rail transitionA few articles have been recently written about Founder to CEO transitions, because not all founders can become good CEOs. Professor Noam Wasserman (Harvard Business School and author, The Founder’s Dilemma) was the first to realize that the skills needed to run a start-up during the early days are different than when the company grows. So, the question becomes whether or not, a founder can evolve with the required company evolution. I’ve been interested in helping young founders become more self-aware of their transition requirements and the stepping-up they need to do, in order to properly lead their startup. Based on interactions with a dozen founders, observing a dozen others, and a review of the recent Blogiography on that topic since 2006, I’ve come-up with a practical Toolset that includes a table on Required Transitions, a Checklist, Skills you need, What doesn’t change, and Mistakes to avoid. The assumption is a starting point of 25+ employees, where the company is about to scale. [Special thanks to Matt Blumberg, author of Startup CEO for reviewing this toolset]. In There are no shortcuts to intelligent founder – ceo transitions., Fred Destin says “entrepreneurs have to write their own story”. So, there is no right or wrong way to evolve to a CEO role, but there are some fundamentals about CEO transitions that do not need to be re-invented. Recently, Ben Horowitz wrote Why Founders Fail: The Product CEO Paradox, focusing on a failure symptom where the CEO wasn’t able to decide between managing, controlling or ignoring their product vision, as the company scaled. But at the heart of this was really a CEO transition failure. So, this is an important topic that has repercussions throughout the organization. This post is about asking your feedback for improving/critiquing the following Toolset. Anything missing? Anything not right? Please use the comments here, or go straight to this public Hackpad I created, and enter your thoughts there. FOUNDER TO CEO TRANSITION HACKPAD (You can edit straight on the Web) After this feedback, I will re-publish an updated version to this post, and add a Self-Assessment interactive tool, similar to the one I did on The Ultimate Guide to a Startup Company’s Culture.

Required Transitions



Doing everything yourself More delegating, and enable them to accomplish tasks
Loose organizational boundaries More functional clarity
Few job descriptions Defined Roles & Responsibilities for each employee
Making most key decisions Holding others accountable for their decisions
Making most hiring decisions Vetting hiring decisions, focusing on short listed candidates
Managing by signals Managing by objectives
No defined processes Start to define (and optimize) processes
Flat structure 2-level structure is OK
Grow by need Plan & model financial impact of your growth
Vision + execution Vision + manage the execution
Managing employees Managing managers
Evaluating the performance of employees Evaluating the performance of managers
Not worrying about profit/loss or budgets Being more aware of budgets and investments trade-offs
Lead by doing Lead by inspiring
Managing the product Managing People (People are your new product)
Sporadic review cycles Disciplined & scheduled review cycles
Managing investors Managing investors and customer relationships
Board relationship Board and market relationship
Sole product visionary Letting others innovate on the product, but staying close to product reviews
Key salesperson & evangelist Hire others to sell & also evangelize
Iterating and tinkering Thinking and planning
Sporadic, informal communications with small groups More regular and formal communications with larger groups in addition to maintaining the sporadic and informal

Checklist that you are Becoming a CEO

  • Spending 50%+ of your time with your people
  • Thinking about your culture and codifying it
  • Becoming self-aware of your strengths and weaknesses
  • Inspiring others to innovate and perform
  • Taking one day per month off to step back and think about where you are, and where you’re going
  • Streamlining new employee on-boarding
  • Managing by Objectives
  • Appreciating operational details
  • Being as passionate about building the company as you were about building the product
  • Running weekly management meetings
  • Reviewing sales progress with the exactitude of a surgeon
  • Process, process, process
  • Joining a CEO peer group
  • Working with a coach or a mentor
  • Starting to think about your brand
  • Recognizing importance of organizational structure design as a lever that ties people, activities and results
  • Hiring a marketing manager, biz dev & sales manager
  • Having a CFO and an HR manager

Skills you Need to Have, or Develop

  • Clarity and effectiveness of communications (strategic + tactical)
  • Appreciation for process and its optimization
  • Believing in and acting on people development
  • Enjoying external networking
  • Not being afraid of selling
  • Liking people
  • Building teams and fostering teamwork
  • Ability to delegate
  • Enjoying recruiting people
  • Can manage sales people (even if you haven’t been one)

What Doesn’t Change and You Need to Continue Doing

  • Making decisions under conditions of uncertainties and ambiguity (but it shifts into the organizational realm)
  • Board Relationship
  • Fundraising
  • Thought leadership with the market
  • Worrying about cash

Strategic Mistakes to Avoid

  • Assuming that your abilities to lead product development or get to product/market fit is equal an ability to manage a company
  • Relying too much on Lean, beyond the product/market fit
  • Not striking the right balance between managing vs. reviewing the product’s evolution
  • Relying too much on being funded instead of figuring out the business/revenue model (need balance)
  • Being focused on product features that don’t contribute to your business model realization
  • Not complementing a geek/technical culture with a sales, marketing or revenue culture