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Questions to ask a CEO

Questions to ask a CEO

James Brogan
James Brogan
CEO and Co-Founder
James Brogan
October 10, 2021

Employee engagement is often described as being at the heart of company performance. 

Engagement is built around a set of values and a vision that drive a common purpose among all employees. But for too long the values and vision were dictated by the C-Suite and senior management. The emotive words painted in the hallways didn’t tie in with the reality of employees daily grind.

In recent years there has been an increasing focus on understanding employee sentiment. The main reason for this is to improve retention rates, arrest falling engagement scores and try and understand the reasons employees might leave, especially in a hybrid world. 

An important element of employee engagement is having an open, honest and transparent culture where there can be great conversations in both a top-down and bottom-up fashion. 

Increasing numbers of organisations are intentionally creating an environment where employees can ask questions of CEOs  - whether that's open office policies, AMA (ask me anything) sessions, town halls, roundtables or other more focused one to one meetings. 

You’ll be surprised how many opportunities there are so we’ll help you make sure you have good questions to ask your CEO.

Questions for CEOs by employees

I have listed below some areas we at PepTalk are passionate about and believe are good questions to ask a CEO of your company. With technology making collaboration and connectivity more accessible, engaging with a CEO is now more important than ever before. 

Employees should be empowered to proactively seek clarity from CEOs on topics that you are passionate about to get an understanding of their position and/or experience. This can help to create a shared vision and purpose across the whole organisation, starting with self change, from the bottom all the way up to the top. It will elevate your connection to the organisation and the people involved. And, maybe most importantly, it will also help give you insight into what kind of leader your CEO is. 

We went out and spoke to a few leaders to get their sense of the best questions to ask a CEO to help inspire you to take that step and engage with your CEO.

Impactful questions to ask your CEO

A well-adjusted team contributes significantly to a company’s success. An engaged and motivated team will go the extra mile without having to be asked. This is what ultimately leads to growth in every sense of the word.

Though it may seem like an afterthought, team culture is an incredibly important part of running a successful business. 

Yet, many people struggle to recognize how important team culture is. 

Questions to ask the CEO about team culture

  • How do you know which team cultures are most effective?
  • Is there a particular team or organization whose culture you admire?

What motivates people to work well together? What can we learn from successful teams? How do we build a team that works well? How can we identify good leadership techniques? These are important topics for discussion at any level of organization. Whether we realise it or not, the things we do as a team impact everyone else on the team and the company. Good team culture helps you get things finished on time, recognises the need to deal with problems quickly, and promotes creativity within a group.

  • What are the signs of a sub-par culture?

If you feel like your company doesn't have a good culture, you may be right. Culture defines what is expected of employees, how social interactions are conducted, and even which activities are acceptable in the workplace

  • What sort of behaviours can improve the culture of a team?
  • What makes a team successful in your opinion?
  • What is the best way to build a great team?

Being part of a team means you do your best when no one's looking, taking responsibility for the success of everyone in the company. It means building respect among peers and earning trust with customers. It means always putting others before yourself.

Learn more about Team Culture HERE

Smart questions to ask your CEO - Ruari Kelleher, CEO Immedis.

"What does a good team culture look like to you?

“This is a great question and one I have spent some time considering. I enjoy answering this one. 

Good team culture is built around strong visions and values that enable behaviours to be actioned every day. It should be articulated simply, ‘how things are done around here’.

There is a strong sense of trust among a great team, the ability to engage in conflict and have powerful and vulnerable conversations. The human experience and understanding the whole person... that is a key part of team culture.

One of the most celebrated leadership books of all time, Patrick Lenoconis “Five Dysfunctions of a Team” talks about the key dynamics of a team.”

What to ask a CEO?

As mentioned in the opening paragraphs, employee engagement is vital to a company’s success. 

Understanding what makes employees happy and engaged can help companies create an inclusive and rewarding work environment. The joy and fulfilment at work come from doing something you care about, being rewarded for it and learning new skills for leadership competency - purpose and drive.

Questions to ask the CEO about employee engagement

  • What is employee engagement?
  • Why is employee engagement important?
  • What is our strategy around employee engagement?

Employees who are engaged experience better relationships with their supervisors and co-workers, and they also have a higher chance of staying. The top 20% of companies with strong employee engagement rates report a 59% lower rate of turnover compared to companies with low engagement scores.

It’s the emotional connection and connection among your workforce, customers and company. The key ingredients for an engaged workforce are motivated people, a supportive environment and opportunities for growth. Engagement is a two-way street. You need to nurture the employees who are willing to fight for your business every day, but you also need to make sure they know that their interests are important and that they will be heard.

Questions to ask a CEO of your company

  • What teams in the organisation do you feel are most engaged? And why?
  • How important is employees’ energy levels to the success of the organisation?
  • How do you listen to your employees?
  • What keeps employees happy in your opinion?
  • How do you motivate people to go the extra mile?  

As the new work dynamic emerges, employee engagement will grow in importance. It will be the essential element to sustain strong levels of commitment and energy among your employees. We are moving from simple surveys to much more action-oriented engagement solutions designed to support ‘in the moment’ action.

Smart questions to ask your CEO - Gillian Doyle PhD, CEO Cerebreon.

What are the unwritten rules of the company?

Questions to ask the CEO about the importance of employee wellbeing

  • How important are wellbeing programs to engage staff?
  • Do you believe poor employee wellbeing can impact employee performance?
  • What does our organization do to understand the wellbeing of employees?
  • What is the most important part of employee wellbeing for you?

The wellbeing of all employees should be a CEOs concern. Equally important is that any wellbeing program is driven by the leadership within the business. It cannot be material objects or services that are handed to employees.

I believe psychologist Barry Schwartz summed this up brilliantly in his book “Why We Work”. 

 “We may not expect business leaders to ask themselves ‘How can I make my employees’ lives better by restructuring their jobs?’ But we surely would expect them to ask themselves ‘How can I make my business better by restructuring employees’ jobs?’”

  • Where do you see workplace wellbeing in three years?
  • How do we engage managers in workplace wellbeing?
  • How can we measure the impact of wellbeing programs?

There is an increasing need for CEOs to foster a positive environment and a sense of wellness for employees. This has only been heightened in a hybrid or remote working environment. We must proactively and intentionally build behaviours that enable employees to be physically, emotionally and mentally ready to do great work. 

Smart questions to ask your CEO - Andy Mackin, CEO Mackin Group

“As a CEO how do you ensure that everyone within your organization is actively involved in employee engagement and do you feel that the employee engagement levels can adversely affect employee wellbeing either way”

Questions to ask the CEO about company success

  • How will we measure achievement from a people perspective?
  • What sort of characteristics in employees contributes to success?
  • What’re your thoughts on rewarding success?

Company success is a topic that gets brought up over and over again in the PepTalk team. We typically see companies only measuring their success from a balance sheet perspective or by looking at KPIs or sales targets. This only tells half the story. 

The health and wellbeing of your employees should be considered part of the success story. Better people make better teams that build better companies. 

We often hear business leaders talk about their people being their biggest asset on their balance sheet. Yet very little is done to develop this asset. We measure performance and contribution without really considering how we can help them perform better.

  • What are the biggest challenges to our success right now?
  • What are the plans to sustain success?
  • How will we continue to have success in the future?

As Barry Schwartz says virtually every job that people do can be seen as improving the lives of customers, even if only in small ways. Therefore, every job that people do can be made meaningful by focusing on how it improves the lives of customers. 

The real success of a company depends on the customer rather than the balance sheet and KPIs.

The best we can do is give our employees a platform to speak honestly about what they think matters most to them as individuals. If we take care of our people this will improve the impact they have on the team. 

Better people make better teams that build better companies. 

Smart questions to ask your CEO - Sarah Martin, CEO Pulsate 

“The question I get asked a lot is “How do you keep going every day?”

Every organisation faces ups and downs and naturally, there will be times when it is hard to see positives.

There is definitely a need at times for grit and resilience but also keeping perspective and focusing on small wins helps to keep a sense of things.

Generally, where you look at things through a longer lens it can help keep you energised and focused on the bigger goals.”

Fun questions to ask your CEO

  • What has been your biggest learning since becoming a CEO?
  • Do you have a secret talent that no one knows about?
  • What do you do for fun?
  • How do you relax?
  • What was your first job?
  • What is the craziest thing you have done?
  • What gets you up in the morning
  • What motivates you?
  • How are you doing today?

Next time you find yourself wondering what a CEO spends his time on, take a minute to reflect on who they are as human beings. What interests them? What gets them excited? What makes them laugh? What do they do to get away from work?

It's these kinds of details that will allow you to truly get to know someone and connect.

Once you’ve done that, at the next appropriate opportunity… ask the question. 

Below will highlight some personal questions to ask your CEO that might just create an impactful and real conversion.

Smart questions to ask your CEO - Garret Flower, CEO ParkOffice 

“How do you manage your mindset in difficult times?”

“The role of a CEO can be complex with a myriad of issues to work through daily. Building your resilience and ability to cope with setbacks and ‘curve balls’ that will no doubt present themselves requires focus and intentional work. It can be interesting to understand some of the techniques that have been used by your CEO over time to help them succeed and assess whether these techniques would be worth bringing into your working routine.”

Questions to ask the CEO about strategy and performance 

  • What strategy helps you perform at your best?
  • Should performance come at a cost?
  • What does performance culture mean to you?
  • How important is wellbeing in employee performance?

There is power in numbers. Every employee is different and has unique capabilities. Team performance is a collective experience that can be leveraged to achieve great things. 

A good CEO, leader or manager will create a visible strategy, a shared vision of what we do every day. This helps everyone know what to expect from the team, and what expectations are set for ourselves. 

A clear strategy is about being accountable for what we do. And accountability is a great driver of performance. Whether it's project managing a team’s daily tasks, leading a project or keeping an attendance record onsite, a strategy that helps keep people accountable is crucial. 

The ambition for any CEO should be to build a team that ultimately cares but especially cares for one another. This can be achieved by developing a strategy that gives signifiers of how we are doing with the work and one another. 

This can help us maintain focus on delivering high-impact work, share positive recognition and support one another through times of difficulty. 

No matter what team you’re on, we know that you can’t do it all by yourself. Communication is a crucial part of team performance. Honestly sharing responsibilities with the rest of the team ensures that everyone has an accurate understanding of what is expected of them and doesn’t feel alone in their efforts.

The best leaders know that employee performance is a huge variable in determining how their organisation will do in the future. 

Asking (or expecting employees) to work with maximum effort on projects comes with tradeoffs. Sure, you get the project completed but at what cost? Research tells us that stress increases in employees in what can be highly emotional experiences. Naturally, these can be negative for our health and productivity. 

The volume of stress people can tolerate varies. But we do know that certain people may be more sensitive to stress and therefore need to be aware of how much their work environment affects them. Senior leaders who are dealing with a lot of day-to-day challenges can find it very hard to rest until the work is done. An unintended consequence is that other employees may feel they have to do the same. Leaders can learn to implement a culture of safety in the workplace to benefit the teams approach to work.

Senior leaders are responsible for setting the tone in an organisation, they need to create an environment that fosters a performance culture but acknowledges the need to balance. There needs to be time for recharging and for creating a positive work-life balance. 

Smart questions to ask your CEO - James Brogan, CEO & Co-Founder of PepTalk 

James Brogan, Co-Founder + CEO PepTalk 

My favourite question I’ve ever been asked is “What are you most proud of regarding the company?”

Understanding what motivates your CEO and drives his/her ambition is a great way to engage around what truly matters to them as people. We are all motivated by different achievements and it can be a chance to understand the common threads that can exist between different people in the organization. Understanding the shared experiences and motivators for your team and leadership can be a powerful way to create a strong sense of cohesion and camaraderie in the team.

In closing

Hopefully, this blog has given you lots of ideas on how to engage with your CEO next time you get the opportunity to ask a question. I know I appreciate it when people take the time to talk to me, and I'm guessing your CEO is probably the same.

If you'd like to connect with me on LinkedIn you can reach me here.

Thanks for reading.


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