Toye Sobande

A manager, mildly irritated on an ordinary Tuesday, fired off a line about a colleague. Nothing dramatic. A little sharp, a little dismissive, the kind of thing people say when they assume they are speaking only to the one person in the “To” field. He hit send, moved on, and never thought about it again.

Three years later that sentence was on a screen in a conference room he had never entered, being read by lawyers he had never met, in a dispute he had not seen coming. Pulled out of its Tuesday, stripped of its tone, laid flat on a page beside a date and a timestamp, it no longer read as a passing mood. It read as evidence. It meant something now that he had never meant by it, and there was nothing he could do, because he had written it in ink he mistook for pencil.

Here is what almost every leader forgets about email, and it is the reason this subject deserves more than a list of tidiness tips. Every message you send is three things at once. It is a message, which is the only part you are thinking about. It is a record, which will sit in a system long after the conversation is dead. And it is potential evidence, which can be summoned, forwarded, and read by an audience you never imagined, at a time you cannot predict, in a mood you cannot control. You attend the first. The other two are the ones that will eventually define you.

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Ponder what actually happens to the words you send. The message is read once and forgotten within the hour. But the record is permanent and searchable, and the evidence is one forward away from a thousand inboxes. You are not really writing to the person in the “To” field at all. You are writing to a future reader you cannot see, in a context that does not yet exist, and you are doing it in the careless rhythm of someone who believes the words will evaporate. They will not. Nothing you write at work ever truly disappears. It only waits.

There is an old and useful principle that if a decision was not written down, it may as well not have happened, because memory is a liar and only the record survives. Leaders lean on that principle constantly, and they are right to. But almost no one says the second half of it out loud, and the second half is where careers quietly bend: if it was written down, it happened forever. The same permanence that protects you when you are careful will convict you when you are careless. The record does not take sides. It simply keeps everything.

Now, the temptation at this point is exactly the wrong lesson. A certain kind of leader hears all this and becomes a coward on the page, hedging every sentence, lawyering every reply, copying half the building to spread the risk, and saying nothing real in writing so that nothing real can be used against them. That instinct feels safe and is actually corrosive. An organisation whose leaders write only to protect themselves produces a paper trail full of fog, and fog protects no one; it only makes the eventual reckoning harder to read. Writing defensively is not the same as writing well.

The higher standard, the one worth building a habit around, is this: write things you would be proud to have read aloud. Not things that are merely safe. Things that are true, clear, fair, and yours, so that if the message ever does surface in a room, you never pictured, it speaks well of you rather than against you. That is a discipline of character, not caution. The leader who writes to be proud writes better emails than the leader who writes to be protected and sleeps better too.

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So, sit with a few honest questions this week, because they cut closer than they first appear. If your last hundred sent messages were read aloud, in full, in a room containing every person they mention, what would you want to take back? Which email sitting in your outbox right now would you quietly rewrite if you knew a stranger would read it three years from today? And when you write, are you informing people or protecting yourself, and are you certain the reader cannot already tell the difference?

Here is your challenge, and it costs you nothing but a breath. Before you send anything consequential this week, run it through a single test: would I be comfortable if this exact message, every word of it, were read aloud a year from now by someone whose respect I care about? If the answer is yes, send it. If the answer is no, do not soften it and do not hide it. Find the thing that made you flinch, and fix that.

I used to think the danger of email was what it recorded. Then I realised the more unsettling truth is not what your emails preserve, but what they teach. Because while you are busy writing messages, your messages are busy writing to your people. That is where we will go next week.

Dr Toye Sobande is a strategic leadership expert, executive coach, lawyer, public speaker, and award-winning author. He is the CEO of Stephens Leadership Consultancy LLC, a strategy and management consulting firm offering creative insights and solutions to businesses and leaders. Email: contactme@toyesobande.com