I’d written a while back about how most organizations reward progress over patience, and shared the simple 2x2 matrix below.
I got an interesting reader question on that post:
What would your questions be to learn if leaders have this kind of thinking baked into their companies' mindset and philosophies?
And I thought I would answer it in the style of my “walk me through” (WMT) interview questions I’ve used before.
“Walk me through a cross-team collaboration you initiated or simplified that resulted in a win-win for each team”
from this you can learn:
how willing they are to work horizontally vs relying on hierarchy
whether they understand that not all work can be owned by 1 team
if they have experience navigating complex dependency management
“Walk me through a series of bets you made that ended up in compounding value for your customer”
from this you can learn:
if they believe in long-term planning and execution vs short term only
whether they’ve been able to break complex problems into chunks
how they get buy-in for making multi-part, phased investments
“Walk me through a strategy shift you undertook that resulted in a step function change for your business”
from this you can learn:
whether they’ve ever even attempted a strategy pivot (successful or not)
if they can articulate what a 10x change (vs incremental) looks like
how they think about top-level business impact and metrics
“Walk me through the last product line / feature set you sunsetted and why”
from this you can learn:
whether they’ve actually killed features and divested bets of any weight
how they navigate customer comms and field perception when removing value
if they think of sunsetting as a way to manage debt, increase focus, improve CX…
“Walk me through an instance of increasing funding / staffing for a team based on promising signals (qual or quant) you saw”
from this you can learn:
whether they have a mental model for when and how to double down
how they handle dialing up 1 investment while dialing down another
if they can blend qual and quant insights or over-rely on 1 signal
“Walk me through a scope change decision you made that resulted in a team slipping its release date commit”
from this you can learn:
if they are willing to change / sacrifice ship dates for a bigger goal
what their bar is for adding / removing scope from a project
how well they handle communication and buy-in for scope change
“Walk me through the last case of regretted attrition on your team and what you learned from that departure”
from this I can learn:
if they have ever even had a regretted departure (no example is either lack of experience, lack of honesty, or lack of learning from that scenario)
whether they can put themselves in the shoes of the departing person and articulate how / why they hit a career plateau and chose to go elsewhere
how they changed their leadership style to prevent from happening again
“Walk me through a hard lesson you learned from your customers / partners / competitors that came later than you liked”
from this you can learn:
how they deal with blind spots and whether they take accountability or blame
what constitutes a “hard lesson” for them (wasted time, wasted resources, etc)
whether they have a growth mindset and a good barometer for healthy pace of learning (some folks are way off in terms of how fast / slow insights should come)
As always, I’d also love to hear from readers about the questions they use to evaluate prospective leaders - please chime in via comments👇 or join the chat via the Substack app.
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further reading / references
you can read the full Patience vs Progress post here
the original WMT interview questions for PMs
I’ve written some satirical essays about leadership in the past if you want a good laugh (Savior Syndrome & The Ineffective Executive)
childish drawing / interpretation
The sketches are only getting better :D
Love these, to reflect on in terms of assessing others and oneself. Thanks!