The first 10 conversations every CEO should have in their 100 days

Intro

In your first 100 days as CEO, it’s tempting to dive straight into:

• strategy decks,

• numbers,

• organisational charts.

All of that matters.But if you skip the right conversations, your strategy will be built on assumptions.

Whether you’re taking over a SME in Flanders, leading a family business in Wallonia, or stepping into a scale-up in the Netherlands, the pattern is the same:

Your first 10–20 conversations quietly define your reality.

In “100 Days to Make Your Mark as a CEO”, I recommend a very concrete mix of internal and external conversations.

Internal conversations you should not skip

1. Your predecessor or key founder (if possible)

If the relationship allows it, have a respectful, honest conversation:

• What were their biggest wins and regrets?

• Which decisions still weigh on the company today?

• What promises were made – to staff, customers, family, investors?

This is not about judging them.It’s about understanding the story you’re walking into.

2. 1:1 talks with each member of your management team

For each person, explore:

• What do you see as the biggest opportunities in the next 2–3 years?

• What keeps you awake at night about this company?

• What would you change first if you were in my role?

Listen for:

• alignment or contradictions,

• personal ambition and energy,

• how they talk about their own team and about other departments.

This will tell you a lot about your leadership bench.

3. A cross-section of frontline staff

Pick people from:

• sales,

• customer service,

• operations,

• support.

Ask simple questions:

• “What does a good day look like here? A bad day?”

• “What makes it hard to serve customers well?”

• “If you had a magic wand to fix one thing, what would it be?”

You will hear the operational reality behind the reports.

4. Your CFO or finance lead

Beyond the standard reporting, ask:

• Where are we really at risk – cashflow, margin, concentration on a few customers, debt?

• What are the “numbers conversations” we are not having?

• What financial patterns worry you the most?

This conversation anchors your first 100 days in economic reality, not just ambition.

5. Your “culture keepers”

These are people who:

• have been in the company for a long time,

• are not always in official leadership roles,

• but clearly influence how people behave.

You can ask:

• “What kind of behaviour is rewarded here? Punished?”

• “What makes people proud? What makes them cynical?”

• “What are the stories people still tell from 5–10 years ago?”

This helps you understand the informal rules of the game.

External conversations that sharpen your picture

6. 3–5 key customers in your core segments

Choose different types (size, sector, country if relevant).

Ask:

• “Why do you really work with us?”

• “Where do we make your life harder than it should be?”

• “If you were CEO of our company, what would you fix first?”

This makes your strategy customer-based, not just inward-looking.

7. 1–2 lost customers

This can be uncomfortable, which is why many CEOs skip it.

Questions:

• “Why did you decide to leave?”

• “What did you choose instead, and why?”

• “Is there anything we could have done differently 12 months earlier?”

This gives you a sharp view on where your value proposition cracked.

8. 1–2 strategic partners or suppliers

Partners and suppliers often see patterns you don’t see.

Ask:

• “Where do we look strong from your perspective?”

• “Where do we look chaotic or hard to work with?”

• “What do you hear about us in the market?”

They sit slightly outside your system, which gives them a useful angle.

9. Your bank, investors or key shareholders

This conversation is about expectations and constraints:

• What does success look like in their eyes (timing, returns, risk profile)?

• What are their non-negotiables?

• How do they see the company’s main risks?

You may not agree with everything, but you need a clear view of the playing field.

10. One external sparring partner

This can be:

• a mentor,

• another CEO,

• a strategist or advisor,

• someone from outside your sector.

The agenda is you:

• how you see the role,

• what you’re afraid of,

• where you might be blind.

Unlike internal players, they have no stake in your internal politics. They can ask the questions others won’t.

How to make these conversations count

A few practical tips:

• Prepare 3–5 core questions and use them across conversations.

• Take notes – not word-for-word, but key themes and phrases.

• Look for patterns, not isolated complaints or compliments.

• Share what you’ve heard later with your organisation:

  • “Across all these talks, I heard these 5 themes…”

In “100 Days to Make Your Mark as a CEO”, these conversations are part of the Discover phase. They give you raw material for strategy, organisation design and cultural work.