Two-Way Opportunity Diligence
Research the role, interview insiders, and test the fit before committing
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- 97%
This method treats a career move as a two-way investigation rather than a one-sided attempt to be selected. Begin with conventional research, then add conversations with people inside and around the organisation to expose motivations, expectations, and hidden challenges. Enter formal interviews with your own questions, checking whether the organisation wants what you want and whether the fit works in both directions. Write down the pros, cons, repair needs, strengths worth preserving, and untapped opportunities before making the decision. If you accept, return to those notes after a few months. That review turns the original diligence into an accountability tool: it shows which assumptions were accurate, what you acted on, and what still needs attention.
Origin
Nicola Mendelsohn described how she evaluates new roles during her conversation on The Diary of a CEO.
Core principles
- 01Treat a senior interview as mutual evaluation
- 02Learn from people around the business, not only its formal pitch
- 03Separate what needs fixing from what already works
- 04Record expectations before hindsight changes them
How to run it
- 1
Research the organisation
Study the business, its direction, and the role before relying on personal chemistry.
Pro tip Look for both stated ambitions and visible constraints.
- 2
Interview the network
Have multiple informal conversations with people in and around the organisation to understand it from different angles.
Pro tip Use several conversations rather than treating one insider as definitive.
Watch out Do not confuse access to senior people with evidence of fit.
- 3
Run a two-way interview
Bring a written question list and test whether their objectives, motivations, and expectations align with yours.
Pro tip Ask directly what needs fixing and what must not be disrupted.
- 4
Write the decision case
Record the pros, cons, challenges, strengths, and opportunities while the evidence is fresh.
Watch out Do not let the prestige of the role replace the analysis.
- 5
Audit the assumptions
After a few months, compare reality with the original notes and identify what you have changed or learned.
Pro tip Turn wrong assumptions into explicit course corrections.
In the wild
A candidate researches the company, speaks with current and former leaders, and asks interviewers which systems need repair and which strengths must be protected. The notes reveal strong mission fit but heavy travel. After agreeing the practical support needed at home, the candidate accepts and reviews the original assumptions three months later.
→ The decision accounts for organisational reality and personal constraints before commitment.
Common mistakes
Treating selection as the only goal
Trying only to impress the employer leaves the candidate's own questions unanswered.
Checking prestige instead of fit
A famous organisation can still offer the wrong work, expectations, or trade-offs.
Is it for you?
Best for
People evaluating a consequential role, partnership, or move into an unfamiliar organisation.
Not ideal for
Routine choices where extensive diligence would cost more than a reversible experiment.
From the transcript
“it's a two-way thing especially at a senior level where they're interviewing me but i'm also interviewing them”
“writing lists you know the pros and the cons of why this may or may not be a good thing”
From the episode
VP Of Meta: Running A Trillion Dollar Business With An Incurable Illness: Nicola Mendelsohn