What is the first conversation with Second Chair™ like?

The first conversation with Second Chair™ is a private conversation with Nikola, arranged through a one-time link in his personal reply to your request. It is a conversation, not a sales presentation. A family can expect to talk about the business, the successor, the transition date and the rooms ahead, and to ask anything about how the six months work. Both sides then decide whether to go further.

It is also the point where the family meets the person who would do the work. Nikola takes on every engagement himself, so there is no hand-over to someone else after the first conversation.

How is the conversation arranged?

It follows a short request on the site. Nikola reads every request personally. Where there is a fit, he replies within three business days with a personal email, and that email includes a one-time link to schedule the conversation. There is no public calendar. The steps before the conversation are set out in what happens after you request a private conversation.

Who should join?

There is no fixed rule, and families arrive at this point in different ways. Some practical considerations:

The parent or current leader is usually the person who made the request and the person who would fund the work. It makes sense for them to be there.
The successor is the client if the work goes ahead. Some families prefer the parent to speak first and alone. Others want the successor involved from the start. Either can work, as long as the successor knows the conversation is happening.
An advisor or private banker who made the introduction may want to be present. If so, say so when you reply to Nikola’s email, so the conversation can be planned with that in mind.

Whatever the choice, a successor who hears about the program for the first time after it has been agreed tends to treat it as something imposed. Introducing a coach to your son or daughter covers how to raise it.

What can a family expect to discuss?

The conversation is not a scripted procedure. These are the subjects that a family can reasonably expect to come up, because they decide whether the program fits.

The business and the transition

What the business does, how the leadership is arranged today, and when the transition begins. The request form already asks for the timing, so the conversation tends to go into what that date means in practice: which role the successor is stepping into, and what changes first.

The successor

Where the successor is in the business, how long they have been there and how they are seen. Most importantly, whether they have decided to take the role. Second Chair™ begins once that decision is made. If it is still open, it is too early for this work, and an honest conversation will say so.

The rooms ahead

The events in the coming months where the successor’s authority will be tested: board meetings, a first company address, the family meeting, conversations with banks, partners and key customers. In the program these become the practice material, so they are a natural part of the first conversation.

What concerns you most

The free-text field in the request is usually the starting point. A parent might be worried that the senior team will not follow, that the board still looks past the successor, or that the family agrees in principle and disagrees at dinner.

What will you be asked?

Expect questions that help both sides judge the fit, for example:

Has the successor decided to take the role?
What is the timeline, and how firm is it?
What would success look like by the end of six months?
Which events are coming up that matter most?
Who else is part of the picture: siblings, a board, long-serving executives, existing advisors?

There is no need to prepare written answers. Rough, honest answers are more useful than polished ones.

What can you ask?

Anything. Families often want to understand the practical side before deciding. Useful questions include:

How do the six months work? The program has three phases: a private diagnostic in weeks one and two, twenty-four weekly sessions of sixty minutes, remote, and a facilitated handover session at the end of month six.
What will I hear as the parent? A private intake in week one, a summary of the diagnostic in week two and a thirty-minute briefing each month. What is said in sessions stays between coach and successor. What the parent sees during successor coaching goes into this.
How is confidentiality handled? Every engagement begins under a mutual NDA. Second Chair™ does not publish case studies or name the families it works with.
What does it cost? Engagements begin at $50,000 for the six months, paid in full by the family or the company.
Is there a guarantee? No. How a board, a senior team or a family responds to a successor is not something anyone can promise.
What is not included? Investment, tax and legal advice. Those stay with the family’s existing advisors, and Second Chair™ works alongside them.
How does it end? With a handover session in which parent and successor write and sign a one-page Handover Charter. What a handover session with both generations looks like describes it.

What makes a good first conversation?

Candour, on both sides. The conversation is most useful when the family describes the situation as it is, including the parts that are uncomfortable: a successor who is not yet sure, a sibling who expected the role, a founder who finds it hard to step back. None of those is a reason the conversation fails. They are what the work would need to account for.

It also helps to come with the next six months roughly in mind. A family that knows its board dates, its announcement plans and its family meetings can see quickly how the program would map onto them.

What happens after the conversation?

Both sides decide whether to go ahead. There is no pressure to decide in the conversation itself, and no offer that expires.

If the family and Nikola agree to proceed, the engagement begins under a mutual NDA. The first phase is the private diagnostic: a parent intake, a successor intake, confidential interviews with three to five people the successor will lead, and a recorded baseline. The written diagnostic follows in week two.

If it is not the right fit, or not the right time, the conversation should make that clear too. Sometimes the honest answer is that the successor needs to decide first, or that the family’s question is one for a different kind of advisor.

In short

The first conversation is private, with Nikola, arranged through a one-time link in his personal reply to your request.
Who joins is the family’s choice. The successor should at least know it is happening.
Expect to discuss the business, the successor, the transition date, the rooms ahead and what concerns you most.
Ask anything: how the six months work, what the parent hears, confidentiality, price and what is not included.
If both sides go ahead, the engagement begins under a mutual NDA with the private diagnostic.

If you would like to begin, the request form is the first step.