Failure-to-Values Postmortem
Process a failed venture, map founder gaps, and encode the lessons before rehiring
- Difficulty
- Advanced
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- 99%
After Grabble failed, Murray-Serter and his cofounder Joel used business psychologists for facilitated sessions across a week. They stated blame, completed personality tests, mapped strengths and weaknesses, and connected their differences to poor decisions. Murray-Serter heard that his lack of focus, unfiltered honesty, and weak commitment to the business had damaged both the venture and his cofounder's motivation. The pair used those findings before building Heights: they clarified that Murray-Serter needed purposeful work, created company values, and wrote hiring processes and interview guidance nine to twelve months before their first employee. The mechanism moves from emotional disclosure to pattern diagnosis and then to organisational design. Its value is not the catharsis alone, but encoding the lessons before pressure and hiring recreate the old system.
Origin
Extracted from The Diary of a CEO
Core principles
- 01Failure should be processed before it is reused as a lesson
- 02Cofounders need room to state blame and hurt
- 03Personality differences can expose operating gaps
- 04Values should shape hiring before the first hire
- 05Purpose mismatch must become an explicit constraint
How to run it
- 1
Create a contained review
Set aside dedicated sessions and consider a neutral facilitator when trust, blame, or strong emotion could block an honest conversation. Agree that the aim is understanding and future design.
Pro tip Use several sessions rather than forcing closure in one meeting.
Watch out A facilitated review is not permission for abuse or unsupported accusation.
- 2
State each account
Let each founder describe responsibility, hurt, and the decisions they believe mattered. Listen for impacts that intention did not reveal.
Pro tip Separate what happened from what each person inferred.
Watch out Premature agreement can hide the lesson.
- 3
Map founder patterns
Use observed behaviour and, if useful, personality assessments to map strengths, weaknesses, motivation, and overlap. Trace those patterns to specific decisions.
Pro tip Ask which operating conditions brought out each founder's worst pattern.
Watch out Personality tests are inputs, not diagnoses or verdicts.
- 4
Define non-negotiables
Write what the next venture must provide for each founder to remain committed. Make purpose, role, communication, and decision boundaries explicit.
Pro tip Reject ideas that recreate the diagnosed mismatch before momentum makes exit harder.
Watch out A commercially attractive idea may still be the wrong company for this team.
- 5
Encode the lesson
Turn the findings into company values, interview prompts, hiring criteria, and operating practices before adding employees. Test future choices against them.
Pro tip Write the hiring system before urgency creates exceptions.
Watch out Values that never affect selection or behaviour are only slogans.
In the wild
Murray-Serter and Joel spent a facilitated week reviewing their failed company, including blame, personality differences, and damaging decisions. Before Heights hired anyone, they had already created values, hiring processes, interview guidance, and a shared requirement that the work fit Murray-Serter's sense of purpose.
→ Painful founder feedback became constraints and hiring infrastructure for the next company.
Common mistakes
Stopping at catharsis
Expressing blame may relieve pressure but does not prevent recurrence unless the lessons become operating changes.
Choosing the next idea too quickly
Momentum can recreate a purpose mismatch before founders agree on what the next venture must provide.
Writing decorative values
Values matter only when they alter hiring, communication, and decisions.
Is it for you?
Best for
Cofounders closing or leaving a venture who may work together again and need a structured account of what failed.
Not ideal for
It is not a substitute for legal, financial, employment, or clinical support where those are required.
From the transcript
“we had facilitated sessions over the course of a week”
“we did personality tests and we looked at where our crossovers were”
From the episode
Overcoming Depression, Burnout, Anxiety and Insomnia with Dan Murray-Serter