You have a job interview scheduled with the hiring manager’s boss. Congratulations on making it to this important stage in the interview process!
Before you get too excited and pop the bubbly, it’s time to prepare for this high-stakes conversation, known as the “skip-level interview.” This crucial meeting requires thorough preparation to maximize your chances of securing an offer.
What should you expect during your interview with your boss’s boss, how do you prepare, and what questions should you anticipate?
In this article, you’ll learn:
- What to expect in a skip-level interview and the purpose of this conversation in the hiring process
- How to effectively prepare for a skip-level interview so you stand out from fellow candidates
- Common interview questions to expect when meeting with a senior leader
- Questions to consider asking during the conversation to demonstrate your strategic thinking, leadership skills, and ability to positively impact the business
What Is A Skip-Level Interview?
Before diving into preparation tips and potential questions, let’s get clear on what a skip-level interview actually is.
Sometimes also referred to as a “higher-up interview” or an “executive chat,” a skip-level interview is an opportunity to meet with your boss’s boss so that you can suss each other out.
This is an important conversation during the interview process, as your skip-level boss will be a key decision-maker in the hiring process.
[Read: 11 Different Types Of Job Interviews (And How To Best Prepare For Each One)]
A quick note: A “skip-level manager” refers to your boss’s boss, because you’re going above your immediate supervisor to the next level of management. While it’s a common phrase used in the tech space, it can extend to other industries. For example, if you’re vying for a C-suite role, your skip-level might be an interview with the board.
What To Expect In A Skip-Level Interview
Now that we’re clear on what a skip-level interview is, let’s unpack what to expect during this high-stakes conversation.
Although many of the questions will be similar to those you’re asked during a hiring manager interview, there will typically be new ones.
Skip-level interviews will typically focus on the big picture. They will often ask higher-level questions, rather than expecting you to get into the weeds. Of course, there may be some exceptions if you’re gunning for a highly technical role or interviewing with a company where senior managers and executives are expected to know the ins and outs of the tech stack.
Skip-level managers are often more interested in your long-term vision, strategic thinking, and ability to drive organizational change.
Because skip-level managers are more senior than hiring managers, they will typically dedicate less time to interviews. Don’t be surprised if there are only 20 to 30 minutes allotted for your conversation. This means your responses need to be concise, which I cover in a subsequent section on how to prepare.
How Many Candidates Make It To The Skip-Level Interview Stage?
Please don’t assume you will be extended an offer simply because you were invited to a skip-level interview.
Although it will depend on how the company orchestrates its hiring process, two to three final candidates typically make it to the skip-level interview with their boss’s boss.
This means you must still impress the hiring manager’s boss and put your best foot forward during this important conversation if you want to increase your chances of receiving a job offer.
How To Prepare For A Skip-Level Interview
So, how do you maximize your chances of success when interviewing with your boss’s boss? Here are 5 tips to make the most of the conversation and leave a favorable impression:
1. Do your research.
While this is a seemingly obvious step, it is often overlooked, even by the most experienced interviewees, given the excitement of the interview process.
Ask your recruiter, headhunter, or hiring manager what to expect, what key points they recommend you highlight, and any tips they have to maximize your success during the conversation.
They want you to succeed, but you must take the initiative to get ready for the conversation.
Of course, like any interview, use LinkedIn to research the person you’ll be meeting, and listen to any podcasts or news articles they’ve been featured in.
2. Reframe your stories.
Although you have likely crafted and recited many stories for your previous interviews, you must reframe them for your skip-level manager interview.
Your boss’s boss will be less focused on the details and more focused on factors such as:
- Your collaboration with cross-functional teams and partners
- Your ability to communicate and influence executives
- Your results and the impact of your work
Addressing these subtle changes in your stories can make the difference between your being perceived as mediocre and being seen as the top candidate they must hire.
3. Learn the art of brevity.
As you get ready for your big day, you want to keep your answers focused on the point, sharing the most important content rather than boring them with unnecessary details.
If you tend to ramble during interviews, you need to knock it off before meeting with your boss’s boss. Consider using a (silent) timer to keep yourself concise and on track.
While you might aim for responses that are 90 seconds to 2 minutes in length when interviewing with a peer or hiring manager, aim for 60 seconds when meeting with a skip-level manager.
Remember that you can always provide them with the opportunity to ask follow-up questions. For example:
- “Does that fully answer your question?”
- “While I can share more about [topic] if you like, I want to focus on…”
4. Distinguish yourself from other candidates.
Your hiring manager is likely not the only direct report to their boss, which means they are likely meeting with many candidates.
Some of my clients who are senior executives report interviewing hundreds of candidates per year! Translation? It’s easy to blend in with the crowd!
Because skip-level managers are so busy, you must distinguish yourself from the many other candidates they’ll meet. Come to the conversation with several unique insights, innovative ideas, or personal anecdotes that showcase your unique value proposition.
5. Don’t skip the practice.
Even if you’ve practiced extensively up to this point, don’t stop now. Spend ample time practicing your talking points and refining them for this specific audience. Meeting with a skip-level manager can make even the most confident interviewee question their abilities.
Importantly, get used to sharing your thoughts concisely and articulately. As an interview coach who specializes in the tech industry, I find that many interviewees have beautifully written talking points, but they struggle to articulate them verbally or talk on the fly.
You must be ready to speak confidently and coherently about your experiences, career accomplishments, and vision for the role.
Common Skip-Level Interview Questions
Anticipating and reviewing questions commonly asked by a skip-level manager can help you approach the interview with confidence. Here are some of the questions you might expect during this conversation:
- Can you describe an instance where you had to influence senior leadership? How did you do it, and what lessons did you learn?
- What’s your approach for communicating technical concepts to non-technical stakeholders and executives?
- How do you align your team’s daily actions with long-term business goals?
- Can you share how you’ve developed and mentored talent on your team?
- What’s your approach to change management?
- Can you tell me about a time when you had to manage a large, cross-functional project? What stakeholders were involved, and how did you gain their buy-in?
- How did you drive innovation in your previous roles?
- What’s the most significant trend you see impacting our industry, and how would you capitalize on it?
- What’s the biggest challenge facing [Company], and how would you address it?
- How do you envision our industry evolving over the next 5 years?
As you respond to the hiring manager’s boss’s questions, remember to keep your responses high-level and focused on strategic impact, your leadership skills, and measurable results.
Questions To Ask When Interviewing With Your Boss’s Boss
The interview is a two-way street, so be sure to bring powerful questions that reinforce your interest in the company, showcase your unique value proposition, and help you assess whether this role and company are the right fit for you:
- What’s your vision for the company/team over the next 3 to 5 years, and how does this role contribute to that vision?
- What current initiatives and projects are you most excited about?
- How can the person in this role make your job easier?
- How will you know the right person was hired into this role?
- What key performance indicators (KPIs) will you use to evaluate success in this role?
I recommend asking open-ended questions that are memorable and accentuate your fabulousness (more commonly referred to as your “unique value proposition”).
Final Thoughts On Skip-Level Interviews
Interviewing with the hiring manager’s boss can feel intimidating, but it’s also a fabulous opportunity to showcase your strategic thinking, leadership skills, and ability to contribute to the organization’s success. Keep in mind that they’re not just evaluating your experience and skills but also how you show up in the meeting and your ability to contribute to the company’s culture and long-term success.
Trying these strategies can make the conversation as successful and memorable as possible, increasing your chances of converting the interview into a job offer.
Need help preparing for your upcoming skip-level interview? Please feel free to reach out or schedule a consultation. I’m here for you! You’ve got this!
