CEOs leading companies over 100 employees dedicate up to half their time to recruiting their executive team. Their primary concern becomes building the leadership layer and designing the organization, a significant shift from the focus of CEOs at smaller companies.
If two people are responsible for watering a plant, it dies from either overwatering or neglect. This is why scaling companies must be zealous about assigning a single Directly Responsible Individual (DRI) for every key initiative. Shared ownership means no ownership, especially for cross-functional projects.
Brian Halligan, Sequoia's in-house CEO coach, uses a five-part framework called 'LOCKS' to assess founders: Lovable (can inspire a team), Obsessed (deep founder-market fit), Chip on the shoulder (driven by something to prove), Knowledgeable (domain expert), and Student (a constant learner).
Hiring executives from large corporations like Google or Microsoft into an early-stage startup almost always fails due to a 'massive impedance mismatch.' Their expectations for established processes clash with the startup's reality. HubSpot experienced a near-100% attrition rate with these types of hires.
Use the formula EV > TV > MEV (Enterprise Value > Team Value > My Value) to guide decisions. Immature leaders optimize for their own team's metrics (TV) at the expense of the company's success (EV). This creates silos. The best leaders always solve for the entire enterprise first.
Brian Halligan reflects that being #1 on Glassdoor's 'Best Places to Work' was a sign of misplaced priorities. The company was too employee-centric, and he was too focused on being liked. They deliberately shifted to be more customer-centric, even if it meant a lower employee NPS.
To assess critical thinking, send C-level candidates your board deck under NDA before the interview. Use the conversation to gauge their feedback. A candidate who only offers praise is a red flag; the best candidates will challenge your thinking and provide constructive criticism.
The 2004 Red Sox won by blending homegrown talent with a few strategic free agents. Startups should apply this model: build a strong core by promoting from within, as internal talent is often underrated, and then surgically add experienced external leaders where necessary.
When you have bad news to deliver—like a down-round valuation—don't soften the blow by revealing it in small increments. Take the hit all at once. 'Rip the darn band-aid off, tell everyone the bad news, they're adults, they can handle it, and get it done.'
C-level hiring is exceptionally difficult, with a high failure rate. Data from MongoDB's CEO shows an average of two C-level turnovers per year. HubSpot's co-founder Brian Halligan estimates that at least 50% of newly hired C-level executives are gone within 18 months.
HubSpot's hiring success improved when they stopped hiring candidates with the fewest weaknesses (e.g., consistent 3/4 scores) and instead chose 'spiky' individuals. These candidates elicit strong positive reactions from some interviewers and weaker reactions from others, indicating exceptional strengths alongside known weaknesses.