Category: Read and Re-read

Trombone Oil & Picking Good Problems

There are these three ideas that are coming together for me right now.

We’ve talked about the importance of novel intersections before – how as you explore different areas, texts, content, relationships, you find places where they approach the same problem in different ways, or you find a similar perspective being represented in unexpected ways across industries.

One of the best ways to drive innovation is to get out of the office, and we need to follow that same pattern when it comes to our information and research diets. We have to get out of the standard operating procedure sometimes, and cast a wide net, find other things that are interesting and engaging outside of our professional day-to-day.

(I think this is why we see such a strong correlation between arts and crafts and winning the Nobel!)

When I joined Disney, I read Bob Iger’s book. In this book there are a number of useful take-aways (although it is a pretty classic business guy book), but one rang out to me and has been hanging around my mind since:

“My former boss Dan Burke once handed me a note that said: “Avoid getting into the business of manufacturing trombone oil. You may become the greatest trombone-oil manufacturer in the world, but in the end, the world only consumes a few quarts of trombone oil a year!” ”

Iger in Ride of a Lifetime

It was a little later that I first read the (now classic) Shreyas Doshi piece on the importance of not only identifying customer problems but also seeking to understand how those problems relate to one another.

After you’ve talked to a customer about a specific problem & possible solutions you could build, ask them to stack rank the problem being discussed vs. the other problems they are trying to solve for their business & org. This is where the real truth will emerge.

Shreyas Doshi

And there was the time that ol’ Brian Chesky scared me into learning about product marketing, which brought me to the very smart, very thoughtful, very valuable podcast and books of April Dunford (which I have recommended before and will recommend again!)

One of my biggest takeaways from Dunford’s Obviously Awesome (which was my Work Book of 2023 by the way!) was the importance of framing a product or solution within the broader context of your target customers or market – and being sensitive to the dynamic and shifting nature not just of your own product being developed, but also how the market itself can shift away from established successful frames.

(I know classically we think about positioning as a skillset for product folks working with external customers, but I’ve started using Dunford’s positioning framework with internal platform teams, and it’s been really valuable!)

These are three ideas that are in the same neighborhood, which is of special interest to product folks, which is the area of Problem Assessment. The most important thing a healthy product organization does is ensure that they don’t build the wrong thing, and it’s easy to hyper focus on a solution, on a product, and lose sight of what problems that real people have, that you can help them to solve.

It feels like every team I talk with, someone has a story about working for months on a project, crunching to hit a deadline, and then seeing the delivered product fail to achieve any interest from the market. We want to avoid this!

When we chat with our customers, when we observe the platform landscape of our companies, there will always be things to improve, areas where we might deploy our resources and time. It’s important that we take the above lessons and leverage them to help consider problems from a few different perspective:

  • “Is this trombone oil?” (Assess business opportunity)
    • We want to consider, if we absolutely defeat the problem, if we build out the absolutely best possible solution and become the dominant player in that market, will that be … a big deal? Would it move the needle for our firm?
  • “How does this rank against other problems? (Assess customer pain)
    • When we talk to our customers, do they consistently report that the problem at hand is more important, more urgent, or more painful than the broad landscape of other problems they have?
  • “Can we appropriately frame this problem?” (Assess market understanding)
    • Even if your firm has the product/engineering talent to build out an exceptional solution to a serious problem, do you know enough about your target market to bring the solution to them in a way that will communicate the value in terms and ways that resonate with that market?

Like any discovery exercise, this assessment can go as deep as you can sensibly prioritize: of course, the framing piece can be improved by learning more about a market and audience, the customer rank piece might be dynamic based on who your target customer is, and even the market sizing piece might change given other larger shifts in the macroeconomic landscape (think about the market for AI Assistants only two years ago!)

They also relate to one another: you wouldn’t want to invest a great deal in learning about the appropriate framing for a customer segment if you aren’t yet sure you have a solution to their most painful problems – and ensuring with relative confidence that you have a significant addressable market probably should come before the other assessments.

I hope bringing these different pieces together this can be a helpful lens in considering the different problems that you might work against: if we can avoid trombone oil, and build things that create real value, and solve real problems, that’s a great start!

The Time Brian Chesky Scared Me So Bad I Bought A Book

When I first heard that the CEO of AirBNB, Brian Chesky, had eliminated the Product Management role, and transitioned that department whole cloth into Product Marketers, I was surprised – and skeptical.

Surprised in part because, AirBNB is a company whose product folks have had a serious impact on me and my own product practice – Lenny of course but also more directly Nick and James from the Transform team (who I got to know during my time in the modern data stack space). To think that a company that produced such thoughtful and successful product folks, was pivoting away from this mindset and methodology (which I’ve built my professional journey on!) was jarring, to say the least.

Was this part of a larger market shift? Was Product Management going the way of the Elevator Operator? Surely a little over-the-top, a dramatic overreaction from a former theater kid. But even so!

A quick Google will give you lots of hot takes and deep dives on what Chesky really meant, and how what they were really doing was shifting from the way that they had found themselves doing product, more intentionally to a revenue- and market-focused direction.

That being said, in hearing the news, my first reflection was more personal – I’ve had the opportunity to work with some world class product marketers, but that part of the overall Product Toolkit was an area where I felt quite weak – not for lack of interest or adjacency, but just, never happened to get around to it!

So, I did the thing any good Product person does when faced with uncertainty; I did some discovery! I reached out to the undisputed most talented product marketing professionals I know, and asked for help.

And help they did – after a few Zoom powered coffee hangouts, I felt as though I had passed through the Dunning Kruger horizon. The depth and complexity of the topic unfolded before me in an exciting (and nervous-making) way, like any topic does once you get close enough.

One aspect of my concern was validated almost immediately: while I had worked closely with marketing teams and marketers, my own toolkit could use some sharpening in this area. So, I set about doing just that sharpening – ingesting a lot of audio and text content, YouTube videos, and overall sort of soaking in the broad Product Marketing Content Ocean – and an ocean it is! There’s no shortage of folks who are happy to opine on the many aspects of the field.

Through this effort I did find two resources to be especially useful and continue to be folks I look to for expertise and value regularly, which I share here:

  • Jason Oakley of Productive PMM – I subscribe to his newsletter, which shares regular quick-hit examples and analysis of interesting things being done in the wild.
  • April Dunford – I will read, write, and listen to anything that April makes! I’ve been so impressed by her thinking, her storytelling style, and her deep and expert analysis. She has a podcast which is a great first stop.

It was through April’s podcast that I first started to think a lot about positioning – not something I had considered with much depth before, but something which, due to the topic itself or perhaps due to April’s natural charisma and engagement around the topic, really drew me in.

I think most folks have the experience of, occasionally, being really taken by an aspect of their own work, some line of thinking or research, or new approach or methodology, that can arise with a sort of renewed energy, a renewal of excitement and a new sort of lens on a great many things that you’ve been doing regularly without much new insight or novelty.

For me, the most recent example of this is positioning – in coming to better understand this line of thought and methodology, I’m find it applying to more and more aspects of my own work.

It has me so fired up, between the great fright that Chesky gave me, and the compelling nature of Dunford’s podcast, I did something I never thought I’d do. I bought a sales book.

I haven’t finished the sales book, but I am already seeing some unexpected intersections of how we thoughtfully market and sell to external customers, and how internal / platform product teams could more thoughtfully represent the value of their partners and work. There’s something here, and I’m stoked to dig in more.

All this to say, if there’s a kerfuffle in your industry, in your place of work, and it makes you nervous or anxious (as Chesky’s shift to Product Marketing did for me) it’s worth sitting with that internal landscape, spending some time interrogating that feeling, maybe having a coffee or two with friends or mentors. You may find there’s something new and exciting behind that anxiety that unlocks a whole new space in your journey.

Paternity Leave and Reading

As you may have noticed via my recent mini tweetstorm, I’m on paternity leave, and feeling thoughtful about it.

(Sidebar, is there an agreed upon definition of tweetstorm? We can all agree that 25 tweets a tweetstorm make, but what about 9? 3?)

Especially having spoken with many of my friends, who work locally, who have nothing like this type of paternity leave – it really is a landscape of gratitude, on my end. This time is special, and important, and I’m so grateful and (frankly) lucky to have it.

When our daughter was born, I didn’t take the three months – I took it in fits and spurts here and there, since the policy is three paid months within the first year of a child’s life.

Rather than take three months at the outset, I took two weeks when she was born, then some time over the holidays, Spring Break to coincide with my wife’s time off, etc. I didn’t end up using the whole three months, and the time I did take off, I could have just as easily taken off with our open vacation policy rather than the “saved pat days.”

With our second child, I was reflective on our daughter Mango’s birth and my reaction, work-wise. Why didn’t I take the time I was afforded?

It was out of fear. Even a few weeks off at a place as fast paced as Automattic meant having to recalibrate, scramble to catch up, and try to figure out how to navigate what seemed like an all-new sea. I was worried that extended leave would jeopardize my chances for advancement and recognition.

Which brings us here – though I’m a Team Lead, responsible for the careers and success of  eleven of my peers, I have chosen to take my full three months of paternity leave. Before he was born, I spent a great deal of time working with my stand-in lead, training and shadowing one on ones and (I’m not proud) linking her to lots of posts on this very blog.

She’s going to do great. I also think that, on a bigger level, it’s important  for the folks on my team to see me take this time – that even in a leadership role it’s safe, and encouraged, to take the time we’re given. Having this time with my kiddos and my wife is important, for me personally but also for me as a long-term contributor to Automattic’s success.

(Our CEO Matt Mullenweg talks a little about hiring folks using a 30-year mindset in the latest Tim Ferris podcast – knowing he sees his employees this way makes me more comfortable taking this kind of time off)

Since I am a terrible A-type monster, three months away from work is a horrifying prospect. I am bad at leisure – especially superfluous leisure.

So, I’m reading. I’m reading a lot. I asked some folks I respect for their recommendations, as well as the world wide Twitterverse. Here’s what I have ahead of me:

Orginals, by Adam Grant, recommended by @mremy
Thinking Fast and Slow, by Daniel Kahneman, recommended independently by @andrewspittle and @ctdotlive
Anarchist’s Tool Chest, by Chris Schwarz, recommended by @blowery
Laws of Simplicity, by John Maeda, recommended by @photomatt
Name of the Wind, by Patrick Rothfuss, recommended by Bill Bounds
The Obstacle is the Way, by Ryan Holliday, recommended by @mikeykrapf
The Score Takes Care of Itself, by Bill Walsh, recommended by @JeremeyD
Deep Work, by Cal Newport, recommended by @thebriankerr

I’ve already finished a few – with 59 days left in my pat leave I’m looking at about 24.3 pages per day to finish them all in time. Which means, of course, I could probably sneak in one more book if you have an excellent recommendation!

Two Book Power Pack

I recently had the experience where two books I read resonated with one another in a surprising way. Right after finishing A More Beautiful Question my friend and colleague Daryl recommended I read Work Rules. 

These two books, read together or in quick succession, results in a gain much greater than the sum of their parts. There are common threads between the two, regarding inquiry and innovation at work, with A More Beautiful Question approaching it theoretically and on a high level, and Work Rules sitting in as a detailed case study.

If you are interested in innovation and organization in businesses today, reading these two together will bear serious fruit.