Jonathan Lowenhar
Jonathan Lowenhar is the co-founder of Enjoy The Work, an executive coaching firm that helps founders become great CEOs. Over the past decade, Enjoy The Work has supported over 165 founders on their journey to becoming better leaders.
Communication Skills
Brain writing prevents the 'founder effect' and loud-voice bias by collecting ideas asynchronously and anonymously before discussion.
"Brain writing is I'm going to expose an idea and I want everyone to now write and weigh in on there... in an async way that no one else can see until it's all combined, maybe even ideally without auth..."
Hiring & Teams Skills
Define a role by its expected outcomes and business impact after one year rather than a list of responsibilities.
"Start with, it's 12 months later, you hired the person, they started today, 12 months have gone by, you're clinking champagne because of how great it's been. What's changed about the business? What do..."
Structure the interview loop into three distinct stages: culture, functional, and technical.
"We think that there is a culture interview, there is a functional interview, and there is a technical interview, but they're designed to get at these notions of have they actually done this kind of wo..."
A candidate's confidence in their former managers' references is a powerful proxy for performance.
"Just to ask the simple question even in the cover letter, of your last ex-bosses, how many would get on the phone and say, you're amazing? If there's any equivocation in the answer, great, move on."
Prioritize candidates with a proven track record of solving the specific problems your company will face in the next 12 months.
"You should hire people who have already done the thing you need to have done next."
High-performers are typically 'pulled' into new roles by former colleagues rather than having to 'push' themselves through job searches.
"If you were an outstanding performer in Job A, it is a high likelihood that in job B, someone associated with you in job A is going to pull you into the next thing and then pull you into the next thin..."
Executive hires fall into three distinct archetypes based on the company's current stage and needs.
"We think there are three types of executives that startups end up hiring over time. We call them the architect, the optimizer, and the scaler."
Culture is the result of codifying founder values and creating consistent rituals to live them.
"Culture at scale is the codification of what matters to a business and the ritualization of living those values. It starts with whoever the founders are and then it will emanate across as long as the..."
Marketing Skills
Effective positioning requires identifying your 'uncommon denominator' against both direct competitors and the status quo.
"What is our uncommon denominator from the enemies? So who are we competing against? Is it actual companies or is it status quo in some sort? What are they great at? What are we great at? What are we g..."
Early-stage success comes from hyper-focusing on a small, highly-satisfied 'white-hot center' of customers.
"All we're looking for in the beginning is a white-hot center of opportunity, a small population that is an enormous fan that's getting enormous impact. We can worry about adjacencies and expansion lat..."
Product Management Skills
Effective planning requires identifying which of the four primary business milestones you are currently working toward.
"In any given time, Lenny, companies are working backwards from one of four things, whether they like it or not. I am working backwards from an exit. I'm working backwards from a next fundraise. I'm wo..."
Avoid 'top-down' goal setting where funnel metrics are just plugs to reach a desired valuation; use historical data for bottoms-up planning.
"Founders often make the mistake when planning for the year ahead of I need to be at this revenue to justify this multiple. And then all of the funnel math is a plug, and that's death, as opposed to he..."
Sales & GTM Skills
The goal of early sales is to codify the founder's 'magic' into a repeatable playbook for others to follow.
"Sales. And this is the codification of a playbook. How are we having the conversation? How are we doing discovery? How are we handling objections? How are we doing demo? How are we moving to close?"