Leadership: Unspeakable

Unit 3, Professor Christina Wing's Unspeakable: Unspeakable: The Taboo Topics We Avoid and How to Talk About Them, and Note on Difficult Conversations in the Family Enterprise.

Some arrangements make perfect sense on the day they're written down. Many years later, they're still sitting there in the documents, while people's lives have moved on somewhere else.

This session's two readings are about how those changes can be seen, and how they can be put into words.

Here goes — enjoy:

Case Summary

The introduction to Unspeakable opens with an email after a funeral.

Luis Garcia founded a successful dry-cleaning business and gave his family a comfortable life. He was thoughtful about many things and prided himself on treating people fairly. But there were a few topics he never wanted to discuss: money, succession, and the fact that one day he would be gone. Whenever his children tried to bring them up, he'd say there was still time, and that they could figure it out themselves later.

A few days after the funeral, the three children received an email from a lawyer they'd never met. The attachment laid out their father's arrangements: control of the business went to the elder daughter, the family home to the son and his wife, and the remaining assets into a trust that benefited all three children but came with quite a few restrictions. Everyone was surprised, and each believed they understood what their father had really intended. The trouble was, they couldn't point to a single conversation they had all been part of that explained why these decisions were made.

The will had been written twenty years earlier. Back then, the elder daughter lived near her father and was well placed to take over the business; the son had just started out in education, with a modest income, and needed the stability a house would bring; the younger daughter's finances were shaky, and her father hoped to protect her through restrictions. Put back in that moment, the arrangements had their reasons.

But twenty years on, the elder daughter had moved out of state, and the son had also left the area and become an accomplished professor. The younger daughter — the one who had originally worried her father — ended up staying on to work in the business and living at home to care for her ageing father. Life had changed, but the arrangements stayed frozen in the past. The original considerations were never revisited, and the father never worked out together with his children what would count as fair now.

According to Wing's account, within a year the three children were no longer speaking to one another. She notes in the book that some names have been anonymised. The problem in this story has a clear time span: a decision that was reasonable at the outset became hard to understand in a reality that went twenty years without an update.

The accompanying HBS note grounds this theme in concrete methods: tell the other person the topic of the conversation in advance, build a shared understanding, stay objective, and agree on next steps at the end. It offers three sample dialogues — on succession, inheritance and a family prenuptial agreement — and lists questions the next generation of a family can ask.

The prep question the professor left us is very direct: think of a conversation you've been putting off, and write down who it's with, why you haven't had it, and what the waiting is costing.

My Thinking

Silence robs a decision of the chance to be updated

The three Garcia children understood the same arrangements differently because the realities they were each holding had already diverged. Who stayed in the business, who took on the caregiving, who needed support — the picture twenty years ago and twenty years later was not the same.

If those changes are never put on the table, a single document ends up carrying several people's mutually incompatible expectations. A decision needs reasons, and it also needs someone to recheck whether those reasons still hold. The same goes for succession plans, partnership roles and key appointments in a company.

My own take is that maintaining an arrangement requires someone to keep questioning its premises. Does this person still want that job? Is the person who originally took on the risk still bearing the same risk? When the facts change, does everyone know where to raise an adjustment?

Paper can preserve a decision. Understanding has to keep happening between people.

Consideration means giving the other person a chance to choose

Maya, in the introduction, is a star employee at a consulting firm. Her manager considers her indispensable, and clients often ask for her by name. When a more senior role opens up, everyone assumes she'll get the promotion.

But she has been back from parental leave for only six months. Her baby often fusses and cries, and she looks exhausted. Her manager thinks adding responsibility now would make things harder for her, and also feels family matters are too private to ask about — so, without discussing it with her, gives the opportunity to someone else.

When Maya later asks about it, her manager says they assumed she didn't want to take on such a role right now. She admits she might well have said no. But she's shocked that she was never even asked.

A well-meant judgement can still take away someone's chance to make their own decision. What's worth talking through here is what the role requires, what she herself wants, and what support she'd like to have. How much of her private situation she chooses to share can be left up to her.

My own take is that consideration should leave room for asking. We can have our observations and guesses, but we also need to give the other person room to correct them.

Being willing to face a problem also means leaving room for the unknown

This session has a premise worth probing: not every conversation that hasn't happened yet is stalled because someone is afraid to speak up. Sometimes we're willing to face the problems we can already see, but don't yet know that another problem exists.

Steve, in the HBS note, is in exactly that situation. He's 29, has worked in private equity, and is about to start business school. He has always assumed he'll take over one day. His mother, however, believes he loves his work outside and doesn't want to join the family business. She herself was once required by her father to join the company, so she wants to give her son more freedom.

His mother also has another successor in mind: John, who already works on the company's sales team. But she has never asked John whether he wants to take over, either. And so three people's futures rest partly on understandings that have never been confirmed.

Being willing to talk about what you know needs to go hand in hand with another ability: discovering what you don't know. For example: "I've always assumed you want to stay on — is that right?" Or: "Is there any part of this that I haven't thought of but that matters a lot to you?"

My own take is that candour also includes uncertainty about your own judgement. Only if you're still willing to make room for new information after stating your position can a conversation change what you understood before.

Once it's raised, agree on who takes the next step

Steve's conversation with his mother doesn't settle on the spot who will take over. The progress it makes is more concrete: in two weeks, get the third-generation members together to find out what each of them wants; Steve drafts the invitation email, his mother sends it, and she has her assistant book the meeting room.

This part deserves attention. Many important issues have already been raised, and have even drawn the response "we should find time to talk about this properly." But who will organise it, what information is needed, and when to pick it up again still have no answers.

After you speak up, the issue still needs to enter a process that can keep moving forward. The HBS note's three steps map onto exactly this.

First, build a shared understanding. Explain why you want to talk and what you hope to clarify, and make it clear you're willing to hear the other person's view. The material suggests that, ideally, you give at least 24 hours' notice so the other person can prepare.

Second, stay objective. Stick to facts that can be confirmed, and avoid presenting guesses as the other person's motives. When emotions run too high, you can pause and give both sides time to regroup.

Third, agree on next steps. Restate what each of you heard, which questions now have answers, which still need information, and who will do what next and when you'll talk again.

My own inclination is that a first conversation can aim for just one small piece of progress that both sides agree on. The cost is accepting that you may not get a final answer this time, and committing time to follow up. But it gives a huge, daunting problem somewhere you can actually start.

Explaining the rules in advance reduces personal misunderstandings

In another example in the HBS note, Crystal is about to get married. Her father suddenly calls her into his office and hands her a stack of prenuptial agreements that she and her fiancé need to sign. Her first feeling is that her father doesn't trust her partner.

Only as the conversation goes on does she learn that this is a uniform family arrangement, and she just happens to be the first in her generation to marry. The father is talking about family rules; the daughter hears a verdict on a specific relationship. That information gap puts the conversation on the defensive from the very start.

The later a rule is explained, the more easily it's taken as an ad hoc judgement about a particular person. How family members join the business, what their pay is based on, how things are adjusted when performance falls short — these run into similar problems.

Explaining rules in advance doesn't mean the rules are necessarily reasonable. They still need to be explained and discussed, and they need to accommodate differing opinions. It's just that when the discussion happens before a specific person is asked to accept a particular outcome, everyone has a better chance of seriously understanding the rule's purpose and its costs.

Takeaways for Arcus42

Treat the questions that haven't been clarified yet as part of the work. Even a fully organised set of materials may still fail to answer what a particular family member really cares about. In discussions, you can separate confirmed facts, each party's understanding, and the questions still to be clarified, so the follow-up work has a clear point of entry.

Give the people affected a chance to speak. A well-meant interpretation one person makes on behalf of others needs to leave room for the people themselves to add to it or correct it. Who takes part in which round of discussion should also match the issue and the wishes of everyone involved.

Let tools help with follow-up; let people carry the communication. In an AI-native way of working, technology can help organise information that people have agreed may be recorded, flag to-dos and track progress. Opening up sensitive topics, understanding emotions, and making the final decisions still require the people involved and the right professionals.

When recording next steps, also record the disagreements that remain. The end of a meeting doesn't mean everyone has reached the same view. Writing down clearly where there is agreement and where there isn't yet lets the next conversation pick up from where things really stand.

As life changes, recheck the premises of your arrangements. Family members' wishes, responsibilities and circumstances change. Building in regular opportunities for discussion helps existing arrangements keep up with reality; where specific legal, tax or investment matters are involved, the relevant professionals need to be part of the judgement.

Before Class

In this session, I want to keep pressing on two questions: how do you discover the problems you haven't yet realised exist? And when an issue has been raised but no arrangement has taken shape, how do you get everyone willing to move it forward together?

My pre-class vote goes to one concrete standard: by the end of a conversation, our understanding of the next step should be clearer than when we started.

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This piece is a pre-class discussion based on the introduction to Christina Wing's Unspeakable and HBS 624-044, Note on Difficult Conversations in the Family Enterprise. The Garcia and Maya stories appear on pages 1–4 of the introduction; Steve, Crystal and the conversation methods are on pages 2–7 of the HBS note. Some names have been anonymised by the original author. The extended reflections here are my personal understanding and do not constitute legal, tax or investment advice.