10 Things I Hate About ConvertKit

24 February 2023

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Ever have a love-hate relationship with a product? 

If you’re a product manager, designer, or UX-conscious engineer, you know how using products that don’t live up to their full potential can drive you crazy.

Today, I want to talk about a product that best personifies that feeling for me: ConvertKit. 

Why I love ConvertKit

First and foremost, I want to emphasize I like a lot about ConvertKit, and I’ve been satisfied with them since switching from Mailchimp a couple years ago.

Mailchimp used to be the *gold standard* for UX. I loved their product and would often point people to their workflows as examples of good UX. I often could hire people with no experience and set them loose and they’d be able to figure out how to do everything they needed to easily. 

Unfortunately, a couple years ago, it seems Mailchimp’s team decided that they needed to fix what wasn’t broken, so as that got worse, and some of their brand decisions also didn’t sit well with with me, I made the switch to ConvertKit.

Their offer to migrate our data was a HUGE selling point and we probably never would have switched without it.

Overall, their performance has been adequate and their support team has been excellent at filling in many of the gaps in the product. I also admire Nathan’s founding story and love some of the stories of what he does at the company, like doing podcast interviews of each new hire to introduce them to the team. 

What I hate about ConvertKit

Now that my team and I are settled in a couple years removed from switching to ConvertKit, and we’re a pretty sophisticated user, there’s quite a few UX things that drive me crazy.

This post is about how ConvertKit could go from good to great, which is how you turn quiet users into raving evangelists.

It’s also how you significantly reduce the workload of your support team, who in many of the cases I’m going to share have to make up for the gaps in the product.

(Note: Wish your product could go from good to great? I’m a product coach and consultant who has helped many teams build the habits that create great products.)

10 Things I Hate About ConvertKit

When you’re using a product, you are trying to accomplish specific tasks. When they are easy and smooth, you often don’t notice and get on with your day. Sometimes, they do something clever and delightful, which then becomes memorable.  It’s why I’ve started a thread of Little Big Details to call them out when I see them.

The following 10 things are a mix of big frustrations that have gotten in the way of key tasks my team wants to do, and those kinds of little big details that are the difference between a good enough product and a GREAT one. 

And because I want this to be a constructive conversation, I try to present solutions where possible. 

Let’s dive in.

1) Reactivating unsubscribes is a tedious chore that could easily be productized

When you have a large list with tens or hundreds of thousands of subscribers, and you have a sophisticated workflow that involves many automations, sequences, and types of emails you send, there are going to be times where someone hits unsubscribe and changes their mind.

And because ConvertKit’s architecture is built around “1 list to rule them all” with many tags and segmentations to manage it, that means that an unsubscribe from one thing also unsubscribes them from everything else associated with our company. Sometimes people didn’t want that.

While looking up the answer to the question of, “Did subscriber X get the email they say is missing?” is a great experience in ConvertKit, fixing an unsubscribe is not. 

Looking up an individual users tells you so much useful information all in one view.

Currently the workflow to get a subscriber reactivated is this:

  1. Click to open up Intercom to ask support to help
  2. Click through 2-3 prompts where Intercom tries to guess if they can automate answering your question
  3. Finally get to chat with a support person
  4. Tell them what the issue is
  5. Provide a screenshot of an email proving the person wants to be resubscribed
  6. Chat with the support person for any clarifications they need
  7. Wait about 20 minutes to a few hours
  8. Get the person resubscribed or deal with another round of questions with another person on the support team

The problem with this is two-fold:

  1. It’s tedious as a user. Half of those steps feel extraneous and that they could be streamlined to make my life as a customer easier.
  2. ConvertKit’s support team is burdened with managing the ticket and manually managing this process.

Now, I understand with spam laws you need to be really sure that someone wants to be resubscribed, and it happens often enough, it’s an option in Intercom. However, it would be better to just give me a form to fill out.

You could even put a button on the individual user’s profile or the Subscriber’s section to take me to the form, so it doesn’t require Intercom yet. 

Then, when you click “Resubscribe” you can pop up a form that:

  • Makes clear the requirements to reactivate a subscriber
  • Asks for the same details the support team has to manually ask (the user’s email, a field to explain the situation, and a way to attach an image or other evidence)
  • Confirms the request has been received and provide an estimate for updates

This could then create a simple system in a very basic admin panel where you can queue up a list for someone on the support team to batch process these. Over time, you can then iterate on it to make their lives easier by both improving and streamlining this process, and adding other customer issues to it as well.

I’ve helped spec out these at multiple companies and they always are built faster than many people projected and save more time than most expected.

Having your support team cover for gaps in your product is a very expensive way to compensate for product issues and missing features. Fixing problems support identifies and making them more efficient at supporting customers are high leverage activities for product teams.

You’ll see in many of today’s items, support at ConvertKit is currently left to cover for exactly these kinds of issues.

2) Import users doesn’t tell me what I need to know

Want to send your support team on a wild goose chase wasting hours of time to support a customer? This is how.

A simple query from engineering would save HOURS.

So now imagine you are importing an important list for a key customer that expects everyone to receive a certain email. You have everything configured in ConvertKit and the spreadsheet looked right to you when you checked it.

Yet, when you imported it, you expected 1,000 emails to be imported, and the confirmation email tells you 998 were. 

Frustratingly, when I import a list, I get an email (like the one pictured above) saying how many were imported.

Yet what I don’t get are:

  • How many people did I try to import?
  • How many failed?
  • Who specifically failed?
  • What errors, if any, you have detected?

Those last 2 are really important. How else will you know who didn’t work. 

Missing MailChimp…

Mailchimp used to do this exceptionally well, so that you could immediately diagnose an issue and fix it. Notice in the email it confirms exactly what ConvertKit does, and it also tells me about a failure, with a suggestion why, and a link to more details.

Typos happen. People are already unsubscribed (see 1!) and more. Letting me know which emails failed, and if possible, why, makes it easy to fix. 

Rather than needing to start a support ticket, I can fix this issue myself relatively quickly.

But without the details MailChimp provides, do you really think I’m going to guess and check line by line myself? Unlikely. 

Telling me how many did not successfully import and who failed at least let’s me try to fix it myself before contacting support. If you also have error messages that are customer readable (like Mailchimp mentioning syntax) you’d save customers TONS of time and mostly eliminate support needing to spend tons of time investigating.

As just one example, recently, I had a ticket run for almost a full week over 1 customer email not importing properly. It was handed off at least 3 times across support before we finally figured out the issue. That was frustrating for me, and costly for the ConvertKit Support team who repeatedly had to start over as they handed off the ticket.

3) #littlebigdetails Make the import flow better

There a bunch of ways to improve the import process. The elements are already there with today’s interface:

The current view when you’re importing a CSV

This is already an efficient pop-up, but when you are a power user and have dozens of each category, it gets unwieldy and mistakes are easy to make.

To improve this view, I would add:

1. Quick search in each section.

This would make my life sooo much easier and faster to import, so I don’t have to scroll through long lists of categories. Best of all, this functionality already exists.

When I add a selected user to a sequence, ConvertKit does have search in that view (pictured below). Why not implement the same in import, too?


2. Show what I picked in the collapsed view.

When you are importing a list, you pick out any forms to assign the new subscribers to, sequences they should start receiving, and tags to add. This is core to making your orchestrations in ConvertKit do what you need it to; this is how you segment your audience, trigger the right emails, and manage your master list effectively.

As you set your forms, sequences, and tags, you expand and collapse them one at a time. Ideally, when I collapse one of those lists, I want ConvertKit to show me which ones I selected so I can quickly review everything before hitting submit.

My crude mockup combining the import pop up with the add subscribers to sequence pop up behavior.

When you are doing an import, it can be a stressful moment, because a mistake will have people get the wrong email (or potentially many wrong emails). Having the clear sanity check (like ConvertKit has when you’re about to send a Broadcast) would help, and this is a simple way to accomplish that.

3. Add a working spinner to the page.

Sometimes I have to click twice on the “Import Subscribers” button, or it’s not clear if it’s working. Adding a spinner (or progress bar) would let me know it worked and to be patient while it works.

Note: Research shows people are MUCH more patient with a spinner or other loading signal; the rule of thumb I’ve found is that customers are willing to wait 2-3 seconds at most on their own, then that grows to 10-15 seconds with a spinner. Add some messaging to read during the spinner and they’ll wait as much as 45 seconds.

Each of these items is a nice win, that in total takes the import process from okay to exceptional. 

These are also the kinds of things that make great quick wins to mix in along with bigger projects. One of these is likely a single point ticket in your project management tool.

Best of all, few things boost the morale of a tired engineering team like feeling like they can ship some things measured in hours or days instead of weeks or months, especially if they also get to hear from happy customers that love the updates they made. 

4) Give more thoughtful ways to manage tags

My team and I have made hundreds of tags at this point. This is only growing, because ConvertKit’s support and account management teams have encouraged us to make more tags to further help us segment, target, and understand our subscribers. 

As it is, these tags are in a massive list that you endlessly scroll in the sidebar of the Subscribers page. The tags are listed in alphabetical order with the number of subscribers there are, and that’s it.

Given the many purposes of tags, the big win would be making it easier to view them for various reasons. 

Organize poll results and other jobs for tags

For example, if you have me do a poll where I’m measuring clicks of various options in the email we send (a clever suggestion from your account management team), allow me to view those results as a special view in the Broadcast results area, instead of having to do a CMD+F in my browser to find it:

Then, for viewing the rest of the tags info in the Subscribers tab, consider the jobs that customers want to get done with their tags.

The goal should be to make it easier to do each of those jobs based on how frequent those jobs are needed across the ConvertKit user base (surveys and understanding the segmentation of your user base are great for figuring this out). 

Create tags when in the flow to tag subscribers

It would also be a big help to be able to create a new tag in the flow of looking to add a tag. Since ConvertKit has a great search here to try and find the right existing tag, you’re less likely to miss one, but then you may also want to create one right there.

Not likely the exact spot for the button, but illustrates it would be helpful to have somewhere in this pop up.

For example, I recently had a broadcast that went to what was a combination of a variety of groups. When I look at the broadcast results, I’d love to be able to tag everyone in that group, and not have to navigate to Subscribers, scroll all the way to the bottom of my list of 160+ tags, and click + Create a Tag, then go back to the broadcast and tag them.

Like much of this list, it’s all about understanding customer workflows and removing friction from the tasks customers are trying to complete.

5) #DesignCrimes Fix the blue on blue stack bar charts

The product team that shipped this missed the mark. Who can make sense of this?!?!?

Let’s look at the issues here with what is supposed to be a breakdown of how our 7 landing pages and forms that drive our subscribers are performing: 

  • The bars are all the same color
  • There are only 2 shades, despite many more than 2 forms
  • There’s no legend to tell what each piece of a bar is (only hover tells you one piece at a time)
  • Sometimes the same color is displayed twice in a row

While I understand if you have a lot of forms you can’t have 500 colors, but you could at least have 8 (ie- ROYGBIV plus black/gray) and then potentially add patterns or shades to the bars, which in particular would help with accessibility (i.e.- colorblind people).

Examples of patterns added to a bar to differentiate beyond color

Add those additional colors with a legend or color code and you’d significantly improve the experience. 

And to truly make this a WOW, let me:

  • Check and uncheck some of the forms to more easily compare some, but not all of my forms
  • Instead of stacking the bar chart, put them side by side so I can more easily tell which bars are clearly the best performing

Helping your customers be smarter is a key part of the process of making a good product, especially in the field of marketing. If your customers can’t understand how their forms and giveaways are performing, nor track the progress of experiments, it’s leaving a lot of value out of the product.

6) Add labels to the Unsubscribes bar chart

Another place to make email marketers smarter is the unsubscribes page. It’s nice that Convertkit added the survey to find out why people unsubscribed, but then the answers are hidden: 

There’s *plenty* of room below those bars (which are standard answers ConvertKit set) so I can immediately analyze it instead of having to hover on each one. 

I would love to be a fly on the wall to understand this compromise that led to a view like this considering:

  • The answers are hard coded. Every customer sees the same 6 options. 
  • The chart is thus displayed the same for each customer
  • All of the options are 8 words or less so could fit in a similar font below each bar.

I quickly made the answers using “Inspect Element” in my browser in and this how they look:

I would take this over the hover as is, but I think a great front end engineer would happily make the couple of longer answers wrap to a second line and center under their appropriate bar.  

You may also want to increase the font of those labels for accessibility purposes; a middle aged marketer with bi or tri-focals is going to have a hard time with that small of a font, and there’s plenty of room below the bars to go with a bigger font.

7) Make form analysis 100X better

This is the “Reports” tab for one of the many ways we get subscribers to Lighthouse:

As you can see, we get a lot of traffic to our blog. Since this CTA was shown to virtually every visitor, we have a low conversion rate, but still got a bunch of conversions from it.

Now, the problem with this is: What do I do with this? It’s not particularly actionable nor helpful: 

  • It lacks enough granularity: Rounding to the fraction of a percent means it’s hard to tell if a change did anything for such a form display. It would help to provide at least 2 decimal places, especially when dealing with large numbers of visitors or a < 1% conversion rate. 
  • No chart nor graph: I can’t track any trends over time. What if I ran a copy experiment? No trend over time means I can’t see if an experiment is winning, nor if a form’s performance is declining.
  • No way to note experiments: Even having a text-based list below a chart with what we changed would give us the context we need (which right now is awkwardly noted in Basecamp and a Google Doc). However, the best would be Google Analytics style annotations to a chart:

Beyond the list of Visitors and Conversions, the other thing you’ll notice is the list of “Top Referrers” on the page.

Unfortunately, this basically says “Search Engines” over and over, which isn’t actionable. It would be much more useful if it told me what page people were on when they subscribed to it. Then, I’d know which blog posts are really converting.  

Especially for some of our custom forms that are for specific giveaways, it would be nice to be able to see if certain pages are doing particularly well or poor. Then we can act on the info it’s providing around conversion rates to recognize any copy tweaks or experiments we should do as well as understand what’s working best.

All of this is about making being a performance marketer smarter, better, and work faster.

The alternative is to do hacky things like my team will track experiments in Basecamp, note the conversion rate, and then check back in a month and see if the displayed cumulative conversion rate went up or down.  All of that could and should be done inside ConvertKit.

8) Give me a way to organize sequences! How about some folders?!?

We have 65 sequences at Lighthouse (and counting). This is because we use ConvertKit for a variety of things like:

  • Drip series for each of our giveaways to grow subscribers
  • A welcome series for every new subscriber to our blog
  • A welcome series for every new trial of our 1 on 1 meeting software
  • A sequence for each of our 8 leadership courses we sell
  • Dozens of variants on our course sequences when customers pay to have various customization made to them. 

As you might imagine, it’s quite unwieldy to have so many sequences. Currently, the only options to organize the view on the Sequences page are sorting in alphabetical order, chronological order, or a variety of options I’ve never found a use for:

Now, this is not a sexy feature, but letting me create folders (or something like them) would be tremendously helpful. I could group things by topics and purpose, as well as archive sequences that are of no use anymore other than as an old record. 

Importantly, this also helps avoid mistakes. Naming conventions are super important when you get long lists, and if you can organize things into folders, you can make it safer by putting things in a set folder for someone.

With extra organization like archiving and folders, your team is much less likely to accidentally choose something named similarly that isn’t what they should be working on.

9) 3 Quick UX wins for ConvertKit sequences

As you can see from the previous item, my team and I use sequences *a lot*.  Because of that, we see a lot of the issues that come up in the UX of sequences.

Here’s 3 simple fixes that would remove points of friction and frustration.

1. Let me scroll in a sequence to switch between steps without having to go to the very bottom of the content.

In a sequence, you have two parts: The text in the email, and the list of all the steps in your sequence in a sidebar. If you have a long email (like our courses) then to scroll and switch from Email 1 to say email 8, 10, or 12 in a sequence, you have to scroll all the way to the bottom of that email, and only then do the additional emails in the sequence become visible and thus clickable.

The simple answer here is to separate scrolling between the two elements.

2. Let me more easily re-send a sequence to a customer when they request it.

Other than re-subscribing people that had issues or accidentally unsubscribed, the number one thing we deal with is people can’t find an email in a sequence, so we need to resend it to them.

The ConvertKit support team company line is that we should copy and paste the entire message and subject line to make a broadcast to send to each person. That’s an incredibly tedious process to send a couple of people an email, especially when links often break and the formatting doesn’t come through in the process.

Now, I can send a “Test Email” easily, but you limit those. I understand this is to protect against spammers, but you can use logic on that, such as only letting me send to people already in the sequence, or subscribed to our general list.

3. When I look at an individual user, and I check their sequence page, add a button to add them to a sequence!

One of the best things you can do in a product is let me do the things I want to do where it makes sense to do them. Supporting our customers often means looking up a specific user to see if they received an email.

When I look up subscriber, it’s great to have all the info on the user available on the subscriber’s profile, like we pictured before:

All I’d like to do is add to the Sequences tab a button for adding this subscriber to another Sequence. This let’s me complete a support activity for a customer where I am. As it stands, I need to take another 3-4 steps to complete the same action.

—

Adding small fixes and improvements in your product are great ways to boost morale for your engineering team and delight customers. Those are 3 that would make a big difference for my team and I when it comes to using sequences.

10) On sequences, tell me who is on what step.

The #1 thing I miss from MailChimp is that in any sequence I can get a pop up of a list to see:

  • Who is in the queue to get a sequence step
  • When they group will get emailed that next step

In Mailchimp, it’s part of the details on a step:

Clicking on the “Queue” then pops up a list of who is in the group to get the email associated with this line in a sequence:

This is big for 2 reasons:

  1. It’s a helpful sanity check to make sure you have your logic correct for a step in the sequence. It can be nerve-wracking to not know for sure it’s right.
  2. Any changes you just made are confirmed by seeing if the way you tweaked the logic now changed the existing members of a given step’s queue.
  3. If a customer has a question or issue, you can confirm they’re properly in a sequence by literally checking the step and seeing for sure that they’re at the step you expect. You can then confidently tell them when they’ll get that next email instead of guessing or having to ask support to check.

In both cases, I currently have to message ConvertKit support and often it gets passed around and escalated before I get a response. This is pretty annoying if I’m trying to close out a customer ticket on my side, and is an expensive task for their support team. 

Why might ConvertKit not have fixed these things?

Now, this is quite the list. It’s hard to expect any company to be perfect, but you can see there’s a mix of big and small things missing from the experience in ConvertKit.

The question then becomes why might ConvertKit not have built or fixed these things? 

Here’s a few thoughts as to why…

1) They have more important things to focus on 

One of my favorite frameworks I’ve ever learned about is “Olsen’s Hierarchy of Needs.” In a simple, easy to understand image, it explains how you should prioritize product development:

This was created by Dan Olsen, who was the VP of Product at Friendster. This was a predecessor to Facebook and MySpace that was very early in the social network game. 

Unfortunately, Olsen created this out of some painful lessons learned. Scaling, product speed, and functionality issues ultimately doomed Friendster. 

I have no idea what the situation may be internally at ConvertKit, but if there are core functionality and scalability issues that they’re putting the majority of their engineers on, then that is 100% the right decision. 

Making sure emails send when they’re supposed to and arrive where they’re sent is more important than any of the things I’ve listed above. 

However, a number of these are what I would expect can be quick wins and quick fixes. Those items are perfect to have your engineers do as a break from, or in between, major tech debt projects. 

2) They commit the cardinal sin of featuring voting.

Feature voting is a terrible way to get product feedback, make prioritization decisions, and learn from customers. I’ve seen it fail so many times I’ve written a 2,000+ word essay on why you never want to use a feature voting system here. 

Not surprisingly, spending even a minute on the ConvertKit feature voting site, I see a number of the common problems:

  1. Spam: Two different consultancies have posted themselves multiple times for reasons I don’t understand. They’re showing on the first page repeatedly, which has nothing to do with feature requests or product feedback….
  2. People feeling unheard: Here’s someone talking about having a problem for *2 years*. And the response basically said, “Sorry, not yet” with no effort to help them with a workaround.
  3. The system is bloated: It’s not just for feature requests, actually. There are 17 categories of things in the “community”, making it incredibly noisy. It’s unreasonable for any customer to expect they’ll truly be heard in all that noise.

And those reasons, are in addition to what typically causes feature voting systems to fail:

  1. Collecting features without understanding the real underlying problems causing the customer to request something.
  2. Distracting people with all the noise of other requests causing them to forget to submit their feedback.
  3. Yet another log in and account to create just to send feedback. Every bit of friction will lose some people.
  4. A lack of context makes it impossible to tell what is a “must have” vs. “nice to have” request. 

And more I wrote about here.

The ConvertKit community site may be great for feeling like they’re listening to and creating a community for their customers, but from a product development perspective, it’s a false idol.

Any time spent by the product team there, and the damage done to not really listening to customers prevents them from making the best, customer and data informed decisions they could. 

3) They don’t seem to talk to a lot of customers

You’d be surprised how many product managers talk to few, if any, customers. You really are in the top 10-20% of all PMs if you make an effort to do so with much regularity. 

I can’t say for certain what the habits are of every PM and designer at ConvertKit. However, I can say my experience as a customer for 2+ years is not good:

  • I’ve never received a survey from their product or design team. I did recently get one from marketing, but none of it included any product questions. It was all demographics.
  • I’ve never received an invitation to a customer development interview, user testing, or even to be added to a list they may draw from for those.
  • I’ve never seen an email, pop up in Intercom, nor any other format where the product team was trying to create direct communication with customers. 
  • I’ve never received a follow up message from a designer nor product manager to ask any questions about feedback that the support team has promised they’ve logged or passed on to product.

Now, it’s possible I’m just unsubscribed from some of those things, and didn’t realize it. Or something about our use case and business type disqualifies us from being a fit for customer interviews.

Or maybe I’m supposed to do something at the community page that I don’t know. However,  if that is the case, then the support team should be better trained to tell me about that, because I’ve asked them before and not been told that. 

Intercom listens to their customers often. Here’s an example I received today.

Regardless of how they do it, the key is that there are opportunities to engage your customers at every step of the way, from prioritization to developing and scoping a feature, to pre and post launch testing.

Many of the issues I covered today could have been fixed by getting closer to the customer during each of those steps. 

And that’s the beauty of making talking to customers a key part of your product development process and culture. You can create all of these benefits:

  • Make sure you build the right features at the right time: When you talk to your customers, you learn if the next feature is actually solving an important problem for them. Prioritization becomes “what’s best for the customer?” instead of internal battles of opinion.
  • Fixing issues before you build them: Interviewing customers can also include getting feedback on mockups, clickable prototypes, and other early designs to make sure you’re on the right track and fix things before costly rewrites are required.
  • Iterating from good to GREAT: You learn about the little big details that matter to customers and the keys to making them super happy when you take the time to speak to them regularly.

Through all of this, you learn how to maximize the time and efforts of your design and engineering teams. Many of the problems and suggestions I’ve made today could have been caught when the features were last iterated on or initially built, if they knew to incorporate them.

Talking to customers is hard. Building a customer driven company is even harder.

As an individual PM, having a strong set of habits to talk to customers and gather actionable data on what to build is a very difficult job. 

Yet, it’s understandable why it doesn’t happen; it’s also a deep set of skills to build. 

This is why so many PMs and companies don’t do a good job of it; many PMs don’t want to do the work, and many others don’t know how. 

If you want to learn how to do it, check out some of these other posts that can help you on your journey to become a customer driven product manager: 

And if you want hands on help or coaching, sign up for a free call to discuss how I can help you and your organization here. 

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

1 Comment

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

1 Comment

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

2 Comments

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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