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
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
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
Does anyone from your team want to move to another team or discipline? How might we support them?
Trust & Support
Let’s review our tech suppliers. Which are we getting value from and which are we not?
Prioritization & Decision Making
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
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
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
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
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
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
What are the top 3 ways-of-working problems our teams are struggling with across the board?
Quality & Execution
In 2 years time, what capabilities would we need that we don’t have today?
Prioritization & Decision Making
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
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
Which companies do we admire in our sector and why?
Quality & Execution
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
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
What is our shared definition of what a “product launch” moment should look like?
Common Goals & Language
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
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
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
Imagine we switched roles. What would we do differently in each other’s role?
Team Health & Dynamics
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
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
