Five Questions to Ask your CEO

The board’s only staff member is the CEO (or equivalent, such as Executive Officer, or General Manager, etc.). The board works with and through the CEO to get stuff done and achieve the strategic goals of the organisation.

On top of the usual monthly questions the board asks the CEO, there are a number of key areas that are beneficial to delve in a little deeper and hopefully increase the effectiveness and improve the work and life of the CEO.

1. How are you going with the Strategy?

At most board meetings the CEO will give the board an update on each of the strategic areas. It may be worthwhile keeping the conversation going on this point during a board meeting, in order to get behind some of the top level “performance on target” or “green-light” dashboard indicators.

Asking questions that get to the heart of what’s working and what’s not working with the strategy and its implementation. Check in with how the CEO’s strategic process (the things they do to implement strategy and realise results) is going against their plan. What’s next for them in relation to strategy implementation? How is their performance against KPIs – the ones they have for themselves, their team, and the organisation?

It’s recommended that the board spend as much time on strategy and strategic issues as it does for compliance and monitoring tasks. As a board you should be ensuring the job’s getting done, whilst supporting and assisting where possible. Approaching this is the mindset of establishing where or how can we do better, rather than trying to catch the CEO out for not doing something, is the way to go.

2. What’s coming on the horizon?

Change, disruption, and innovation all have the potential to impact the organisation to some degree. Asking the CEO what’s coming that we need to be aware of opens the door for the conversation around the offensive and defensive measures. For example, is there an innovation that we can adopt into our work practices that will allow us to do more with less [offensive]? Or, do we need to introduce long-term contracts because a new competitor is looking to enter the market [defensive]?

Further to this, what are the opportunities coming from disruption and innovation? Is there a new product we can offer? Is there a new market we can enter?

3. How are you developing / improving your team?

The CEO gets their work done with and through the staff of the organisation. It is prudent for the board to check in with the CEO regarding the organisation team, particularly the CEO’s direct reports. The areas that are worth reviewing are: succession planning activities (key positions in particular); the capacity of current staff to meet future organisation needs; their performance and how the CEO is managing high and low performers; the culture and how that’s being actively managed; and the team’s performance against KPIs.

Organisational talent is your most important asset and should be given the appropriate amount of focus by the board.

For more on the board’s role in organisation talent development, watch this clip from Inside America’s Boardrooms.

4. How are you doing?

Mental health and psychological safety is a modern concern for every workplace. The CEO’s job is multi-faceted and often times highly stressful. An empathetic and prudent board recognises that the CEO is a human being and, as such, takes the time to check-in with the CEO. It’s worth asking about their mental wellness, physical health, family, and their workload and expectations placed on them by the board.

If there are indications – or outward admissions – that the CEO is struggling, the board must take action. This could be easing back on expectations, bringing in an expert to assist with the CEO personally or with the organisation.

Remember, “the person taking care of everyone else needs someone to take care of them”. That ‘someone’ is the board.

5. What do we [the board] have to start doing, stop doing, and continue doing?

I see the role of the board as that of enablers; providing resources, strategic input, expertise, and a sounding board to the CEO. This also means that sometimes you can be standing in the way of the CEO, or you could be doing something that the CEO wants you to do more of. Asking this question creates a candid environment for the CEO to ask for explicit help – either by starting or continuing to do something positive, or stopping you doing something that’s not working.


This list of questions goes beyond the usual questions asked at the regular board meetings. It is also by no means exhaustive. It is, however, a great place to start to introduce more meaningful and impactful conversations with your CEO that will benefit the organisation.

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