One of the first conversations that comes up in my leadership coaching programmes is about managing upward: how to talk to your boss, how to present to senior management without losing your way, and why you sometimes walk out of an important meeting without the decision you needed.
The story people tell me is often the same. You've prepared everything and you know the project better than anyone, yet ten minutes into the meeting you realise you're still explaining the background, someone has started looking at their phone, and it all ends with "interesting, keep us posted". The problem is almost never competence. It's that we talk to the people above us the way we'd talk to a colleague who already knows everything we know, while the person listening has far less context and far less time.
The higher you go, the less time there is
Each level needs something different, and this is one of the first things we work through together in sessions. Your manager needs to know where you stand, where they need to step in and what they need to decide, so what works is a 1:1 with a clear agenda, where decisions come first and updates go by email. The typical mistake here is walking through all the work you've done, or showing something half-finished without saying so.
With senior leadership the conversation changes: someone running an area wants to understand what changes for them and what risks they're taking on. What works here is a summary with the options on the table, ideally prepared with a few one-to-one conversations before the meeting, while things go wrong when you take the context for granted or walk in with nobody on your side.
At the very top, finally, what's needed is a clear decision, tied to numbers, strategy and risk. The request comes first, the material fits on one page or a handful of slides, and the details go in the appendix. What doesn't work is starting with the history, getting lost in detail and leaving without having asked for anything specific.
The hardest thing to accept for people who work hard is that none of them really cares how much work went into it. The journey matters to you, because that's where you learned things and solved problems, but the person making the decision needs to know where you've ended up and what you're asking them for.
There's also a brake I see often, and it comes from within. We tell ourselves things like "I can't bring a problem without already having the solution" or "I can't go over anyone's head", and we behave accordingly, even though many of these rules were never actually given to us. It's worth stopping to ask whether they really exist in your organisation, or whether you've simply assumed them.
Start with the end: Minto's pyramid
The most useful change is also the simplest one: say what you're asking for straight away, and leave the explanations for later, if they're needed. The person who put this into shape better than anyone is Barbara Minto, who developed the Pyramid Principle while working at McKinsey. At the top of the pyramid sits the main message, below it two or three arguments that support it, and below those the data for each argument, so the listener can stop at whatever level they need: a director might stop at the top, while someone who has to check the details goes all the way down to the numbers.
Minto adds three simple rules: each idea must summarise the ones below it, ideas in the same group must be of the same kind (all reasons or all steps, not a mix), and they must follow a logical order, whether of importance or of time.
To get to the top of the pyramid, she suggests opening in four steps, which she calls SCQA. You start with the situation, the context everyone already knows; move on to the complication, what has changed or no longer works; from there a question arises, which often doesn't even need to be said out loud; and finally comes your answer, which is the top of the pyramid.
Here's an example: "The new ERP goes live in March, but two key suppliers won't be ready before June. How do we keep deliveries going in the meantime? I propose handling those two suppliers manually for three months: it costs us two part-time people and we don't have to move the go-live." Right after come the reasons, meaning the risk you avoid, what it costs and the alternatives you ruled out, each with its numbers. If they stop you after the first sentence they already have what they need, and if they don't, you have your outline ready anyway.
Of course, it isn't the only way. When you need to bring people along on a change, rather than just inform them, it works well to alternate between how things are today and how they could be, closing with what you're asking for. For really complex decisions, on the other hand, there's Amazon's approach: no slides, but a document of a few pages written in prose, which everyone reads in silence at the start of the meeting before discussing it.
When you present to senior management
The request goes on the first slide, not the last one, and it's worth preparing a two-minute version as well as the twenty-minute one, because you'll very likely be interrupted. It happens almost every time and it isn't a bad sign: everything else stays in the appendix, and you'll need it when the questions come.
In slide titles, write the conclusion rather than the topic: "Logistics costs are up 12%" already says something, while "Cost analysis" leaves the audience to work it out for themselves. One slide, one message. And speak their language, which means what changes for strategy, revenue, costs, risks and timing, leaving the technical detail for later, if someone asks.
Bring two or three options and say clearly which one you'd choose and why, because decision-makers want to know what you think, not just be handed a menu. Before the meeting, have a few conversations: talk to the key people one at a time and listen to their objections, because many important meetings are decided before they even start. Finally, remember that your slides will travel without you, so they need to make sense even when you're not there to talk them through.
Prepare, and rehearse out loud
This is the part almost all of us skip, convinced that knowing the subject well means tidying up the slides the night before is enough. For a TED talk, which lasts eighteen minutes at most, the TED team starts working with speakers as much as six months ahead: people who speak in public for a living spend months writing, cutting and rehearsing. You don't need to go that far for a meeting with senior management, but it gives you an idea of how much work sits behind a talk that looks spontaneous.
My advice is simple: rehearse out loud in front of someone. It can be a colleague you trust, or even your boss, if the presentation is for their own superiors. Ask them what stuck, where they got lost and what they would have wanted to hear earlier. After just a few rounds like this, the way you present really changes.
The 1:1 with your manager
The 1:1 almost always drifts because we want to tell too much. A question I really like to ask is: if your manager had just joined, what would you tell them? The answer is usually much less than you had in mind, and that's where to start. It can help to split the time into three parts.
Start with decisions, the things where you need a yes, a no or a choice, presented with the options, your recommendation and the date by which you need an answer. Then leave room to discuss one or two topics at most where you want their view, being clear about how mature the work is, with a simple "this is still rough, I'd like your view on this point". Updates, the things they need to know but don't need to discuss, can go by email before or after, so they don't take up the time you have together.
Pay attention to how they prefer to receive information, too, because some people understand better by reading first and others need to listen and ask questions, and choose the channel accordingly. Then ask them to come with their own points as well, because the 1:1 belongs to both of you, but propose the format yourself.
The most common traps
The most frequent one is telling the story of the process instead of the result, followed closely by starting with the background, so that the request comes at the end, when time has already run out. Then there's bringing in half-finished work without saying it's half-finished, leaving the meeting without having asked for anything specific and, finally, reading a silence or a distracted look as a judgement on you, when it's only an interpretation and worth checking.
Before you walk in
Before a meeting that matters, try answering these questions in writing:
Who will I be talking to, and what's on their mind right now?
What is my message, in one sentence?
What am I asking for, and by when?
What are the two or three arguments that support it?
What objections do I expect?
What can I cut?
If you can't answer in a few lines, the message isn't ready yet. And after the meeting, three minutes are enough to ask yourself whether you got what you needed, how much time you spent on things you could have sent by email and what you'll change next time.
