In Italian business culture, selling a company is still often seen as a failure.
For many SMEs, it feels like surrendering, walking away, ending a chapter with a bitter aftertaste. The reality is different, but the prejudice remains.

So even when the entrepreneur starts thinking about it, and it happens more often than one might think, they prefer not to talk. They postpone. Wait. Set it aside.

Until when? Often until it is too late to approach it with clarity.

Professionals who work alongside entrepreneurs (consultants, accountants, external CFOs) face an often-overlooked responsibility: to be the first to bring up the subject, without pushing, without breaking trust, without using the wrong tone.

Here are five ways to do it constructively.

1) Frame the future, not the exit

Simple questions like “How do you see yourself in five or ten years?” or “What role would you like to have in your company a few years from now?” are not directly about selling, but they lay the groundwork.

They encourage the entrepreneur to reflect on time, priorities, and the balance between business and personal life.
They open up a neutral space where the idea of selling can emerge without immediately touching a sensitive nerve.

2) Talk about others, not about them

Those who sell rarely talk about it. But everyone is curious to hear stories.
Bringing up the example of another entrepreneur, ideally from a similar sector or region, creates the emotional distance needed to bypass the taboo.

“A client of mine considered selling while the company was still growing. Today he is still active, but in a different role, with capital for new ventures.”

Telling a concrete, relatable story helps normalize the topic.

3) Offer a conversation, not a decision

The goal is not to lead the entrepreneur toward selling. It is to give them the tools to assess whether it might be worth thinking about.

A confidential conversation with an advisor specialized in M&A, with no pressure and no commitment, helps turn a latent thought into a real evaluation.

The words to use: valuation, control, confidentiality.
Never say “sale” on the first call.

4) Remove urgency, create space

One of the main reasons entrepreneurs avoid discussing a possible sale is the perception that a decision must follow immediately. Dismantling that urgency is essential.

“No one says you have to sell. And certainly not now.
But if it might make sense one or three years from now, it is worth starting the conversation today.”

5) Ask: “What if someone made you an offer?”

This is the question that shifts the perspective. Saying “Have you ever thought about selling?” is too direct.
Instead, ask:

“If a serious offer to buy your company came in tomorrow, would you consider it?”

It puts the entrepreneur in front of a realistic scenario. That is often when the real conversation begins.

The real risk is not talking about it

Today, selling a company is not an anomaly.
It is a concrete, legitimate and, in some cases, strategically sound option.

But as long as it remains taboo, it will continue to be an emotional decision. Reactive. Or worse, denied altogether.

Those with a trusted relationship with the entrepreneur have a duty to open that door.
Avoiding the topic out of fear of “losing the client” after the sale means stepping back from your role as advisor and settling for the more comfortable one of executor.

But those who have built real trust know that a sale does not end the relationship. It simply changes form.
It opens new paths where value can still be created: reinvestments, new projects, liquidity management, or the start of a new venture.

Talking about it the right way is not a risk. It is a mark of professionalism.