The Surprise You Never Want
This is about the heart-stopping moment you realize the big role you accepted comes with surprises: misalignment, closed-mindedness, closed inner circles, lack of resources, underlying beliefs, and other obstacles to success.
Or the flip: the heart-stopping moment you realize the key executive you hired comes with surprises: misalignment, closed-mindedness, lack of awareness, conflicting beliefs, and other obstacles to the team’s success
This post is a critical reminder to do your due diligence, be truly curious, and to have real conversations up front.
And for CEOs and hiring executives, these are great questions to candidly debrief before you start the recruiting process. by Arpad Szakal,
The biggest risk in any executive job move isn't the compensation.
It’s not the title. It’s not even the scope.
It’s the team you’re walking into.
The politics. The support you’ll get when the heat’s on. And the battles no one warns you about.
And yet.
Too many seasoned candidates ask questions like:
“What’s the 90-day plan?”
“What’s the company vision?”
“What’s the culture like?”
Nice. Polite.
Useless.
If you want the real story behind the role
Ask better questions.
Here are 15 questions for C-suite and top-flight talent to work with:
1. “What’s the real reason this role is open now?”
Reveals: political landmines, failed predecessors, or strategic pivots.
2. “What will make this hire fail—regardless of their skill set?”
Reveals: hidden risks, culture misalignment, power dynamics.
3. “What surprised the last person who took this role?”
Reveals: unspoken expectations and reality-vs-pitch disconnects.
4. “Who stands to gain most if I succeed? Who might feel threatened?”
Reveals: internal alliances and opposition—before you step in.
5. “What’s one tough call I’ll need to make in my first 90 days?”
Reveals: real priorities and where the pressure lies.
6. “When the last crisis hit, what did this leadership team get right—and wrong?”
Reveals: leadership resilience, transparency, and how they handle stress.
7. “What’s the most important thing I’ll need to protect?”
Reveals: the company’s sacred cows—and potential no-go zones.
8. “What’s broken, but no one has had the courage to fix?”
Reveals: where change is needed—but politically risky.
9. “Who has a strong voice in this company without a title?”
Reveals: informal power structures that matter just as much as the org chart.
10. “When was the last time someone said no to the CEO—and what happened?”
Reveals: the real openness to dissent and challenge.
11. “What’s a leadership behaviour you quietly reward here?”
Reveals: values in action, not just on posters.
12. “Which functions are seen as profit drivers—and which are tolerated overhead?”
Reveals: where influence lives—and where it doesn’t.
13. “What does success in this role not look like?”
Reveals: the missteps others made, and how to avoid them.
14. “Who are the top 3 internal stakeholders I must win over early?”
Reveals: where political capital must be built fast.
15. “What would make you say—12 months from now—‘Hiring you was the best move we made’?”
Reveals: expectations, hopes, and how they’ll judge you when the honeymoon ends.
These aren’t just “smart” questions.
They’re strategy tools.
Don’t just be impressive in interviews.
Be informed. Be intentional. Be in control.