The Questions I Asked When I Interviewed Executives
And what I was actually listening for
There are two questions I lean on when I am interviewing somebody for a leadership role, and I have been asked both of them myself. They are hard on purpose. There is no single right answer to either one, and there are a lot of wrong ones, and the wrong ones almost never sound wrong when you say them out loud. That is the part that should worry you.
If you are preparing for an executive interview, these two are worth sitting with before somebody asks you a version of them across a table.
Question one
What do you do when you see an issue with how the company is being run, it does not directly relate to your role, and the culture is stay in your lane?
Here is the most common answer I get, and I want you to read it and notice that nothing about it sounds bad.
I respect my coworkers and I offer to help when I can, but I also accept that they are professionals like I am, so I don't do anything that would step on their toes. If I see something that is really off I will find a creative way to bring it up without making the other person feel bad. But generally in an organization with a stay in your lane culture, I stay in my lane unless somebody asks me otherwise.
That is a reasonable answer. It is respectful, it is self-aware, it is the kind of thing that gets nodded at. And I have a problem with it, because you were hired to make the business better, and while you are employed there you have an obligation to do everything in your power to do that. That does not mean bulldozing people. It means using every skill and tool you have, everywhere you can reach, and finding a way in when the front door is closed.
The candidate who tells me they stay in their lane is telling me they will watch something fail politely.
What a good answer sounds like
I was on an executive team once where one of my peers seemed to object to everything I asked, suggested, or did. On the IT side I was solid, there was nothing more I could do without a bigger budget, and what I was trying to do was help in areas outside IT because I wanted to see every part of the business succeed. I had actually done a lot of the work we were struggling with. The culture leaned hard on stay in your lane, so the problem I had to solve was not the business problem anymore, it was how do I help when I am continually rebuffed, chided, and dismissed.
Other than how this person treated me, I liked their work. High octane producer, hundred miles an hour, real attention to detail, hard worker. Our company had a system where you could nominate somebody for extra effort or for doing something better than expected, so I dropped two notes in the box. My submissions were not anonymous, but the review committee only saw the action, not who did it or who submitted it. They picked mine, and then they read them out to the company.
After that, this person started accepting my input.
I did not go around them, I did not escalate, and I did not go quiet either. I found the one door that was open.
And here is one where I got it wrong
I was working with a company that was struggling financially, so they went looking for new product offerings that might generate revenue. They found a real gap in the market and started exploring it. Early on I asked whether we were doing any reports, investigations, or reviews to gather actionable information about the offering, and I was told that one member of the team had been gathering it and was the expert on the subject. I asked to see the data. I was told not to worry about it, it had nothing to do with my role.
Several months later it came up again in an executive meeting. I did not raise it, but I asked follow up questions and got rebuffed again. What I asked that day was whether we were going to put together a business plan for this, with goals and objectives.
Three months after that the rest of the team came to me and asked me to prepare the technical tools, because we were going live in a week.
I do not get this right every time. What I failed to connect was that nobody on that team had ever built a plan for the work they were doing. That company operated by being told what they could sell, so nobody there had ever done that simple step, and they were not hiding the plan from me, there was no plan. If I ran into it again I would write the business plan myself, or offer to write it with the people who needed it, instead of asking whether one was coming and accepting the answer.
A year later the program had generated zero revenue and cost over a hundred thousand dollars.
Two stories, same question. One where I found a way in and one where I asked politely and let it go. You already know which one I would rather tell.
Question two
How do you make sure your direct reports are purposefully engaged, and how do you track that?
This is one of the best questions to ask or to be asked in an executive interview. When it was asked of me, I answered it and then turned it back on the person asking, who was a future peer. Months later she came to me and asked for help getting her own team more engaged. I walked her through my process and helped her build her own version of it, and a few months after that she told me she was seeing the shift, both in engagement and in what her team was getting done.
Here is what I told her.
First I have to understand who I am working with. I build a relationship with every member of my team, a professional one, because I do not have the time to become anybody's out of work buddy, but I am spending eight or nine hours a day with these people five days a week and I should know them and understand what they want. In too many cases I find that people have never been taught how to set a goal and reach it, any kind of goal, and that sits at the top of my list of what causes somebody to disconnect from their work. When a person is interested in what they are doing, has goals, and has somebody acting as a guide or a mentor, they stay engaged.
Then tracking is easy, because you are just touching base on the goals.
For me that is a regular one on one where we go through their goals, which are mostly professional, and where we look at my involvement in their success. The bigger part is that a leader has to actually lead. I take the time to meet with them and I take the time to go find meaningful projects that move them toward what they said they wanted.
Sometimes the company has real metrics you can apply. Sometimes it does not, and then I am measuring by how well the work gets done, how much of myself I have to put into somebody's work, and how often I have to correct mistakes. Which means there are situations where the absence of issues is the only metric available.
I would rather say that in an interview than invent a dashboard that does not exist.
What this means for how you prepare
Everything you have done in your career is material. The good, the bad, the productive and the unproductive, all of it. When you are young you have less to offer, that is just true. But with time even your mistakes start carrying insight into how to make things better, if you are willing to use them that way.
The hundred thousand dollar story is not a story about being right. I tell it because I learned something in it that I would not have learned by winning.
So before your next interview, go back through your own history and find those. Not the highlight reel, the actual moments where something worked or something did not and you saw why. That is where your best answer to a hard question is already sitting, waiting for you to remember it.
That is also the exact thing ApplyEdge's Skills Assessment is built to do — it asks you the kind of question that surfaces a buried moment like these, keeps your answer once it's told to you, and never makes you dig it back up from memory for the next interview.
Related: Your Experience Already Qualifies You — on translating what you've already done into the language of the role you want.