I used to think good communication was about telling everybody everything as soon as possible. The logic seemed reasonable enough: people cannot complain that they were not informed if you have given them all the information, problems are less likely to develop when people know what is happening, and decisions should be communicated quickly so that everyone understands what is expected of them. For a long time, I associated good communication with speed, completeness and transparency, which meant that when I had something important to share, my instinct was to communicate as much as possible.
That instinct has not entirely disappeared, and one of my weaknesses as a leader has always been writing long emails. I do not particularly like sending four or five messages about the same subject, so I tend to put everything into one place: the background, the context, the decision, the reasoning behind it, the actions required and, quite often, the answers to questions that I anticipate people might ask. From my perspective, this is efficient because everything is available in one place and there should be little opportunity for misunderstanding.
The problem, of course, is that I am not the person receiving the email. Some people appreciate having all the information together, while others see a wall of text, struggle to identify what matters most, read part of the message and miss an important detail, or intend to return to it later and never do. Over time, I have had to accept one of the more uncomfortable realities of leadership communication: providing information and creating understanding are not the same thing.
When Communication Does Not Land
Recently, I communicated information about an annual event that we had also discussed the previous year. It was not a new initiative, there was already organisational knowledge and experience behind it, and I believed the information I had provided was sufficiently clear. Nevertheless, several members of my immediate team were confused about what was happening and what was expected of them.
My initial internal reaction was probably the same one many leaders experience when this happens. I wondered why they did not understand something that seemed obvious to me, particularly when the event had happened before and the relevant information had already been provided. Experience, however, has taught me to recognise that reaction without allowing it to determine what happens next. Whatever I thought about the clarity of the original communication, the reality was that several people had not understood it, and defending the email was not going to resolve their confusion.
I could have sent another message, highlighted the relevant paragraphs or reminded everyone that we had discussed the same event the previous year. Instead, I spoke face to face with the two or three people who were unclear, and the misunderstanding was resolved relatively quickly. Earlier in my career, I suspect I would have spent longer demonstrating that the information had already been communicated; now, I am more interested in changing the method when the original method has not worked.
Part of the difficulty is that leaders often know far more about an issue than they realise. They have attended meetings, read documents, participated in discussions, seen earlier versions of plans and had informal conversations with colleagues, which means that by the time a decision is communicated they may have been thinking about the issue for weeks or months. The person receiving the communication, however, may be encountering it for the first time, without any of the background knowledge that has made the decision appear increasingly obvious to those involved in making it.
Familiarity creates assumptions about what other people know, remember and understand. We assume that previous conversations are still fresh in people’s minds, that organisational language has a commonly understood meaning, and that words such as accountability, flexibility, quality, improvement or success mean roughly the same thing to everyone. In reality, many workplace disagreements continue for far longer than necessary because people are using the same words to mean different things, or different words to describe essentially the same idea, without ever checking whether they are actually discussing the same issue.
Tone creates a similar problem because the warmth, expression and context that exist in a face to face conversation largely disappear when communication moves to email or messaging. A sentence that sounds efficient to the person writing it may appear dismissive to the person receiving it, while directness can be interpreted as anger and brevity as impatience. Even apparently neutral phrases can carry meanings that were never explicitly written. Few people, for example, read “per my last email” as nothing more than a helpful reference to previous correspondence, because the frustration behind the phrase is often inferred whether the sender intended it or not.
The longer I have led people, the less convinced I have become that intention is a useful final measure of communication. I may know exactly what I meant, but the person receiving the message can only respond to what they experienced, and when those two things are different, insisting on the purity of my intentions does little to repair the misunderstanding.
Who Needs To Hear It, And How?
Communication becomes more complicated as organisations grow because information rarely travels directly from one person to everyone who needs to receive it. A leader communicates something to a senior team, members of that team communicate it to their teams, and those people explain it to others until the original message has travelled through several layers of the organisation. Along the way, details disappear, different elements are emphasised, individual interpretations are added and, occasionally, the message that eventually reaches people bears surprisingly little resemblance to the one that began the journey.
Written communication can reduce some of this distortion because everyone receives the same information, but it creates different problems. Emails become longer because leaders try to remove every possible ambiguity, people skim because they receive too much information, important actions become buried among explanations, and questions that might have been resolved in a short conversation develop into lengthy email exchanges. There is no perfect communication method, which is why leadership requires judgement about whether something should be communicated through an email, a meeting, a private conversation or, as is often necessary, through several methods over a period of time.
The same judgement is needed when deciding who should receive a message. Few workplace communications frustrate me more than the blanket email sent to an entire group because one or two people have failed to meet an expectation. One person misses a deadline and everybody receives a reminder; two people ignore an agreed process and the entire organisation receives another explanation of something that most people were already doing correctly.
If two identifiable people are the problem, my preference is to speak directly to those people rather than making everyone else wonder whether they have done something wrong. Leadership involves having conversations that are sometimes uncomfortable, and communicating with fifty people because we would rather avoid speaking directly to two of them is rarely a good substitute for addressing the actual issue.
There are occasions, however, when an individual incident exposes a wider organisational misunderstanding. What initially appears to be a problem with one or two people may reveal that an expectation was never as clear as leaders believed, in which case broader communication becomes necessary. Even then, I think it helps to acknowledge that many people already understand or are already meeting the expectation, rather than communicating in a way that makes an entire group feel collectively reprimanded.
The important question is whether we are dealing with a people problem or whether the incident has revealed a communication problem. The answer should influence not only who receives the message but also the method used to communicate it.
Trust is also affected by decisions about who can see a communication. BCC has legitimate uses, particularly when privacy needs to be protected or large groups of people are being contacted, but hidden audiences can change the nature of workplace conversations. When people discover that an exchange included recipients they did not know were present, they may become more cautious about what they say, less willing to communicate openly and increasingly concerned about how their words might be interpreted by people who are observing the conversation from the background.
For that reason, I have increasingly valued working relationships in which communication is direct enough for people to challenge me openly. I have been fortunate to work with personal assistants who had no difficulty telling me when something did not make sense, needed changing or should not be sent. Those relationships did not happen accidentally because we discussed the expectation before we began working together. I wanted them to challenge me, and they knew that telling me I was wrong was part of doing their job well.
There is a significant difference between telling people that they are allowed to disagree with a leader and creating a working relationship in which they genuinely believe they can do so. Experience has not stopped me from miscommunicating, but it has taught me the value of surrounding myself with people who are willing to notice it before the communication travels any further.
Silence, Speed And The Weight Of Words
I have sometimes taken too long to respond to people, not because I was ignoring them but because I needed more information, had not made a decision or simply wanted time to think. The mistake was not necessarily taking time because some decisions deserve careful consideration; the mistake was failing to communicate how long I expected that process to take.
A colleague once pointed this out to me directly by asking that, if I was going to take my time, I at least give some indication of when an answer could be expected. It was useful feedback because people can cope with waiting far better when they understand how long the wait is likely to be. When no timeframe is provided, silence creates a space that people inevitably fill with their own explanations: perhaps the answer is no, something has gone wrong, the leader has forgotten, or a decision has already been made and nobody has bothered to tell them.
I have experienced this from the other side recently while going through recruitment processes, and it has reinforced how uncomfortable silence becomes when the outcome matters to you. Waiting is one thing; waiting without knowing whether an answer is coming tomorrow, next week or at all is something quite different. Leaders and organisations do not need to have every answer immediately, but if an answer is going to take time, acknowledging the delay and providing some indication of what happens next is part of communicating responsibly.
At the opposite end of the spectrum, I have also responded too quickly on more occasions than I would like to remember. Earlier in my career, an email would arrive that frustrated me, a decision would annoy me, or someone would communicate something I believed was unfair or inaccurate, and I would feel compelled to respond while the issue was still fresh. The response might have been professional, the language carefully chosen and the argument entirely reasonable, but communication sent while emotions are still shaping our judgement can create problems even when the content is technically correct.
Over time, I have become better at recognising when not to communicate immediately. Sometimes that means walking away, allowing the initial emotion to settle, speaking to someone whose judgement I trust and returning to the message when I am clearer about what I actually want the communication to achieve. My wife has often been that person for me, not because she automatically agrees with my perspective but because she is calm, rational and willing to challenge it. We do not always see matters in the same way, which is precisely why discussing them with her can prevent me from becoming too convinced by my own interpretation of events.
The value of having people who will challenge us applies equally to professional relationships. Leaders benefit enormously from having someone who will tell them not to send an email yet, question whether a message will be received in the way it was intended, or point out that winning an argument is unlikely to improve the situation. Responsiveness still matters, but I no longer believe that the quickest response is necessarily the most professional one, particularly when a short delay can produce a better judgement and a more useful conversation.
The emotional weight of communication is also evident when leaders give corrective feedback. Nobody particularly enjoys criticism, regardless of whether it is described as feedback, professional dialogue or development, and even carefully delivered conversations can be experienced personally by the recipient. That does not mean leaders should avoid difficult conversations because honest feedback remains essential for improvement, but the way those conversations are framed can influence whether people leave feeling defensive or capable of reflecting on what they might do differently.
I prefer to focus conversations on improvement by asking what could be different, what could be better, what has been learned and what support might be needed. The underlying issue may be exactly the same, but framing the conversation around future improvement creates more opportunity for productive reflection than simply listing what someone has done wrong.
Leaders also need to remember that corrective feedback often carries considerably more emotional weight than praise. Someone may have received regular encouragement, recognition and thanks over a long period of time, yet one difficult conversation can become the interaction they remember most clearly. We cannot control every reaction to our words, but we should not underestimate their impact simply because giving feedback has become a routine part of our role.
Choosing The Moment
There used to be a phrase in one organisation where I worked: Bad News Thursday. Difficult messages had a habit of arriving just before the weekend, leaving people with several days to think about what they had been told without being able to ask questions, seek clarification or do anything practical in response. Organisations sometimes create the same problem by sending significant messages during holidays, technically fulfilling their responsibility to communicate while leaving recipients to carry the uncertainty until normal working arrangements resume.
I have also deliberately told people before a weekend that we needed to discuss something significant when they returned. My reasoning was different because I did not want to ambush someone on Monday morning with a conversation they had no opportunity to anticipate, particularly when the matter was serious enough that some reflection might be useful beforehand. Nevertheless, I have never been entirely comfortable doing it because giving someone advance notice of a difficult conversation also means asking them to carry that knowledge through their weekend.
There is no perfect rule about timing because the same decision can be considerate in one situation and unnecessarily harmful in another. What matters is why the leader has chosen that moment and whose interests the timing is serving. Sometimes waiting protects the person receiving the message, while at other times advance notice gives them the dignity of preparation; equally, both delay and speed can become convenient ways for leaders to avoid dealing properly with difficult communication.
That uncertainty is probably one of the biggest changes in how I think about communication after nearly thirty years in education. I used to believe good communication was about telling everybody everything as soon as possible, whereas now I think it is about choosing your moments without using timing as an excuse to procrastinate, choosing the right method, deciding who genuinely needs the information and recognising when an email should become a conversation.
It also means accepting that leaders need safeguards around their own communication. I have benefited from personal assistants who were prepared to tell me that something was wrong, colleagues who pointed out when my silence was creating uncertainty, team members whose confusion showed me that an email had failed, and a wife who has often encouraged me to wait, reconsider or look at an issue from another perspective. None of those people removed my responsibility for communicating well, but they helped me recognise occasions when my own judgement needed challenging.
Perhaps the most important lesson has been accepting that intention is not the final measure of whether communication has worked. I can believe that I explained something clearly, point to the email where the information was provided, remind people that we discussed the same issue the previous year and defend every word I used, but none of that changes the fact that something needs to be done differently if people have not understood.
Good leaders will miscommunicate because leadership involves communicating frequently, across different relationships, under pressure and in circumstances where people do not always share the same information, expectations or interpretations. Experience does not remove that problem, although it can make us quicker to recognise when communication has failed and more willing to change our approach.
Earlier in my career, I was more likely to defend the message I had sent. These days, I would rather change the method and create understanding.
I am still learning when to do which.
If you enjoyed this article, you can continue exploring these ideas through the growing collection of short leadership videos published across TikTok, Instagram, YouTube, Facebook and LinkedIn. Wherever you choose to follow, I hope the reflections encourage you to think a little differently about the quieter moments that shape leadership every day.