MemCast

How to be a CEO when AI breaks all the old playbooks | Sequoia CEO Coach Brian Halligan

Brian Halligan shares hard-won lessons from scaling HubSpot and coaching top CEOs, focusing on leadership traits, hiring strategies, and adapting to AI-driven changes in business.

1h 14m·Guest Brian Halligan·Host Lenny Rachitsky·

The LOCK(S) Algorithm for CEO Success

1 / 11

Brian shares his framework for evaluating successful CEOs, emphasizing lovability, obsession, chip-on-shoulder mentality, deep knowledge, and being a perpetual student. This reflects the evolving nature of leadership in fast-moving industries.

Successful CEOs inspire followership through lovability, not just likability
  • Lovability (the 'L' in LOCK) means people would crawl across broken glass to work for them
  • Examples include Steve Jobs who inspired despite being rough-edged
  • Contrasts with traditional charisma; more about creating gravitational pull
  • Measured by whether young talent would enthusiastically join their team
Could I envision a 28-year-old me graduating from business school going to work for this person? Would I crawl across broken glass? Brian Halligan
Steve Jobs, you would say, is kind of rough and maybe not lovable, but he would inspire followership Brian Halligan
Deep founder-market fit outperforms opportunistic entrepreneurship
  • Obsession (the 'O' in LOCK) requires years of immersion in the problem space
  • Skeptical of founders who discovered their problem recently
  • Looks for lifelong patterns of obsessive rabbit-hole diving
  • Evidence includes personal history of deep domain immersion
I'm a little negative on people who came up with this problem to solve six months ago and started a company Brian Halligan
I like people with deep founder market fit who've been thinking about it for a long time and have evidence in their lives of going deep down obsessively down a rabbit hole Brian Halligan
Modern CEOs must be perpetual students of their craft
  • The added 'S' in LOCKS stands for student mentality
  • Top CEOs constantly learn from history and peers like LLMs
  • Studies beyond immediate needs (e.g., Winston Weinberg studying historical business strategies)
  • Contrasts with know-it-all founders who plateau early
They're like LLMs - constantly constantly learning Brian Halligan
They go way back in time and have a lot of history on stuff Brian Halligan

Hiring Like the 2004 Red Sox

2 / 11

Brian advocates for blending homegrown talent with strategic external hires, warning against over-indexing on big-company pedigrees. He shares HubSpot's painful lessons about impedance mismatches in scaling organizations.

Homegrown talent dramatically outperforms big-company hires in scaling startups
  • HubSpot had 100% attrition rate on hires from Salesforce/Google/Microsoft
  • Internal promotions understood cultural context and growth stage
  • Big-company hires expected polished systems that didn't exist
  • Successful exceptions (like David Ortiz in baseball) were rare strategic additions
We hired so many people from Salesforce and Google Microsoft like 100% attrition rate on all those folks Brian Halligan
There's just a massive impedance mismatch when you hire them on what their expectations are versus your expectations Brian Halligan
Spiky candidates with clear weaknesses outperform uniformly 'good enough' hires
  • HubSpot initially hired candidates with no red flags (all 3/4 ratings)
  • Switched to hiring spiky profiles with 4/4 and 2/4 ratings
  • High-performers had glaring weaknesses paired with extraordinary strengths
  • Required cultural tolerance for uneven skill distribution
Almost every time we hired the three out of four, like the person with the least amount of weaknesses Brian Halligan
We went with people with weaknesses. We went with people with challenge stuff Brian Halligan
Blind references reveal truth when conducted with surgical precision
  • Most reference checks are 'box-checking' exercises
  • Effective questions: 'Would you enthusiastically rehire?' (1-10 scale)
  • Parker Conrad's NDA+board deck tactic surfaces real thinking patterns
  • Requires willingness to hear negative feedback before hiring
Would you enthusiastically rehire this person for that role? which I think is a really good question Brian Halligan
Parker Conrad has a good hack...he has them sign an NDA and sends them the last board deck and schedules a half-hour interview about the deck Brian Halligan

The CEO's Evolving Role in the AI Era

3 / 11

Brian analyzes how AI accelerates decision cycles and changes the fundamental rhythm of leadership, requiring faster adaptation and more frequent strategic pivots than ever before.

AI enables more projects but creates a tax on strategic optionality
  • Teams accomplish in 2 months what took 1 year pre-AI
  • Creates pressure to pursue multiple strategic paths simultaneously
  • Paradoxically reduces focus on core business
  • Requires conscious pruning of initiatives (e.g., OpenAI refocusing on ChatGPT)
Something that used to take you a year takes two months now Brian Halligan
There's a massive tax on optionality when you can move this fast and try a lot of things Brian Halligan
Quarterly planning cycles have replaced annual strategies
  • AI-driven pace makes annual plans obsolete within weeks
  • CEOs must make irreversible decisions faster
  • Requires comfort with committing despite uncertainty
  • HubSpot shifted from yearly to quarterly planning cadence
The planning cycles used to be a year. I think the planning cycles now are 3 months long Brian Halligan
It puts pressure on the CEOs to be faster and better decision makers Brian Halligan
Five-tool CEOs are becoming the new norm in AI startups
  • Rare previously (e.g., Jobs couldn't code, Bezos wasn't technical)
  • Now common: Brett Taylor types who code, sell, and inspire
  • AI lowers some skill barriers but raises expectations
  • Creates bifurcation between superstar founders and others
The thing that's kind of new now are five tool CEOs like Brett Taylor's one Brian Halligan
You can code, you have taste, you have vision, you can sell the product, you can convince employees Brian Halligan

Scaling Through Crisis

4 / 11

Brian reframes crises as opportunities for organizational growth, sharing how HubSpot's worst moments led to its most significant improvements in product quality and operational rigor.

Never waste a good crisis - they force necessary overcorrections
  • HubSpot's major outage led to complete deployment process overhaul
  • Crises provide political capital for radical changes
  • Requires willingness to 'swing pendulum hard the other way'
  • Most durable improvements came from worst moments
Most of the good things that happened at HubSpot came out of a crisis Brian Halligan
We purposely swung the pendulum hard the other way Brian Halligan
Public vulnerability builds trust during organizational trauma
  • Brian cried publicly after HubSpot's major outage
  • Showed team the human cost of failure
  • Created shared ownership of recovery
  • Contrasted with traditional 'strong leader' persona
I remember that company meeting. I cried in front of the whole company Brian Halligan
He couldn't believe it happened to us. And I remember using the next play slide on that one Brian Halligan
Companies more often die from overeating than indigestion
  • Most failures stem from overexpansion vs. competition
  • HubSpot's pivot to CRM revealed operational immaturity
  • Requires recognizing when growth outpaces capability
  • Analogous to sports teams making unforced errors
Companies are far more likely to die of overeating than indigestion Brian Halligan
Most of them are self-inflicted Brian Halligan

The Feedback Imperative

5 / 11

Brian identifies giving direct feedback as the most critical yet underdeveloped skill in young founders, sharing frameworks to make difficult conversations more natural and effective.

Giving feedback is the #1 skill young founders must master
  • Founders often avoid difficult conversations
  • Creates compounding organizational debt
  • Requires normalizing regular feedback at all levels
  • Best CEOs develop this skill within first 2 years
It's that feedback thing. All of the CEOs are building their teams Brian Halligan
Those types of conversations are very tricky and quite unnatural for homo sapiens Brian Halligan
Peer groups accelerate feedback skill development
  • Sequoia's 'kids table' (under 100 employees) shares struggles
  • Normalizes that all founders struggle with feedback
  • Provides safe space to practice
  • More effective than top-down coaching
Misery loves company on this...they talk about this with each other Brian Halligan
It's actually much more effective when their peers weigh in Brian Halligan
Founders must learn to detect organizational BS
  • Scaling creates information asymmetry
  • Teams 'sell' their version of reality
  • Requires developing BS detection through pattern recognition
  • HubSpot used cross-functional metrics to surface truth
They're constantly being spun. Everyone's trying to sell to them Brian Halligan
They have to all get good at the inspiration thing over time Brian Halligan

Cultural Evolution at Scale

6 / 11

Brian traces HubSpot's intentional shift from employee-centric to customer-centric culture, revealing how metrics and rituals must change as companies grow beyond startup phase.

Companies must choose their primary constituency: employees, customers, or investors
  • Early HubSpot over-indexed on employee happiness (#1 on Glassdoor)
  • Realized customer NPS of 25 vs. employee NPS of 60 was misalignment
  • Shifted comp plans to tie to retention/NPS
  • Requires conscious tradeoffs between constituencies
We were very employee centric more than customer centric in the first several years Brian Halligan
I would give up 10 points of employee net promoter score to get 10 points of customer net promoter score Brian Halligan
Customer panels should directly inform executive decisions
  • Monthly management meetings featured customer panels
  • Brian personally asked 'tricky questions' to surface pain points
  • Board meetings included live customer feedback
  • Prevented insulation from market realities
We would have a customer panel come on and that customer panel I would run the panel and ask very tricky questions Brian Halligan
My favorite question is what do you love about HubSpot and then what do you hate about HubSpot Brian Halligan
EV > TV > MV framework prevents organizational silos
  • Enterprise Value > Team Value > My Value
  • Counteracts natural tendency to optimize for local metrics
  • Must be reinforced in performance reviews
  • Example: Sales prioritizing bookings over implementation pain
Where they would fall down was they didn't solve for EV but they'd solve for TV over EV Brian Halligan
The immature managers who didn't scale really saw for themselves and sub as they saw for themselves kind of suboptimized for their peers Brian Halligan

The DRRI Principle

7 / 11

Brian explains why 'Directly Responsible Individuals' must own cross-functional outcomes, using the vivid metaphor of plant-watering to illustrate accountability pitfalls in scaling organizations.

If you want to kill a plant, have two people water it
  • Shared accountability creates diffusion of responsibility
  • Results in either overwatering (micromanagement) or neglect
  • Scaling requires clear single points of ownership
  • Especially critical for cross-functional initiatives
If you want to kill a plant, have two people water it Brian Halligan
The plant would either be over watered and die or not watered at all and die Brian Halligan
DRRI becomes religious doctrine at scale
  • Small teams can operate without formal DRRI
  • Beyond 100 employees, ambiguity causes systemic failures
  • Requires empowering owners to direct other teams
  • HubSpot reduced interview panels from 8 to 4 to clarify ownership
Once it gets to the adults table, people get deep religion on DRRI Brian Halligan
Everything important happens cross-functionally inside a company at scale and you need someone powerful to own it Brian Halligan
Founders must overcome trust issues to scale delegation
  • Brian admits only trusting small inner circle
  • Created scaling bottleneck at HubSpot
  • Requires systematic verification vs. gut checks
  • Parallels to moving from founder-led to process-driven sales
I have trust issues. I only trusted a small number of people at HubSpot Brian Halligan
That was a scaling limit. That was a limit for me Brian Halligan

The Founder's Journey

8 / 11

Brian reflects on the psychological toll of building HubSpot over two decades, offering unvarnished perspective on the sacrifices required to build a lasting company.

Founder obsession requires surrendering work-life balance
  • Brian worked 60-70 hour weeks for 20 years
  • Current founders even more intense (7 days/week)
  • Only exception: Kareem from Clay advocates balance
  • Tradeoff between extraordinary outcomes and personal cost
People talk about 996. It's way more than that. The founders are seven days a week Brian Halligan
I don't know any of the founders I work with that have work life balance Brian Halligan
Near-death experience clarified CEO succession timing
  • Snowmobile accident forced existential reflection
  • Realized misalignment with later-stage CEO role
  • Prompted transition to Yamini Rangan
  • Demonstrates importance of self-awareness in leadership transitions
I don't really like being CEO of an 8,000 person company. Doesn't really suit me Brian Halligan
If I make it out of here alive, I'm out. And so that's exactly what happened Brian Halligan
Constructive dissatisfaction drives perpetual improvement
  • Board described Brian as having 'perpetual state of constructive dissatisfaction'
  • Current generation of CEOs more humble than predecessors
  • Combines ambition with relentless focus on gaps
  • Different from toxic perfectionism
Perpetual state of constructive dissatisfaction Brian Halligan
They're always a little bit dissatisfied with where they are and very focused on the end state Brian Halligan

AI's Impact on Go-To-Market

9 / 11

Brian predicts how AI will transform sales and marketing funnels, from avatar-driven customer education to AI-assisted sales calls, while preserving the human element in enterprise relationships.

Enterprise sales will be the last white-collar job AI replaces
  • AI excels in software dev, customer support, legal
  • Trust-based sales relationships resist automation
  • Requires nuanced understanding of organizational politics
  • Even with AI tools, human judgment remains critical
Ye old enterprise sales where there's actual trust built up between two carbon based life forms will be very very very late to go Brian Halligan
Enterprise sales hasn't changed that much since the 1990s Brian Halligan
AI avatars will revolutionize top-of-funnel education
  • Customers will start research in AI interfaces (Gemini, ChatGPT)
  • Company websites will feature all-knowing avatar guides
  • Stores conversations in CRM for human follow-up
  • Requires rethinking content strategy for AI consumption
I think every website will change and there'll be an all-knowing avatar on that homepage Brian Halligan
They will stay in there and do lots more research and be incredibly well educated Brian Halligan
Deployment engineers are the new sales engineers for AI products
  • AI tools require significant implementation support
  • Renamed from 'sales engineers' to reflect hands-on work
  • Critical for enterprise adoption despite title change
  • Parallels to early cloud adoption challenges
They're technical. They help you implement it. They connect all your systems. They customize it Brian Halligan
They call their SEs or their system consultants for deployed engineers Brian Halligan

The Scaling Paradox

10 / 11

Brian articulates the fundamental tension between starting and scaling companies today - while technology makes founding easier than ever, building durable institutions has never been harder.

Starting companies has never been easier; scaling has never been harder
  • Cloud/AI reduce technical barriers to entry
  • Explosion of new companies creates noise
  • Distribution becomes primary constraint
  • Requires exceptional execution to stand out
Starting a company has never been easier. Scaling one into a durable, high impact organization has never been harder Brian Halligan
The number of companies formed is going to mushroom over the next 10 years relative to the last 10 years Brian Halligan
Founders dramatically underestimate scaling complexity
  • Early stage focuses on product-market fit
  • Scaling requires entirely new skills (org design, process)
  • Most first-time founders lack frame of reference
  • HubSpot's scaling challenges were self-inflicted
People are very bad at this and HubSpot was too Brian Halligan
I didn't know that was going to be the case Brian Halligan
Two steps forward, one step back is the reality of scaling
  • External perception: smooth upward trajectory
  • Internal reality: constant crises and setbacks
  • Requires resilience and long-term orientation
  • Pattern holds across companies and industries
Inside it was two steps forward, one step back, two steps forward, one step back Brian Halligan
A lot of times it was a crisis that caused that step back Brian Halligan

Practical Hagganisms

11 / 11

Brian shares his collection of memorable leadership principles forged through experience, from 'don't nibble the sandwich' to 'never waste a good crisis' - each with hard-won lessons behind them.

When eating a sandwich, don't nibble - rip the bandaid off
  • Ruth Porat's principle for decisive action
  • Applied to layoffs: better one deep cut than serial small ones
  • Prevents prolonged organizational anxiety
  • Requires courage to deliver full bad news upfront
When you have to eat a sandwich, don't nibble Brian Halligan
Tell everyone the bad news. They're adults. They can handle it and get it done Brian Halligan
Next play mentality prevents error compounding
  • From Duke coach Mike Krzyzewski
  • After mistakes, focus immediately on next action
  • Prevents defensive overcompensation
  • HubSpot used visual reminders during crises
Next play because there was an unforced error and we need to deal with it and kind of move on Brian Halligan
Make their error, forget about it, and move back down the other side of the court and run the play Brian Halligan
There are no silver bullets - only lead bullets
  • Scaling requires consistent execution of fundamentals
  • No single hire/feature/event creates breakout success
  • Contrasts with founder hopes for 'magic moments'
  • Builds appreciation for compound growth
I always thought incorrectly that we would have one hire or one investor or one event that would be a silver bullet Brian Halligan
Inside it was two steps forward, one step back Brian Halligan
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