Category Archives: Practical Product Podcast

Practical Product Ep 11: JTBD (Jobs to Be Done) – What it is, why it matters, how to use it, and a real life example

6 January 2023

“I don’t want a drill, I want a quarter inch hole.”

If you’ve worked in product long, you’ve probably heard that phrase talking about Jobs to Be Done (JTBD). The goal of the framework is to help you think deeper about why your customers buy or use your product. Often, it goes much deeper than you’d expect, and are even more significant than wanting a “quarter inch hole.”

Over the years, I’ve found learning the Jobs to Be Done for your product to be incredibly helpful not just for product teams, but also to inform sales and marketing materials. When you know the true, full buyer’s journey for your customers, you can attract more of them faster, and know how to better meet their needs.

Yet, most PMs are terrible at Jobs to Be Done, even if they claim to know what it is.

They pay lip service to the phrase, kind of like how some people think they’re a “lean startup” because they keep a tight budget. 🤦‍♂️

That’s why ever since I learned how to properly do a JTBD interview from the creators Clayton Christensen and Bob Moesta at a seminar in 2012, I’ve taught many friends, colleagues, and clients how to do Jobs to Be Done interviews, too.

In my experience, doing a live example is the best way to learn it, which is why I’ve typically taught people by doing an interview of them with a recent purchase.

While that works, it doesn’t scale well.

That’s why this week’s episode of Practical Product is a live recording of doing one of these interviews.

How to do a Jobs to Be Done interview: Why it matters, how to use it, and a live example for you to follow along to

On this episode we sit down with my former client, Ryan Findley, to go through the buyer’s journey and Jobs to Be Done for Ryan buying a new mattress.

Ryan, who is the Chief Learning Officer at Learn to Win and has spent his career working at startups and scaleups. He’s a builder who helped launch his current company, Learn to Win, and served as the company’s founding Head of Product (which is when we worked together).

In this episode, we show you:

  • How to do a JTBD interview
  • How to map what you learn to the buyer’s journey
  • What to do with what you learn in an interview
  • Common pitfalls to avoid and key moments to recognize

Highlights of the episode include discussing:

  • (0:35) – Introducing JTBD: What is Jobs to be done?
  • (3:03) – Setting the stage with the product Ryan recently bought
  • (3:45)- When did you first start thinking it was time for a new mattress?
  • (4:34) – Who was involved in the purchasing decision?
  • (7:51) – How did budget play a role here?
  • (9:14) – Where did you go to get ratings and reviews?
  • (13:45) – Zooming out: Black Friday & Forcing Functions
  • (21:36) – The purchase moment
  • (33:37) – How did this purchase differ from other things you buy?
  • (47:17) – Did you visit any third party locations when you were in the process?
  • (48:39) – Digging into Ryan’s experience using what he purchased
  • (49:59) – Advice for marketers applying JTBD
  • (54:53) – Ryan’s thoughts on this experiment

Key Show Notes & Further Reading:

We covered a lot of ground in this episode, so we have a ton of links for you to check out.

Mapping the Buyer’s Journey

The image above is the timeline we discuss in the episode. As you do a JTBD interview, you will learn what the various steps were in your buyer’s journey from “First Thought” all the way to “Buying” and “Consuming.”

If you want to follow along more closely in the interview, open up this companion post on how to do the jobs to be done interview. I use this post and the questions listed there every time I do an interview.

Additional helpful links:

Learn more and connect with Ryan Findley

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Practical Product Ep 10: ChatGPT and AI: The latest applications and what they mean for PMs feat Lazar Stojkovic

28 December 2022

Are you following what’s happening in the world of AI? Have you been asking questions of ChatGPT and trying out the various text to image AIs?

Whether you are new to the field of AI, or an eager follower, you’re going to love this episode of Practical Product.

In this episode, my good friend and fellow product-minded founder, Lazar Stojkovic talk about all the exciting things we’re seeing in AI. We talk about what we’ve liked and not liked, the controversies and opportunities, and most importantly, what every PM should be doing to think through using AI in their job, and at their company going forward.

The most exciting developments in AI + what product leaders need to be thinking about

On this episode, we dive deep into the latest developments in AI. Lazar and I have both spent a bunch of time trying various AI powered tools, so we’re able to provide a realistic evaluation of them, and help point you to the best ones to check out.

We also tackle the most important questions for you as a product manager and leader:

  • What should PMs do to prepare for a world with AI?
  • How can PMs get their teams involved in discussions about AI?

Highlights of the episode include discussing:

  • (1:09) – Introducing Lazar
  • (3:05) – Thoughts on ChatGPT
  • (8:19) – Is AI actually taking people’s jobs?
  • (18:44) – The pictorial side of  AI
  • (30:31) – 10x-ing AI, applications and potential negative outcomes
  • (46:27) – What to look forward to with AI
  • (53:44) – How will the costs of AI impact pricing and how you can use them in your product?
  • (57:51) – How should Product Managers be thinking about AI in their products?
  • (1:21:12) – What could the future of AI may look like?

Key Show Notes & Further Reading:

We covered a lot of ground in this episode, so we have a ton of links for you to check out.

The AI basics:

  • ChatGPT – A chat based system by OpenAI that can provide written answers from a text-based prompt
  • GPT-3 API – An API by OpenAI that allows you to bring GPT into your product or service.
  • Replicate – Open source cloud API for running AI models
  • Lore AI Newsletter – A free newsletter discussing business and creative applications for AI

Tweets and Threads on AI discussed:

Articles and Blog Posts about AI:

Examples of AI tools you can try:

Learn more and connect with Lazar Stojkovic

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Practical Product Ep 9: The Harsh Truth of Interviewing & Hiring Product Managers

3 December 2022

Unfortunately, the product management interview process at most companies is poor. Navigating the interview process, or creating a good one at your company is a tall task.

In this wide-ranging interview we cover both perspectives to help you think about both the perspective of the interviewer and the interviewee. You’ll learn how to prepare to run a great interview process, when a project is appropriate and how to make it effective, as well as tips for your resume, and how to handle imperfect interviews for your next job.

This episode is with Willis Jackson, a long time friend of mine who has been the first PM at recently IPO’d Grove Collaborative, as well as VP of Product at Apto. He’s now hard at work on his own startup, but he took some time to share a lot of hard earned knowledge on the interview process in this episode of Practical Product.

The Product Management Hiring Process: How to thrive as the interviewer or interviewee

On this episode, we cover terrible PM interview practices, the key fundamentals of hiring you need to follow, how to ask behavioral questions the right way, making good PM assignments, and how to build your resume like a pro.

Highlights of the episode include discussing:

  • (0:44) – Introducing Willis Jackson 
  • (2:18) – The different types of Product Management and how they affect interviews
  • (8:09) – Recommended resources to learn to be great at hiring.
  • (17:15) – Handling ridiculous hypothetical questions and what to do instead.
  • (26:51) – The importance of networking, reputation and interviewing stories
  • (38:33) – How to make good, fair PM assignments for your interview process
  • (52:43) – Whether you should include company problems in your interview process
  • (59:13) – Resume crafting do’s and don’ts for PMs
  • (1:22:45) – Finding the right type of PM roles and filtering opportunities to save all sides tim

Key Show Notes & Further Reading:

We covered a lot of ground for both the interviewer and those seeking their next job, so some key takeaways are grouped below for each.

For the interviewer:

  • If you know you’ll be hiring down the road, start planning now. Think about the skills you want, the values you want, and the process you’ll follow. 
  • Interviewing is a skill. Spend time reading and learning how to do it well. 
  • It’s much easier to create your interview plan in small, incremental steps leading up to when you need them than being buried, desperately needing help and spread too thin.
  • Avoid puzzles, brain teasers, and hypothetical situations that are nothing like the job they’d have. Research shows it has no bearing on evaluating candidates effectively.
  • If you’re going to make an assignment, make it:
    • A reasonable time request (a few hours, not days worth of effort)
    • Consistently applied to everyone (don’t give one person a day and someone else 2 weeks)
    • Involves what the job would really include. (Willis’s example is a plan after an experiment / launch fails) 
    • Extremely clear what you’ll evaluate them on and what you will not. (Like whether you care about design or format)
  • Be proactive in communicating with your recruiting team. Enlist their help and expertise to find & close great candidates.
  • Remember that hiring the wrong person is extremely expensive in time wasted by your team, cost on your budget, and setbacks on your projects. 

For the interviewee:

  • Make your resume succinct and include data & numbers as much as covering skills and actions
  • If you do not have numbers now, start working on it now. Get in the habit to look up numbers and see what work you did has moved the needle.
  • Your resume becomes talking points and great questions in the interview.
  • Prepare good questions to ask an interviewee to make sure the company does the kind of product management you like doing.
  • Reflect on your current job regularly. Willis recommends weekly journaling on subjects like:
    • What wins have you had recently? What happened?
    • What did you learn from a project that recently didn’t go well?
    • What do you enjoy about your work and want future jobs to also offer you? 
    • What’s changed over time in my notes?

Helpful links mentioned in this episode:

Learn more and connect with Willis Jackson

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Practical Product Ep 8: How to Write Product Specs Your Team & Executives Actually Want to Read

23 November 2022

Are your product specs high quality? Do they succinctly and clearly convey what you’re working on, why you chose them, and what your engineering and design partners need to do their jobs well?

Or are they kind of random, with each one different than the last?

I’ve helped dozens of PMs improve their product specs, and I’ve been lucky to learn from one of the best how to make a great product spec. Which is why I knew I needed to do an episode on the subject to help everyone improve their product specs.

Today, we cover:

  • The most common mistakes PMs make in their product specs
  • How I learned the right way to make a spec
  • The key, fundamental concepts underlying good product specs
  • and most importantly: Exactly what goes into a great product spec (aka- Product Thesis)

How to Write Product Specs Your Team Actually Wants to Read (AKA – The Product Thesis)

Everyone writes product specs regularly in their job as a PM, but few do a great job with them. These poorly constructured specs then cause all kinds of problems on product teams including:

  • Engineers and designers confused and uninspired about what they’re making
  • Delays in shipping due to misunderstandings and miscommunication about priorities
  • Disappointed execs who don’t get what they expect

And a lot more. Yet, it keeps happening because PMs don’t realize that the root cause in their specs that:

  • Do not cover the right topics
  • Are wayyyyy too long, and filled with fluff
  • Tend to be overly prescriptive on the solution instead of collaborating with your team on it
  • Lack data to back up your decision
  • Fail to share an inspiring WHY to motivate your and convince your team
  • Are inconsistent spec to spec making it harder to read and digest

That’s why we need to hit the reset button and reshape how you make product specs with something called The Product Thesis. Listen in to learn more about it:

Highlights of the episode include discussing:

  • (0:49) – Mistakes made on the average Product Spec
  • (3:17) – Introducing you to The Product Thesis 
  • (10:06) – What goes into a Product Thesis?
  • (12:05) – Section 1: Why are we working on this next?
  • (14:57) – Section 2: When and how do people use this feature? (Aka – what are the use cases?)
  • (18:24) – Section 3: What problems do we need to solve, and in what priority?
  • (24:19) – Section 4: How much time is budgeted for this project? When does this need to be completed by?
  • (25:56) – Section 5: What are the future considerations that must be accounted for?
  • (27:28) – Section 6: What is our KPI or metric for this thesis?
  • (29:59) – Optional: For larger companies: Who are the stakeholders and how/when do they need to be involved?
  • (31:14) – Optional: What kind of launch or marketing/sales efforts go with this feature?
  • (32:27) – Section 8: Further Reading

Key Show Notes & Further Reading:

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Practical Product Ep 7: How to Supercharge Growth with Free Tools & Side Products with Michael Novotny

11 November 2022

Have you ever thought about building a free tool for your company? Do you want to build more buzz, get a ton more inbound SEO links, or drive signups and leads for your core business?

Or maybe you are a free tool skeptic, worried it will distract your team, take to much time, or not pay off?

I’ve always been curious about free tools, but haven’t been directly involved in many myself. So when I met Michael Novotny, who has become an expert in creating free tools, I knew I had to have him on the Practical Product podcast.

Michael is a product manager turned founder, who has helped build and launch dozens of free tools / side products now and studied hundreds of others with his company, Product and Build Co.

In this episode we go deep on this topic covering everything including keys to success, pitfalls to avoid, tons of examples, and how to convince yourself or your boss to take a shot at making some free tools or side products.

How to Use Free Tools & Side Products to Grow Your Business

Today we talked about how building free tools (aka – side projects) for your company can help drive major growth for your company.

Building these tools helps you a few ways:

  1. People who use your free tool may directly sign up for your paid product when they see you made the free tool.
  2. People using your free tool may give you their email address, which you can market to later.
  3. Others will link to your free tool, boosting your SEO through improved backlinks.

Michael shares a lot wisdom and experience doing these, and the most important tips are:

  • Build a portfolio: You need to launch many tools (ideally 4-5 or more) so that some will hit, and others won’t. If you only launch one, the odds work against you on the moon and stars aligning for you. 
  • Build in public/test with your community: To increase your success rate, validate and test the ideas you have for tools to see if they resonate and what are the most important things it needs to do to provide value. 
  • Use low and no-code tools: You can build and launch a lot faster using these tools, and since it doesn’t touch your core product, it doesn’t need the perfect architecture. 

There’s a lot more to this episode, so I encourage you to give it a listen on your favorite platform or in the player below:

Highlights of the episode include discussing:

  • (2:04) – How Michael discovered the power of free tools to drive sign-ups for another product
  • (11:46) – What are a couple of your favorite examples of these tools?
  • (16:31) – Cases where free tools didn’t work out.
  • (21:55) – Are there businesses that shouldn’t be creating free tools?
  • (29:05) – What is Michael’s Side-Product Framework?
  • (34:56) – How should PM’s think about budgeting for Side-Products?
  • (42:08) – How do you come up with good ideas?
  • (47:55) – How can you start to validate some ideas for tools to see if you’re on the right track?
  • (54:09) – What should people do to make these free tools successful?
  • (58:05) – What are the best ways to tie a free tool to your product?
  • (1:03:32) – How much ongoing maintenance should you expect?
  • (1:09:18) – What are your favorite tools that help you piece this process together?
  • (1:13:58) – Keys to convincing your boss or peers to try free tools.

Key Show Notes & Further Reading:

Case studies and examples of Free tools:

No Code and low code tools to help you build your free tools:

– Connect with and learn more about Michael Novotny:

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Practical Product Ep 6: Succeeding as a Remote Product Leader w/ Valentina Thörner, Product Advisory at Klaus

5 November 2022

Were you ready to be a remote PM when COVID struck? Are you finding yourself still remote 2 years later?

Or maybe you’re back in the office, but your company embraced remote work, so some of your team is distributed elsewhere?

Regardless of your situation, if you or part of your team is not co-located with you right now, you have special challenges as a product manager. What works in office doesn’t always work remotely.

That’s why I knew we needed to bring in an expert to talk about remote product leadership during this season of Practical Product.

And Valentina brought the knowledge. She’s been leading remote teams for over a decade and teaching others with her courses and consulting for much of that time.

We had an amazing, 95-minute conversation covering a wide range of topics that any manager leading a fully or partially remote team needs to hear.

And if you’re thinking about changing jobs and joining a remote organization, you’ll want to listen in too, because we specifically talked about the transition you’ll have to make as well.

How to Succeed as a Remote Product Leader (even if you’re new to it)

Some jobs are not that different doing them remote versus in person. For example, a sales rep may have to sit and make the same calls, send the same emails, and generally have identical tasks that if anything, might be easier in a quiet environment remotely.

For a highly collaborative role like product management, that’s not the case. A LOT changes.

What works in person, doesn’t always work remotely, and often, the solutions aren’t even a 1 to 1 trade. Instead, you have to reinvent entire workflows and processes to fit the different way of working remotely.

Today’s discussion with Valentina Thörner goes deep on exactly these things.

You can listen on your favorite platform or in the player below:

Highlights of the episode include discussing:

A deep dive on remote vs. in person communication advice, and great team construction:

  • (1:43) – What are some of the biggest changes when someone shifts to a remote PM role?
  • (11:38) – How can a Remote PM be successful?
  • (14:55) – How can Remote PMs understand how their team is feeling and reacting to their work and communication in an asynchronous environment?
  • (24:00) – Do you think the ideal product team size is different for remote vs. in-person?
  • (26:54) – How do you avoid meeting & Zoom fatigue / overload?
  • (42:16) – How do you create the collaborative juices from a whiteboarding session for a remote team?
  • (48:48) – How often do Remote product teams need to be together in person?
  • (51:53) – How much would you think about geolocation when it comes to constructing pods?

If you’re thinking about working as a remote PM or want to find a great remote company:

  • (58:49) – What are ways PM’s can prepare themselves for the shift to a remote-first organization?
  • (1:04:54)- What questions would you recommend asking when sussing out if a remote company is the right fit?
  • (1:14:15) – What skills would you recommend developing for folks looking to become remote PM’s?
  • (1:20:32) – What are good ways for folks to build their writing and communication skills?
  • (1:27:10) – Are there any more skills people need to develop to be great Remote PM’s?

Key Show Notes & Further Reading:

– Books and other helpful links from today’s episode:

Many books and great blog posts were mentioned in this episode. Here’s a rundown of the books:

And blog posts for you to read:

– Connect with and learn more about Valentina Thörner:

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Practical Product Ep 5: Why intellectuals are wrong about AI, the Bundling Phase & What it means for PMs, and more.

29 October 2022

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What are the consequences of AI making our lives easier and better? What jobs will be lost and what happens when they are gone? And how should product managers think about the new, bundling phase we’ve entered?

In this week’s episode of the Practical Product podcast, you’ll hear my thoughts, and some quotes from others related to a few key topics that have been top of mind lately:

  1. What it means to now be in a bundling phase for tech and how PMs should adjust their strategies.
  2. A problematic mindset I see and hear in too many PMs.
  3. The truth about AI and the future of work. Will we really see jobs disappear?

Practical Rants: Why intellectuals are wrong about AI, what PMs must do as we enter the Bundling Phase, and a key mindset PMs must avoid

This episode is a collection of my thoughts on some trending topics I am seeing in the world of tech and product management relevant to PMs:

1. We are in a Bundling Phase: How can we as Product Managers bundle our offerings for consumers who are concerned about economic instability? We need to establish our products as absolute must have’s in the eyes of our customers and recognize the new market dynamics to survive and thrive .

2. Let’s stop the Self-Deprecation in Product Managers: Don’t be the “this is fine” dog meme, be part of the solution when you see negative trends within the culture or product at your organization.

3. The Truth about AI & the Future of Work: I break down a clip from Yuval Noah Harai and his horrendous take on the “Useless Class” of folks he predicts will grow as technology continues to advance. We must shut push back on this rhetoric and build tools for an abundant AI future.

You can listen on your favorite platform or in the player below:

Highlights of the episode include discussing:

  • (1:27) – Bundling within companies amidst economic uncertainty
  • (6:34) – What to do as a PM when you see customer churn due to bundling
  • (10:23) – Understand your secret sauce
  • (12:37) – Self-Deprecation in Product Managers
  • (17:29) – Yuval Noah Harari on the “Useless Class” & The future of work with AI
  • (29:22) – Product Managers can be part of the solution
  • (32:04) – Final Thoughts & Recap

Key Show Notes & Further Reading:

1) Now entering the Bundling Phase…

I saw a tweet from my old boss and mentor, Hiten Shah, that really hit home:

That got me thinking…why now?

Now you have the combined argument of:

  1. We had too many tools to manage. IT hated this. It was a security and info management nightmare.
  2. Budget cuts. You’d rather cut a tool than an employee. And there’s an easy case to make to decision makers that, “hey, this big system does all these things. Let’s cancel all the other tools and consolidate on this.”

And for PMs, this means you need to consider a few key tactics to navigate this reality:

  • Look for breadth over depth in feature building. In a consolidation phase especially, you’ll be competing against a lengthy feature checklist, where one system that does everything gets the purchase, and there’s no second place. 
  • Take advantage of integrations and APIs. If you integrate with tools they use, it helps keep you sticky. And if you have an API and others build on top of what you’re doing that’s also a great, viable strategy to expand your functionality faster than your own team can build. 
  • Build for the right ecosystems. Microsoft and Salesforce are two of the biggest heavy hitters. They’re exactly what people are going to consolidate on because it’s so easy to. Be prepared for push back though…both are miserable to build on. 
  • Tighten your relationship with Sales and CS. You need to know how you’re winning and losing deals. Find out how account management is doing trying to retain key accounts and what they’re saying they’re thinking about. 
  • Understand your secret sauce and champions. What’s unique about your company? What do you do better than most? What critical thing do you deliver that will have someone with influence at a customer banging the table to keep you? If you don’t have it you better get it. If you do, make sure that feature stays great. Don’t let the goose that lays the golden eggs get hurt. 

2) The problem of self-deprecation for product managers.

While this meme can be funny, it shouldn’t be your main identity as a product manager:

It sends a bad message to everyone around you if you’re constantly self deprecating about your job:

  1. It makes you sound like a victim, and potentially setting you up to welcome more abuse
  2. It creates a self-fulfilling prophecy where you look for confirmation of this negative way of living as a product manager. Build for and focus on the positive direction.
  3. It sends a bad external message to other PMs that “this is the job.”

And maybe in some cases “this is the job” but ask yourself if that’s what you really want? 

3) Why AI is NOT going to cause massive unemployment.

Harari is a monster disguised as an intellectual.

The ignorance of Harari is staggering. He oversimplifies things and has such an out of touch view of reality.

These changes always happen. Every time there’s talk of this concern.

There used to be tons of jobs for horses before cars: Poop shovelers, veterinarians, horse feed, etc. 

And cars of course created jobs: car dealers, mechanics, all the many parts needing manufactured, car washes, windshield repair, gas stations and the entire oil industry, etc. 

There were floors and floors of accountants and bookkeepers, and then the spreadsheet came along…and with the rise of computers, I think we can all see the many jobs they created, and how information and services were democratized. 

There are plenty of jobs to fill

In today’s world, it’s crazy for someone to argue there are no jobs. There are tons of opportunity all around us:

  • We have organizations like Bloomtech happily training people, many coming from “low skill” jobs.
  • Most tech jobs are self taught, too! Can you major in sales or product management?
  • There are tons of labor jobs that no robot will take for some time, which as of now is estimated to be over 4 million jobs, and once again there are training jobs like Mike Rowe Works.

This means that even if some jobs are displaced by AI, there’s no reason to believe there won’t be work for these people.

AI makes jobs more efficient, not eliminated.

Not one reply to this great question about copywriting AI mentions *anyone* losing their jobs:

And similarly, Github’s AI is making engineers faster, not taking their jobs:

When you free up a worker’s time, they can do more and different things.

Product Managers can be part of the solution.

If you’re working on a product that uses AI, think about how you can help make a better future for workers:

  1. Build your tools to make their jobs faster and better, not replace them. You’ll get less adoption resistance and they’ll become your loyal fans.
  2. Make your interfaces more accessible and easy to use. This will allow newcomers to use your product, and speed up adoption.

Harari is a monster and a terrible human being.

Harari is an example of an intellectual monster. He is giving speeches like the video embedded above to world leaders at places like the World Economic Forum. He has a large platform and the ears of people that make his ideas very dangerous.

Did you know that part of Nazi eugenics called some people, “useless eaters”? To use phrases like the “Useless Class”, is the first step to genocide and should be condemned fully, especially in intellectual conversations as we all develop technology people will be using every day.

Do not fall for those false pity ideas from false intellectuals. There will always be jobs. And every new technology creates new jobs and opportunities as much as it may eliminate a few old ones.

We as product managers have the opportunity to be a part of the solution and create the future that helps everyone, and does not consider anyone “useless.

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Practical Product Ep 4: The Curse of the 1st PM – Part 2: The PM View with 4-time 1st PM, Hostos Monegro

21 October 2022

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Why is it such a struggle for 1st PM hires to succeed? What are the challenges from the perspective of a product leader who has done this before? How can you avoid being a casualty of the 1st PM curse?

Today, we answer those questions and a lot more.

A chance meeting…

Back in 2019, I was living in New York City. I was meeting other PMs in town, and by chance was connected to Hostos Monegro. As it turns out, we had a lot in common, as we’d both been a 1st PM multiple times at startups.

As the conversation continued, we realized there was *a lot* in common between our experiences. It helped me realize that the situations I experienced were possibly less about me, and more about the nature of the job. It ultimately led to the inspiration for the now oft-discussed post, “Why you want to be the second 1st PM.”

Knowing how much credit Hostos deserved for inspiring and helping craft the ideas of that post, I knew there was no one better to talk about the product manager perspective than him. When I started planning this podcast, he was one of the first people I asked to come on the show, and this week’s episode is the product of that discussion.

The Curse of the 1st PM – Part 2 w/ Hostos Monegro, 4-time 1st PM

If you haven’t read it yet, the best place to start is reading my 2019 post, “Why you want to be the Second 1st PM” to get context on this unique role that comes with special challenges, and sometimes a lot of baggage. You can also check out Part 1, with a CEO who hired (and fired) a 1st PM recently here.

Today’s discussion with Hostos dives into lessons learned on having made the majority of his career being either the 1st PM, or as our original post called it, the *second* 1st PM (who comes after the first one didn’t work out).

If you’ve ever thought you wanted to try being a 1st PM, or already are one, this is a great episode for you. We cover key topics like how to screen for the right founders to work with, why this role can be awesome and fulfilling, and how to avoid some of the common pitfalls that come with the curse of the 1st PM.

Highlights of the episode include discussing:

  • (2:14) – What is it like being a 1st PM the 4th time around?
  • (5:53) – How did you think about filtering the Founder when looking for a 1st PM role?
  • (9:14) – What are the awesome parts of this kind of role?
  • (15:07) – What are some of the hardest lessons you’ve learned as a 1st PM?
  • (25:17) – Advice for someone interested in taking on the 1st-PM role
  • (38:40) – What should potential PM’s look for in a company to determine if it’s a good fit?
  • (46:52) – Recommendations if you think some of these 1st PM pitfalls apply to your situation
  • (48:11) – Advice for founders thinking about hiring their First-PM
  • (54:00) – How the First-PM be set up for success

You can also learn more about Hostos or get in touch with him on Linkedin and Twitter.

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Practical Product Ep 3: The Curse of the 1st PM – Part 1: The Company View with Pulkit Agrawal of Chameleon

13 October 2022

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Why is it such a struggle for 1st PM hires to succeed? What are the challenges from the perspective of the CEO who hires them? What do founders learn in the experience when seemingly inevitably, the 1st PM they hired with the best of intentions didn’t work out?

Pulkit Agrawal mentioned me and my post on “Why you want to be the 2nd 1st PM” when he lived this challenge firsthand:

And knowing he had just gone through this, I knew we had to talk about it on the Practical Product podcast. That’s why this week’s episode is all about it.

The Curse of the 1st PM – Part 1 w/ Pulkit Agrawal, CEO of Chameleon

If you haven’t read it yet, the best place to start is reading my 2019 post, “Why you want to be the Second 1st PM” to get context on this unique role that comes with special challenges, and sometimes a lot of baggage.

Today’s discussion with Pulkit helps answer the question you may have from the post, “How does this happen?” Pulkit read my blog post, new the risks, and yet it still happened.

Are all 1st PMs doomed? Probably not, but the challenges and unique factors of being an early stage startup do make for an ever-changing set of circumstances that can make someone who was the right choice when hired no longer the right person 6-18 months later.

Pulkit and I have a really candid conversation about what happened, what he learned, and most importantly what he’ll do differently with the second 1st PM (who he just hired).

Highlights of the episode include discussing:

  • (5:35) – How has your approach changed for hiring PM #2?
  • (6:27) – What got you excited about the person you ultimately hired for the #1 role?
  • (13:52) – When did you start to realize things may not be working out?
  • (18:28) – How did you handle the transition of a PM leaving the team?
  • (25:13) – Is it inevitable that the first PM will never be a perfect fit?
  • (34:02) – How are you thinking about changing your hiring process the second time around?
  • (35:44) – What advice would you give a founder who’s considering hiring their first PM?
  • (43:17) – How can the founder set the PM up for success?
  • (45:03) – What advice would you have for PM’s interviewing for a first PM role?
  • (48:52) – What are some red flags candidates need to look out for?

You can also learn more about Pulkit’s company at Chameleon.io, and check out their blog to learn more product management and user onboarding tips.

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Practical Product Ep 2: The “Impossible” Product Manager w/ Jason Cohen of A Smart Bear + WP Engine

5 October 2022

“A great product manager is… 🧵 ” <- You’ve probably seen more than a few threads like this on Twitter. The challenge is that the whole list is impossible to be in one person; even if you did somehow manage all the skills needed, you’d still end up with not enough hours in the day to do it all.

Jason Cohen, cofounder and CTO of WP Engine knows this tradeoff well. He wrote about the challenge in his blog post, “The Impossible Product Manager, a.k.a. the “Great” Product Manager.”

Reading it resonated a ton as I’ve seen in my career and coaching other PMs, so I knew I had to reach out to Jason to talk more about it on the Practical Product podcast.

The “Impossible” Product Manager w/ Jason Cohen of A Smart Bear + WP Engine

The demands of a product manager can be overwhelming. You can often be expected to be more things to more people than any one person can truly master. And even if you can do those things, there’s not nearly enough hours in the day nor the week to do all of them. 

Read Jason’s full post here. Today’s podcast discussion is focused on the consequences of the post and what to do about it.

As a quick summary, there are 4 key areas of responsibility that can fall under product managers that Jason outlines:

  1. Strategist
  2. Customer Whisperer
  3. Scrum Product Owner
  4. Orchestrator

The key to those for is that as Jason puts it, “a “Great PM” is excellent in one area, good in at least one other, and doesn’t have time for more than two.”

So today we’re diving into what that means for product managers.

Listen in the player above, or you can find all your favorite podcast platforms with links to them by clicking the “Subscribe” text in the player.

And as you search for that balance of the right areas to focus on, keep in mind this great visual from Jason on finding your ideal situation:

When you find this intersection, you’ll maximize your happiness *and* thrive in your career.

You can read Jason’s expanded post on this topic, which he wrote after the recording of this episode here: “Finding Fulfillment”

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