Six Interview Red Flags That Still Trip Up Senior Leaders
After more than 25 years in executive search, you’d think I’d have seen it all when it comes to interviews.
Yet even now, I regularly hear stories from clients about seasoned, accomplished leaders who interview very badly.
Not the ones we’ve represented and worked closely with, I should add. But nonetheless, I hear of the same issues coming up time and again.
My advice is simple: if you accept an interview, treat it like an interview. Unless it’s explicitly framed as an informal, exploratory conversation, assume it matters. Because it does.
You never lose by making a good impression — but you can lose a great opportunity by making a bad one.
A recent Harvard Business Review article by Boris Groysberg and Robin Abrahams, “6 Red Flags That Keep Good Candidates from Getting Hired,” summed this up beautifully. Their research with hundreds of senior executives identified six recurring red flags that derail otherwise strong candidates at the in-person stage.
They echo many of the mistakes I’ve had clients and companies share with me over the years, and they’re all entirely avoidable.
If you’re actively (or even passively) considering your next move, take note:
1️⃣ Poor self-awareness
Senior leaders are expected to know themselves, their strengths, weaknesses, and how they show up under pressure. Yet it’s remarkable how often even experienced candidates struggle to clearly articulate their own impact.
Overly rehearsed answers or relentless name-dropping can be as damaging as vague ones. The most compelling leaders combine confidence with humility, owning both their achievements and their mistakes.
If you’ve never reflected on a failure, it’s not a good look, either you’re lying, or you’re missing one of the core traits of leadership: self-awareness.
2️⃣ Lack of preparation
Even for initial conversations, some basic preparation is essential. Understand what the company does, what problem it solves, its culture, its investors, and its leadership.
At a senior level, “I had a quick look at the website” doesn’t cut it. Know the market context, ask informed questions, and show you’ve thought about how you can contribute. Turning up unprepared isn’t just careless, it’s disrespectful.
3️⃣ Poor manners or lack of professionalism
Small lapses leave big impressions. Being late without apology, dressing inappropriately, interrupting, or treating an “informal” interview too casually are all avoidable.
One that always makes me wince: arrogance or rudeness toward reception, assistants, or anyone else in the process. Many companies check back with every person who interacts with a candidate.
Professional courtesy and presence matter. Listen, be composed, and treat every exchange as meaningful. How you behave in the process is how people assume you’ll behave in the job.
4️⃣ Excessive self-interest
Ambition is attractive; entitlement isn’t.
Bringing up salary, flexibility, or benefits too early sends the wrong signal.
The best candidates know their priorities but focus first on how they can add value. Contribution comes before compensation.
Money matters, of course, in my experience it’s usually a top three criteria, but for the strongest leaders, it’s rarely the number-one motivator. We tend to filter anyone out of a process if it’s their sole motivator.
5️⃣ Problematic relationships with past or present employers
Badmouthing current or former employers never lands well. It hints at arrogance, bitterness, or lack of self-awareness, none of which inspire confidence.
You can be honest about difficult experiences, but frame them around what you learned rather than who you blame. Professionalism and perspective go a long way. Be honest, personalities clash, unforeseen problems arise, If everything was perfect you wouldn’t be interviewing.
6️⃣ Job-hopping without context
Career changes aren’t automatically a concern, but they do need to make sense.
What matters is the story you tell, the thread that links your decisions and the lessons learned along the way.
If you’ve made a few wrong turns (and who hasn’t?), explain them honestly. What did you learn? How did you grow? A coherent story builds confidence in your judgment.
Final thoughts
At senior level, interviews aren’t about proving you’re qualified, that’s usually a given. Of course skills and experience needs to be questioned and validated, but they’re about alignment, authenticity, and clarity.
The leaders who stand out in my experience show three simple things:
Clarity about their strengths, weaknesses, and goals
Courtesy in how they engage with everyone they meet
Coherence in how they connect their past, present, and future
The fundamentals of great interviewing haven’t changed, but the stakes have.
Small signals carry big weight.
So before your next interview, take the time to reflect, prepare, and show up as the best version of yourself.
Because even after 25 years in this industry, I still see these same red flags, and I still see them cost great people great opportunities.
It’s simple really:
When someone comes to meet you, what do you expect of them?
Apply the same standard.
—David