What to Expect in a Skip-Level Interview and How to Succeed
Tiffany Cheng
Mentoring Expat Directors in Large Organizations Advance to Senior Executive Roles | ex-Volvo, Atlas Copco
So, by now, you’ve probably gone through 3 or 4 rounds of interviews—starting with the recruiter, then the HR business partner, your future line manager, and maybe even a couple of your potential peers. Chances are, you’ve also completed a case study assignment and sat through a panel interview. Now, you’ve been invited to the final round—the grandparent interview, which is with the skip-level manager. This person could be the CEO or another very senior executive. It’s the last step in the process, so how do you prepare for it?
In this video, I shared how I prepared for the final round of my job interview with a board member from the group when I was interviewing for the Vice President position at the largest organization in Sweden by market cap.
1. The Difference Between a Line Manager Interview and a “Grandparent” or Skip-Level Interview
So, what’s the difference? One of the biggest differences is understanding that the roles of the interviewers are different. In my case, my direct manager was the President of the division, and he was the one who made the hiring decisions. He had ownership of the division’s business and was directly responsible for the P&L. He knew exactly what kind of profile he needed in his management team to help lead the division and solve specific problems.
During my interview with the President, the focus was on my technical competence, past track record, leadership, and strategic insights—particularly how I could contribute directly to the success of the division. The interview was operationally focused, covering topics like selling the next generation of renewable energy solutions, uplifting digital marketing strategies, and expanding into new markets through our online and offline sales channels.
The interview was really about evaluating whether I could set the right direction for my function and lead the organization’s digital marketing strategy to hit its ambitious targets over the next three years and achieve the revenue growth we had committed to. He wanted to see if I had the vision and leadership to make that happen.
But when it came to the grandparent interview with the board member, the focus shifted.
The grandparent’s role in the interview wasn’t about assessing my ability to meet immediate business needs; instead, this interview was less about what I could do today and more about how I would fit into the company’s future and continue to develop there.
The tone of the conversation was much more casual. It felt more like a conversation than a structured interview process. The board member seemed to be trying to get to know me as a person. We talked about my values, what drives me, and how I saw myself fitting into the company’s culture. There wasn’t much discussion about immediate business outcomes.
2. Create a Memorable Experience
When you approach an interview, especially at the executive level, it’s important to see it as more than just a standard Q&A session.
Think of the entire interview as an event where your goal is to create a memorable experience for your audience. It’s not just about what you say but about how you make them feel.
You want to transform the interview into a genuine, engaging conversation—something that stands out in their day. Imagine being a senior executive with back-to-back meetings all day long. What you want to do is make this one hour of the interview a pleasant experience for them, not another draining session filled with self-promotion.
So, instead of treating the interview as a simple question-and-answer exchange, make it interactive and engaging. Ask thoughtful questions that show your passion, curiosity, and collaborative mindset. Remember, people love talking about themselves, and the more you let them speak by asking good questions, the better they’ll feel about the conversation.
Have you ever noticed how good it feels to talk about yourself or share your ideas in a conversation? Well, there’s a scientific reason for that. When we talk, especially about ourselves, our brain releases dopamine, which makes us feel good.
Psychologically, this is self-disclosure—revealing personal information to others. When we self-disclose, we build trust and rapport in relationships, and it also gives us a psychological boost. According to research, the more we engage in self-disclosure, the more dopamine our brain releases, making us feel even better.
In an interview setting, this is why it’s important to create opportunities for the interviewer to talk as well. When they share their thoughts and experiences, you’re not only making the conversation more engaging but also making them feel good because of this natural dopamine boost. The more positive feelings they associate with the conversation, the more they’ll associate those feelings with you as a candidate.
This not only strengthens your connection with the interviewer but also gives you more insights into the job. You can then tailor your next questions or answers to align even more closely with what they’re looking for.
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3. Deep Research on the Executive
The first thing you need to do—and this might seem obvious—is to look up the executive who will be interviewing you online. But don’t just skim the surface—go deep in your research. Understand the roles they’ve held, the challenges they’ve faced, and the impact they’ve made. Go beyond the basics.
By this stage of your job interview process, I’m assuming you’ve already got a good grasp of the company’s financial situation, its challenges, and the background of most of the leadership team.
Now, when it comes to the senior executive or CEO who will interview you, I want you to take it a step further. Go to the company’s investor relations page and listen to at least the last 3 to 4 quarterly earnings calls. Pay special attention to the questions asked during the Q&A sessions—these are often the best way to uncover the company’s pain points. It’s very likely that the executive or CEO who will be interviewing you spoke at these events.
During your research, make sure you also check out any media articles, videos, interviews, or quotes featuring the executive. This will give you insights into their priorities and leadership style. Use this information to ask non-generic, specific questions that go beyond what you could just Google.
For example, instead of asking, “What’s your leadership style?” you might say, “I noticed in your recent interview with the Financial Times that you emphasized the importance of innovation as a key enabler of profitable growth. Given the 20% profitability target, can you share how you see the leadership team fostering a culture that encourages innovative thinking across the organization?”
4. Articulate Your answers
Even if you’re using storytelling, keep your responses concise—do not go longer than two minutes, and preferably keep them around 30-60 seconds. Simplicity and conciseness are key.
I understand that as a leader with over 20 years of experience, it’s easy to overload your answers with unnecessary details, technical jargon, or in-depth explanations about projects at your current or previous company that others do not fully understand.
Remember, your audience doesn’t need as much background information as you think to grasp your point.
When you overwhelm your interviewer, it can leave an impression that you are junior and too operational, which doesn’t help reinforce your executive presence.
5. Make Them Picture a Future with You
The interview isn’t just about your past; it’s really more about the future. Many of you are excellent at preparing to showcase your past successes and how strong you are as a candidate.
But here’s the thing—the more you talk about your past achievements, the harder it is for them to see how you’d operate in their environment.
As you describe your past successes and the challenges you’ve overcome, they might be thinking, “Sure, you were great at handling those challenges in your previous organization, but we’re different. What worked back then might not work for us.” They have different solutions, products, customers, and an organizational culture that might be completely different from what you’re used to. So, as you expand on your past, you could be unintentionally creating objections in their minds.
That’s why it’s crucial to shift your focus. Transition your answers from just talking about what you’ve done in the past to explaining how your experience, leadership, and lessons learned can be leveraged in their specific context. Move the conversation from one of evaluation to one of collaboration. Help them visualize how having you on their executive team can positively impact their future. Show them what it would be like to work with you and lead the organization together.
Remember, decision-making is more about emotions than logic. People often make decisions based on how they feel first and then use logic to justify those decisions.
Typically, they already have a sense of whether they like a candidate. Once they feel good about someone, they start backing it up with logical reasons like the candidate’s track record, relevant experience, or industry background.
So, when you help them visualize your presence in the leadership team and how you’ll function within their organization, you’re engaging the emotional side of their brain in your favor.
6. Do Not Ask What It Takes to Succeed in This Role
It’s common advice to ask at the end of an interview, “What does it take to succeed here?” This approach can work well when you’re interviewing for a middle-management or more junior position. It shows that you’re eager to understand what’s required to thrive in the role.
However, if you pose this question during an executive job interview with one of the most senior people in the company, it can raise concerns.
The reason is that they might wonder why you don’t already know what it takes to succeed. Executives are expected to lead and possess the experience and competence to support their directions and vision for the organization. When you ask a question about what it takes to succeed in the role, it may signal a lack of leadership. It could imply that you require guidance and a clearer definition of the role, indicating a need for direction from others.
For instance, during my interview for the Vice President of Communication position, the final interviewer was the manager of the division Presidents, a board member. I was expected to be the advisor who defined what it takes to succeed in the role.
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