CEOfriend - Playbook

Playbooks

Hiring Your First Senior Leaders

The challenge: You can't do everything yourself anymore, but hiring wrong at this stage is expensive and demoralizing.

Hire for the next 18 months, not 18 years. The person who can run a 50-person team is rarely the right hire when you have 12 people. Ignore the VC advice to "hire ahead" — you need someone effective now.
Write the scorecard before the job spec. Define the 3-5 outcomes this person must achieve in year one. If you can't articulate what success looks like, you're not ready to hire.
Do the job yourself first. Never hire a Head of Sales before you've closed deals yourself. You need to know what good looks like to recognize it in candidates.
Back-channel aggressively. The references a candidate gives you are rehearsed. Find people who worked with them that they didn't suggest. LinkedIn makes this easy.
Spend 15-20 hours with finalists before deciding. Have them do real work — a 90-day plan, a strategy memo, a mock board presentation. Chemistry in interviews doesn't predict performance.

Go deeper:

a16z: The First Principles of Executive Hiring — comprehensive 2025 guide to scaling your leadership team
a16z: How to Hire a Strong Founding Team — recruiting as a core founder skill
Delian Asparouhov: How to Interview an Executive — practical Khosla Ventures framework
"Who" by Geoff Smart — the A Method for Hiring

Discuss with: Leadership Architect

Managing Cash & Runway

The challenge: Revenue is growing but cash is tight. You're not sure whether to invest or conserve.

Know your "default alive" number. If you stopped all growth spending today, would you reach profitability before cash runs out? This single question clarifies every decision.
Run a 13-week rolling cash forecast. Monthly P&L is for accountants. Weekly cash position is for survival. Update it every Friday — it takes 20 minutes once you have the template.
Separate growth spend from operating costs. Know exactly what you're spending to grow vs. what you're spending to run. This lets you cut intelligently if needed.
Invoice faster, pay slower (within reason). Tighten payment terms for new customers. Negotiate longer terms with suppliers. The cash conversion cycle is free money.
Keep 6 months runway as a floor, not a target. Below this, you're fundraising from weakness. Above 12 months, you're probably under-investing. The sweet spot is 8-10 months.

Go deeper:

Scaleup Finance: How Much Runway You Really Need in 2025 — updated benchmarks for today's funding environment
"Simple Numbers, Straight Talk, Big Profits" by Greg Crabtree — clearest book on SME finance
Float — cash flow forecasting tool

Discuss with: Investor & Finance Advisor

Preparing Board Meetings

The challenge: You've got a board now, but meetings feel performative rather than useful.

Send materials 48 hours ahead — and expect them to be read. If you're presenting slides in the room, you're wasting expensive time. Calibration should happen before the meeting.
Structure around decisions, not updates. Every board meeting should have 1-2 decisions you need the board's input on. "For information" sections should be minimal.
Lead with lowlights, not highlights. Boards add most value when discussing problems. If you're hiding issues, you're paying for advisors you're not using.
Use the same metrics every time. Pick 5-7 KPIs and show them consistently. Changing metrics looks like you're hiding something (even when you're not).
End with specific asks. "I need an intro to X," "I need help thinking through Y," "I need you to approve Z." Vague asks get vague help.

Go deeper:

Sequoia: Preparing a Board Deck — gold standard from day one
Lenny Rachitsky: Investor Update Template — simple monthly format
"Startup Boards" by Brad Feld — the definitive guide

Discuss with: Governance Advisor

Making Big Strategic Decisions

The challenge: You're facing a fork in the road — new market, acquisition, pivot — and the stakes feel high.

First, decide if it's reversible. Reversible decisions should be made fast by individuals. Irreversible decisions deserve slow, collective deliberation. Most decisions are more reversible than they feel.
Run a pre-mortem. Imagine it's a year from now and this decision was a disaster. Write down why it failed. This surfaces risks your optimism is hiding.
Seek out the strongest opposing view. Find someone smart who disagrees with you and understand their reasoning fully before deciding. If you can't steelman the counterargument, you haven't thought hard enough.
Set a decision deadline. Parkinson's Law applies to decisions too. Without a deadline, analysis becomes procrastination. "We'll decide by Friday" focuses the mind.
Write down your reasoning. Not for others — for yourself. In six months, you'll want to know why you decided this way. It also forces clarity you won't get from just thinking.

Go deeper:

Farnam Street: The Pre-Mortem — Kahneman's favourite technique
Farnam Street: Reversible vs Irreversible Decisions — Bezos's Type 1/Type 2 framework
"Thinking in Bets" by Annie Duke — decision-making under uncertainty

Discuss with: CMO Advisor, Investor & Finance Advisor

Founder Effectiveness & Energy

The challenge: You're working harder than ever but feel less effective. Something needs to change.

Audit your calendar for a week. Categorize every hour: creating, managing, selling, administering, firefighting. The results will horrify you — and show you where to cut.
Protect your mornings. Do your most important thinking work before 11am. Meetings, emails, and Slack are for afternoons. This single change is worth weeks of productivity.
Give away your Legos. The tasks you're best at are often the ones you most need to delegate. Holding onto them feels safe but stunts both you and your team.
Distinguish urgent from important. Most "urgent" things aren't important. Most important things don't feel urgent. Block time for important-but-not-urgent work or it will never happen.
Schedule recovery like you schedule meetings. Exercise, sleep, and time off aren't luxuries — they're infrastructure. Burnout is expensive; prevention is cheap.

Go deeper:

Sam Altman: Productivity — short, practical, from someone who knows
First Round: Give Away Your Legos — the emotional side of delegation
"The Effective Executive" by Peter Drucker — still the best

Discuss with: Leadership Architect

Pricing & Commercial Strategy

The challenge: You suspect you're underpriced but fear losing customers if you move.

Price on value, not cost. What your product costs to deliver is irrelevant to what customers will pay. Focus on the value you create for them, then capture a fraction of it.
Raise prices for new customers first. Test higher prices with new prospects before touching existing accounts. You'll learn price sensitivity with lower risk.
Segment your pricing. Different customers get different value from your product. One price for everyone leaves money on the table with high-value customers and prices out low-value ones.
Communicate price increases with confidence. "Due to increased costs" is weak. "We've invested significantly in X, Y, Z" positions the increase as justified. Never apologize.
Watch for the "too easy" signal. If no one ever pushes back on price, you're too cheap. If you're closing 80%+ of proposals, raise prices until you're closing 50-60%.

Go deeper:

"Confessions of the Pricing Man" by Hermann Simon — the master class on pricing
"Monetizing Innovation" by Madhavan Ramanujam — how to price before you build
ProfitWell — pricing analytics (free tier available)

Discuss with: CMO Advisor

Letting Someone Go

The challenge: You know it's not working, but you've been avoiding the conversation.

If you're asking "should I fire them?" — you already know. The question in your head is the answer. You're just looking for permission. Delaying makes it worse for everyone.
Own the failure. In most cases, you hired wrong, set unclear expectations, or failed to address problems early. This framing is fairer and makes the conversation easier.
Preserve their dignity. You can take someone's job; you don't need to take their self-respect. Let them shape the narrative. Offer a reasonable reference. Be generous with notice.
Be direct and brief. "I've decided this isn't working and we need to part ways" is clearer than 20 minutes of preamble. They know why they're in the room.
Communicate to the team quickly and consistently. Your remaining team will care deeply about how you treat departing colleagues. Handle it poorly and you'll lose their trust. Handle it well and you'll earn it.

Go deeper:

a16z: Preparing to Fire an Executive — Ben Horowitz on doing it with dignity
a16z: It's Never Too Early to Fire — why waiting makes everything worse
ACAS: Dismissals — UK employment law basics
"Radical Candor" by Kim Scott — Chapter 6 on difficult conversations

Discuss with: Leadership Architect, Governance Advisor

Fundraising & Investor Relations

The challenge: You're considering raising, or managing existing investors who want more than you can give.

Fundraise when you don't need to. The best time to raise is when you have momentum and options. Desperation is visible and expensive.
Your narrative matters as much as your numbers. Investors buy the story of where you're going, validated by proof of where you've been. Craft a compelling arc before you open the deck.
Target 20-30 investors, not 100. Research deeply. Personalize outreach. A warm intro is worth 50 cold emails. Quality of conversation beats quantity of meetings.
Send monthly updates even when you're not raising. Building relationships before you need them is the whole game. Updates take an hour; the trust they build is invaluable.
Know your walk-away terms. Before you start, decide what terms you won't accept. Negotiating without a bottom line means you'll regret whatever you sign.

Go deeper:

Lenny's Newsletter: A Playbook for Fundraising — comprehensive guide
Lenny Rachitsky: Investor Update Template — monthly format
"Venture Deals" by Brad Feld — Chapters 4-7 on term sheets are essential
DocSend — track who's reading your deck

Discuss with: Investor & Finance Advisor

Scaling Operations

The challenge: What worked at £2M is creaking at £8M. You need systems but hate bureaucracy.

Document when it hurts. The third time you explain the same thing, write it down. Not before (premature process) and not much after (you'll forget the pain).
Build for 3x, not 10x. Over-engineering systems for future scale you may never reach wastes time. Build what you need now plus a bit of headroom.
One throat to choke per problem. Ambiguous ownership kills execution. Every project, process, and metric should have exactly one person accountable.
Meetings are a smell. If you need recurring meetings to coordinate, your structure is wrong. Good systems reduce meeting load; bad ones increase it.
Let go of the early chaos (a little). Some founders love the scrappy early days. But your team needs clarity to do their best work. Process isn't bureaucracy; it's kindness.

Go deeper:

First Round: Give Away Your Legos — on letting go as you scale
"The E-Myth Revisited" by Michael Gerber — Part 2 on systems thinking
Ramp: The Art of Hiring — scaling insights from top founders

Discuss with: Leadership Architect

Competitive Pressure

The challenge: A competitor is making noise, or a bigger player just entered your space.

Don't panic. Most "threats" aren't. Press releases and funding announcements are designed to scare you. Look at actual customer behaviour, not headlines.
Double down on your wedge. You can't out-feature a bigger competitor. Own one thing so completely that customers with that need can't imagine choosing anyone else.
Talk to churned customers, not just retained ones. If you're losing deals, find out why. The pattern will reveal whether competition is real or imagined.
Compete on speed, not resources. Big companies are slow. Your advantage is cycle time — faster releases, faster customer response, faster decisions.
Consider whether to fight or differentiate. Sometimes the right response to a competitor is to move into adjacent space they can't follow. Not every battle is worth winning.

Go deeper:

"Good Strategy Bad Strategy" by Richard Rumelt — what strategy actually is
"7 Powers" by Hamilton Helmer — understanding sustainable competitive advantage
Crayon — competitive intelligence platform

Discuss with: CMO Advisor

Monthly Briefings

Each month, we publish a short take on one challenge founders are facing — with curated resources and a prompt to discuss with your advisor.

January 2025: Annual Planning That Actually Works

The challenge: It's January. You know you should have a plan for the year. But last year's plan was obsolete by March, and the year before that you never really finished it. How do you create something useful without disappearing into a spreadsheet for two weeks?

Start with the one question that matters: "What would make this year a success?" Not ten things. One thing. If you achieve nothing else, what would make you look back in December and say "that was a good year"? Maybe it's hitting £5M ARR. Maybe it's hiring a leadership team you trust. Maybe it's getting to profitability. Everything else flows from this. Write it down. Make it specific. Make it measurable. If you can't say whether you achieved it, it's not clear enough.
Work backwards from the goal, not forwards from today. Most founders plan by asking "what should we do next quarter?" This produces incremental thinking. Instead, ask: "If we're going to hit X by December, what must be true by September? By June? By March?" This reveals the critical path — and often shows you're not being ambitious enough about the early milestones.
Identify the 3-5 bets that will determine the year. A "bet" is a decision with meaningful uncertainty and meaningful upside. "Hire a VP Sales" is a bet. "Keep doing what we're doing" is not. Your annual plan should make explicit what you're betting on and what you're betting against. If everything in your plan is safe, you're not planning — you're coasting.
Build in quarterly resets, not annual reviews. The plan you make in January will be wrong by April. That's fine — but only if you've scheduled time to revisit it. Block a half-day at the end of each quarter to ask: "Given what we now know, would we still make the same choices?" This isn't failure; it's learning.
Communicate the plan in one page, not fifty. If your team can't remember the plan, it doesn't exist. Distil everything into: the one thing that defines success, the 3-5 bets you're making, and the key milestones for Q1. Everything else is appendix. Complexity is where plans go to die.

The Annual Planning Conversation

Before you build your plan, try answering these questions. Better yet, discuss them with your leadership team — or with one of your CEOfriend advisors.

On last year:

What actually drove our results — was it what we planned, or something else?
What did we say we'd do that we didn't? Why?
What do we know now that we didn't know in January?

On this year:

What's the one thing that would make this year a success?
What are we betting on? What are we explicitly not doing?
What's the biggest risk to the plan? What would we do if it materialised?

On the team:

Do we have the right people to execute this plan?
Where are the gaps? When do we need to fill them by?
Is everyone aligned on what matters most?

Go deeper:

Burkland: Annual Financial Planning Resources for Startups — comprehensive 2025 planning guides
Sam Altman: Productivity — "Picking the right thing to work on is the most important element of productivity"
Farnam Street: Reversible vs Irreversible Decisions — helps identify which bets need deep analysis
"Good Strategy Bad Strategy" by Richard Rumelt — particularly the section on "the kernel" of strategy

Discuss with: Investor & Finance Advisor (for financial targets), Leadership Architect (for team planning), CMO Advisor (for commercial assumptions)

February 2025: The 90-Day Senior Hire

The challenge: You've just hired someone senior — a VP, a Head of, a C-level. The search took months. Now they've started, and you're not quite sure what to do with them. How do you set them up for success without micromanaging, and spot problems before it's too late?

Agree on 90-day outcomes before day one. Not activities. Outcomes. "Understand the business" is an activity. "Present a diagnosis of our sales pipeline with three recommendations" is an outcome. Write down 3-5 things that, if achieved, would make you confident the hire is working. Share them explicitly. Ambiguity is the enemy of success.
Front-load your time together. The instinct is to give them space: "I hired someone senior so I don't have to be involved." Wrong. The first 30 days should have more CEO time, not less. Daily check-ins in week one, then twice-weekly, then weekly. You're not micromanaging — you're calibrating.
Expect them to listen before they fix. A great senior hire spends the first 30 days asking questions, not proposing solutions. If they're telling you what's broken in week two, they're either a genius or (more likely) they're pattern-matching from their last company without understanding yours. Be suspicious of early confidence.
Introduce them to the business, not just the team. They need context you take for granted. Set up sessions with customers, walk them through the financials, explain the history. The biggest mistakes new executives make come from missing context, not missing skill.
Have the honest conversation at day 45. Don't wait until day 90 to give feedback. At the halfway point, be direct: "Here's what's working, here's what's not, here's what I need to see more of." If they're defensive or dismissive, that's data. If they're curious and adaptive, that's also data.

Signs It's Working (by day 90):

They're teaching you things about your business you didn't know
The team is energised, not anxious
They've made at least one decision you wouldn't have made — and it was right
You're thinking about bigger problems because they've taken things off your plate
They're asking for more responsibility, not more guidance

Signs It's Not (by day 90):

You're still explaining basic context you covered in week one
They're blaming the team, the product, or the market for lack of progress
The team is coming to you with concerns — or worse, going quiet
You find yourself doing their job "just this once" repeatedly
Your gut says something is off, even if you can't articulate it

The Uncomfortable Truth

Most failed senior hires are visible by day 60. Most founders don't act until month 6 or later. The cost isn't just salary — it's the opportunity cost of the right person not being in the role, plus the damage done to the team's trust and momentum.

If it's not working, the kind thing — for everyone — is to act quickly.

Go deeper:

a16z: The Hiring Process — step-by-step guide including onboarding executives (2025)
W Talent Solutions: Executive Onboarding 90-Day Guide — practical month-by-month framework
First Round: Give Away Your Legos — what you need to let go of for them to succeed
"The First 90 Days" by Michael Watkins — the classic guide (give it to your new hire)

Discuss with: Leadership Architect

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Last updated: December 2025