52 Questions For Your First 90 Days

As part of a case study interview presentation (for head of product at a Series A/B stage startup), I've been asked to share what my first 90 days would look like. I took the traditional "People, Product, Process" structure and added "Context" as its own section. I also used the Lean Canvas as a guide. Let me know what you think! What am I missing?

Context

What do we think PMF looks like?

1. How are we defining the market? How big is it?
2. Who are the users? What do we know about them? What do we need to know about them?
3. What user problems do they have? How painful are those problems?
4. How are we monetizing our solution to those problems? Will that scale?
5. How are we acquiring those customers? What’s our CAC and LTV? What level of retention / repeat engagement do we need to hit the target LTV? Will that scale?

How are we defining the product?

1. What’s the user journey look like??
2. Which JTBDs do we want to focus on?
3. What are our solutions to the JTBDs we’ve identified?
4. When we bring our solutions to market, how do we talk about them? What’s the response?
5. How do our solutions compare to alternatives and competitors in the market?
6. What qual and quant data do we have to believe we’re right?
7. Are there network effects or defensive moats that will grow over time?

Where are we today vs. where we need to be?

1. Do we have PMF and it’s just a matter of scaling? Why do we think that?
2. If we don’t have PMF, are we using every tool to get there?

What’s our strategy to get from today to our goal?

1. Let's dig into (or build) the operating model to understand the levers, timing, and assumptions. What feels easy vs hard? Why?
2. How are we validating and prioritizing these opportunities?
3. To what degree is the organization aligned on the same goals and strategy? Is everyone moving in the same direction? How good are we at alignment and focus?
4. How might we unlock a new gear, to learn faster, grow faster, deliver greater value?

People

Who’s who:

1. Who are the 1-2 dozen people I’ll be working with the closest?
2. Who are the 50-150 people that form the larger effort I’m a part of?
3. As a remote team, how might I best build relationships, trust and rapport with everyone, individually and in teams?

Talent:

1. Organizationally, what are we good at? Where do we need coaching / training? Where do we need new talent?
2. Individually, what drives someone? What is rewarding to them? What frustrates them? How can I help?
3. What programs, budgets, and opportunities can we create to accelerate the growth of our people?

Exec team:

1. How are we performing as a First Team?
2. Do we have trust, rapport, good communication, alignment, safe debate + disagree and commit?
3. How might we get better as a First Team?

Product

Execution:

1. What have we built?
2. What have we learned?
3. What’s working and what’s not? What do our users say?
4. How good is our data, analytics, and reporting?
5. What’s the state of our tech? What’s on fire now, and what will be on fire soon?

Culture:

1. What’s the product culture within the product team?
2. What about across the company??
3. What do we want it to be?
4. How outcomes focused and hypothesis based are we??
5. Is Product held accountable for delivering results??
6. Is Product given the autonomy to deliver results, abstracted from specific features?

Process

Product Process:

1. What’s our template for writing product briefs??
2. How good are we at product strategy and writing OKRs?
3. How are we identifying and prioritizing opportunities?
4. How are we identifying and validating assumptions and hypotheses?
5. How are we using qual and quant data as recurring feedback loops?

Communication & Collaboration

1. Do we know what the rest of the org is doing? How do we know?
2. Does the org know what we’re doing? How do they know?
3. Are we all aligned? If we’re not, why not? How good are we at correcting misalignment?
4. What are all the touch points for stakeholders and the broader team to be involved with us, and us with them? How often are they happening, and how often should they be happening?
5. How well are we working cross-functionally??

Tools

1. Do we have the right tools to be a high performing team?
2. Are there tools we should be using more?
3. Are there tools we were / are using that we’ve outgrown??
4. Any opportunities to cancel and save money?