The Toolshed

A place for visioning, tinkering, and building around the topics of education reform, technology, and female entrepreneurship.

Month: December, 2014

Good Managers Are Made, Not Born — And Other Discoveries.

I went on my first run in over 2.5 months this past week while visiting family in Naples, FL for the Christmas holiday.  Earlier this fall, I struggled with an unfortunate health situation that prevented me from exercising.  It was simultaneous torture and joy to be told, frankly and dispassionately by my doctor, that I could not run for the next three months.  I actually despise running (“How can I have only run .63 miles?  It feels like I’ve been out here for hours!”) but know that exercise is good for body and mind and have the Catholic discipline to force myself to do it.  My father one time told me: “You can cure almost anything with water and exercise.”  I’ve clung to that potentially spurious adage for years, likely to my own detriment at times.  (I’ve prolonged many a cold by running in frosty climes prior to recovery.)

At any rate, on the four-mile loop around my parents’ neighborhood, I found myself stopping multiple times to jot down things I’ve learned at work on my iPhone notepad to bring to bear here in this toolshed over the coming year.  Some of them are bits of wisdom I’ve inherited from folks much wiser than I; others are half-formed observations and intuitions from my own direct efforts — flotsam and jetsam circulating and surfacing, some of dubious use and others, likely, a meaningful component of the lifelong professional credo I suppose I’m seeking to build through this blog.

At any rate, my taking stock from this past week:

1.  Good managers are made, not born.*  At my previous place of employment, the sharpest tools in the shed were promoted quickly to managerial roles.  I recall an HR consultant that was working with us on a range of unfortunate (and, in retrospect, petty and frustratingly time-consuming) personnel issues saying to me: “You know, too often, people that are good at what they do are promoted to a management role.  But what few realize is that management is a skill, and many of these people need support and training to be effective supervisors.”  I internalized this for some time.  On the one hand, I felt foolish for not recognizing this myself.  On the other, it made me feel relieved — I made so many mistakes as a green manager that I almost want to send thank yous and apologies now, five years later — and this wisdom made me realize that no one can be expected to knock it out of the park as a manager right out of the gate.

*Except for maybe my husband.  My husband may defy this truth.  He is a seriously talented people manager, and has always been.  It exhausts him, but he is wicked good at it.  He has incredible intuition when it comes to addressing people and situation in the workplace.

2.  A managerial promotion should not necessarily be a reward for good performance.  Related to the above, I read this fascinating post that makes the case that, especially in technical environments, management should not necessarily be the reward for strong performance.  I asked a friend of mine who works at Yammer about this, as I knew he’d been promoted from a senior programming position to management recently, and had encountered some challenges in the transition.  (We’d talked previously about the gaping differences between maker’s time and manager’s time.)  He had some interesting corroborative thoughts:

“About 3-4 years after college, I had the opportunity to manage people probably due to similar circumstances outlined in the blog post. At the time, I had no idea what I was doing and, now after looking back, know I definitely did certain things very poorly. At Yammer, I passed up my first opportunity to manage because of my first experience with management. I had a second opportunity at Yammer and decided to jump into it because I made a decision that I didn’t want to code my entire career. I went in knowing that I would have to learn how to be a good manager, so I had a different perspective than my first foray into the role. Going back to the blog, there are definitely senior coders that never want to manage. I have a few on my team. I tend to “reward” them through similar means (give them the projects that have a lot of impact), but I also force them to grow by challenging them to not be “owners” of the code. There are definitely some truths in that blog post, but everyone is a snowflake and sometimes people need to learn by getting burned (like me).”

3.  We may need to think outside the box to imagine an org structure not oriented around the idea that management is the only path for career progression.  When I first heard Matt Mullenweg, CEO of WordPress, talking in an interview at last year’s Lean Startup Conference about his truly distributed, remote, and flat organization, I probably shared the same amount of confusion and bemusement that his interviewee, Sarah Milstein, displays.  At times, Mullenweg comes off as a disconnected and spacey hippie, but there is some beautiful synchrony and integrity between his open-source product and his organizational ethos.  At WordPress, everyone works in small and fluid teams, and team leaders occasionally emerge and then step back.  There is no rigidity or structure to this, and becoming a lead does not mean higher compensation or my authority.  It’s difficult for me to imagine this sort of organization working well in any industry outside of technology, and even within technology, it makes me wonder about productivity.  But still, there’s something intriguing about his anti-hierarchical tack that resonates with the above observations.

4.  If someone else can do it 70% as well as you can, you should delegate.  I have to admit that my main struggle as a manager is relinquishing control.  I am a perfectionist and I will embarrassingly admit that I occasionally hold the unhealthy, rude, and overly egotistic view that I can do certain things better than the people reporting to me.  That’s why this bit of wisdom I picked up from a blog I read a few months ago was incredibly useful in terms of making the judgement call as to whether to delegate or own it yourself.

5.  A start-up is a human institution developing something under conditions of great uncertainty.  This comes from the maestro, Eric Ries, and I think this will prove to be a useful definition to have on hand.


Taking Stock: 12.19.2014

I recently attended The Lean Startup Conference in San Francisco.  I learned a lot that I have brought back to my work in Chicago, the most powerful of which is the liberating discovery that everyone fails in the product space, and that your strength as a product lead stems from resiliency and faith in the process of iterative design.  (As an aside, it makes me wonder if we shouldn’t call product people “process people.”)  I took away a lot of gems, some useful activities and frameworks, and a newfound appreciation for the art of the presentation.

My favorite quote of the entire event came from Dan Milstein, who said:

“Lead by owning the questions, not the plans.”

Despite a broadly positive experience, I did bristle at the cultish-ness of the event.  There was something distasteful about the “us” vs “them” rhetoric woven throughout the presentations, as though all conference attendees were of the enlightened ilk while the rest of “upper management” and “the establishment” were blindly and mindlessly using antiquated, problematic, and unsuccessful techniques.  I do happen to believe that the lean startup methodology should be the ethos of the modern tech company, but there is also the question of what happens when a company grows up and necessarily needs to focus on efficiency vs. innovation in order to scale cheaply.  Perhaps it’s unfair to position these two forces at opposite ends of the seesaw, but there was something in the language of many-a talk that made we want to push back a bit, made me want to understand whether there are certain environments, timeframes, situations, etc., where lean needs to take a backseat to other forces for growth.

But this is probably the contrarian voice in me that draws back at any “us vs. them” formulation.

At any rate, one of the most helpful practices I picked up and will apply to my own work moving forward is what I will rename as the weekly learning inventory: a five minute activity each Friday to pause and take stock of major/top-of-mind learnings from the previous week.  I will be sharing these here each week.  A good hook to draw me back into writing more liberally about my observations and experiences.

Today I will share two weeks’ worth of inventory:

December 12, 2014

  • Lead by owning the questions, not the plans.
  • When it comes to pricing, ask for as much as you can with a straight face.  (Great advice from a mentor of mine out in SF.  I’ve been selling our technology to willing, like-minded partners and, despite a fair amount of research and consultation and thinking and reading, still feel insecure about the pricing model we have in place.  The process of validating it through customer conversations is not only time-consuming but also, from a personal standpoint, challenging for me.  I’ve never been in a position to ask for money.  My mentor had the above advice to offer, alongside the general provocation: “Ask for twice as much as you feel comfortable asking for.”  A speaker at LEAN corroborated this advice when he said: “If you’re not uncomfortable asking for money, you’re asking too late.”)
  • Our app is the space between nothing and a financial product. (Our COO Joe pointed out that our technology is sort of a stepping stone towards having a student open a financial product; I hadn’t been thinking of the technology as a trainer of sorts, but he’s onto something with this framing.)
  • Piloting something is a series of unpleasant encounters with reality. (#truedat)
  • Our app is best-suited to drive results around saving and mindful spending.  (We have been pushing to conceive of the app as a one-stop shop for issuing challenges across a range of financial habits and practices, but the photo-centric nature of the technology really fits in best for saving and spending habits.  It’s frankly challenging to envision interesting, generative challenges around safe financial product use or making money, though I’m open to pushback.

December 19, 2014

  • High achievers own the process, not the end product.
  • Most (even highly traditional) schools and folks that work in them view financial education as “dry.”  (An interesting re-framing of our value proposition.  I think that if we can sell them on the idea that we’re doing something fun, light, different to have huge, real impact, we’ll see lots of hand waving.)
  • At the end of the day, we are all humans with complex psychologies.  Business is not as rational as one might expect.  (I have been slowly coming to this perspective over the past six years.  Everything we do is driven by humans, their motivations, their passions, and their hatreds.  This is so basic that it’s almost embarrassing to write, but I have been recently struck by the power of truly thinking through the motivations of the person across the table, whether it’s a partner, a mentor, a student, a staff member.)
  • “I wish access was enough.  I wish education as enough.  But they’re not.”   (An interesting speaker from Ounce of Prevention mentioned this during an event I spoke at earlier this week.  She was provoking some of the students that had completed a class on human centered design and put together project pitches to think beyond education, beyond access — what will really drive change in a community?  This gets to the point above.)
  • Lean methodologies are a continuation of the human centered design process.  (I see them as tightly related, and possibly not in a temporal sense.  There are a lot of different overlaps.  I think that HCD is centered upon a language of empathy whereas lean is more about analytics and growth, which shade them in different ways, respectively.)