Put me in, coach - or Put the coach in?: Operating vs. Advising

What is the difference between advising and operating? Until this year I thought it was Leverage vs. Ownership respectively - but no longer.

If you’re weighing these paths, the real tradeoff to interrogate is: Do you get more fulfillment from working in a team 🧑🤝🧑 or individually 🧑? If you choose that properly for yourself, your work is more personally rewarding and more likely effective of course. In my case, a standing team is more rewarding and more naturally available in an operator context. But through a fortunate set of recent projects, I've seen both Leverage and Ownership is possible in either operating or advising modes, it's a false choice I realized one can design to avoid.

1. Ownership in advising: Deliverables that can tie to immediate, regular outcomes drive this feeling (over, say recurring hours on the weekly top priority, or a major capstone result)

2. Leverage in operating: Because you own the problem regardless, solutions that have leverage (e.g. a broader solve, or less time to solve next time) should always be the goal.

🧑: What I mean by “leverage” is the thing I love most about being a consulting advisor, both with a large firm (Booz Allen) and as a sole proprietor of an LLC. You come in at a crucial point, and for short bursts of time - either a couple hours a week or as many hours as you can in a set period. You work to add something critical that takes things to the next level or stage.

🧑🤝🧑: And while “ownership” is technically available in advisory - e.g. when you get a share of upside, hit the engagement's goal - being an operator you own the problem and the solution. You wake up with it as your main mission, accounting for it every day with action. Checking in on your investment is nice, but it’s like passive income. Great for a portfolio, but definitionally not life’s work.

🍕: Ownership in advisory is not about getting credit, equity stakes or a billing level that says you’re vital. It’s more about ensuring what you are consulting about has outcomes immediately built in. Even meetings, and especially incrementally-valuable deliverables. Help close a hire, a deal, hit a weekly number. Your client / advisee may or may not take the next major step successfully no matter how you’ve empowered them, but framing the work and the value as what happens in the moment (alongside a final business or equity outcome) makes a better engagement for everyone. With advisor equity being more commonly granted over a vesting schedule these days, it's also more aligned anyway.

🚑: When family health crises prevented me from doing more than some fractional work for most of 2024, I was fortunate that my work with a couple folks (like Mike Meaney, PhD and Lisa Luedde - and others who know who you are) showed me that you can have ownership of an outcome even when you don’t get to ship everything yourself. Unlike a time-bound consulting arrangement, these engagements and the nature of their goals would force me to think of what could be done (or failing that, decided) in every single interaction to move the ball forward. This is a discipline to carry forward, and mimics a rule I adopted in operating for ensuring every meeting has a goal outcome asserted from the outset.

🧢: I’ve coached my kid’s baseball team for a few years - definitionally, I'm not on the team. We coaches think we’re helping them develop skills, master a rule, but really we’re teaching them how to love learning something that they can do without us coaches, but they can’t do without the others on their team. With the basics understood, we realized very quickly that the kids do best and enjoy it most when we get them helping each other. We now create practice schedules and provide roles on the team so that this happens not just organically, but automatically in the process of having a great experience and outcome.

Go Dragons!

⛏️ vs 🤖: Similarly, in reflecting on my recent operating roles - and to a lesser extent in AI-related advisory - it’s amazing how much leverage can be gained in strategies to add and calibrate for that by design. E.g., summarize user feedback and tie it to your roadmap automatically in a tool. Or just track the multiple of time it takes digging for it (vs simply reviewing it) when the process is manual. Reinforcement Learning with Human Feedback (or RLHF) isn't just for robots or an GenAI buzzword - visible work product and living documentation has helped human agents for much longer.

Or lastly, think (I do almost every day) about following the first, most shocking principle a long-retired mentor gave me: Never make yourself indispensable. Whether advising or operating, that’s leverage AND ownership.

Creating a Creative GPT

Since the capability to build your own GPT was introduced by OpenAI, I have created a few private GPTs just to play around and test the limits of what was possible. One saved me from accepting a doomed consulting project. My favorite — that I continue to use — is one that takes the supposed ‘bug’ of generative AI — ‘hallucination’ — and turns it into a feature. It’s my brainstorming-when-I’m stuck partner, Creative Gap Minder:

https://chatgpt.com/g/g-rw8PngZ4v-creative-gap-minder

As a longtime product professional, I am generally practiced and confident in coming up with a reasonable, high-internal-integrity plan and approach for a new product strategy or project plan. But how can one ever know what one might still be missing?

Many diverse eyes on your plan is really the only way outside of actual experimentation — so let’s add a robot eye to our diverse perspectives. This GPT both suggests frameworks to smoke that out both for yourself or with your team, as well as ideas you may not have considered. Play with it and LMK what you think!

Whether you should have considered whatever ideas this GPT comes up with... your mileage may vary! It certainly fails embarrassingly for me at times — and I wouldn’t have it any other way. Since hallucination is really not deterministically different than non-hallucination, it is something you need to actually want as part of the product, not just to guardrail around and pray. Otherwise an LLM is almost certainly the wrong tool for the job (even if AI more generally is likely right). Here, my own limits as a RAG expert notwithstanding, it’s a great tool for the case, in principle.

Some qualitative observations through iteration:

• Settled on and strongly recommend a framework (I unfortunately cannot attribute) for completeness of your custom GPT’s prompt. Include statements for all of the following: Role, Task, Context, Format, Tone, Examples. Do them under these titles in #markdown.

• The GPT’s occasional disobeying of what I have provided in the RAG context I provided seems unlikely related to the prompt’s instructions to be provocative, or due to a high ‘temperature’ setting (especially as OpenAI has guardrailed temperature risks themselves in a number of ways since 3.5).

• GPT 4o improved the result markedly off the same bank of QA prompts — it both adhered to my prompt instructions and seems to do a better job chunking and understanding the PDFs I have given it as context and reference material. Misalignment fails are non-zero but rare however. This seems like a good tradeoff for now, but the trendline suggests other foundation models that offer more configurability and control will be better long-term for the creative demands I have even with a safe use case like this.

So Llama probably ultimately but Perplexity next — it’s time to baseline what I could do there (to Mind the Gap?) with what they have out of the box…

Voice of the Customer in our Product Development Process

(Another blog post - like “Product Management in 5 Questions” I wrote a bit ago in service of promoting the new SaaS-era Product practice at CrowdFlower — which eventually exited via acquisition by Appen. A bit basic perhaps — the cool thing is how much easier it is to schedule and administer this stuff with tools like LoopPanel, Monterey.ai and ChatGPT — but makes it even less valid to avoid it!)

January 27, 2016

Late last year, we hosted the Rich Data Summit. Fundamentally, it was an industry event where we brought in some of the smartest speakers in the data science landscape to share their views on the present and future of the field. After announcing the Beta release of our new AI offering, my attention turned to our customer panel on ‘The State of Data Science’, where in a moment of shameless self-interest, I used the fact I was tabbed as moderator to frame that session as an opportunity to understand the voice of the Data Scientist. It was important that every CrowdFlower employee in that room heard how they work, what interests, motivates (and de-motivates) them and their teams.

For product people, sessions where you learn about your core users are incredibly valuable. But most would agree it is disappointingly hard to get these kinds of sessions scheduled. We often have to spend many hours of logistics and protocol development (and give away a few Amazon gift cards of high denominations), all just to get a small handful of 15-to-60-minute interviews done.

But it’s completely worth it.

Here’s why and how those sessions are essential to the product development process.

1. You get a user story about an actual user

If you’re not familiar with the Agile concept of a User Story, Broadcom’s Rally Software can help. But the TL;DR is that in our process, Product people ask Engineers for code that fulfills a need for an actual (type of) person.

We might describe those people as “a new visitor who is frustrated with our security requirements” for example, but that persona doesn’t feel real until you actually talk to one such person. They make the User Story real.

Of course, it’s important you make sure to control for Cognitive Bias problems deriving from the small sample size and interview format, but once you have, you can do a better job of describing your user to other people on your team and discovering their real needs, even beyond the ones they can articulate.

2. You learn whether our goal is being met

Good product management starts with a thoughtful definition of the goal behind the time and money you’re proposing to spend. The reason why would merit a whole separate post, but suffice it to say, when you ask people “what is it you want to accomplish?” and “how would you go about doing that?”, it becomes very clear whether what you’re building can solve the problem you thought it would.

3. You learn whether your goal is the right goal

A happy outcome of any interview about whether a goal can be achieved is that you can also learn whether that goal actually matters to the people you think it should matter to.

In a user research session where you’ve crafted behavioral questions about what someone wants to do and tries to do, a good listener can also hear what the subject is pointedly not saying, or what they’re glossing over because they think something else is more important. When you notice that happening, you get a more valuable initiative gift-wrapped for you to work on instead.

4. You often see patterns very quickly

While it can be painful to get one interview scheduled, thankfully, it doesn’t take many of them to see the most valuable themes are for the people you’re trying to understand.

Specifically in usability testing (where you’re trying to figure out how easily people can complete a task you’ve laid out in your product), noted researcher Jakob Nielsen quantified why you often only need 5 such sessions. When you spend the time to schedule these interviews, it’s usually good to mix in both discovery-related, open-ended questions and task-oriented hypothesis tests on a related product or prototype. Hearing about both the problem as well as the symptom gives a better view as to which level’s common themes are most important.

5. You put yourself in a position to get lucky

I can count at least 4 times in my career where we’ve conducted behavioral interviews and uncovered something surprising that ended up being more valuable than the whole initial project. At OpenTable, for example, we realized we didn’t need to spend millions to acquire and load restaurant photos for all of our listings in search results — because when asked, people consistently said they only truly cared about seeing them for an individual restaurant that already met other criteria.

At CrowdFlower we saw that users didn’t want or need lengthy onboarding videos, product tours or tutorials for building a job that we had considered creating. They just wanted to get their hands dirty and needed us only to organize our job templates into a couple easy-to-understand use-case categories.

So, as the folks at Lean Startup would say, when you’ve got an important problem to solve for your customers, get out of the building. Nag, beg, demand, and work hard to get in front of just a couple real people. It may not go easily or even the way you thought it would, but it’s always worth the time.

And if you’re one of those customers at CrowdFlower, I’d love to hear from you — and our Product team just might happen to have a highly-denominated Amazon Gift Card with your name on it.

Product Review: The Franklin RexPro (1999)

(while Microsoft was still trying to figure out editorial content, I got in the rotation to write up pre-millennium tech for the MSN “Geek Chic” column. This one is a howler about a pre-iPhone great from my early career and reminds me how far we have come in just 25 years.)

I may work for a Web site, and I like my computers simple, and more to the point, I like my appointment and address book to be… the size of an appointment and address book. Only then, in my mind, does technology obviate the need for that 19th-century innovation known as the little black book.

If you’re like me and think that no matter how many bells and whistles a Palm Pilot or Windows CE-style personal data assistant may have, both are too bulky and too buggy, then the solution for you may well be the Franklin RexPro.

If you’re looking into the PDA market for the first time (or if you’re considering a switch), ask yourself these questions: Do you often need to enter things in your portable organizer, or can it wait until you get to your laptop or desk? Do you really need half-baked Internet and e-mail access at all times? And do you want to learn the Cyrillic-style lettering a pen-using PDA requires?

The incredible PCMCIA technical marvel, with rich display, in its well-appointed leather case!

The RexPro is the size of a credit card (although it’s about three times thicker) and it has an appointment calendar, address book (it can store up to 6,000 entries), to-do list, note pad and world clock. And you can enter data in a pinch. It requires using six handy buttons to navigate options and the alphabet, which is, admittedly, time intensive.

It comes with a CD-ROM by Starfish Corp. that provides a sophisticated desktop-organizer application and translator program that work on their own or can be easily set up to synchronize data between the RexPro and most major organizer applications (such as Outlook, Sidekick, Schedule+, ACT! and Lotus). Visit Franklin’s Web site (www.franklin.com/rex/) for further information on specifications. In addition to online vendors such as ZDNET, you can purchase the RexPro for less than $200 at many office supply and computer stores. It comes with batteries that last about six months and a docking station for a COM port (a computer-output microfilm port, which you won’t need if you have a Type II PC-card slot, since the RexPro is essentially a PC card itself).

My favorite feature, however, is the folded leather carrying sleeve, which has little pockets that can be used to hold business cards, note paper for quick scribbles (I usually enter information into RexPro in a spare moment later) or whatever else your functional little heart desires.

The RexPro is available at Office Depot, Staples and CompUSA.

— Jack Shay

Postscript: The good people over at r/retrobattlestations reminded me of this thing a couple years ago so I dug it up. As always on Reddit, the comments are pretty great too.

Measure For Measure - Directors Note

(I wrote this as a junior at Georgetown, directing my first full-length play. It’s interesting to think about what the world looked like back then, especially to a Foreign Service undergrad on the DC Hilltop)

In 1995, we cannot stage Measure for Measure as Shakespeare did. We are not under the constraints he was, nor do we have the same values as his audience. Why, then, do we continue to stage his works, and why do they still possess the power to move us? I think Measure for Measure answers this question brilliantly: Shakespeare understood human beings, and the essence of humanity is timeless. We cannot restrict that understanding to our time any more than Shakespeare could restrict it to his.

Measure for Measure is such a multi-layered piece, so open to interpretation that I believe it to be the most under-rated piece of theatre in Shakespeare's repertoire. It may not be the favorite piece of many scholars, or even considered a masterpiece on the level of King Lear or Hamlet. But as an honest portrayal of people, it need not have garnered such accolades. However, if we are to attempt to make this story into some sort of a fairy tale, or a treatise on government, or a diatribe on the decay of morality (all of which are certainly valid interpretations), I feel I would have been denying the beautiful, pure understanding of the human spirit imbued in this play. The story of Measure for Measure presents questions to which there are no easy, or even right, answers, and that is the essential problem with which the people in the story must come to terms. Perhaps now, more than any other time in history, we know that one cannot approximate the truth by judging the story to be black or white; the world is almost always more complex than that. The people in Measure for Measure live in a world of shades of grey, and so do we.

What such a world demands is courage and strength. Such traits are in short supply, and understandably so. To look at ourselves for what we are, and to try to understand what other people feel and why they feel it are noble and mighty tasks. Some of us are too weak to do it, some of us will never try, and none of us can do it all the time. We are human, and we make mistakes. We can all identify with people who make the wrong decision; we understand what it feels like. Sometimes, we try to forgive and move on. Measure for Measure is about real people like you and me, and the choices they make when confronting their own weaknesses.

Thank you very much for coming, and enjoy the show.

—Jack Shay (SFS '97)

2019 Volunteer Trip to the El Paso-Juarez Border

Friends and Family: I have heard more interest than I expected to regarding the trip I just took to the border in El Paso — so it seemed worthwhile to try to get some thoughts down — it’s probably a good thing to do anyway. You’re getting this because (I think?) you asked in some way. I really did try to make this as short as possible (but happy to chat more anytime), I timed it at 6 minutes reading.

This writing comes out of 15 days in a sprawling warehouse that currently receives between 40 and 140 people a day. Families with kids only — predominantly Brazilians and Mexicans — who were released from detention by ICE, Border Patrol, CBP or some combination. These daily numbers have ranged wildly between four digits and single digits in the past year, but the "Migrant Protection Protocols" have achieved some brutal effectiveness that has kept this <100/day range and nationality mix constant over the last couple months.

The facility was in as undisclosed a location as possible. The threat of gang retaliations plus the anti-immigrant-motivated mass shooting just up the road in August rightfully spooked the organization into no-photos/no-disclosures policies — or I could have shared more. For example, the faces of the inspiring and amazing local and other volunteers, and some really stunning community art in the facility that brought some focus away from the seas of Red Cross cots — some pics might have saved some of these thousand words.

At the warehouse’s office, we would receive 0-15 minutes warning before a van or bus would show up, after which point our entire contribution was to:

1. Get our guests to understand that they were no longer prisoners (even despite the tracking ankle bracelets often attached)

2. Ensure we identified who needed medical assistance, who was separated from still-detained family members, and who may have suffered other depredations to try to get them at least the first step toward remediation.

3. Provide cleaning supplies, showers, food, a bed and a change of clothes.

4. Communicate with their sponsors to get them on their way to their US destination.

5. Get them safely to the bus station or airport and secure their tickets from their sponsor.

It is surely in everyone’s interest for our government to perform these 5 basic functions for asylum seekers once we’ve admitted them for a hearing. But non-profits have to do it — most likely because cruelty is the point.

Every volunteer and staff member had their ways of handling this environment; mine was mostly to stay task-oriented and ensure I had a backlog of facilities- or process- improvement projects to work on during lulls in the action. In turn, this parade of confused humanity tried with varying degrees of success to preserve their own wits, dignity or whatever resource was most dear to them at the time. But a little heartbreaking moment would creep through just about every day. Something precious seized or stolen, someone missing, hurt or dead, someone’s last dollar spent, someone’s sponsor disappeared. There were also happy moments of people speaking to their relatives for the first time in a long time, unexpected humor, kids having fun in the playroom, etc. but at least in my experience, these were sadly outnumbered.

Overall, I would estimate about 1/3rd of those I personally did ‘intake’ documentation for escaped with just a few days in this ordeal thanks to proper functioning of the bureaucracy involved. Another 1/3rd were victims of incompetence, errors of omission or common misunderstanding that resulted in some major loss — these were rarely recoverable. The final 1/3rd had suffered active malice at the hands of criminal predators or perhaps worse, trusted officials who simply decided they could do something other than what was supposed to be their job. Of the latter, the most common evils were disappeared property and apparently-intentional court-date mishandling.

On my last night there, I was asked by one of the other volunteers what my single biggest takeaway was. After instantly realizing that I probably was a long way from extracting any real insight from the hall of mirrors I had just spent 2+ weeks inside, a first draft just popped into my mouth: It was how completely and constantly all these harmless and industrious people — and their families — are screwed at every turn. The criminals, government and mostly-broken community they fled, as well as the criminals, government and mostly-broken community at and beyond the border who profit by their flight all get turns — and will continue to get turns for months or years to come. Just a little mercy or counterforce is what we as American citizens and fellow human beings can hope to apply when we can recognize an opportunity to do so.

What can you do? Donate money not things (they really do take extra bandwidth to deal with even if its what's needed) if you cannot offer time. The organization I worked with was Annunciation House -- despite an old post you'll see on their site, are now accepting short-term volunteers and I'd be pleased to refer you. But there are many other worthy organizations that may resonate, including the ACLU and RAICES. Or maybe just do what you can above market rate when interacting with someone who may be somehow caught in this sorry situation (a hotel housekeeper, delivery person, anyone really).

If you do have time -- and even better, could advocate legally or professionally for asylum seekers -- by all means spending some hours on that (or in the case of Annunciation House, 2 weeks minimum) is worthwhile. I can say that being a productive part of the Sisyphean flow of support services does bring real help to individuals, and is its own reward. But working for change at the system level is the only real way to abate this onslaught of human suffering — because this administration is not done inflicting cruelty and barriers to asylum yet.  Which is why I suggest advocacy and/or dollars first. At the same time, the percentage of us who have any means to do anything at all is so, so small (the retired, the just-graduated, and those with any savings at all), that your help whatever you can spare will not see diminishing returns, and every bit will make a difference somewhere to someone.

Thanks for reading -- I hope you found the time worthwhile.

Music Review Archives: Ian Brown - Golden Greats

(published offline in 2005 — Lost in the Grooves, edited by Kim Cooper and David Smay)

IAN BROWN

Kim and David’s zine spawned a great collection of essays — and one from me.

Golden Greats (Polydor, 1999)

In typically iconoclastic fashion, Ian Brown does his Stone Roses–based experimentations with dance backbeats one better on his second solo effort. The album forges a marriage of pop-rock accessibility and electronic fluidity that has seldom been achieved before or since.

Golden Greats is an inscrutably interesting animal from its first moments: versatile Aziz Ibrahim’s muscular guitar heroics burst from his jangling quasi-Asiatic introduction, while Brown the singer abandons his previously trademarked fey tonality, projecting a newly strong, moody and confident artist. As usual, his lyrics are often utter bollocks (“Dolphins were monkeys/That didn’t like the land”), but in the mode of muse-worship (e.g., “Set My Baby Free”), Brown delivers occasional poetry as welcome counterweight.

Words notwithstanding, the genius here is the songcraft. Masterful pop chord progressions guide the rhythmic side of a heavily electro mix, producing a relentlessly engrossing, Moby-esque effect. Although Brown is contextually closer to Seal than Moby—and more complex and rough-hewn than either artist—the appeal is to the same self-serious club-goers and couch-stoners. Brown’s real talents aren’t vocal or instrumental—they’re collaborative. On most tracks here, Dave McCracken, Tim Wills and Inder Goldfinger alternate guitar, percussion, keyboard, and production with a recently self-taught Brown. Why the work was so alchemically catchy this time around, however, is a true enigma.

Despite its innovative meld of rock bombast and trance-inducing electronics, Golden Greats was doomed almost immediately after release by Brown’s unfailing knack for self-sabotage. The Roses’ debut full-length inarguably changed the tone of British rock, but Brown and company waited four years to release a follow-up, during which time Oasis famously stole the Roses’ swagger and the Beatles’ songbook. If Golden Greats, which debuted in the UK at #9, might have given Brown a second chance to reclaim British music stateside for the forces of good, we’ll never know. Citing family obligations, he pulled out of all promotion of the album mere days before major PR for his U.S. tour was to begin.

Same Stuff Different Day

In the great tradition of looking backward in order to look forward for the New Year, I dug up and updated a blog post about good product management to see how far we've come and what's next.