The #family channel

About 4 years ago, when an Allovue team member was expecting his first child, we created a #family channel in Slack as a repository for baby pictures while he was on paternity leave. As our team has grown and evolved over the years, the #family channel has remained one of my favorite bastions of our corporate culture.

Importantly, the #family channel leaves “family” open to interpretation. Diversity and inclusion are celebrated company values, so everyone’s definition of family is a little different.

In the #family channel, we share the joys of life milestones big and small: graduations, weddings, babies, haircuts, piano lessons, first days of school, vacations, meltdowns at the dinner table, science projects, new homes, workouts, renovation projections, pet snuggles, and all of the silly just-because moments that make us feel grateful and loved every day.

Because life happens, the #family channel isn’t all happy moments. We also share moments of grief: a death in the family, a relative in the hospital, a friend diagnosed with a terrible illness. While I welcome the daily dose of cute children and animals, the more somber updates have convinced me how critical the #family channel is to our work.

I’m not sure anyone has ever successfully siloed their “work life” and “home life”; it’s all just life. And frankly, why should we want to? To pretend that these categories exist in an emotional vacuum is to ignore the basic humanity of our coworkers and deny our team the opportunity to connect and empathize on a higher level. Our company culture is richer and our work is more fulfilling because we get to know our colleagues not just through their professional skills and contributions, but also who they are as parents, spouses, friends, siblings, caretakers, and fur-parents. We grow to understand each other as whole people.

The #family channel makes us better colleagues and managers. We subscribe to Kim Scott’s philosophy of Radical Candor – a management approach that exists at the intersection of caring personally and challenging directly. It’s naïve or delusional to dismiss the impact of personal matters (good or bad) on someone’s productivity at work. As managers, we must care about who people are outside of work and understand the circumstances of their lives in order to support and grow our team members to their full potential.

If your team doesn’t already have the equivalent of a #family channel, I encourage you to start one. Come for the cute pictures, stay for the meaningful connections.

5 years ago was my last day of “work”

5 years ago today I did a crazy thing.

I walked away from a great job to pursue an inkling of an idea. This was a clean (psychotic) break from the first 25 years of my life, during which I played by all the rules, colored inside the lines, and took well-trodden paths. Goodbye to all that.

I didn’t feel compelled to recapitulate the details of what’s transpired since then. Instead, I was going to reflect and summarize what I’ve learned over the past 5 years, but I found myself at a loss for words. What could I possibly say to capture the love and fury and joy and indignation and on-the-brinkness and sheer thrill and terror and sense of purpose I have felt (sometimes all at once) during these years?

Everything boils down to platitudes: be yourself; trust your gut; never give up; get some sleep; hustle; surround yourself with the right people; blah.

The platitudes are true but utterly devoid of meaning until they’re colored by personal experiences (usually mistakes) that you just can’t cheat. Entrepreneurship has a way of making you learn things the hard way and kicking you when you’re down. And then there are these barely perceptible yet completely addictive glimmers of progress that make you feel on top of the world. It’s either sadness or euphoria.

In an acute moment of doubt, a great advisor, and, later, an investor once said to me:  “Well, I like an entrepreneur who burns her ships on the shore. Just keep going.”

Onward.

Be Unhappy.

Each day, I skim through the headlines of the Aspen Institute’s Five Best Ideas of the Day newsletter. One caught my eye this morning:

The secret to office happiness isn’t working less—it’s caring less

The premise is unnervingly true. Caring less is the cultural aspiration du jour in a time when many of us are suffering from outrage fatigue. The “zero fucks given” meme entered internet vernacular in late 2010 and surged during the last election season:

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The Subtle Art of Not Giving a F*ck has sold over a million copies, is a New York Times #1 Bestseller, and has spent 29 weeks on Amazon’s Most Read Nonfiction Chart, where it currently occupies the #1 spot.

I lead a startup focused on education resource equity where there is no shortage of outrage about the status quo. We care deeply about the injustices, inefficiencies, and inequities we witness every day – in the education system and as a woman-led startup. We would love to care less. If I cared less, maybe I could lay off the antacid, sleep well, lose 10 pounds, and have some emotional capacity left over for personal relationships.

We fantasize about this so often that my business partner and I have even dreamed up a fictional business that we could run without caring at all: a personalized nail-polish business called Nailed.it. Oh, to run a business with products of zero consequence.

Here’s the ugly truth about progress: if those driving it cared less, we wouldn’t make any. Social impact work is difficult, enraging, slow, and often thankless. As Dr. Seuss tells us, one has to care a whole awful lot to make change in this world.

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While we make jokes and wish for occasional relief from the crushing anxiety of caring so much, I don’t want to live in a world where people doing important social work care less. I do not want to live in a world where people doing the grueling unhappy work to cure disease or educate children or develop clean energy solutions or alleviate poverty or advocate for civil rights wake up in the morning and ponder, “Maybe a nice forest-bath today.” I want to live in a world where people wake up angry and go to work.

When I feel depleted and daunted and start daydreaming about a happy, care-free life, I remind myself of this passage from Brave New World:

“But I don’t want comfort. I want God, I want poetry, I want real danger, I want freedom, I want goodness. I want sin.”

“In fact,” said Mustapha Mond, “you’re claiming the right to be unhappy.”

“All right then,” the Savage said defiantly, “I’m claiming the right to be unhappy.”

#Firstthirtyjobs

I have always been obsessed with working. My very first job was “Mother’s Helper” for my neighbor at age 9 and I just started collecting hustles from there. Unlike most young entrepreneurs, I wasn’t really in it for the money. I liked making money, but I viewed it as buying my independence to shop and travel where I pleased. I mostly liked collecting experiences, though, and I racked up quite a few:

  1. Mother’s helper/Babysitter (through most of middle school and high school)
  2. Face-painting/Nail painting at children’s birthday parties
  3. Cat-sitter
  4. Referee for Lincroft Soccer
  5. Umpire for Lincroft Little League
  6. Closet cleaner (for a hoarder – my job was literally never done)
  7. Secretary at a law office
  8. Marketing & box office sales for a local theatre
  9. Hype girl for a DJ – basically, got paid to do the electric slide at Bar Mitzvahs
  10. Salesgirl at Victoria’s Secret
  11. Bank Teller
  12. English teacher in Thailand
  13. Caterer (roommate and I catered campus events from our dorm room kitchen)
  14. Admin/coffee maker at Penn English Language Center
  15. Research assistant in South Africa
  16. Research subject in South Africa
  17. Kaplan SAT-prep teacher
  18. House cleaner/cook for a Penn professor
  19. Freedom School kindergarten teacher
  20. Netter Center assistant for Academically Based Community Service program
  21. Baltimore City middle school teacher
  22. Ann Taylor Loft salesgirl
  23. Adjunct professor at Towson
  24. ABS Capital Marketing coordinator
  25. Photographer
  26. AirBNB host
  27. Grant writer
  28. Director of education at Betamore
  29. Entrepreneurship bootcamp teacher at Towson
  30. CEO of Allovue

Magically Redefine Your Team Roles and Responsibilities

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Last quarter, a few things happened at once with our team at Allovue. 1) We were at a major inflection point, shifting my focus as CEO from mostly on product development to mostly on sales & marketing 2) Our CTO’s wife was 7 months pregnant, so we wanted to free up some of his time to spend at home once the baby arrived 3) One of our senior developers expressed interest in more autonomy and more responsibility. Here’s how we redefined our roles & responsibilities in a process that we completely pulled out of thin air and resulted in everyone on our leadership team being happier and more productive in their jobs. I’m telling you: magic.

I gathered the leadership team into the conference room and started by writing our names on the whiteboard. One at a time, we went around the room and each person named every process or category over which he or she currently felt ownership and responsibility.

After everyone listed responsibilities, we made a list called “No Man’s Land” for processes that we felt someone needed to own, but no one had named. (Note: We also put things on this list that people forgot to name earlier, because we figured this was an indicator of a responsibility that was not high priority or top of mind.)

This next step is the most critical ingredient of the magic. DO NOT SKIP THIS STEP. I went around to each person again and asked them to tell me “Yes” for things on their list that they felt were the right fit for them, and “No” for anything on their list that they wished for any reason was NOT on their list – you don’t like it, you don’t think you’re good at it, you think it’s stupid… whatever. “Yes” items got a check and “No” items got an X and were moved to No Man’s Land.

At this point in the process, everyone had a list of responsibilities that they loved and felt were appropriate for them to own. Now we had to contend with No Man’s Land: all the things we felt were important for somebody to own, but either no one did, or the person who owned it until now didn’t want to own it.

For the final step of this process, we went through each item on the list and decided to either 1) assign it to someone else on the team 2) find a way to make it suck less for the person who crossed it off their list 3) hire someone to do it.

And that’s when the magic happened.

As we went through the list, my team’s secret interests, skills, and talents emerged as, one by one, people volunteered to snap up items from No Man’s Land and take ownership of them. Rosalyn admitted to secretly enjoying close-reading of legal contracts, whereas I hated it and had been slogging through them. Jason volunteered to take on Sprint Planning, a process that was a total drain for Ted, but a natural fit for Jason. Jake took ownership of all front-end and design processes, which had been awkwardly and inefficiently split between me and the dev team. Ted reclaimed some technical processes, once we realized that a week of time could set up playbooks to automate all the stuff that was wasting his time.

At the end of this exercise, there were only four items in No Man’s Land, and they exactly mirrored the job description I had just written up for our new Venture for America hire. MAGIC. We went around once more to confirm that everyone felt comfortable with their new roles. Ted said, “Wait – that list is my job now?” “Yes…” I said hesitantly. A huge grin spread across his face. It’s a really good day when your CTO is happy.

This entire process took 45 minutes.

A few months in, here are some things that have resulted:

  • Our dev team velocity is higher than it has ever been. I attribute this to a combination of the fact that Jason enjoys Sprint Planning, and Ted has more time freed up to write code.
  • We have fewer errors in legal documents, because Rosalyn is a true Eagle Eyes and catches every. single. thing.
  • Rosalyn has also taken major ownership over customer on-boarding and project planning, demonstrating her unique strengths as a leader in this area
  • Jake has streamlined design processes, which has further contributed to increased velocity
  • My time has been freed up to focus on sales and marketing

Here are some of my key takeaways from this exercise:

  • Don’t let corporate dogma dictate the roles and responsibilities of your team.
  • Making people do something because “they’re supposed to” will drain your employees and slow down your team’s velocity. Sure, everybody has to do some things once in awhile that they don’t love… but make sure it’s really “once in awhile” and not “most of the time.”
  • Take a strengths-based approach. Hopefully, you hired people who are uniquely qualified to contribute to your team. Play to their strengths. They will thrive, and the whole team and company will thrive right along with them.
  • Listen when people ask for more responsibility. Don’t let talent and leadership sit dormant in the organization. This doesn’t mean promoting everyone to an executive position, but find ways to give people opportunities for leadership when they crave it. This might mean giving someone a leadership role over a single project or feature in the short term, and it might unleash new skills and talents you never saw before.
  • Just because someone “can” doesn’t mean they “should.” Founding team members tend to be multi-skilled individuals. It’s easy to assume that because someone is capable of doing something, it makes sense for them to keep doing it. Take inventory of these things regularly – can someone else on the team do it faster, with more joy? This goes back to the strengths-based approach: are people spending their time in the most efficient way, given the skills and talents of the team as a whole? Make sure that people who are uniquely qualified at high-value, mission-critical tasks are spending as much time as possible on those tasks.

I expect that we will return to this process as we grow, consistently reevaluating how team members are spending their time, and ensuring that we’re leveraging leadership capacity across the organization – because a happy, healthy, productive team is nothing short of magic.

If you try this magic process, or have done something similar, I’d love to hear about it!

Everything I know about being a CEO, I learned being a teacher

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“How can you be a CEO when you were just a teacher?”

This is one of the most common questions I have fielded as the CEO and founder of Allovue, an early-stage financial analytics company. Initially the question offended me; I prickled at the insinuation of all the worst teacher stereotypes: teachers aren’t as smart or shrewd as other professionals, teachers are lazy, teachers are fluffy.

Now, I’m amused by the question. After all, teachers are the unsung CEOs of the world. Teachers manage hundreds of people every day (who are not paid to show up!) Teachers prepare and present 4–6 hours of unique content every day, and are evaluated based on those hundreds of students’ ability to process and retain this new content. Teachers make all their own agendas, PowerPoints, and reading materials. They often buy their own presentation tools and office supplies — for over a hundred people. Sorry, no T&E reimbursements! They make their own photocopies of materials they created or purchased themselves. They give individualized feedback to over a hundred people on a regular basis. Hey, CEOs — when was the last time you reviewed and evaluated the daily work of +100 employees after doing all your own work and meetings for the day? And don’t forget to call all of your employees’ parents at least once a week to let them know how they’re doing at work! Great teachers are virtually superhuman masters of management and logistics.

I’ve come to realize that most of my favorite management strategies were fire-tested in the classroom, not a boardroom. Having taught students from kindergarten age up to the graduate level, I’ll let you in a little secret: managing adults is not all that different from managing children.

Public praise, private punishment

This is a staple of classroom management. Can you remember a time that you were called out in front of your peers for doing or saying something wrong? Can you feel your cheeks getting warm just thinking about it? Now, think about a time that someone praised you for a job well-done in front of all your colleagues. I bet your chest is still swelling with pride. This is a pretty basic tenet of human psychology: most people appreciate public recognition for good work, but feel humiliated by screwing up in front of their pals. Publicly chastising people for mistakes might create results in the short term, but it’s no way to build a strong culture in the long term.

As often as possible, we make an effort to let our team know about all the awesome things their teammates are doing — we also share a weekly newsletter with team shout-outs and appreciations, ranging from small helps (“Thanks for giving me a ride home”) to big wins (“Great job closing that sale! Coffee for everyone!”)

On the contrary, if something is going awry with process or performance, we address these issues privately with team members, and we focus on figuring out why something isn’t working and what steps need to be taken to fix the problem. It is difficult to consistently do this without egos and finger-pointing. We are not perfect at it, but couching these discussions in terms of finding solutions instead of allocating blame goes a long way.

Give credit, take blame

As a general rule, when something good happens, my team did it. When something goes wrong, it’s my fault. As the CEO, you have little to lose by accepting blame. It takes pressure off the team and frees up their mental space to focus on solving the problem. Are you sensing a theme here? People don’t function well when they’re embarrassed or scared.

As for giving credit, let’s harken back to Obama’s “you didn’t build that” decree. No matter how much of a 10x-programmer-visionary-wünderkind you are, it’s extremely unlikely that you built something great alone. Give credit where credit is due — and then some. Elevating others does not diminish you. Take every opportunity to credit your team, investors, advisors, and customers because this is an all-ships-rise-win-win situation.

Bring cupcakes

I don’t care if you are 5 or 50 — people love cupcakes. I have studied this extensively, and the effects of cupcakes on a classroom or office are the same: good cheer and a burst of productivity. We are lucky enough to have the gourmet cupcake shop La Cakerie down the street from our office and we are frequent patrons. Birthday? Cupcakes! Engagement? Cupcakes! Good press? Cupcakes! Thursday? Cupcakes! Celebrate each other. Celebrate wins, big or small. Celebrate just because you are all in this together, doing the hard things, fighting the good fight, and goddamit, you deserve a cupcake.

If You Can’t Do Anything Else

Every theatre kid has a moment (or many moments) when they consider pursuing a career in acting.

I had my moments. Every few months or so for the decade between middle school and college graduation (the heyday of my theatre career, as life would have it), I would threaten my parents with pursuing acting. I even declared a second major in Theatre second semester of freshman year (which I later demoted to a minor).

I remember the popular maxim that often accompanied these ambitions: “You should pursue a career in acting if you can’t do anything else.” It wasn’t until several years post-college that I learned there were actually two interpretations of this adage.

I had always interpreted the phrase to mean that you should pursue acting if you couldn’t breathe without it; if you felt as though you would truly perish from asphyxiation, choked by your own unfulfilled potential on the screens and stages of the world. (I was a little bit of a drama queen, and perhaps prone to hyperbole.)

Another friend interpreted it more literally: you should pursue your thespian ambitions if you simply have no other skills with which to barter in the game of Life. If that is your one talent, then you may as well play your hand. If you can do something – really, anything else – definitely do that instead.

I still like my version better. It has poetic conviction: give me the Backstage listings or give me death!

In any case, my theatrical ambitions didn’t pass muster by either definition – I loved (and still love) theatre, but felt I could be happy leaving it as a hobby. In fact, I feared the opposite: that I would rely too heavily on the art as a meal ticket, take parts I didn’t love in shows I didn’t believe it, and slowly start to resent it altogether, the way people spoke of being sickened at the sight of ice cream after a summer scooping sticky globs of the stuff. And supposedly, after four years of a good college education, I had other marketable skills to lean on. (Time will tell, I guess.)

I spoke to a young(er) entrepreneur-in-waiting last week, and he told me he had a list of about a dozen business ideas he was thinking about pursuing. Without seeing the list, I told him none of them was the right one. He asked how I knew, and I said that when he found the right problem to solve, he would unquestionably know it to be the one to pursue. He wouldn’t be able to do anything else.

Two years ago, that is how I felt about a problem that I later started Allovue to solve. I couldn’t sleep. I couldn’t stop thinking about it. I felt certain of my impending death, crushed by the weight of regret (there’s that hyperbole again!) It’s a feeling not so unlike lovesickness. I couldn’t do anything else.

I think founding a business is a pursuit worthy of hyperbole. There’s plenty of rejection, the odds are not ever in your favor – it’s really not so different from a career in acting, when you think about it. For every break-out celebrity, there are thousands of people getting typed-out all day. For every Uber, there are thousands of wantrepreneurs honing their “Uber for X” pitches. Unless you’re Richard Branson or Elon Musk, you probably can’t just pick an idea off a list.

You should only pursue your business idea if you can’t do anything else.