Top 10 Frightfully Scary Product Manager Nightmares

Halloween is just around the corner. I love watching scary movies this time of year, especially the original Halloween movie starring Jamie Lee Curtis. There are so many scary movies to choose from, I usually watch one almost every night during October… which always leads to nightmares. This got me thinking… what are the top nightmares product managers have? What keeps you up at night?!?

#10 – Having dinner with your extended family and suffering through questions about “what exactly do you do”?

#9 – Coming back from a rare lunch with a co-worker only to find someone from your support team has convinced your dev team to squeeze this bug fix into the sprint even though they’re already behind schedule on everything else they thought they would get to.

#8 – Interviewing a UX design candidate who insists the onboarding experience for your app is outdated and would be the first thing she would fix if hired.

#7 – Finding out via a post on Slack that the Sales team promised your biggest client their pet feature will ship in the next release.

#6 – Sitting in a quarterly planning session to discuss OKRs while people keep suggesting tasks as KRs.

#5 – Finding a typo on your landing page … 12 hours after deploying to production.

#4 – Being asked to put together a roadmap presentation for your company’s board meeting … and the CEO needs it in 4 hours.

#3 – Getting a rejection notification from the app store 5 days after you submitted it for approval … and your big launch is happening tomorrow.

#2 – Writing a strategic plan for the future of your product … while sitting in coach on a 5-hour flight and the person in front of you has reclined their seat ALL.THE.WAY.BACK … and your laptop battery dies before you saved your document.

#1 – Someone from Customer Success just created a new Slack channel called “Feature Requests” and invited the entire company to it. AND… your boss thinks it’s a great idea and asks you to keep track of everything that’s requested.

What are some of your scary product manager stories? What spooks you the most? Share in the comments below.

Also, please follow me on Instagram. I share product management posts almost daily and you don’t want to miss out! Click here to follow me

What do Tom Brady and Oprah have in common with product managers?

It’s football season, once again (American football to be precise), which reminds me of a podcast episode of Oprah Winfrey’s “Supersoul Conversations” with Tom Brady. I’m not much of a football fan (college basketball is my jam), but I was interested in hearing what Tom had to say since he’s such an incredible athlete.

Tom spoke about how he had not always been the best football player. When he played for Michigan, he knew the areas he had to work on, but he also knew his strengths: he had a strong work ethic, he was a natural at leading people, and he had perseverance. Probably sounds like a great product manager you know, right?

He went on to talk about how he led his NFL team, the Patriots, when they were down by 25 points in Super Bowl LI against the Falcons. Rather than worrying about the huge gap and questioning if they could do it, they tackled (sorry, had to go there) each play one at a time and ensured they made the right move for that particular play: Score one touch down. Stop the defense and get the ball back quickly. Get to a first down… you get the picture. That 25-point comeback was the biggest in Super Bowl history.

As a product manager, you may aspire to be the greatest of all time (like Tom Brady is one of the greatest football players of all time). To get there, you must be able to lead your teams by identifying the key plays needed to win and focusing on those plays one at a time.

If you and your team are trying to deliver a monolithic release, you are setting yourself (and your company) up for failure.

The key to winning is to lead your team to focus on the right solution for the first opportunity you need to deliver before moving on to the second one, and the third one and so on. Prioritize and focus on incremental activities that put you closer to your goal (whether it’s delivering a more engaging experience for your customers, increasing revenue for your company, etc.).

Want to learn more about how to lead cross-functional teams? Sign up for my 1:1 coaching program designed to advance your career.

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Revisiting habits of successful product managers

I wrote a post at the very beginning of 2020 about the habits of successful product managers. Given we are more than halfway into the year and 2021 is just around the corner, I wanted to revisit some of these habits as a gentle reminder because there is still time to make the most of this year that has turned out to be completely different than what we expected!

With the vast majority of us working remotely, many of these habits have become increasingly more important as we struggle to maintain connections and relationships via Zoom. Here are the habits I encourage you to establish if you’re not already doing so. These habits will go a long way towards helping you become the best product manager you can be. 

Identify the day’s non-negotiables

Spend a few minutes each day prioritizing a small number of ‘must-dos’ to ensure you get those items checked off your to-do list. Working remotely brings the new twist of trying to get those ‘must-dos’ done while dealing with kids clamoring for your attention, your dog wanting to be walked or your wifi is maxed out because so many people in your home are online at the same time. 

Identifying your non-negotiables is key to making time for things that often get shoved to the back burner, such as talking to customers or reaching out to that one stakeholder you’ve been meaning to have a better relationship with. Speaking of which…

Schedule regular check-ins

As a product manager, you are the glue that connects the people inside your company. Make it a priority to check in on a regular basis to build and strengthen relationships with your stakeholders, teammates, and peers. With most us working remotely these days, it’s even more critical to make a concerted effort to stay connected with the people you don’t see in the office. Try doing virtual coffee or happy hours as a way to socialize informally.

Treat your career like a product

If you’re a product manager responsible for products that already exist, you know the importance of monitoring how those products are doing and developing ways to improve and optimize those products, right? You should treat your career the same way!

Make time each month to reflect on your wins and lessons. Keeping track of those will help you when it’s time to do your quarterly or annual performance review. This will also help you keep your resume updated with your biggest accomplishments and achievements.

I also recommend setting quarterly OKRs for yourself just as you would your products. Perhaps Q4 2020 is the time you target for looking for a new job? It’s just around the corner, so use September to start developing your game plan and working on your resume. 

I’m a huge fan of Dolly Parton. She once said, “If you don’t like the road you’re on, start paving another one.”

Are YOU happy with the road that you’re on? Do you wish you could be on a different road? Or maybe you would just like to get from point A to B as quickly as possible?

Spending time monthly to reflect on where you’re at in your career and identifying improvements and optimizations you’d like to make is one of the smartest habits you can develop as a product manager. 

If you’d like help with making a career change, I’ll be offering a 6-week Launch Your PM Career Bootcamp in September. You can learn more about it here, as well as get on the waitlist.

Podcasts for Product Managers

Whether you’re trying to break into product management or simply looking to improve your skills so you can be promoted eventually, it’s hard to find time to squeeze learning in when your juggling so many other things. Listening to podcasts is one of my favorite ways to expand my mind because I can do it while doing other things that don’t require a lot of thought, like folding laundry or walking the dog.

Here are the podcasts I recommend for improving your skills and advancing your career.

My favorite product management podcast currently is The Product Experience by Mind the Product. I love how coshots Lily Smith and Randy Silver extract the juiciest nuggets of golden information from their weekly guests. I always look forward to new episodes.

This is Product Management is brought to you by Alpha, an on-demand user insights platform for product teams. Hosted by Mike Fishbein, each episode features an in-depth interview with a product management leader on topics such as innovation, leadership, and user research. is a collaboration between and Product Collective. The co-hosts dedicate each episode to a deep-dive on topics such as finding product market fit, key metrics you should be using, and conducting customer interviews.

100PM podcast on product management

100 Product Managers began with a mission to interview one hundred active product managers in Los Angeles – from startups to enterprise. Host Susan Abade interviews product leaders from organizations such as Audible and Women Who Code.

p.s. I was a special guest on one of these episodes in 2017. Give it a listen!

What is YOUR favorite #product podcast? 🎧 Let me know in the comments below or send an email to

How To Make Product Management Connections On Linkedin

Raise your hand if you dread contacting someone you don’t know to get career help. 🙋‍♀️

“What’s the best way to connect with someone on LinkedIn to set up an informational interview” is one of the most frequently asked questions I hear. 

Check out my tips and templates below to become a networking Ninja. 🙅🏽‍♂️

The best way to connect with someone is via a mutual connection which is where the power of LinkedIn comes in. When you’re looking at the profile of the person you wish to contact, you can quickly see who you might know in common. Let’s say I wanted to contact Reid Hoffman, the founder of LinkedIn. Wow, we actually have seven mutual connections! Using the template below, you could then craft an email to your mutual connection with a request to introduce you. 

How to ask for an introduction to someone you’re mutually connected to:

Here’s a short and specific email template you can use when you would like to ask a mutual connection to introduce you to somone:

Hi {name},

I was looking to get introduced to {person you’re trying to connect with} from {that person’s company} and saw you were connected to them. I’m not sure how well you’re connected to them, but if the relationship is strong, I’d really appreciate an introduction to chat about {topic that you’re interested in].

Please let me know if you feel comfortable doing this and I’ll forward a proper request for the introduction that you can forward to them.

How to follow up after an introduction has been made via a mutual connection:

Once you’ve been introduced, it’s fairly straightforward to contact the person directly to let them know your interest and, more specifically, why you want to speak with them. 

Let’s say you are interested in a better understanding of career opportunities or how product management works at a particular company. Setting up an informational interview with someone on the product management team at your targeted company is a good next step. Once you find someone who looks like they might be able to provide some insight, take the plunge and use the following template to send them a request. 

Hi, {contact name}, I’m so glad {mutual contact name} introduced us! I’m a {job title or aspiring job title} and I’ve been considering making a career change. I’ve been following {company name} for a long time now and am wondering if it might be a good place for me to explore further. Would you be open to having a 15-minute call with me sometime in the next two weeks to discuss product management at {company} and what your experience has been there? 

How to connect with someone stone cold — without having a mutual connection introduce you

This is the moment that strikes fear into most of us… trying to connect with someone who you’ve never met before, with whom you share no mutual connections and that you really don’t know anything about other than that they work at the company you’re interested in.

Don’t worry… I’ve got you! Here are a multitude of different email template you can use to connect with someone, depending on your situation.

Hi, {contact name}, I’m a fellow product manager and have been considering making a career change. I’ve been following {company name} for a long time now and am wondering if it might be a good place for me to explore further. Would you be open to having a 15-minute call with me sometime in the next two weeks to discuss product management at {company} and what your experience has been there? 


Hi, {contact name}, I’m an entrepreneur-turned product manager who’s looking to connect with people who’ve made a similar career change. I see that prior to becoming a product manager, you started your own company. I would love the chance to learn more about your experience as I contemplate whether this career change is something I should continue to pursue. Would you be open to having a 15-minute call with me sometime in the next two weeks to discuss product management at {company} and what your experience has been there? 


Hi, {contact name}, I’m an aspiring product manager with a background in {marketing/project management/your current job title}. I see you made a similar transition yourself. Would you be open to having a 15-minute call with me sometime in the next two weeks to discuss how you went about transitioning to product management at {company}? I’d love to learn how I can better prepare myself based on conversations with people like you who’ve been successful at this.”

Want to follow up on a product manager job application?

Use this email template for when you want to contact the recruiter and/or hiring manager for a role you’ve applied for. Also, be sure not to follow up too soon. I recommend waiting 1-2 weeks before reaching out so that you give the person time to review your application first. 

Hi, {name of contact}. I’ve been interested in working for [company name} for a long time, so when I saw that you were looking for a Product Manager, I applied right away. I haven’t yet heard back on my application so I thought I’d reach out to introduce myself directly because I believe my experience is very relevant to what you’re looking for based on the job description. 

Thanks for connecting and I hope you have a great day!”

When you simply want to build your network and make connections to other product managers — which I highly recommend you do, regardless of where you are in your career!

Use the following simple template:

Hi, {contact name}. My name is {Name} and I’m a {Title/Product Manager/Aspiring Product Manager}. Just looking to connect and share with others in the product management industry at this time. I hope you have a great day! 

Whatever you do, keep the communication short, sweet, and to the point. And if you’re not sure about how to find people to connect to in the first place, you may want to consider joining my next Launch Your PM Career Bootcamp in September. This is one of the many things I teach in the program. You can get on the waitlist now and be one of the first to learn when registration opens up. 

6 Simple Steps To an Attention-Grabbing Cover Letter

You may be asking yourself, why bother with a cover letter? 🤷🏼‍♀️ Maybe you’ve heard companies don’t care. After all, most job postings include uploading a cover letter as optional. You might believe that since you’re applying online, you only need a resume.

According to a recent study by ResumeLab, 83% of hiring managers who responded claimed that a great cover letter can land an interview even if your resume isn’t good enough!

And consider this…While the hiring manager might have indicated the cover letter is optional, not sending one is a sign of laziness.

Your cover letter is the best opportunity you have to make a good first impression on the hiring manager. Don’t squander it.

You might feel uncomfortable writing a persuasive letter to someone you likely have never met. Or perhaps you’re simply unsure of how to write about yourself without sounding arrogant. Don’t worry. With these step by step tips, you’ll have a winning cover letter in no time at all! And make sure you read the entire article so that you can get to the free checklist I’ve included at the bottom of this page!

Step 1: Use a standard format

Keep your cover letter to a single page with plenty of margin space. The more white space, the easier it will be to read. If needed, do a little Marie Kondo on your letter and eliminate anything non-essential.

Use a font size no smaller than 10 points. Avoid decreasing the font size just to make the cover letter fit a single page. Your font should also be one that’s easy to read, such as Helvetica or Times New Roman. And be consistent! Use the same font throughout the letter… and use the same font as the one you use on your resume.

If there isn’t an option to upload a separate cover letter, copy and paste the body of your cover letter into the box on the application where you can enter free-form text if that is available.

Step 2: Address the letter to the hiring manager

This is a key step because in addition to addressing the letter to the correct person, you also will need the hiring manager’s name so that you can follow up (more on this later).

If you’re not sure who the hiring manager is, this is your chance to hone your research skills and find out. Go to LinkedIn and search for the company name and 2-3 keywords that would likely describe the title of the person in charge of hiring for the position you’re applying for.

If you’re not sure you’ve found the right person, find someone who works at the company (ideally who you are connected to in some way) and ask them if they know the best person to contact to learn more about this role.

You can also try calling the company’s main phone number and asking the person answering the phone, but I’ve found that most people on that first-line of defense are protective of employee information.

Step 3: Open with a meaningful sentence

Starting a cover letter with “I am writing to apply for the product manager position at [company x]” is stating the obvious. Instead, use this initial sentence to grab the hiring manager’s attention by offering a glimpse into your unique value proposition. Here are some examples:

“In my 5 years at [prior company], I increased our annual recurring revenue per user by [percentage].”

“My approach to creating products is based on combining design thinking frameworks with qualitative and quantitative data.”

You should start with a sentence that makes the reader want to know more about you so they keep reading and, more importantly, are compelled to review your resume.

Step 4: Customize for each and every job application

It’s okay to use the same general cover letter template for each job, especially if you’re applying to several at a time. The easiest — and most effective — tweak is to review the skills and traits listed within the job description and craft 1-2 sentences that illustrate how you have used those skills and traits successfully with concrete examples.

For instance, this job description lists the following qualifications for a product manager role:

You can create a killer opening sentence, building on the example here, by tying in your own experience that matches the qualifications listed above. This would make you stand out from the crowd of applicants.

One last related tip: Be sure to mention the specific job title. The people reviewing your resume may be trying to fill dozens, if not hundreds, of job openings.

Step 5: Close graciously YET assertively

Show appreciation for the recruiter and hiring manager’s time and consideration by thanking them. But don’t stop there. Be assertive and let them know you will follow up in one week to answer any questions they may have.

And be sure to follow up with the hiring manager if you haven’t heard back within a week from submitting your application!

Step 6: Review for typos

This last step before submitting your resume and cover letter is crucial. As a product manager, you are expected to be a master of details, big and small. If you have even one typo in your resume, that screams a lack of attention to detail. It also implies that you didn’t take your time writing the resume which then implies that you don’t care about the job. Spend a few minutes carefully reviewing your cover letter for grammatical mistakes and typos. If you’re unsure, try a service such as Grammarly.

That’s all there is to create a winning cover letter.

Ultimate PM Resume Starter Kit Download

If you found this article helpful, download my free 7-step checklist to
crafting the perfect resume for product managers!

Define Your Product Management Career Path

Many companies provide a single career path up the proverbial corporate ladder where the only way to get ahead is by moving up in title, rung by rung. In product management, this usually takes the form of something like this:


For most of my career, I worked at startups that had single-track product management career paths like this. Luckily, most of these companies were small enough that I was able to manage small teams while being hands on, defining products, and collaborating with designers and engineers to bring those pro

ducts to life. On two different occasions, though, I was faced with choosing between being a manager or an individual contributor (often referred to as an IC). Both took place at different times in my career, so depending on what stage you are at, my hope is that you find my experience useful.



I joined Spinner, the world’s first streaming music service, in 1998 as one of a dozen or so employees. This was my first job as a product manager and I was thrilled to have finally made the transition from marketing to product management. We were a small but mighty team that grew the business and the company rapidly. Within a year, we had grown to over one hundred employees. I managed a team of product managers, designers, and front-end developers. It was an exciting time leading a collaborative team, as we created numerous versions of our music player that was branded for a variety of partnerships.




In 1999, American Online acquired the company. As part of the transition process, AOL brought in a few executives whose job it was to evaluate their newly acquired staff in an attempt to integrate Spinner into their organization. I vividly remember the day I was called into a conference room with one of these individuals who asked a few questions about my role and responsibilities. At one point she said “Ah, you see, at AOL, you’re either an IC or a people manager. You can’t be both. You have to choose.” I felt like I was in the movie The Matrix, choosing between the red pill or the blue pill. I knew once I made my decision, there would be no turning back.


Based on what I had seen so far of the AOL culture, I did not think I was cut out for the politics that seemed to dominate daily corporate life. Although I loved finding and hiring talented people to join my team, the work I enjoyed the most was creating something from scratch. Creating a vision, solving problems, building products that people loved — that is what drove me each and every day. I chose to give up my reins as a manager and spent the remainder of my career at AOL as an individual contributor. Looking back, I think the decision was easy because I was fairly new to product management at that time. Frankly, I wasn’t sure what the career path of a product manager even looked like back then. What I did know is that I wanted to have a direct impact on products that would be used by millions of people.




I was eventually recruited away from AOL to join another music start-up called Musicmatch. Musicmatch was another pioneer in the digital music space with it’s CD ripping and burning software called the Musicmatch Jukebox. Similar to my experience at Spinner, I managed a small team while being hands-on with the product development process. One of the highlights from there was creating an in-house usability testing facility and hiring a UX researcher to help us better understand how customers were using our products and how we could make them better.




Shortly after leaving Musicmatch, I was asked to join another digital music start-up called Sonos. When I joined in 2005, I was the only software product manager. The team at Sonos sought me out because of my experience with streaming music services. I had a strong network built from my days at Spinner/AOL and was able to leverage those relationships to establish new partnerships for Sonos. I also had experience developing software for hardware, which was an uncommon thing back then, before there were smart phones and IoT products. I jumped right in, wearing a number of hats. One moment I would wear a business development hat, negotiating with Pandora. Another minute, I would be working with a designer, sketching design ideas for our remote control software. The minute after that, I would be working with our acoustics team to figure out how we could tweak the EQ settings of our speakers to deliver the optimum sound quality.


When I look back on those days, I’m honestly not sure how I did it all, but I loved every minute of it. At some point, however, it became clear that I was spreading myself too thin and we needed to expand the team. To organize the work, my boss and I decided to split music service integrations into its own work stream. I hired and managed two additional people — one who would be responsible for the music service partnerships and the other who would be responsible for our 3rd party developer APIs and website. In addition to managing those new employees, I was the hands-on product manager for all other aspects of Sonos software. Again, I reached a breaking point where I was not being the best manager I could be to my staff nor was I doing my best work as the PM for the Sonos software. I remember the CEO of Sonos telling me that one of the worst possible outcomes in promoting a great software engineer to being a manager is that you gain a mediocre manager and lose a talented engineer. The same could be said for product managers. My boss was extremely supportive and gave me a few weeks to do some much-needed soul searching to figure out what the best path forward would be for me.


I am a deeply introspective person to begin with. Having the time and space to reflect on where I was at this particular stage of my career was such good fortune. I figured out the right path to take by asking myself one simple question:


What are you working on that gets you out of bed?


Looking back, I realized that I was focusing my energy on redesigning our apps and defining new features. Thinking about our customer needs, collaborating with designers and engineers, launching new products — these were the things that got me out of bed in the morning. At the same time, I was not spending enough time filling the open positions on my team. I would block out a few hours each week for phone screens and the occasional interview and then wonder why it was taking months to fill the position.


Again, I was faced with choosing between management and individual contribution. Even though I had made this decision once before, this time it wasn’t as easy. For one thing, Sonos didn’t have a 2-track career path for product managers at the time. They did offer a dual-career path for engineers, however. Another reason this was a difficult decision was my ego. At this point in my career, I had worked as a product manager for more than ten years and had some preconceived notions about my future that were based on the continuous climb up that invisible ladder. For me, this had less to do with power and more to do with money. The loftier the title, the higher the compensation.


Ultimately, I knew that money wouldn’t make me happy. What made me happy was thinking about, “How can I help people listen to more music every day?” Deciding to be an individual contributor (again!) was the best decision for me, because I was happiest having the most direct impact on the product. It was also the best decision for the company because they didn’t have to worry about further developing my management skills and, instead, they could unleash me on special projects, such as creating a ground-breaking retail experience for the flagship Sonos store in New York City.


As Shakespeare wrote,

“To thine own self be true.”


In order to know which path you should take, you need to be honest with yourself. Set aside a few days for some deep introspection. Grab a journal and a pen and ask yourself these three key questions:


1) What are your strengths as well as your blind spots?


Be open to the feedback you’ve been given, the good and the bad. Take a co-worker out for coffee and ask them for feedback. Review those performance reviews again. If you already manage people, provide them with a way to give feedback.


2) What do you enjoy doing the most?


Ask yourself what gets you out of bed every day. Is it thinking about how to help your newest team member grow? Or do you thrive when brainstorming ideas for helping your customers use your product more easily?


3) Where do you want to be in 5 years? 10 years?


Do you have dreams of becoming a CEO or starting your own company? If so, the manager track might be best for you. Perhaps you’d rather be a subject matter expert in a particular field, speaking at conferences and being sought after for your brilliant insights.


Whether you decide to focus on managing or would rather be an individual contributor, I encourage you to champion a dual-track path at your company, if it doesn’t already offer it.


Here’s what dual-track paths might look like based on my experience:


Having a track that rewards senior individual contributors helps retain a critical aspect of your company’s brain trust while ensuring people becoming managers are doing so because they want to.


In my particular case, Sonos did eventually develop a dual-track path for product managers and I was the archetype for the Principal Product Manager role. It was gratifying to be recognized and rewarded for my contributions as the most senior product manager at the company in terms of tenure and experience.


After leaving Sonos, I decided to pursue yet another career path by leveraging my extensive experience to start a consulting business. Being my own boss while having a direct impact on the success of my business offers me the best of both worlds.


Does your company offer different tracks for product managers? Have you ever faced the challenge of deciding if becoming a manager is right for you? What do you think?


Originally published at on April 23, 2018.

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