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Organization Planning with Dan Ross

Organization Planning with Dan Ross

In this session, we were joined by Dan Ross, cofounder and fmr Head of Operations at Headway! Dan walked us through a rapid fire session covering an array of topics like Values, OKR's, Team Structure, and Hiring.


Values tend to fall into three buckets:

  • Who we are
  • How we work
  • How we decide

The first two are generally nice to have's - they make the team feel good by identifying cultural norms and behaviors.

"How we decide" is the most important of the three - it should be prescriptive and give direction for small and large decisions made across the organization. Amazon's relentless focus on customer experience is a great example of this. That is a core value for them, and give the other important elements of their flywheel provides the necessary weight for the whole company to make decisions that always put the customer first. Much of Amazon's success can be attributed to this value.


  • Firs trap most company's fall into with OKR's is trying to cascade goals across the org.
  • The process of creating OKR's is less important than the actual Buy-in!
  • Important things to remember about OKRs
  • Bottoms up. Top down & bottom up goals.
  • CEO & exec team set company objectives (top down)
  • Manager sets ~50% of goals for reports
  • Not evaluative. No tie to performance cycle.
  • Flexible. Can change mid period.

Goal Setting: important to recognize the difference between optimization goals and the more ambitious goals that unlock new thinking. Strike a balance and measure against time.

  • Common mistake - too ambitious goals set for short periods, not ambitious enough goals for longer periods

Team Structure

  • best to have one leader with autonomy and no competing priorities.
  • Focus enables much higher productivity.
  • Hire faster and better to enable your manager to have this lvel of focus.


  • Keep the top of your funnel as tight and narrow as possible.
  • Maintain storng diversity in candidate pool, but be very clear on the skillsets you are looking for and test against these qualities as early as possible
  • Kevin Ryan - founder & CEO at AlleyCorp - "“When I’m hiring a CEO, I put more weight on references than on interviews.”
  • Weight references much higher than interviews.
  • Reference early in the process and broadly both with provided references and backdoor references
  • Avoid the Reference Challenge (former manager is a champion of the candidate and will only say positive things to help them out).
  • Build trust - go longer than you think in the reference call (45+mins)
  • Use the reference call to sell the importance of the role and the mission of your company. ABS!
  • Express the importance of confidentiality
  • Create openings with open-ended questions, stack ranked qualities/behaviors, and by generating controversy.
  • Dan includes a reference call guide in the appendix in the below deck!


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