Jasmine explains the trigger for hiring a COO: she had seven people reporting to her and had shifted from doing all the work to managing people, yet felt more drained rather than freer. She frames this transition, not raw headcount, as the moment a founder needs an integrator.

Seven direct reports pushed her past capacity
She moved from doing the work to managing people who do the work
More management did not equal more time; it meant feeling more drained

“I went from doing all of the work to managing people, do all of the work, and I didn't feel like I had more time.…”
Jasmine Star · 0:02:08

#scaling#operations#founder

Explainer0:04:21

Why trust is the foundation of the CEO-COO relationship

Citing the HBR article, Jasmine highlights that the single most important success factor is a high level of trust between the CEO and COO, built by meeting obligations on both sides. The CEO must support the COO's vision, keep ego in check, and execute, while the CEO grants real authority and decision rights.

Trust is the most consistent success factor across interviews
Trust comes from both sides meeting obligations
The founder must grant real authority and not stymie the COO's career

“the most important being a high level of trust between the CEO and the CEO. Trust comes from meeting obligations on both sides.”
Jasmine Star · 0:04:21

#trust#leadership#delegation

Story· 3

Story0:00:00

The COO who asked 'what would make you fire me?'

Jasmine opens with her COO Jade sitting across from her on a Zoom call and asking what would make Jasmine fire her. The question came after Jade read a Slack thread in which Jasmine described their working relationship in the third person. It sets up the episode's exploration of hiring and defining success for a right hand.

Jade read about herself from a third-person Slack narrative Jasmine wrote
She asked directly what would get her fired
The moment caught Jasmine off guard and framed the whole episode

“She sat across from me and she said, can I ask what would make you fire me? that caught me off guard.”
Jasmine Star · 0:00:00

#leadership#trust#coo

Story0:14:06

Why Jade took a pay cut to become an executive project manager

Jade was in contention to become CEO at her prior company but saw Jasmine's Facebook listing and took both a pay cut and a title demotion to join as an executive project manager. She did it because she believed she could work her way up to running the company, which she ultimately did as COO.

Jade was on track to be CEO elsewhere before applying
She accepted a pay cut and a demotion to start as EPM
She bet on working her way up, and became COO

“Jade, our CEO, took a pay cut and she took a position demotion to work at Social curator.”
Jasmine Star · 0:14:06

#hiring#ambition#coo

Story0:16:19

Jasmine's honest answer: only broken trust would get you fired

Returning to the opening question, Jasmine tells Jade she would only fire her for violating trust, including even small lies. She lists what trust means to her: no stealing, speaking the truth even when unwelcome, pushing back on disagreement, and doing what you say you'll do. She adds that Jade is better at her role than Jasmine could be, so she simply needs her to stay ahead.

The single fireable offense is any violation of trust
Trust includes honesty, pushback, and reliability
Jasmine trusts Jade to be better at the role than she is

“I need you to push back on me when you disagree with me. I need to trust that you will do what you say you…”
Jasmine Star · 0:17:28

#trust#leadership#feedback

Q&A· 1

Q&A0:09:38

What KPI to set for a pure operations role

Responding to a mastermind member's question about KPIs for operational roles, Jasmine explains her cascade: the COO sets KPIs for all leadership and each leader sets KPIs for their team. For a person focused purely on operations, she suggests their KPI could be that 90% of all team KPIs are met, since their job is ensuring everyone has support to hit their goals.

COO sets leadership KPIs; leaders set their teams' KPIs
A pure-ops KPI can be a percentage of all team KPIs being met
The ops person's role is to make sure everyone gets the support they need

“their KPI might be our 90% of all KPIs across the team being met”
Jasmine Star · 0:11:53

#kpi#operations#management

Tool· 1

Tool0:12:58

Turn 'what would make you fire them' into a KPI

Jasmine offers a practical question for defining an ambiguous ops role: name the things this person could do that would make you mad or fire them. Once named, you can make the person responsible for ensuring that thing doesn't happen and turn it into a KPI.

Ask what would make you mad enough to fire the person
Name that specific thing
Make preventing it their responsibility and a measurable KPI

“What are the things that this person can do that would make you mad or fire them.”
Jasmine Star · 0:12:58

#kpi#accountability#hiring

Takeaway· 2

Takeaway0:03:07

The seven reasons companies hire a COO

Jasmine reads from a Harvard Business Review article listing seven reasons companies hire a COO, from implementing the CEO's strategy to testing possible successors. She advises founders to pick just one of the seven to focus on when assessing candidates, because it aligns the candidate's goals with the founder's.

Seven distinct reasons range from executing strategy to retaining a valued executive
No standard set of great-COO attributes exists, so the role has huge variance
Founders should focus on one reason to guide their search

“there are seven basic reasons why companies decide to hire a CEO”
Jasmine Star · 0:03:07

#hiring#strategy#coo

Takeaway0:11:53

The three things Jasmine measures herself on as CEO

Jasmine shares her own KPIs as CEO of the holding company: recruit top talent, get attention for the businesses, and build trust with an audience. She contrasts this with her COO's KPI to underline that every founder's KPIs are different and role-dependent.

Recruit a pipeline of top talent
Get attention for the holding company's businesses
Build trust with an audience

#kpi#ceo#leadership

Frameworks in this episode

Stay Ahead of Me KPI

The Executive-Project-Manager Audition

Insights & moments

✶Explainer· 2

The signal that it's time to hire an operations right hand