Do not tell them. Show them. Play ten seconds of their own recording back, pause, look at them, and ask what they think. Most executives will name the problem themselves, far faster than they will accept your version of it. Then hand the decision back, because the choice has to stay theirs.
Communications people know this meeting. The chief executive has a presentation in the morning. You have watched the run-through. It is not working. And you have somewhere between thirty seconds and no time at all to decide whether to say so.
In a two-day session with a federal agency in Washington DC in this past month, this was the question that would not go away. It surfaced on the first morning and was still on the whiteboard at the end of the second afternoon. How do I tell my principal that this is not landing. The people asking were career communicators, several of them very senior, and not one of them had a reliable answer.
I have been on both sides of it. For thirteen years I produced at ABC, NBC and Fox, which meant standing in a green room with a guest who was ninety seconds from making an avoidable mistake on live television. For twenty years since, I have coached executives at organizations including AIG, AARP, Gartner, the ASPCA and the Social Security Administration. Seniority does not make people harder to advise. It makes them harder to advise badly.
Why does communications advice bounce off senior leaders?
Because you are not giving advice. You are making a sale, and you have not treated it like one.
Two things sell: why someone should care, and how they avoid pain. Both work. Pain works better.
Tell a chief executive that a tighter open would be more engaging and you are selling the first one: abstract, pleasant, easy to decline. Tell them the room will decide inside the first twenty seconds whether this is worth their attention, and right now the first twenty seconds are housekeeping, and you are selling the second. You are describing something they do not want to happen, in a room they walk into tomorrow.
There is a second sale underneath the first. You are also selling yourself as the person worth listening to, and every note either builds that standing or spends it. Which is why the order of your suggestions matters more than their quality. Lead with the one easiest to accept, not the one that bothers you most.
How do I tell an executive their presentation is not working?
Start with the mildest version that could possibly work and escalate only if you have to. Here is the ladder, roughly in the order of how much nerve each rung costs.
- Offer rather than instruct. "Would it help if I pulled the three numbers you are most likely to get asked about?" is an offer. "You need to know these numbers" is an instruction. An offer can be declined without anyone losing face, which is why it gets accepted.
- Name the pain gently. Not "this is boring." Try "there is a stretch in the middle where I lost the thread, and I know this material." You are reporting your own experience, which cannot be argued with, rather than delivering a verdict, which can.
- Hand the decision back. "If you are comfortable seeing that tomorrow, then it is fine with me." That sentence ends the contest, restores their authority, and still leaves the observation sitting in the room where they have to look at it.
- Ask permission to help. "Tell me how I can best support you." Some principals want a rehearsal. Some want one page. Some want you silent until they ask. You will not guess right, and asking costs nothing.
- Ask rather than tell. The most reliable and the hardest to remember under pressure. "What do you want them to do when you finish?" beats any note you could have written.
Not one of those rungs contains a correction. They are questions, offers or reports. That is not politeness, it is the mechanism.
The move that beats all of them: make them say it
Everything above is technique. This is the one I would keep if I had to give up the rest.
Record the run-through. Then play back ten seconds. Not the whole thing. Ten seconds, chosen carefully. Stop the playback. Look at them. Say nothing except four words: what do you think?
Then wait. Actually wait. The silence is the tool.
What happens next is remarkably consistent. They say "I am boring." Or "I am rambling." Or "I have no idea where I was going with that." They deliver the harshest possible version of the note you were afraid to give, about themselves, out loud and unprompted.
I have been running this with chief executives for twenty years and have never found anything that works as well. When you say "that ran a little long," they hear an opinion, and opinions have an author who can be disagreed with. When they watch ten seconds of themselves and arrive at the same conclusion, there is nobody on the other side of the table. The recording has no agenda, no career, and no stake in the outcome.
It also solves your problem, which was that you needed to say something difficult. Now you do not have to. The judgment is theirs, and your job from that second onward is not to pile on. It is to say "what would you rather it did?" and start building.
- Record on whatever is in the room. A phone on a stack of books is enough.
- Choose ten seconds, not thirty. Long enough to show the pattern, short enough that they cannot escape into "well, later on I get to the point."
- Pick a representative stretch, not the worst moment. Ambushing someone with their worst ten seconds buys one honest reaction and no second use.
- Ask the open question. "What do you think?" Never "was that a bit long?" The moment you name it, you have taken the judgment back off them.
- Sit through the silence. Three seconds will feel like a minute. Do not fill it.
One caution: it only works if the clip is representative and the person believes you are not building a case. Use it as a gotcha once and you will never use it again. More on rehearsal in how to practice a presentation.
What do you say when you have to say something they will not like?
Sometimes there is no recording, no run-through and no time. Keep one sentence ready and use the same one every time, so it becomes a familiar signal rather than a warning shot.
It works because it concedes the outcome before the argument starts. You are not asking them to agree. You are asking for thirty seconds of hearing, and you have already committed to what follows: they decide, you comply. Declining that looks worse than granting it.
Say it in that order. Concession first, information second. Reversed, it reads as a retreat rather than a frame.
What if they throw the talking points away?
They will. Some principals treat a prepared script as an insult to their own fluency, and some of them are right. Read talking points sound exactly like read talking points.
Do not fight the behavior. Change the format. A leader who rejects a page of prepared remarks will very often accept a page of bullets, because bullets read as raw material rather than a leash.
Then do the one thing that makes the format work. Put five bullets in bold and say it plainly: if everything else falls out, these five have to survive. Five is not arbitrary. It is roughly what a person can carry while also reading a room, and more than a real question period is likely to reach.
You have converted a control fight into a priority conversation. They keep their own delivery. You keep the message. The same logic drives how teams build key messages for media interviews.
Should you have a signal?
For the moments when it is happening live and there is no time for any of the above, agree a signal in advance. A hand flat on the table. A tap on a notebook. Something that means "land this answer" or "you are drifting."
The important part is not the signal. It is how you obtain one. Do not arrive with a system. Ask: "should we have a signal?" That phrasing hands them the invention. If they choose it, they will use it. If you assign it, they will forget it, or they will spot it mid-answer and read it as being managed in front of other people, which is the one thing no senior leader tolerates. Agree what it means and what it does not, because a signal that could mean three things means nothing at live speed.
What if none of this works?
Sometimes it does not, and the honest thing is to say so rather than pretend a technique is universal. In that room in Washington, people had tried most of this with a particular principal and got nowhere. We did not solve it. What we agreed on was narrower: keep the offer standing, keep a record of what you advised, and choose your moments. You cannot spend your standing on an internal all-hands and still have it for the appearance that matters.
There is also a version of this that is not a communications problem. If a leader takes input on nothing, not just delivery, that is an organizational issue and no playback exercise will touch it. Knowing which of the two you have is worth more than another technique.
The shift that makes all of it easier
Stop trying to be right in the room. Start trying to be the person they come to before the room. The first wins one uncomfortable conversation. The second wins every conversation after it, which is where the influence lives.
For more on building that standing, see executive communication coaching and how to get buy-in from your audience. If your leaders have a high-stakes moment coming, tell us about it here.