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If you can’t master executive comms, you can’t become a world class marketer. 

It doesn’t need to be your strongest asset, but you must become good at it in order to move forward in your career. Many years ago when I was a teaching assistant for Power and Negotiations at MIT, I gained an even deeper understanding of the importance of communicating effectively in order to get an outcome you desire. And this ability is useful across every facet of life, not only professional. In your career, your ability to communicate up, down and across the org chart in a manner which is effective will pay dividends for your career. 

In most of my past roles I’ve often found myself pulled into communicating with the executive team — CEO, COO, CMO, CPO. Whether it’s projects I’m leading (expected), projects I’m a key stakeholder to and  the team enlists me me to drive executive comms (flattered), or it’s my boss or skip level boss (flattered and a bit annoyed) who have asked me to communicate progress or outcomes to CxOs. I have often found myself being the one selected to lead and craft executive comms. It may sound like a humblebrag, but I think it's a skill that comes natural to me and one I’m fairly good at and I want to share with you some of what I’ve learned so you can leverage them to become a better communicator. 

Today I will share my playbook for effectively communicating with executives on your team and at your organization. I break these into three buckets: general principles, written communication, and executive presentations. 

General Principles 

Know your audience 🔎 

The first and most important rule of all communication is know your audience. Who are you communicating to and what can you learn about them – this includes their goals, their concerns, their timeline, their personality and more. If you have little or no previous interaction with this stakeholder, you must do some research. There are dots you can connect to better understand your executive audience. All hands recordings, documents they’ve authored, comments in forgotten google docs and slides, and quick checks in with others in your orbit who  have a relationship with that executive. Being familiar with the content of your presentation or writing matters but also understanding the personality of the executive matters to. For example, what is their general inclination around the thing you’ll be discussing – are they worried and what specifically worries them, are they excited about the opportunity and how can you lean into this etc. Doing this work will be incredibly helpful so you can ensure your preparation is tailored to the expectation and temperment of that person. 

Reduce response time ⏱️

From my experience there is a direct correlation between response time and the successful execution of the ini. Obviously your response should be thoughtful, substantive and move the conversation forward. But all else being equal, the person that responds quicker is more likely to drive more impact and advance quicker over the arc of their career. If you are not able to craft a thoughtful response without input from others which will take time, a general rule, you should respond to confirm receipt with a note on when they can expect an answer. As Sriram notes, response time is often a very accurate signal for competence: 

Calendar symbiosis 📆

A corollary of response time is understanding when executives are online and active. Execs have full schedules. But they have patterns, like replying to slacks and emails late at night. For some execs, their review time is 8-10am on Saturday mornings. While others are Sunday evening-ers between 8-11pm. Know the pattern for each executive you work with. This will help you be more effective when your message is delivered and a tighter feedback loop for their comments. There have been multiple instances where the CEO/COO/CPO is in my memo or Google Slides asking questions at 9:30pm on a Sunday night. I was in there <5 mins later with a thoughtful response which solicited a 👏 or 👍 response minutes later. It built rapport. And it helps build a line between you and that executive. The confidence that the exec had in me was slightly higher after each interaction. And the Monday review meeting was a breeze compared to those folks who left the CEOs questioning hanging for 24 hours. 

Written Communication 

Be Direct ➡️

You should be direct and succinct — executives are busy. The pyramid principle from Barbara Pinto at McKinsey, does a fairly good job outlining how you should structure your written comms to have the most important information at the top. Be explicit and do not bury your ask. They have no time to search for the TLDR. Make it clear what you need from them, when you need it by, why you need it and the implications of not getting it Your proposal or ask should be substantiated and backed up by analysis, data and evidence whenever possible 

Sweat the details 😥 

If you include an attachment, does the executive and their chief of staff have access? Do all your links work correctly and link to the appropriate slide or page? Did you spell check everything? If you need a response from them to unblock the team – did you make that explicit and include a specific date and time of when a response is needed? These may seem like common sense but I assure you I have had failure points across the board here, on multiple occasions and so have my reports and my peers. We’re human, we make mistakes. Spend a few extra minutes to mitigate these errors and you’ll be glad you did. 

Peer to peer 🤝

Communicating with executives, especially when you have established rapport and are more senior in your career (Director+), should be more peer than subordinate to executives. In the book The Courage to be Disliked, which profiles Adlerian psychology, authors Ichiro Kishimi and Fumitake Koga share a similar perspective: 

I have noticed colleagues that continue to interact and communicate with execs in a hierarchical manner, putting them on a pedestal. Oftentimes the email to them is too long and convoluted. Instead, match their formality. If they are texting you in all lower case text and using emojis, do the same. I often match the tonality and formality of the exec I’m communicating with. From my CPO texting on weekends to the COO using emojis in Google comments, match their tone and treat them like competent peers. 

The exception here is If you are much more junior than your executive audience and don’t have a rapport or an existing relationship with them, generally you should be more formal and to the point in your communications until you’ve established credibility & rapport. 

Executive Presentations 

Executive meetings are not a one time event, I like to think of them in three phases: pre meeting, meeting, and post meeting. 

Pre Meeting: Do your homework & be crystal clear on the purpose 

Do the Meetings Before The Meeting 🔄 

This simply means prep, prep and more prep. This goes without saying but not only must you be intimately familiar with the contents of whatever you’re presenting, you must ensure those in the meeting are pre-aligned or at least ‘warmed’ going into the meeting. This means you should know and understand every attendee’s role, their POV and anticipate their questions and/or pushback. In my experience, presenting to the CEO, COO, CPO and CMO of Instacart – this means you need to meet with the other stakeholders (formally or informally) and prep them on what you are going to present and address their concerns before the meeting so you are not surprised or caught off guard with in the moment opposition. Here are things you can do to achieve this: 

• Know the players and ensure they are read in prior to the meeting. Most should be aligned to your POV but it’s perfectly okay if not everyone is as long as you understand their perspective and will be ready to address in the room

• Anticipate objections and be prepared to handle them gracefully and thoughtfully in the moment – this will be abundantly evident if you have not done the work here and will reflect poorly on you 

• If you include a complex chart, data set or information in your appendix or support documentation, be fully prepared for an executive to ask you the most minute question about it so you better understand it inside our or ensure you have someone in the room who can speak to it in detail 

• Send a Pre-Read Do this 24-48 hours prior to the meeting and ask the attendees to read it so you can move into discussion to ensure an efficient use of time. This can be in a memo or slide format and companies usually have a style or preference so know what that is. 

• Designate a note taker if there is not one officially assigned. In critical executive meetings, someone will be taking the notes and managing the AIs post meeting. Find out who that is and if there is not someone, find someone to do while you present and facilitate the meeting. You want to ensure your post meeting hygiene is on point and trying to balance the presentation and note taking will make you less efficient at both. 

Be clear on the purpose of your meeting 🥅

What is the goal of this meeting and what do you want to get out of it? Make sure you are clear on what this is and ensure everyone else in the room (pre & during) the meeting is on the same page. Every org has their own flavor of how executive meetings are run – many require pre-reads, some involve silent reading in the room for the first 15 minutes, many limit the number of attendees etc. Understand the nuance for your executive team and organization. There are also different types of meetings: 

• Decision meetings where you are seeking a gating decision from a CMO, CPO or CEO

• Inform meetings where you are seeking to bring an executive along on the progress of a project initiative

• Pivot meetings where the strategy in place requires a significant change and your CEO must weigh in

• New venture meetings where you are presenting a plan or proposal which needs executive alignment and approval. 

• Is it a decision making meeting in which you’re trying to achieve a decision in the meeting? If this is the case, who is the decider? Who is accountable? They should have been briefed ahead of time and likely already have a POV going into the meeting. If it is a decision-making meeting, make sure you facilitate a discussion with dissenting viewpoints. 

• Is it a resource ask meeting where you’re trying to move forward with a new plan? This could be annual or half planning, or a product launch or campaign that needs more resources. 

• Is it an approval meeting, such as a go/no-go meeting or final review of marketing assets before the campaign is set to go live? Sometimes these approval meetings can be done async via slack/email. 

Meeting: Establish context, facilitate seamlessly and master executive presence 

Set the context 📕

In the same vein as executives are short on time, you should have a succinct intro for your meetings. Set the context, remind them of past decisions, and highlight the key decisions and topics meeting will focus on. Clarify the constraints to guide the conversation, and make it clear what success will look like at the end of the next 30/60 minutes. You and the working team may know the subject like the back of your hand. The CEO or CPO doesn’t. They are constantly context switching as they have upwards of 15 meetings and hundreds of slacks a day. While the meeting may be the most important meeting of your day, or your week, it’s just another meeting for the CEO. 

Facilitate with elegance ⭐️

Executive meetings can go down rabbit holes. Executives like to double click  into esoteric nuances, assumptions and love to ideate. The pro is they’re engaged. The con is that the meeting can go sideways if not managed properly. While it’s important to engage and hear  ideas which have nothing to do with your objective, it’s also critical to steer and correct course quickly and appropriately. The nuance here is to make that CEO feel heard but gently point their attention back to the matter at hand. . Remember your goal is to get to X within Y timeframe and it entirely your job to ensure this goal is met.  One tactic that can work well in facilitation, when used appropriately, is humor. It can help lighten the mood and allow folks to let their guards down a bit which removes unnecessary and rigid formality. IIt’s also a way to demonstrate confidence and control over the facilitation. 

Executive presence 👩🏽‍💼

A corollary of being excellent at facilitation is having a strong executive presence. It’s one of those elusive terms that no one can articulate yet everyone in the room knows it when they see it. It’s that magical combination of competence, likability and engagement. You know your stuff and present it confidently yet you’re open to disagreement and welcome objection. You can read the room well and know when to pause, when to engage in discussion and how to bring the group back together. It’s a bit like conducting an orchestra when not all eyes are on you so in this sense it’s even harder. If you are presenting to a CEO, CPO, CMO etc, you are probably a high potential leader at the company and make no mistake that your executive presence will be assessed – how you speak, how you address questions, how to move the meeting forward– all of that will be noticed and can help build your credibility with this audience or diminish it. 

Make it real ✅

In meetings with executives, marketers oftentimes get stuck in strategy theater. Slides and frameworks dominate the conversation. The consternation on the faces of CEOs and executives is apparent. Instead, you should make it as real as possible as quickly as possible — execs want to see the final product — the GTM plan, campaign, press release, the homepage, the words of the keynote. The framework and supporting rationale should be in your back pocket, but don’t make it the focal point of your meeting.

Expect interruption 😬

Many marketers come to executive meetings with an expectation of sequentially presenting a 20 slide deck.  I have never seen this happen once in 15 years. At every single meeting I led with a VP, CEO, CMO, CPO etc – we are never going through a slide deck or memo neatly and chronologically. You will be interrupted and oftentimes immediately. At both Instacart and Google, I’ve presented to SVP (Google) and CEO (Instacart), where in both instances they wanted to start with a topic that wasn’t even on the agenda. You have to be prepared to accommodate this and again, steer the conversation appropriately. Assuming you’ve sent a pre-read, your role will be to ensure folks have read it and then focus on discussing open questions or concerns the team has. 

• Sometimes meetings can do off track because of unexpected opposition to your proposal. Of course, you’ve aligned with the key stakeholders prior to the meeting to ensure you’re on the same page and perhaps you’ve even had a stakeholder ‘warm the executive’ or presell the takeaways to them. At Instacart, this was common. Our CMO would ‘pre sell’ ideas to our CEO or COO prior to a major presentation so nothing is surprising in the moment. However, I’ve been in meetings when a previously aligned on idea or proposal with a key stakeholder comes into question in the room because that stakeholder changes their position in the room. This is a tough situation and will 100% catch you off guard. There are many ways to handle this but generally, you should always remain calm, receptive and engage in a discussion even when you’re caught off guard. 

Post Meeting: Proactively follow-up & Manage AIs 

Written Follow-up ✍️

Within 24 hours of the meeting, send a detailed follow-up outlining key decisions, outcomes, next steps and clarity on what the executive should expect and when. If there are AIs for others who were not in the meeting, include them in the follow-up (send context prior to the email of course!) and be crystal clear on AIs other stakeholders in the meeting will need to do. 

Informal Follow-up 💬

Sometimes in between a critical gating meeting and the next meeting with that executive team, the executive or key stakeholders will want an informal check in on how things are progressing. You can do this via a Slack channel or a less formal email with progress. This can be done weekly or monthly. It’s not required but I highly recommend it especially for high visibility and timely initiatives. 

BTW, check our consulting service if your company needs support with fractional marketing. And if you’re looking for 1:1 coaching or advice on GTM, team building & recruiting or interview prep, please reach out.