Teach Me How To Dougie (Part 2)
Teach Me How To Dougie (Part 2)
But this time, more like "1,2 Step"
Ladies and Gentlemen… *ooooeee* (this is a Jazze Phizzle Productshizzle..)*
This week’s email subtitle has me off on a Missy/Ciara tangent already.
Back to the newsletter at hand! A fun update to share: This week I’m featured on the Substack homepage, which is pretty cool! Substack is all the rage recently, though I was definitely not familiar with the company when I started the newsletter. A good friend basically tech-shamed me into launching the newsletter on here.
Substack is a platform for writers to maintain independence and to own their content and their audience without worrying about the forces that have encumbered creative writing and journalism in recent years (editors, advertisers etc). This is less relevant for me (I’m just here for the easy user interface), but it’s a great platform that has attracted a lot of established talent as well as burgeoning writers and creators, so hopefully it'll be an interesting means of content discovery for you. (Substack)
Onto the newsletter! This week we pick up where we left off last week - Mentors!
Musings
This week I want to introduce a framework of mentorship that alleviates some of the time commitment and barriers that exist to forming mentor relationships later in our careers.
In college and early on in our careers, the opportunities to connect with mentors are more plentiful. As we move further ahead, these opportunities are fewer and further between: everyone generally has less spare time, and there are fewer formal opportunities to meet mentors.
One possible solution to this is to dismantle the need to have a single mentor to rely on all the time, and instead create a multiple-person council of sorts.
This concept of cobbling together various attributes of many people to serve a singular purpose, was highlighted in an article published by The Cut in 2015….(Ok, so the article is actually about casual dating… but I feel strongly like it can apply to mentors too**.)
To summarize:
The famous 1980s cartoon Voltron: “Defender of the Universe” is about a team of warrior robots that would assemble themselves into one giant, unstoppable super-robot to defeat their foes.
The Cut uses the analogy to posit that the goal of dating isn’t necessarily to find a single person that embodies all of the traits that you’re looking for, but instead encourages you to look for individuals that each embody some of the traits that you value.
Exhibit A:
Can we apply this framework of mashing together a few different sources into a ‘Voltron Boyfriend’ to mentorship aka. using a few different sources to create the perfect ‘Voltron Mentor’?
It lessens the pressure of looking for a single source of inspiration, and reduces the time commitment required from any individual mentor.
** P.S. I will never stop drawing job/dating parallels. Here’s another lol example:
Conversations
This week’s conversation was with a woman in my network who is the living embodiment of applying the Voltron theory to mentors… but has a much more professional name for it: A Personal Board of Directors
She is creating a small group of people to consult for advice, that she hopes will provide her support in the way that a corporate Board of Directors provides a company’s CEO support. She intends to lean on them to bounce decisions off of (both personal and professional), to keep her aligned in her goals, and help her design a professional and life roadmap of sorts.
It’s a good framework from a time commitment perspective as well: As a baseline, corporate boards tend to only meet quarterly, meetings are scheduled far in advance, and when they convene, the agenda is highly focused. Ad hoc meetings might be called if there is a more pressing issue at hand (in the case of your career, that might be evaluating a job change or move etc).
We talked about other similarities to a corporate Board of Directors that she wanted to emulate. We discussed a team that was:
Diversified.
The need for diversity in personal and professional contexts is a no-brainer. We all improve and learn more when we interact with people who aren’t like us.
Functional diversity (and perhaps the most literal embodiment of the Voltron theory) is one such lens through which you can think about board construction.
At my fund, for example, we have a stellar Board of Advisors, who is diverse in many ways, but also diverse by their specific subject matter expertise within healthcare. For example, we have an expert in diagnostics, an expert in insurance, and an expert in medical devices, just to name a few.
We invest in all sectors of healthcare, and we are able to leverage the Board’s expert knowledge to look at deals across modalities, and can cross pollinate insights across all the subsectors.
If we think about the discrete sectors of our lives, shouldn’t we apply that same logic and find experts in those specific lanes? Your Personal Board of Directors could have someone you strongly admire as a parent + someone you strongly admire as a manager + someone you strongly admire as a recreational runner, for example.
We discussed how in order to find these diverse sources of mentorship, sometimes you have to sign up for completely atypical activities. She describes one particularly unique place where she has sourced mentorship to complement the more traditional finance professionals she works with:
“I serve on my neighborhood’s Rotary Club. Average age… late 60s? Early 70s? (I’m in my late 30s for context). The advice and perspective I get from women in the club is lifechanging.
I could be having a bad day at work, and later at the Rotary meeting, I’m reminded that there’s a lot more to life than work. On the flip side, a lot of these women have accomplished a ton in their career, and they remind of what’s possible and there are so many years ahead to “achieve” and learn.”
(Somewhat) Independent.
Usually a corporate board of directors is comprised of both affiliated and independent members. Independence meaning members that are not employees of the company, or affiliated in some way. These members don’t stand to materially and directly benefit from the company’s day-to-day operations and can therefore give unbiased advice.
In that same vein, while you might really admire and respect someone you are working with at your current company, you can’t necessarily get unbiased advice on decisions like quitting, or switching roles, or dealing with a difficult coworker from them.
Yes, some of your professional and personal challenges have nuance that can only be understood by people that know your industry (or even the specifics of your company and team), but some challenges can benefit from a completely independent and fresh perspective.
We discussed how one of the best profiles of mentor is a hybrid of knowing the business, but being independent: old coworkers, professors or bosses. They care about your success and have broader knowledge of your company and industry, but aren’t impacted by your day to day career decisions. My friend describes one of her most memorable mentors:
“Someone I go to for advice time and time again is my very first boss! Before he was a portfolio manager, he was a social worker, and I’ve always admired his deep sense of empathy above any of his other traits, even his investing acumen.
Revisiting old bosses is also the easiest one in terms of reengaging - people love reminiscing, and I’d imagine would love to receive an email with an update about what you’re up to.”
Impermanent.
Corporate boards swap members out from time to time. The company has different needs over time. Directors themselves have varying interests over time. In that same way, mentors that have a long term view of your success are great, but mentors don’t necessarily need to be a lifetime assignment.
More on this approach below, but setting up a mentor relationship as being a yearlong commitment can be really effective, and less daunting. My friend frames it like this:
“The typical corporate board meets 4x a year. Once every 3 months? That’s not a huge commitment for any one person.
And for you, if you have 2-3 people on your ‘board’ sharing the responsibility, that’s 8-12 touchpoints in a year, which equates to a once-a-month cadence to keep you on track.
Of course you can meet more frequently if it naturally makes sense to do so, but the baseline expectation of quarterly just seems digestible. Also, it’s likely that people think about their other work and personal obligations on a quarterly basis, so you can align to that and make it easier for them to plan.”
Actually Popping the Question…
Formally asking someone to be your mentor can be awkward.
One approach I like when engaging in conversations with potential mentors, is to focus only on the year ahead. It’s a much less open-ended ask than “Will you mentor me?”
Sharing what you’re working on and where you need help in the near term gives focus and timeliness to the conversation, and can alleviate the formality of asking someone to be your mentor.
Some examples:
“This is my first year as a working mom.”… and I’d love to know how you handled that
“This is the year I’m dabbling in a side project.”… and want to know how you’ve successfully grown yours.
“This year I’m exploring if I change industries altogether.”…given your experience doing so, where should I start?
It also makes clear why you are approaching this person for advice. They presumably have experience navigating that specific struggle.
Having the year timeframe in mind also creates a natural way to schedule follow-ups and sets up a future cadence of checking in. At the end of an initial conversation about what you’re focused on, you can ask to touch base in a few months to provide an update, or ask more questions as you’re further along in your process.
By asking to touch base, you’ve set up an expectation for a future meeting to discuss progress, and can leave it somewhat open-ended to how they want to engage (e.g. put a formal placeholder on the calendar now, casual quarterly coffee, ad hoc emails etc.)
Resources/Links:
A Personal Board of Directors framework from a VC blog that offers a few other tips (visible.VC) :
Make a long list of board candidates and don’t be disheartened if people say no (just keep moving down the list!)
Choose someone who might be a designated ‘critic’ whose main job it is to provide constructive feedback so you get stronger in your conviction
“How to Successfully Ask Someone to Be Your Mentor” … (Psychology Today): ask someone to be your mentor without actually asking. Everyone agrees, it’s intimidating and awkward!
Cool ladies doing cool things: “A Mother and Son Hug After a Year of Isolation” (SF Chronicle) Marjorie Mann is of the quiet heroines of the pandemic. She is a nonagenerian in the Bay Area (and a diehard Oakland Raiders fan) who just received her second vaccination in April and is able to reunited with her son (and can go to Kohls again!)
Tell Me About You
Who would be on your dream Personal Board of Directors?
Have your typical mentorship relationships lasted more or less than one year?
If this was helpful to you or you think someone could benefit from the conversation (and you read all the way to the end!) I’d love if you’d share the “To-Woo” List!