What is a good question to ask an executive?

Questions to ask a CEO (or yourself):

Do all problems go through you, or is the team empowered to fix problems?
How are problems in the company surfaced to you and other leaders?
What's your biggest people problem you're trying to solve right now?

Table of Contents Show

Questions to ask a CEO (or yourself):
3) What does your company's hierarchy look like?
Questions to ask a CEO (or yourself):
4) Are you and your managers having 1 on 1s with your staff?
Questions to ask a CEO (or yourself):
5) What kind of example are you setting for your team?
Questions to ask a CEO (or yourself):
Promoting from within vs. Hiring outside talent
Questions to ask a CEO (or yourself):
What questions will a CEO ask in an interview?
Ask now – before it's too late
Further reading

3) What does your company's hierarchy look like?

Hierarchy is not a bad thing. Done well, it makes decision making and key responsibilities clear. It also shows clear career paths for your people that want to grow and advance.

Unfortunately, too much hierarchy slows a company down. However, rarely is that the problem today. Many companies instead try to be as flat as possible, sometimes trying to have no managers at all. This was a recipe for disaster, as many found out the hard way.

Zappos, Medium, Buffer, and others tried to make various types of flat organizational structure work, in an effort to get away from corporate politics and the dangers of bad bosses. They all ended as failed experiments that cost them big.

As Wistia learned:

"Every company has a structure. If you don't explicitly define your structure, then you are left with an implicit one, and that can stifle productivity. We had hoped that being flat would let us move faster and be more creative, but as we grew, we ended up with an unspoken hierarchy that actually slowed down our ability to execute."

And Wistia is not alone as companies like Github and Buffer have had similar problems they've shared publicly.

Being intentional about the communication architecture and hierarchy of a company is a key responsibility of a leader and a healthy discussion to have.

Questions to ask a CEO (or yourself):

What org structure do you have in the company today? What will it look like in 6-12 months?
Who are leaders you see developing in your current staff?
How do you think about the design of your organization? Do you tend to be intentional with it, or look for it to emerge organically?

4) Are you and your managers having 1 on 1s with your staff?

1 on 1s are an essential tool to fix problems, coach people, build relationships, and talk about all the things that no one gets around to otherwise. It's why we write about 1 on 1s so often on the Lighthouse blog and built a product to help you have awesome 1 on 1 meetings.

When a company is in its early days, it's easy to think that getting beers, social outings, and a tight-knit team is enough. Unfortunately, it's not. As investor and former serial entrepreneur Jason Lemkin writes:

The place to ask is in private, 1 on 1 conversations. It's why so many CEOs and investors swear by 1 on 1s like Ben Horowitz, Andy Grove, Michael Wolfe, and Tomas Tunguz.

If you have more than 5 employees and don't have them, you're on your way to trouble. It's only a matter of time.

Don't have time? Can you afford to lose your best people? Remember: by the time people are frustrated and go get a job offer, it's too late.

[Ed note: if you're new to 1 on 1s and need help getting started, this free e-book on having amazing 1 on 1s here can help.]

Questions to ask a CEO (or yourself):

Do you and your leaders have one on ones with their staff?
What usually gets talked about in your company's one on ones? How do you know?
How are you training new managers? What are they expected to do with their teams?

5) What kind of example are you setting for your team?

The gift and curse of being a startup founder or CEO is that your team will emulate you. If you work hard, they'll work hard. If you're kind to customers, they will be, too.

It also has its downsides. If you struggle with something, so will they. If you have a bad habit, they'll pick it up.

It's hard to build up self-awareness, but it's essential to being a great leader. If you're trying to help a CEO, look for these signals:

Word choice: Do they say "We" or "I" did something? Is it "our" or "my" accomplishment?
Responsibility: Do they take responsibility for problems, or is it always someone else's fault?
Hypocrisy: Have they done everything they ask their team to do, or are they headed down the path of "do as I say, not as I do"?
Approachable: Are they open to feedback? Do they tend to reward, or shoot, the messenger delivering bad news or problems?
Character: When someone leaves, is it good riddance, or do they treat past employees with respect?

Little things add up. While many of these can seem subtle on their own, they either add to the health of a company's culture or its slow poisoning.

Over time, working on the example a leader is setting is the best way to fix any problem they're facing and change their culture for the better.

Questions to ask a CEO (or yourself):

Have you noticed how your habits are picked up by your team?
How did you handle the departure of (person who left)? What do you say about them around the team now if they come up?
What did you say and do the last time someone brought you bad news?

Tapping into an employee's goals and core drivers is the best way to maximize their motivation.

The desire for growth and career development is universal across ages, as a Towers Watson study found:

The better a company supports its employee's growth and development, the more those employees are then willing to invest their own time to move the company forward.

According to a 2012 study by The Alliance (P. 44), "75% of employees say that they're willing to use their own time to further their careers and take on additional learning that would benefit them at work.”

As a leader, this means that not only can you retain talent longer, but you'll get greater effort by your employees when you help them grow.

Promoting from within vs. Hiring outside talent

One of the most important choices a CEO can make throughout a company's growth is whether to promote from within or hire outside talent for each role. While outside talent is required at times, promoting from within allows you to provide more and larger opportunities for career growth and advancement. This leads to many benefits for the company.

According to a study by Wharton management professor Matthew Bidwell, "external hires” tend to be the all-around worst for a company:

External hires typically get "significantly lower performance evaluations for their first two years on the job than do internal workers who are promoted into similar jobs.”
And the external hires have "higher exit rates, and they are paid about 18% to 20% more”

This means your external hire costs you more money, is less likely to stick around, and is more likely to underperform. A CEO that tends to hire externally is bound to have a number of those underperformers in senior roles.

However, above it all, the biggest impact promoting from within has is on morale and retention.

This is because one of the biggest reasons people who are otherwise happy leave their job is a lack of growth. If you're interviewing now, keep in mind you'll be much more likely to stay if you know the company invests in your growth, regardless of how exciting the role you're interviewing for is to you.

And for the investors reading, recognize it's helpful to know the founder's philosophy on growth because it changes their cost structure.

Uncovering diamonds in the rough from within and growing them to be stars can save the company a lot of money, and build deep loyalty. Meanwhile, hiring in senior talent, which so many investors like to advocate for, can do a lot more harm than good as the Wharton study shows us.

Questions to ask a CEO (or yourself):

How much do you look to promote from within vs. hiring in senior leaders?
Do you and your leaders invest in the growth of your team? In what ways?
How often do you expect managers in your company to talk to their team members about their careers?
How do promotion decisions get made here?

* Want to encourage your portfolio companies to promote from within or want to learn to apply it in your company? Learn more here:

What questions will a CEO ask in an interview?

If you're interviewing for a new position and you're trying to impress (and the questions we've discussed will help to that end), you might also be wondering what kind of questions the CEO could ask you in an interview.

First, expect they'll ask about your interest in the company. It's often their baby they started, or something they live and breathe 24/7. Be ready to answer questions like, "Why do you want to work here?” and "What are you looking for in your next role?”

If you're an important hire, the CEO may also be involved in the closing process. Once you've passed their filter for why you want to be there and you'd fit their culture, they'll be asking you questions to find out how they can get you to join their company over others.

Prepare accordingly, and you're more likely to not only get the job, but get an offer that matches what's most important to you.

Ask now – before it's too late

A CEO I met once remarked, "every company is a mess"; unfortunately, they saw that as the end of the conversation instead of the start of one on how to get better. That mindset led to them losing wave after wave of staff until their own departure after they had turned over almost the entire staff.

No company is perfect. Even the best company with a great culture will still have some work to do in some of the above areas.

The point of all of this is to make sure leaders are thinking about these things and doing something about it. Making positive progress in these areas is meaningful to their employees and the health of their company's culture.

If you're a CEO growing your company, get out in front of this. Start asking yourself these tough questions and get help making some of these needed habits a reality. (Need help and have more than 40 employees? Sign up here or email jason at getlighthouse dot com with your questions.)

If you're an investor, advisor, friend, or mentor, help the leaders you're working with by being proactive about these questions. Don't wait for them to come to you. Get them thinking about it so they catch the issue sooner. Even if they don't buy in now, they will down the line when things get worse.