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The Conversation You Are Not In
CEO Briefing #123

The Conversation You Are Not In

The Conversation You Are Not In
Short answer

A CEO brand is built in public but verified in private, by people who worked for the CEO. Investors, candidates and corporate buyers check it through current and former employees. Iskender Dirik explains why your team is a separate audience, four questions that reveal what they would say, and three levers that change their answers.

An investor is a few days from signing a term sheet. The data room is clean, the numbers hold, the CEO presented well.

So the investor does the last thing on his list. He calls someone who left her company two years ago.

Not one of the references the CEO put forward. Someone the investor happens to know, through someone else. And someone with nothing left to protect.

One question: what was she actually like to work for?

The answer takes about ninety seconds. And it carries more weight with that investor than every post she has published, every keynote she has given, every interview she has done.

She built her reputation in public. It got decided in private.

Built outward, verified inward

A CEO brand gets built for the outside. Profile, posts, stages, podcasts, press. All of it reaches investors, customers, and candidates.

None of it is what they check it against.

They check it against people who watched that CEO on ordinary Tuesdays. A candidate weighing an offer does the same, through a friend of a friend. So does a corporate buyer, once a price is on the table and the question moves from what the company does to who is running it.

Which means the people who work for you, and the ones who used to, are an audience of their own. They rarely show up in the plan.

Why they are a different audience

Three things separate them from investors, customers, and candidates.

1. They cannot scroll away: A stranger who finds your thinking irrelevant moves on. Your team reads all of it, because their work depends on you. A thought you post casually on a Sunday arrives on Monday as an instruction.

2. They can check every word: What you claim in public about your standards runs against what they watched you do last quarter. The bigger your reach, the more expensive the distance between the two.

3. Their number only grows: Everyone who has ever worked for you stays reachable, and the ones who left speak the most freely. You add to that group every year. You never take anyone out of it.

Finding out what they would say

Here is the hard part. You cannot ask them yourself. When the boss asks what it is like to work for her, people answer the boss.

So someone else asks. A chief of staff, an HR lead, an external coach. Six people across three levels of the company, twenty minutes each, and no answer gets attached to a name.

The interviewer asks about you, by name. Four questions do the work:

1. When you think of [name], what comes to mind first? Whatever someone says without being prompted is your actual brand. Every answer after this one is already shaped by the question.

2. What does [name] stand for here? This shows whether your position made it into the building or only onto your profile.

3. Can you remember a time [name] stopped something or said no? What was the reason? Anyone who can name your reason can predict your next decision. That is the real test.

4. What gets said about [name] here that nobody would say to their face? This one collects what the first three leave behind.

You are reading the answers for three things: the words that keep coming back, the conviction you consider central that nobody mentions, and the thing several people name that you never claimed.

What moves it

Three levers change those answers. Two of them cost nothing.

1. Say it the same way for years: Your position exists on paper. The test is whether someone on your team can state it accurately while you are on a plane. That takes the same wording, quarter after quarter. A conviction rephrased every time reads as a new conviction, and people stop trying to hold on to it.

2. Give the criterion, not just the decision: Announcing a decision informs the company. Naming the standard behind it lets people predict the next one. A leader with unremarkable but stable standards is easier to work for than an impressive one whose standards move.

3. Consider a channel that is yours alone: The idea is a recurring internal note – written, filmed, or spoken – that goes to your company on a fixed rhythm and carries one thing: what you are watching in the market and how you read it. The all-hands belongs to the company. A note like that belongs to you.

The first two levers correct how you are already read. A channel of your own builds something over years. And the details decide whether it holds up: which format, how often, how personal, and what stays out of it. That is the next issue.

The market decides whether it believes you. Your own people decide whether that belief survives the first phone call.

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Episode page with show notes on id.vc

Frequently asked questions

How do investors check a CEO’s reputation before signing a term sheet?

Beyond the references the CEO puts forward, an investor may call someone who used to work for the CEO and ask what the CEO was actually like to work for. That answer can carry more weight than every post, keynote and interview.

Why are employees a different audience for a CEO brand?

They cannot scroll away, because their work depends on you. They can check every public claim against what they watched you do. And their number only grows, because everyone who has ever worked for you stays reachable.

How can a CEO find out what employees really think?

Someone else has to ask, such as a chief of staff, an HR lead or an external coach. Six people across three levels, twenty minutes each, with no answer attached to a name, and four questions about the CEO by name.

How can a CEO change how the team sees them?

Say your position the same way for years, give the criterion behind a decision and not just the decision, and consider a recurring internal channel that is yours alone.

Iskender Dirik
About the author

Iskender Dirik

CEO advisor for fundraising, exits and executive branding. Venture Partner at EQT Ventures, previously led the global Gen AI practice at Samsung NEXT and was Managing Director of Microsoft ScaleUp. Host of DEALMACHER, the podcast with the dealmakers who sat at the table when big capital moved.

EQT VenturesSamsung NEXTMicrosoft ScaleUp
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