Lexi Reese on Leading Leaders

A. Leadership and the CEO Role

Leadership is about making other people better and is built on a foundation of trust

Leadership is about making other people better, first as a result of your presence, but in a way that lasts into your absence. First, you need to figure out how to unleash the potential of one person. Once you have done this, the next step is to figure out how unleash the potential of many people, via systems
Trust is the foundational ingredient to make this happen. In Lexi’s experience: “Build trust in substance (what you say and do) and style (how you say and do it)”
Teams with diverse backgrounds and perspectives perform better. It’s easy to default into hiring people like yourself because it feels comfortable and familiar. As you build out your team, prioritize building a team with diverse perspectives

Lexi on prioritizing building diverse teams

“But the core piece for all of you and for all of us is, there is an edge that you can get competitively if you are able to bring perspectives that are different from yours, and make people feel welcome, safe, and valued to bring that difference, because that's what will help you build a better product and a better commercial moment. And that, I think, is one of the hardest things to do at scale.”

Your role will evolve, but articulating vision, mission, and plan remains constant

The CEO job changes at every stage. Mostly in the form of how you prioritize and spend your time
- As this happens, remember where you spend your time (and resources) signals priorities to the rest of the company
What doesn’t change is your responsibility to communicate and articulate the vision, mission, and plan
- What is the vision for the future that you have?
- What’s the mission of the company to make that future a reality?
- What is the plan for making the vision and mission happen?
It’s also important to connect everyone’s roles to the vision, mission, and plan
- Connect qualitatively by establishing clear values and cultural norms
- Connect quantitatively by establishing metrics/KPIs for each team/function
Most of this exists in your head, and you think it's clear. It’s not. Write it down and socialize it.
- Values are “code” for structuring and guiding human behavior

Case Study: Lanai’s Values and Behavioral Norms

Curiosity
We question openly, learn quickly, and share generously.

Community
We celebrate differences, and unite in purpose.

Commitment
We have high standards and 100% say/do ratio.

Clarity
We communicate honestly, directly, and with care.

B. Driving Alignment with Leaders

Set clear expectations with your direct reports.

Set expectations with your direct reports and clearly communicate them with your direct reports
You can use these to hold executives accountable when they are not meeting your expectations
This also helps create trust. Expectations/plans/norms give people structure to operate within

Case Study: Lexi’s expectations of her direct reports

Lexi sets 6 expectations with her direct reports. She uses these to guide her team and hold them accountable.

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I have a high degree of confidence that [your function] will consistently execute well.

It’s not that I don’t want to be involved in the details of your work (I do!) but I’m confident your team’s execution will be stellar regardless. This doesn’t mean mistakes won’t happen, but the quality of output from your team and their response to setbacks is consistently amazing.

You have the skills, commitment, and leadership necessary to lead your team for the company we aim to be in two years.

When we reach that place — that promised land — we’ll have a [your function] team that is beyond the best in the industry, and we’ll be ready to push to the next level.

You’re chronically discontent with where the company and your department is today.

I don’t spend a lot of time challenging you to do more or to do better — you’re the challenger. I more often find myself at the receiving end of aggressive plans from you to do more, to take your department — and in fact the whole company — to the next level.

You exercise great judgment and wisdom when it comes to what’s critical to our business.

You and your team are focused on the right things. You’re cool headed and able to absorb the ups and downs of startup leadership.

You have a paranoia and sense of urgency matching my own.

I’m constantly in a state of mild panic about the company and how we’re doing, and you share this with me and in some sense help relieve me of it. You can operate in this vigilant and paranoid manner while maintaining an eternal optimism that our company can solve any problem that comes our way.

I’d trust you to meet one-on-one with our most critical constituencies on the most difficult topics.

Be it customers, board members, investors, or future employees, I know you’ll think on your feet and represent the company well.

Define role charters and success KPIs for yourself and each of your directs

Start by writing your role charter and a role charter for each of your executives / direct reports

A role charter includes the following information:
- 1. Purpose–The reason the role exists
- 2. Accountabilities–Qualitative expectations for the role
- 3. Parameters for Success–Quantitative metrics they will be held accountable for
- 4. Key capabilities and behaviors–Behavioral norms and expectations
- 5. Decision rights–Where do they own the decision versus the CEO/others
Circulate these charters with your team. You learn a lot when focusing on the role and not the person
These role charters become a system you can use to hold your directs accountable
- Role charters clarify expectations and leave no room for interpretation‍
- “Design the game (and rules) for your team"

Example: Gusto's COO Charter

Problem

When Lexi first joined as COO of Gusto, Josh (CEO/founder) initially struggled with trusting Lexi to make certain decisions. He couldn’t articulate why and Lexi didn’t understand the hesitancy

Solution

Lexi and Josh came up with the role charter for the COO
They defined accountability, KPIs, values, and decision making boundaries
This helped them understand the hesitancy came from Lexi making decisions quickly based on patterns
Josh preferred to make decisions based on data and first principles

COO Role Charter

Set up 1-1s (or other accountability checks) to drive further alignment and regular feedback

Lexi uses 1-1s and believes they are critical – “hold them sacred even when you don’t want to do it”
1-1s create a shared vocabulary and become a way to share feedback and drive accountability
If you don’t want to do 45 minute 1-1s with every executive, consider the office hours framework
- Vlad, Webflow’s founder, sets up 2-hour office hour blocks each week
- Vlad asks his direct reports to pick time if they’d like to catch up with him
- Invariably, he ends up speaking 1-1 with each of his reports on his team
- For leaders that don’t pick time or might need more accountability, he’ll tell them to pick a time
Try to batch 1-1s on a single day (e.g., Monday) if you feel they will be a drag on energy

Example: Lexi’s Approach to 1-1s

Running a great 1-1

Good 1-1s start with you building a deep understanding of your direct reports
- 1) Ask each leader to write a user manual – a document that outlines their working style
- 2) Understand their key strengths – Maximize these strengths by aligning them to the right tasks
- Link 1) and 2) to the top of the 1-1 document, so these can be revisited regularly
Spend the first 5 minutes understanding engagement level, energy drainers/boosters, and feedback
- How are you doing? Scale of one to five? What's your engagement level?
- What's giving your energy, what's draining your energy?
- Do you have any feedback for me?
Shift into accountability (action items review, KPI progress, team updates) and feedback from you
- This becomes a great place to drive cadence/execution and share specific feedback examples
- Don’t forget to highlight successes – data shows 5 positive to 1 critical feedbacks is ideal
Lastly, leave room for open discussion

1-1 Template

Reference Links:

User Manual
Personality/Strengths Assessment
Development Plans

[Date] Agenda (Note: FYI, For Discussion, or ASK - help/hear/handle)

Personal Check-in
- Engagement level (1-5)
- Energy boosters
- Energy drainers
- Feedback for me (help/hear/handle)
Action Items Review
- Follow-up from last meeting
- Administrative updates
Business Progress
- Key metrics and OKRs (team and individual)
- Quarterly review: How do you want me involved in major objectives?
- Situational leadership assessment
Team Updates
- Sub-team health: Pulse, OKRs, metrics
- Highlights and lowlights
- Early warning signs (customer impact, team dynamics, attrition, promotion)
Feedback from Me
- Discussion topics
- SBI (Situation, Behavior, Impact) feedback
Hot Topics
- Weekly/monthly/quarterly focus areas
- Your skill/competence assessment and desired coaching
Open Discussion
- New ideas
- Organizational improvement suggestions
- Product feedback
- Personal satisfaction and growth

Quarterly Career Coffee (Offsite)

Dedicated to personal development and career growth

Remember: This meeting is primarily for you. Feel free to modify the format to best suit your needs. The essentials are progress against objectives, your personal check-in, and identifying areas where you need support.

Failure mode over lack of alignment or regular check-ins

Lack of communication drives unhappiness and misalignment.

Three failure modes

1. Swoop and Poop

The CEO flies in and gives heavy criticism on a project they haven’t been involved in‍

2. Simon Cowell

You haven’t been focused or involved on a project. It launches and you judge it very negatively
Builds resentment as people think “if you care this much, why weren’t you involved earlier?”

3. Mushroom

Drop in randomly give feedback and go missing again
Again, it builds resentment because people see you sporadically and don’t know where you are

Preventing Failure Modes

Communicate. Communicate. Communicate. Expectations need to be set clearly
Say what you do and do what you say. This drives clarity and understanding
Treat others the way they want to be treated. Helps you understand their decision making/actions

Framework for deciding when to intervene with leaders

Default to Trust, Verify with Data:

Establish expectations. Start by giving executives autonomy
Set clear, measurable OKRs and use regular data check-ins
Increase oversight if metrics show consistent issues

Evolve Your Role Deliberately:

Actively "give away your Legos" to create space for strategic work (as trust is built)
Clarify decision-making authority using frameworks like RACI
Adapt your involvement based on the executive's proven competence and the task's criticality

Build a Culture of Transparency and Growth:

Implement regular feedback loops, including weekly check-ins and quarterly deep dives
Encourage open discussion of challenges and proactive problem-solving
Model vulnerability by sharing your own learnings and struggles

Tactics for reducing your direct reports

Look at your reports and figure out who absolutely needs to report to you
Look for points of leverage (i.e., who else in your company might be able to manage your reports)
20 direct reports works early on, but won’t as your company grows and you will become the bottleneck
When communicating the decision, remember that it's the first time others are hearing it,
Communicate clearly by addressing:
- Purpose of the change: Why is it happening?
- Picture of success: What will success look like for everyone?
- Plan: What is the timeline for the change? (e.g., tomorrow, next week, etc.)
- Individual roles: What is each person’s part in making it successful?
Acknowledge that the process may feel difficult or unfamiliar, but ask for their support by explaining the need to reduce your touchpoints to focus on key priorities. Being open and human will help your current reports understand and support the change

Tactics for hiring a leader for a team (e.g., sales) that currently reports the CEO

Clearly communicate the vision and rationale:

Articulate why hiring a sales manager is necessary for the company's growth and success
Explain how this change will benefit the existing sales team (e.g., more support, structured development, better resource allocation)
Be transparent about your need to focus on closing deals while ensuring the team has proper management

Involve the team in the process:

Seek input from the existing sales team on what they need from a manager
Consider including key team members in the interview process for the new sales manager
Use this as an opportunity to reset expectations and get buy-in for the future sales organization

Ensure a smooth transition and integration:

Clearly define the new sales manager's role, responsibilities, and decision-making authority
Create a detailed onboarding plan for the new manager, including introductions to the team and key stakeholders
Establish regular check-ins with both the new manager and the existing team to address concerns and ensure alignment
Gradually transition responsibilities to the new manager while maintaining visibility and involvement in key decisions

Example: Responsibilities and Onboarding (Sales Leader)

Role Charter

Responsibilities:

Sales Strategy and Execution

Develop and implement comprehensive sales strategies aligned with company goals
Establish and optimize sales processes and methodologies
Set and communicate clear sales targets for the team

Pipeline Management

Oversee and optimize the sales pipeline
Implement and maintain a robust CRM system
Ensure accurate and timely reporting of sales activities and forecasts

Customer Relationships

Build and maintain relationships with key accounts
Oversee customer success initiatives to ensure high retention rates
Gather and act on customer feedback to improve products and services

Revenue Forecasting

Develop accurate sales forecasts
Analyze sales data to identify trends and opportunities
Provide regular updates to leadership on sales performance and projections

Team Leadership and Development

Recruit, train, and mentor sales team members
Conduct regular performance reviews and provide ongoing feedback
Foster a culture of high performance and continuous improvement

Key Performance Indicators (KPIs):

Sales Revenue: Meet or exceed quarterly and annual revenue targets
Conversion Rate: Improve lead-to-customer conversion rates
Average Deal Size: Increase the average value of closed deals
Sales Cycle Length: Reduce the average time from lead to closed deal

Decision-Making Authority:

Full authority over sales team hiring, firing, and performance management
Autonomy in developing and implementing sales strategies
Authority to negotiate deals within predefined parameters
Input into product development and pricing strategies

Reporting Structure:

Reports directly to the CEO
Direct reports include all sales team members (until further structure is developed)

Onboarding

Note: In the early stages of growth, it’s unrealistic to assume a leader doesn’t start executing until day 90. Adjust the onboarding plan accordingly. Key is to stay close early and to sufficiently transfer context.

Week 1-2: Orientation and Introduction

Day 1-3:

Welcome meeting with CEO
Review role charter, responsibilities, and authority
Introduce company vision, mission, and values
Tour of office and introduction to immediate team
Set up necessary accounts and tools

Day 4-5:

One-on-one meetings with each sales team member
Introduction to key stakeholders (e.g., Product, Marketing, Customer Success leads)
Review current sales processes, pipeline, and CRM

Week 2:

Deep dive into current sales strategy and performance metrics
Review of top accounts and ongoing deals
Begin shadowing sales calls and meetings

Weeks 3-4: Deep Dive and Assessment

Conduct a thorough analysis of current sales operations
Review historical performance data and identify trends
Meet with cross-functional teams to understand product roadmap and marketing strategies
Attend customer meetings to gain firsthand insight into customer needs and pain points
Begin formulating initial observations and potential areas for improvement

Weeks 5-8: Strategy Development and Team Building

Develop a preliminary sales strategy based on initial observations
Hold a team offsite to build rapport and gather input from the sales team
Begin implementing any quick wins identified in the assessment phase
Start one-on-one coaching sessions with team members
Establish regular team meetings and communication rhythms

Weeks 9-12: Execution and Refinement

Finalize and present a comprehensive sales strategy to CEO and leadership team
Begin implementing new processes or strategies
Conduct first round of performance check-ins with team members
Start contributing to revenue forecasting and pipeline management
Identify key metrics for ongoing performance tracking

Throughout the 90 days:

Weekly check-ins with CEO to discuss progress, challenges, and alignment
Regular updates to the sales team on observations, plans, and changes
Feedback sessions with team members and key stakeholders
Documentation of learnings, decisions, and plans for future reference

End of 90 Days:

Comprehensive review meeting with CEO
Presentation to leadership team on state of sales org, strategy, and future plans
Team meeting to reflect on the first 90 days and align on go-forward plan

Tactics for dealing with cofounder and executive tensions

Co-founders don’t need to be kept happy; they need to deliver and align with the vision and mission.
At work, hierarchy exists, and one person, typically the CEO, is the final decision maker on most things
Outside of work, relationships can be equal, but at work, roles and responsibilities must be clear
Use a role charter to clarify expectations for everyone on the team, including your cofounders
Establish decision making rights and where each leader provides input versus making decisions
- Example: A technical founder may have input on hiring, but the VP engineering is ultimate DM
Cofounders have special status in certain areas (e.g., board decisions) and you can determine these
- Figure these out for you and your cofounders. Make it known, so it’s not misunderstood

B. Useful Meetings

Set expectations and norms around meetings to make them effective

At Lanai, Lexi told the team 80% of time is spent building product / growing customers, 20% is internal and that meetings only happen for three reasons:
- Cadence–Weekly staff meetings. Meetings for driving pace, keeping plans on-time/under budget
- Catalyst–Product reviews, decision-making forums. Meetings for making decisions
- Context–All-hands, offsites. Meetings for sharing context and driving alignment
Every meeting has an agenda based on its purpose (Cadence, Catalyst, and Context)
- In the agenda, mark information as type 1 (informational) or type 2 (requires a decision/discussion). This clarifies whether something needs to be debated
Encourage teams to always consider the outcome/result versus the effort put in
- Example: We delivered X, Y, Z results for customers versus we did all these tasks
Every meeting is an opportunity to hold people accountable, and you must set that expectation.
- Lexi demonstrates this by consistently sharing feedback during meetings or in public settings
- Her general approach is to praise in public and offer critique in private (immediately)
- Don’t wait for 1:1s or the next meeting to deliver critical feedback—bad behaviors can fester if not addressed promptly.

Example: Lexi’s Leadership Meetings

Lexi designed her leadership meeting to be 45 minutes. She finds meetings get sloppy at 60 minutes
Lexi uses the meeting to drive accountability and alignment amongst her executive team

Weekend Updates (5 minutes)

Share personal updates, pictures encouraged

CEO Headlines (7 minutes)

Main priorities and progress against goals: Product Market Fit, Team, Customers, Funding
Competitive Developments
Team Developments

VoC - Customer or Prospect Debrief (7 minutes)

Review event goals and outcomes
Discuss what worked well and areas for improvement

Round the Horn (10 minutes)

Team members share write in advance what is Type 1: Informational updates (async, written), Type 2: Discussion and decision-making (synchronous)
- Accomplishments
- This Week's Priorities
- Help Needed
- FYI items

Final notes (5 minutes)

Calendar
Recap of AIs, owners, deadlines

Tactics for preventing meetings from changing purpose

Meetings typically bleed when expectations are unclear (e.g., leader doesn’t agree with a goal)
For example, you are in a business review and your sales leader begins clarifying the goal
This is avoided with better planning, expectation setting, and agreement upfront with leaders
If a leader agrees with the goal and understands it – they are less likely to question it in the future

Lexi on when meetings bleed

"What I think happens when meetings go off track is that you think you're in a cadence meeting, but people are actually clarifying the goals. You’re a little bit in dispute, without saying you're in dispute, about what is a reasonable goal. You’re saying, 'That looks really low,' and your head of sales is like, 'Fuck off, that sounds really high.' All of that could have been avoided if you had first had the discussion about what is a reasonable expectation for us to deliver this product, what is a reasonable expectation for us to sell this product, and what is a reasonable expectation for us to serve it profitably, durably, and within the financial position we have.”

C. Inspiring Leaders

Ambition starts you setting the “art of the possible” for your team

Ambitious goals start with you presenting the "art of the possible" to your team
If you want to hit an ambitious revenue target (e.g., $150M ARR), it’s important to say it to the team
That said, it must be grounded in reality, or you risk losing credibility with your leaders and team
This happened at Gusto – at one point the team said they could do $200M and the founders asked for $400M without detailed backups. This created animosity between the founders and the leadership team

How to approach the team with ambitious goals?

Begin with a small group (CFO, senior operator, yourself, Chief of Staff)
Create a one-page document outlining customer and revenue goals
Break down the goals into a decision tree showing the key inputs to understand how it will happen
Share the document and decision tree with the team to make ambitious targets more believable

How to deal with an executive you think is lowballing?

If someone thinks the target isn’t possible, they must provide data to support their view, rather than simply saying no
Lexi recently encountered this issue with her Head of Design. She expected him to create a design partner program with 12 partners, but he proposed only 2, which she felt was too conservative and not viable
To address this, Lexi asked him to explain why he believed 2 was sufficient, as she saw it as lowballing
After he broke down the tasks, there were interconnected decisions that Lexi hadn’t considered
While 12 was indeed unrealistic, they both agreed that 2 was too conservative, and they compromised on 7

Tactics for driving executives to be more ambitious

Use situational leadership approach:

Adapt leadership style based on the development level and needs of each individual
Employ different styles like directing, coaching, supporting, or delegating as appropriate

Have alignment conversations:

Discuss and align on development goals, leadership vision, and performance expectations
Ensure clarity on objectives and desired outcomes

Set SMART goals:

Create Specific, Measurable, Achievable, Relevant, and Time-bound goals
Provide clear targets to work towards

Diagnose development levels:

Assess current competence (skill) and commitment (will) levels for the actual goals
Identify areas for growth and improvement

Match leadership styles with the development level of the person for the task

Enthusiastic Beginner (D1):
- Characteristics: Low competence, high commitment
- Leadership style: Directing
- Description: The leader provides specific instructions and closely supervises performance. This approach is best for those who are new to a task but eager to learn.
Disillusioned Learner (D2):
- Characteristics: Some competence, variable commitment
- Leadership style: Coaching
- Description: The leader explains decisions, solicits suggestions, and continues to direct task accomplishment. This approach helps those who have gained some skills but may be experiencing frustration or setbacks.
Capable, but Cautious, Contributor (D3):
- Characteristics: High competence, variable commitment
- Leadership style: Supporting
- Description: The leader facilitates and supports the individual's efforts toward task accomplishment and shares responsibility for decision-making. This approach is for those who are skilled but may lack confidence or motivation.
Self-Reliant Achiever (D4):
- Characteristics: High competence, high commitment
- Leadership style: Delegating
- Description: The leader turns over responsibility for decision-making and problem-solving to the individual. This approach is suitable for highly skilled and motivated individuals who can work independently.
Have regular conversations:
- Discuss goals, diagnose development levels, match leadership styles
- Provide ongoing feedback and adjust approaches as needed
Focus on continuous improvement:
- Encourage learning and development at all levels
- Foster a growth mindset and desire for ongoing progress

Chapters