This Week #3: Finding product/market fit, interviewing for a Director of PM role, and structuring discussions with senior leaders

Hello and welcome to my weekly newsletter, where I tackle your questions and share advice about building product, driving growth, managing humans, and anything else that’s challenging you at work. I’ll answer three questions each week (keeping your name and company anonymous) until you stop sending me questions. If you have anything you’d like advice on, or just want to say hi, simply reply to this email and ask! I won’t have all of the answers, and I’ve still got much to learn myself, but through this experience I hope that together we can all become better at whatever it is we do.

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On to this week’s questions!

Q: I have a startup idea and I’ve started talking to potential customers about it. What should I be asking them to know if I have Product/Market Fit?

Oh, that fabled Product/Market Fit (PMF) 🔮 Many seek it, few find it. The search for PMF is not so different from a treasure hunt — you’re pretty sure there’s gold somewhere out there, you find vague clues along the way, and you have to keep your crew/team/investors from mutinying before you discover it. If you do find it though (and you can manage to keep it), glory and treasure await 🤑

What is PMF? It just means you’ve created something that people want. You can read more about why it’s important in this legendary article by Marc Andreesen (who coined the term).

How does one know if they’re indeed building something people will want? In my experience, you never really know you have PMF until you’ve built the thing, gotten people to use it, and enough people continue to use it for an extended period (here’s a way to measure this once you have enough users). Also, it’s not a binary, big-bang, event — you simply get clearer and clearer about what the market wants, build it for them, and hope that it has lasting, differentiated, value. Remember the Yo app? or CryptoKitties? Lots of initial traction, and then a quick fade. It felt like PMF, but that there’s fools gold. 😏

What you want to do at your stage, up until you can measure things like long-term retention and level of “disappointment” if your product disappeared, is to build increasingly greater confidence that you’re heading towards treasure. You do this through the initial conversations you’re having now, and later with wireframes, prototypes, and having people use the actual product.

When talking to potential customers early on, here are the three things I’d look for to build confidence that you are heading towards PMF:

  1. Passion: How excited do people get when you describe your idea? You want to see people get visibly excited. You want them to ask you how soon this thing will exist. You want to hear them offer you money for it. This will be hard to miss. If you can’t find a handful of people that act this way, you either don’t have PMF, you aren’t pitching it well, or you haven’t talked to the right people. Adjust one or two of these things and see if you can get there. Try to find at least five people who are very excited. As Paul Graham famously said, “It's better to have 100 people that love you than a million people that just sort of like you.”

  2. Skin in the game: Are people willing to pay you for this product? Ask them this directly. Even try to get them to pay you now (i.e.. literally send them an invoice) to get early access to the product. Nothing will be a better signal of interest and PMF if you can do this successfully. Try this even if it’s a consumer app that you won’t charge for — it’ll show you how much value you’re creating in people’s lives.

  3. A clear why: As you talk with these potential users, keep asking “why.” Why are they excited about your product? What specifically is it going to do for them? Why is this problem a big deal? Why aren’t they using something else instead? This will both help you make sure you’re understanding what they are saying, and help you get to the core of their pain point.

Concrete questions I’d ask in your interviews after you describe your idea:

  1. How are you currently solving this problem?

  2. What annoys you about your current approach?

  3. If you had a magic wand, what would you wish for to solve this problem?

  4. How much would you pay for this if it existed?

  5. Why is this a problem for you? [Listen for answer] Why is that? [Listen for answer] Why is that? [Listen for answer] Why is that?

Final tip: Pick the people you talk to carefully. Figuring out the target audience for your product is very much part of this search, so be careful getting discouraged by talking to the wrong group of people.

Q: Any advice on interviewing for a director-level PM position?

As you progress in your PM career, moving from an individual contributor (IC), to a manager of PMs, to a manager of manager of PMs, your gaze rises from the week-to-week, to months out, to years out. You’re increasingly looking further out into the horizon — laying ground-work, anticipating challenges, and working towards a long-term vision. You focus less on day-to-day execution and more on putting place strong vision, strategy, and people. With that in mind, when interviewing or hiring for a director-level PM, the five most important traits to nail IMHO are:

  1. Long-term strategic thinking: As a Director of PM, you will be asked to take on large complex problems (e.g. growth is slowing on a marquee product, launch a critical new product from scratch, build out this key piece of infra), and find a clear path to solving those problems. Unlike doing this as an IC PM, the scope will be bigger, the stakes will be higher, and the number of people involved will be larger. When interviewing, expect to be asked about times you’ve defined strategies for problems in the past, and to be given complex business problems that you’ll need to tackle either at home or in-person. Focus on your approach to breaking down the problem and your strategy for addressing it, not on having the perfect solution in the end.

  2. People leadership: As you move up the career ladder as a PM manager you become increasingly distant from the actual product. More and more your impact comes out of the work of other people. As Andy Grove famously shared in High Output Management, “the output of a manager is the output of the organizational units under his or her supervision or influence.” Thus, your ability to lead and influence people becomes ever more critical. When interviewing, expect to be asked about your leadership style, how you’ve navigated people challenges in the past, and what your reports and peers would say about working with you, if asked.

  3. Stakeholder management: Similarly, you’ll be spending a lot of time working with senior external leaders. Sometimes, even more time than with your own team. When interviewing, expect to be asked about times you had to push back on stakeholders, when you had to go along with something you didn’t agree with, and how you’ve set things up for success when presenting to execs.

  4. Impact: As a de-facto leader of a large number of resources (i.e. engineers, designers, data scientists, researchers, etc.), you will be expected to drive significant impact (i.e. changes the trajectory of the business). Expect to be asked how you’ve prioritized for impact in the past, how you align your team behind the most impactful work, how you set goals, and how you think ahead to make sure you’re always working on the highest impact opportunities.

  5. Communication: Your ability to communicate clearly, concisely, and convincingly will be essential to being successful at every one of the above attributes. Expect to the asked about concrete tactics you’ve learned for communicating with your team and stakeholders, how you keep your team and stakeholders up to date on what’s happening, and how you communicate bad news. Also, be cognizant of how you’re communicating during the interview — that itself is an important signal to the hiring team.

Q: When you were doing check-ins with senior leadership, did you often find decks were necessary to communicate? If so, curious if you found certain content/structures to be best.

Check out the McKinsey Situation-Complication-Resolution (SCR) Framework. My last manager introduced me to this and it’s changed the way I present information ever since. You can apply this to any medium, and in many different contexts.

In terms of the actual medium, that decision depends so much on what your audience is expecting (are decks encouraged? are they banned?), what sort of information you’re communicating (designs? strategy? a bunch of data?), and your personal style of communication (do you like to point to things on a screen? do you like the attention to be on you?). My advice is to pick whatever you’re most comfortable with, tell the story you want to tell, see how it goes, and iterate. Watch to see if the leaders stay engaged and understand what you want them to understand. If not, ask for feedback from those leaders or your manager, and try something different next time.

That’s it for this week! Have something you’d like some advice on? Just ask by replying to this email. 🤔

Inspiration for the week ahead 🧠

  1. Book: No Hard Feelings: The Secret Power of Embracing Emotions at Work — A deeply researched, beautifully illustrated, and immediately actionable guide to turning emotions at work from a liability into an asset, for you and your team.

  2. Blog post: Cross the world four times — A (rare) new blog-post Derek Sivers. It’s a tear-jerker.

  3. Podcast: Dan Carlin's Hardcore History - If you have any interest in history at all, start with this episode and just try to stop listening.


Lenny 👋