Interviewing at senior levels

Originally posted Aug 13, 2019

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In my last newsletter, I wrote about a few skills that indicate someone is distinctly more senior in their role:

• Comfort working within ambiguity, and creating clarity for your team when none is given to you from above
• Comfort setting direction, without waiting for a strategy or vision to be handed down to you
• Making impossible calls, where there’s no obvious right answer, and folks’ livelihoods might be at stake
• ‘Being more strategic’, which could mean so many different things, in different organizations, and to different people. Usually, this means you have a hand in setting the future vision for your organization. (This could be about the organizational design, product roadmap, business goals and objectives, how everyone works together, etc.)

Take a look at that list, and how intangible some of those skills are. It’s hard enough to recognize if you’re performing any of them at any given time, and it’s equally hard to spot someone else performing them.

This means that it’s also pretty difficult to hire someone who’s experienced in and effective at those skills. If you’ve ever interviewed for a senior management or leadership position, you’ve probably met interviewers who had no idea how to accurately assess your fit for their role or their organization.

When I was last interviewing for VPE positions, I met with a bunch of companies who needed a VPE to tackle their engineering team processes, management skills, and org design, but still emphasized hands-on-keyboard interviews rather than behavioral interviews. They got lots of data about how I might speed up their front end, and zero data about whether or not I could help tackle their organizational challenges (which is what they needed the most).

So I’ve dedicated this newsletter to what can you do to adequately prepare for interviewing at senior levels, and help give others an accurate picture of who you are and how you lead. I hope you find the resources in here valuable, whenever you’re ready to start interviewing at senior levels!

—Lara

Develop a pithy one-liner + a story for likely topics

There are a few common topics/questions that you’ll encounter as you’re interviewing. Some examples:

• Delivering feedback (and sometimes more specifically, dealing with a Brilliant Jerk)
• Hiring fast, dealing with organizational growing pains
• Diversity/inclusion
• Tackling infighting/factions around technical decisions
• Improving the org design (PM on every team? Matrix management? Centralized platform/service teams like mobile or security, or distributed among teams?)
• Team vs team (Product vs Infra, Marketing vs Engineering, etc.)

Of course, these will all depend upon the stage of an organization and their current pain points. Things like creating a career ladder, permitting or supporting remote employees, identifying compensation bands, etc. might come up more often depending on the size or age of the organizations you’re interviewing with.

As you begin interviewing, scour job descriptions for common pain points or skills required, and develop:

1. A pithy one-line philosophy/approach you take
2. An example/story/anecdote

Here’s a great example of a pithy philosophy/approach to a question like, “how do you define leadership?”:

Leadership skill is really about comfort with handling ambiguity. Handling it for yourself alone is enough in many contexts. To be a great manager/leader you must handle it well yourself and also help the team handle it by providing confidence and clarity
—Camille Fournier

A related story might be a time when you had to provide confidence and clarity to your team amidst news of an acquisition, and how you chose what information to communicate and when, and in what medium.

Some interviewers only want your pithy “how do I think about this topic?” statement. Other interviewers will want the story. I have been in innumerable post-interview-huddles where interviewers said, “they talked a lot about how they think about team friction, but couldn’t give any examples!” or “they kept on going on and on about how they scaled their organization, but I couldn’t figure out how they would do that here!”

So come prepared with both; when you’re asked a question, start with your pithy one-liner, and then share your example.

Figure out what you want to acquire or gain in your next role

In her phenomenal slide deck, “WHAT AM I GOING TO DO WITH MY LIFE???”, Millie Tran provides a ton of amazing prompts to help you figure out what you want next. I’m including two examples here, but you should really check out the entire deck!

Firstly, some questions Millie invites us to ponder:

• what skills do I want to learn?
• what do I enjoy?
• what do I want to do more of?
• what do I care about?
• what’s just interesting to me?

Each and every person is going to have a different set of answers here. And these answers will, naturally, evolve over time. The way I usually frame this set of questions to my coaching clients boils down to: what do you want to gain or aquire next? Maybe a skill, maybe a title, maybe an experience (like scaling an organization to twice its size, or creating a career ladders for managers that’s distinct from an IC track), maybe just… some downtime, a break from fast-paced growth.

In her deck, Millie includes a great list of categories to answer this question, from an HBR article called “How to build a meaningful career”:

• Legacy: This is about the concrete outcomes of your work. What do you want to achieve?
• Mastery: These are the strengths that you want to improve.
• Freedom: This is about the salary, benefits, and flexibility you need to live the life you want.
• Alignment: This last category covers the culture and values of the place you work. This is not the same as mission, but is about whether you feel like you belong.

Knowing what you want to grow, or experience, or acquire is invaluable as you think about your next steps. Kathryn McElroy had an “introspective happy hour” where she reflected on what she wants to optimize for:

I optimize for money (least expensive) for my personal life, but I’d rather optimize for time so I have more quality time with my family and daughter. I’ve been slowly chipping away at this already by delegating (hiring out) some life tasks (cleaning).

When I was interviewing for VPE positions, I wanted to acquire that VPE title, and I wanted the chief focus of that role to be shaping an engineering management culture at the company. This level of clarity was invaluable when I began interviewing; it was easy to decline to interview at places where they needed a VPE to primarily set technical direction, scale up from a handful of engineers, or fix their maintenance roadmap. Those challenges of course, can involve leveling up managers (and these challenges pretty much exist at every technical organization, so it’s important to know how to tackle them). But I really wanted to work at a place that was primarily hungry for a management culture, and ready for a VPE to join and immediately get to work on it.

Spend a good chunk of time introspecting and figuring out what you want to acquire, gain, or optimize for in your next role. Then ask lots of questions in interviews to assess whether each new role will be an opportunity to do so.

Define YOUR leadership one-liner

Millie Tran included this definition of a competitive advantage in her deck (which is expanded upon in this blog post):

Your competitive advantage is the intersection of three different, ever-changing forces: your assets, your aspirations/values, and the market realities.

Y’all know how I feel about leadership philosophies (here’s a worksheet!)—and these REALLY come in handy when you’re interviewing. What are you great at? How do you show up as a leader? What are you optimizing for as a leader?

Your leadership one-liner, your competitive advantage… your interviewers want to hear it. They’re going to be trying to distinguish you from the rest of the candidates. They’ll want to know how you’re uniquely positioned to tackle this senior leadership role.

Everyone’s philosophy is going to be different, and some one-liners sound more gross or fake or people-pleasing than others. Just like earlier when we talked about developing a one-line philosophy or approach to common leadership situations and a story, you’ll want to do that here, too. How has your leadership one-liner manifested at work? What are some stories about when it’s helped, or when it’s failed you or the team?

As you define and illustrate this leadership approach for your interviewers, there’s a chance that they won’t like it, or think you’re a good fit based on it. That’s okay! That’s why it’s so important to go through this exercise. You want to find the right organization or opportunity or problems to solve next, and they want to find a leader who’s right for them, too. It’s MUCH better to be real and find it’s not a fit during the interview stage, than to skip this exercise and not have it work out in the long run.