. He immediately asked where I planned to apply, and upon hearing my choices he quickly chimed in “well, you should have no problem advancing your career coming from any of those”.

Then before I knew it, we had launched into a mini discussion about the GMAT, median scores, whether I should retake, etc. Before it was all over he was giving me positioning strategy tips on why I felt I needed the MBA to go the next level. He also corroborated why and how my story and trajectory made sense, which put a very nice period on the discussion before I grabbed my empty lunch bag and walked to the elevator, trying to pretend like I wasn’t (emotionally) pumping my fist like Tiger.

Next Steps

So, I’ll invest some time this weekend putting together a really nice packet for my boss to make his job a lot easier. What’s also nice is that my secondary recommender–who just left his job at my company for a new gig a week ago (and no one wonders why he did it because it was expected behavior)–agreed to write rec’s for me a week ago before taking a week’s vacay back in his homeland of India.

So now I’ll only need to recruit my 3rd interviewers for my Stanford and HBS apps. Everyone else is committed; BIG ‘OLE hurdle jumped. Now, if I can just get everyone to turn in their stuff ON TIME.

I really hate being pressed up to the last minute; ugh, we’ll see…

MBAOver30 offers the perspective of a 30-something, California-based entrepreneur who is applying to Harvard, Stanford, Wharton, MIT, Northwestern, Chicago, Dartmouth, Yale, and Berkeley.. He hopes to gain acceptance to the Class of 2015 and blogs at MBAOver30.

Previous posts on Poets&Quants:

How I Totally Overestimated The MBA Admissions Process
Musings on MBA Failophobia
Letting Go Of An MBA Safety School
When A Campus Visit Turns Off An MBA Applicant
Yale, Tuck and Booth: The Next Leg of My Pre- MBA Research
 My Countdown: Less Than 30 Days To The GMAT
From Suits To Startups: Why MBA Programs Are Changing
Why I’m Not Getting Either A Part-Time MBA or An Executive MBA
Preparing To Sit For The GMAT Exam
Falls Short of GMAT Goal, But The 700 Is A Big Improvement
A 2012-2013 MBA Application Strategy
Celebrating A 35th Birthday & Still Wanting A Full-Time MBA
A Tuck Coffee Chat Leaves Our Guest Blogger A Believer
Heading Into the August Cave: Getting Those Round One Apps Done 
Just One MBA Essay Shy Of Being Doe