How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work)

1. Distinguish Founder from CEO

Accept that being a founder (a state of being, an attitude) is separate from being a CEO (a craft). Both are equally important for building an ascendant startup, so actively work on developing CEO skills like hiring, financial management, and growth strategy.

2. Cultivate Your CEO Craft

Actively work on developing the skills required to be a CEO, such as hiring, managing financials, growth strategy, roadmapping, planning, and people management. Do not use ‘Founder Mode’ as an excuse to avoid learning these essential operational skills.

3. Listen to Your Intuition

In existential moments, get still, quiet, and alone to listen to your ’little voice’ (intuition), which comes from a deep understanding of self, not just your brain. Trust this voice, especially when well-resourced (rested, fed, loved), as it’s often right and fear is a poor decision-maker.

4. Counter ‘Ready Fire Aim’

Overcome improvisational tendencies by engaging in basic business design and planning. Start by defining what you’re working backwards from (exit, fundraise, profitability), quantify what needs to be true, identify required actions/resources, and shorten feedback loops.

5. Master Startup Acquisition (Magic Box)

Instead of putting your company ‘for sale,’ seduce a buyer by making them fall in love with a future fantasy. Learn their needs, prove how your solution enables their fantasy with easy evidence, and then quantify the future value to their business, shifting focus from past performance to future potential.

6. Avoid Puncturing the Fantasy

During acquisition talks, do not do anything that might break the buyer’s fantasy. Ensure your books are in order, investors are aligned, key team members are committed, and you are a positive presence to work with.

7. Negotiate Asynchronously with Corp Dev

When dealing with corporate development, who are expert negotiators, always move negotiations offline. State that you need to see proposals in writing to socialize with advisors and co-founders, avoiding live negotiation where you are at a disadvantage.

8. Entice, Don’t Push, Buyers

When trying to move an acquisition forward, avoid ultimatums or pushing for a compelling event. Instead, use enticing language, such as mentioning an upcoming fundraising round that would make your company too expensive, to create urgency without being confrontational.

9. Define Hiring Success First

When hiring, don’t start with a job description. Instead, work backwards by defining what success looks like for that role 12 months from now, then seek candidates who have already achieved similar outcomes in their past roles.

10. Hire ‘Pulled’ Candidates

Prioritize candidates who have a history of being ‘pulled’ into new roles by previous bosses or colleagues due to their outstanding performance. This indicates a track record of creating ‘raving fans’ and high value.

11. Assess for Core Values

Codify your company’s core values and integrate them into your hiring process, using specific interview stages or a dedicated team to evaluate candidates’ alignment with these values.

12. Filter Candidates with a Simple Question

For recruiters, use a quick filter by asking candidates how many of their last ex-bosses would get on the phone and say they are amazing. Any equivocation in their answer should be considered a red flag.

13. Hire the Right Executive Archetype

For senior roles, understand the three executive archetypes: Architect (builds playbooks from scratch), Optimizer (refines existing playbooks), and Scaler (finds leverage for 10x growth). Hire an executive who has explicitly performed that specific type of work before to ensure success.

14. Work Backwards from Business Milestones

Remember that hiring is never the goal itself; it’s a means to an end. Tie all hiring needs back to specific business milestones (fundraise, exit, profitability) and quantified goals, defining the resource gap before seeking a new hire.

15. Define Your Ideal Customer Profile (ICP)

Before selling, clearly define who you truly want to sell to, including their qualifications, discovery questions, and ‘kill criteria’ (reasons not to sign them). Focus on a ‘white-hot center of opportunity’ with a small, highly satisfied customer base before expanding.

16. Identify Your Uncommon Denominator

For marketing and positioning, clearly articulate what makes your company great that your competitors (or the status quo) are not. Represent this unique differentiation consistently in your branding, artifacts, and identity.

17. Diversify Demand Generation Experiments

Broaden your approach to demand generation beyond familiar methods. Explore various channels and use a high-impact/low-effort matrix or ‘brain writing’ to identify and run 3-4 experiments per channel.

18. Codify a Repeatable Sales Playbook

Systematize your sales process by codifying a playbook that outlines how to conduct conversations, perform discovery, handle objections, deliver demos, and move to close. This transforms individual selling into a scalable machine.

19. Avoid Plugging Funnel Math

When planning for growth, do not start with a desired revenue target and then plug in funnel math backwards. Instead, use historical data (3-12 months) to make reasonable assumptions about funnel changes, building up to future projections for a more realistic financial conversation.

20. Embrace ‘One Life’ Mentality

Adopt the motto ’there is only one life’ to show up consistently as yourself across all settings (work, social, family). This fosters genuine connections and helps you enjoy your work more by breaking down artificial boundaries.

21. Practice Brain Writing

When ideating or brainstorming, use ‘brain writing’ instead of live discussion. Expose an idea, then have everyone write their opinions, comments, and edits asynchronously and anonymously to dampen the ‘founder effect’ and include diverse processors (introverts, extroverts, fast/slow thinkers).

22. Address CEO Failure Modes

Recognize and work on common CEO failure modes such as being a Robot (emotionless), Pleaser (avoiding hard decisions), Perfectionist (slow to act), Angry (toxic), Laissez-faire (ignoring management), Riding the Brake (too slow), Riding the Accelerator (too fast), Ready Fire Aim (poor planning), or Micromanager (disrespectful). Self-awareness and targeted development are key.

23. Establish Company Rhythm

Learn how to run a company well by establishing a clear, unmistakable rhythm in its operations. This consistent pattern is evident in every well-run business.

24. Ensure Sustainable Job Fit

For sustainable success in any job, ensure three things are true: you are good at it, you like it, and the market cares about it. If any of these are off, you likely won’t stay in that role long.

25. Work ‘On’ the Business

Regularly step back from the day-to-day operations (‘in the business’) to work ‘on the business.’ This involves defining where you’re headed, why, and how you’ll measure progress, which is crucial for strategic direction.

26. Prioritize Company Health

Actively address the four common company failure modes: choosing the wrong market, failing to build something people want, founder dysfunction (e.g., co-founders not getting along), and poor execution. These are critical for survival and growth.