What would our core user persona(s) think about our current priorities? How do we feel about that as a leadership team?
Prioritization & Decision Making
Alissa Reiter
Alissa Reiter
|

CMO @ Evernow;

Ex–Sr. Dir Product, Growth @ Ancestry.com

What are the major risks you see in the high-priority initiatives our teams are currently working on? What can we do right now to help de-risk them?
Prioritization & Decision Making
Tom Willerer
Tom Willerer
|

Ex-CPO @ Opendoor;

Ex–VP Product @ Netflix

What does being “data-driven” actually mean to you? What is the opposite of being data-driven? Can our organization be customer-driven and data-driven?
Common Goals & Language
John Cutler
John Cutler
|

Product Evangelist & Coach @ Amplitude

What practices do we have in place to ensure we are always looking to the horizon, iterating today and keeping the house clean?
Quality & Execution
Shruti Ramiah
Shruti Ramiah
|

Head of Design @ Zalando;

Ex–Head of Design @ N26

What’s a recent win from our team that we haven’t really celebrated? How can we give it the recognition it deserves?
Team Health & Dynamics
Alissa Reiter
Alissa Reiter
|

CMO @ Evernow;

Ex–Sr. Dir Product, Growth @ Ancestry.com

When should we make investments in our technical infrastructure and scaling vs new value for users?
Prioritization & Decision Making
Barron Ernst
Barron Ernst
|

Head of Growth @ Figure;

Ex–Dir of Product @ Booking

How are we mixing our portfolio of work to focus on our present and future customer?
Prioritization & Decision Making
Shruti Ramiah
Shruti Ramiah
|

Head of Design @ Zalando;

Ex–Head of Design @ N26

Do we both have the same story of what we are trying to do long term? What common analogies do/should we use?
Common Goals & Language
Janet Balneaves
Janet Balneaves
|

Product Director @ Shopify

What does [your team/org] think of [my team/org], and why?
Trust & Support
Louis Bennett
Louis Bennett
|

EIR @ Reforge;

Ex–Head of Engineering @ Intercom

What is the biggest assumption we are making in our product strategy?
Prioritization & Decision Making
Shaun Shirazian
Shaun Shirazian
|

CPO @ Pipedrive

Where do we have opportunities for the team to have more fun and feel like they're having more impact?
Team Health & Dynamics
John Cutler
John Cutler
|

Product Evangelist & Coach @ Amplitude

When it comes to data, which key insights are you missing in order to better lead our teams together? How can we make access to this data this a clear priority?
Prioritization & Decision Making
Olivier Maître
Olivier Maître
|

Head of Product & Design @ Cash App (Block);

Ex–Head of Product @ N26

What shared language, tools and processes do we need to ensure our disciplines understand each other and collaborate smoothly?
Common Goals & Language
Shruti Ramiah
Shruti Ramiah
|

Head of Design @ Zalando;

Ex–Head of Design @ N26

Are we applying each teammates' talents in the most impactful way? (e.g. Do we have back-end heavy work on the plates of mostly front-end teams?)
Team Health & Dynamics
Janet Balneaves
Janet Balneaves
|

Product Dir @ Shopify

Does anyone from your team want to move to another team or discipline? How might we support them?
Trust & Support
Andrew Moll
Andrew Moll
|

Head of Product @ Abacum

Let’s review our tech suppliers. Which are we getting value from and which are we not?
Prioritization & Decision Making
Matt Fenby Taylor
Matt Fenby Taylor
|

CPO @ Clearscore

What stops us from moving as quickly as we could be?
Quality & Execution
Barron Ernst
Barron Ernst
|

Head of Growth @ Figure;

Ex–Dir of Product @ Booking

How can we get better at starting smaller - i.e. with prototypes - rather than over-investing in scalable solutions by default?
Quality & Execution
Sam Bower
Sam Bower
|

Dir of Product @ Hotjar

What can I do to make your job easier?
Trust & Support
Elena Luneva
Elena Luneva
|

GM @ Braintrust;

Ex–Head of Product @ Nextdoor

An exposé is written about our company. What would you be most embarrassed/proud of?
Trust & Support
Andrew Moll
Andrew Moll
|

Head of Product @ Abacum

What is one thing you’ve wanted to share with me but have held back? What gave you pause to say it?
Trust & Support
Brian Balfour
Brian Balfour
|

Founder & CEO Reforge;

Ex–VP Growth @ HubSpot

What % of the company do you think can explain our goals and priorities for the next 3, 6, 12 months?
Common Goals & Language
Andrew Moll
Andrew Moll
|

Head of Product @ Abacum

Who are our high-potential people we’d bet on for the future? Who’s struggling and what can we do to help them?
Trust & Support
Matt Fenby Taylor
Matt Fenby Taylor
|

CPO @ Clearscore

Where do we have opportunities to reduce uncertainty where it is causing drag for the broader team?
Common Goals & Language
John Cutler
John Cutler
|

Product Evangelist & Coach @ Amplitude

How can we make observability and system performance top-of-mind for non-engineers?
Common Goals & Language
Sam Bower
Sam Bower
|

Dir of Product @ Hotjar

How are we creating similar work cultures of expectations, evaluation and psychological safety within our disciplines?
Team Health & Dynamics
Shruti Ramiah
Shruti Ramiah
|

Head of Design @ Zalando;

Ex–Head of Design @ N26

How can we ensure that our teams build with scalability and availability in mind whilst balancing scope and velocity?
Quality & Execution
Tamara Amorin Almeida
Tamara Amorin Almeida
|

Head of Product @ TIER Mobility

What are the top 3 ways-of-working problems our teams are struggling with across the board?
Quality & Execution
Matt Fenby Taylor
Matt Fenby Taylor
|

CPO @ Clearscore

In 2 years time, what capabilities would we need that we don’t have today?
Prioritization & Decision Making
Matt Fenby Taylor
Matt Fenby Taylor
|

CPO @ Clearscore

How can we frame the value of tech debt in a way that delivers value not just technically, but also for customers and for the business?
Common Goals & Language
Barron Ernst
Barron Ernst
|

Head of Growth @ Figure;

Ex–Dir of Product @ Booking

If engineering/product/design had a magic wand, what would it change about design/product/engineering?
Team Health & Dynamics
Matt Fenby Taylor
Matt Fenby Taylor
|

CPO @ Clearscore

When are you most productive? Least? Why?
Trust & Support
Elena Luneva
Elena Luneva
|

GM @ Braintrust;

Ex–Head of Product @ Nextdoor

What’s your succession plan?
Trust & Support
Matt Fenby Taylor
Matt Fenby Taylor
|

CPO @ Clearscore

Which companies do we admire in our sector and why?
Quality & Execution
Matt Fenby Taylor
Matt Fenby Taylor
|

CPO @ Clearscore

Are our Product and Engineering teams flexible enough to change rapidly to support changes in business priorities? How can we all become better shape-shifters?
Quality & Execution
Narek Verdian
Narek Verdian
|

CTO @ Glovo

What is holding your team back from doing their best work? How can my team help them go from good to great?
Team Health & Dynamics
Shelby Bower
Shelby Bower
|

Head of Product Design @ Docusign

What is our shared definition of what a “product launch” moment should look like?
Common Goals & Language
Christy Roach
Christy Roach
|

Head of Product Marketing @ Airtable

How can we measure the scope and impact of non-feature related initiatives so that we’re able to prioritize them against others?
Prioritization & Decision Making
Tamara Amorin Almeida
Tamara Amorin Almeida
|

Head of Product @ TIER Mobility

On a scale from 1-10, how much does our organization’s current work advance our company strategy? Help me understand why you chose that number.
Prioritization & Decision Making
Shelby Bower
Shelby Bower
|

Head of Product Design @ Docusign

How well do you think our teams’ current work supports our broader mission?
Prioritization & Decision Making
Alissa Reiter
Alissa Reiter
|

CMO @ Evernow;

Ex–Sr. Dir Product, Growth @ Ancestry.com

We hold ourselves to a high UX standard for our users externally. How can we apply the same UX standard of the code we write for its users internally?
Quality & Execution
Imran Omari
Imran Omari
|

VP Engineering @ Hotjar

Imagine we switched roles. What would we do differently in each other’s role?
Team Health & Dynamics
Shaun Shirazian
Shaun Shirazian
|

CPO @ Pipedrive

How do we draw a line every quarter to know what the most important tasks are to do as a team, as a business unit, and as a company?
Prioritization & Decision Making
Barron Ernst
Barron Ernst
|

Head of Growth @ Figure;

Ex–Dir of Product @ Booking

What is our definition of a great team? Do we still agree with it?
Team Health & Dynamics
Matt Fenby Taylor
Matt Fenby Taylor
|

CPO @ Clearscore

Regardless of our existing team structure, stack-rank your top 5 priorities across Product and Tech. Help me understand the “why” behind each one.
Prioritization & Decision Making
Partho Ghosh
Partho Ghosh
|

Sr. Dir of Product, Growth @ Hootsuite