Leadership, Observed
We treat the interview as the most revealing conversation in a leader’s career.
It is also the most rehearsed.
In investing, we underwrite for what we cannot see.
In hiring, we keep underwriting for what we can.
The more I have worked across investing, development, and talent, the more I believe most hiring misses are visible much earlier than we admit.
We just don’t frame them that way.
The data has been pointing in the same direction for years.
89% of hiring failures come down to attitude and cultural misalignment, not technical skill.
40–50% of leaders struggle within the first 18 months.
Roughly 70% of transformations fail, largely due to people and execution, not strategy (McKinsey & Company).
And still, we default to the same evaluation criteria.
Experience. Pedigree. How someone shows up in the room.
Because “fit” feels uncomfortable.
It sounds subjective. It risks being misused. And it forces a harder question.
Do we actually understand how our organization works?
Not the version in the deck.
The real one.
Typically, assessments are used at the end of the process.
A final step. A way to confirm there are no obvious red flags. Often, more about coverage than conviction.
A subtle form of CYA.
Useful.
But not decisive.
As I started building my own advisory work, I found myself going back to first principles.
What actually drives success once someone is in the seat?
Not during interviews. Not in curated conversations.
But:
under pressure
over time
inside a system with real incentives and trade-offs
That is where most evaluation breaks down.
At more senior levels, this becomes even more pronounced.
People know how to position themselves.
They understand how to interpret questions. They know what good looks like. They present a version of themselves that is thoughtful, composed, and aligned.
And that version matters.
But it is still a version.
What matters just as much is:
who they are when they are under pressure
how they operate when they are not being observed
what happens when things go wrong
how they respond when the environment becomes uncertain or breaks
Because that is the version the organization actually gets.
This is where tools like Hogan Assessments started to matter more to me.
Not as a validation step.
But as a way to drive the work.
Done well, an assessment does not ask one question.
It asks three.
Who you are at your best.
Who you become under pressure.
What you actually want from the work.
The first explains how you show up.
The second explains how you break.
The third explains why you stay, or why you leave.
Most processes only ask the first.
And then wonder why the answer keeps being incomplete.
The version that emerges under pressure is rarely a hidden flaw.
It is usually a strength, miscalibrated for the moment.
Conviction that becomes resistance.
Diligence that becomes paralysis.
A bias for action that becomes recklessness.
Most derailers are not who someone is.
They are who someone becomes when the environment stops rewarding the very thing it once hired them for.
Used this way, assessments shape interview strategy. They force the right questions. They help uncover the personality that shows up at work, not the one that shows up in the room.
At their best, they don’t validate decisions. They change them.
Over time, I found myself building a more integrated lens across investing, development, and talent.
What I think of as the HASKIL view.
Fit is not a feeling. It is a pattern.
Between:
the individual
the environment
and the role as it actually operates
And this is where most organizations get it wrong.
They evaluate people in isolation.
They rarely evaluate the system with the same rigor.
At HASKIL, this is increasingly where the work sits.
Not just helping organizations hire.
But helping leaders step back and ask a harder question.
Am I in the right seat?
And if exploring something new:
Do I actually understand what environment I perform best in?
Because this is not a one-sided decision.
In reality, it is closer to alignment.
In some ways, it is like dating.
It has to work for both sides.
And yet, most interview processes are one-sided.
Candidates adjust. They optimize. They present what they think the organization wants to see.
Often focused on getting the offer, they can lose sight of what actually makes them effective.
Most candidates have spent years preparing answers to the first question.
Far fewer have asked themselves the third.
What environments actually energize me?
What kind of work compounds, and what kind quietly drains?
Where do my natural patterns add value, and where do they create friction?
That data exists.
It is just rarely the data we use.
What gets missed is just as important:
What kind of environment do I actually thrive in?
What types of teams and leaders bring out my best?
Where do my natural patterns compound versus create friction?
This is a muscle most leaders are not trained to use.
But it matters.
Because fit is not something an organization determines on its own.
It has to work in both directions.
Bottom line
Most hiring and leadership failures are not surprises.
They are patterns we chose not to fully examine.
Interviews reward control. Leadership tests what happens when control is gone.
If you are thinking about what fit looks like for you, or questioning whether you are in the right seat, I would be happy to explore it together.