Recently, I was part of a search for an executive-level role where the internal candidate was passed over, and afterwards she asked me why. On paper, she seemed to be crushing it: exceeding targets, managing a well-performing team, and sustaining a good reputation with partners. But after the search, the feedback came in: “She’s a great operator, but we need someone more strategic.”
Between my interim leadership work and my executive coaching practice, I spend a lot of time with executives, as well as senior leaders gunning for the C-suite, working through what’s holding them back from commanding the trust and respect they need to advance their careers and lead effectively.
The thing I find most often blocking folks? Their communication practices. When you move into leadership, you need to rewire how you show up and communicate. What made you successful up until this point in your career can potentially become a blocker if you don’t adjust.
Below I’ve tried to distill the 10 lessons I give most often. Some might be obvious… but others might be things people are too polite or too politically cautious to tell you to your face, but it boils down to (1) Say what you think (2) Show up like you belong, and (3) Manage your reputation.
Let’s go!
Say What You Think.
Bring a point of view to the work, master brevity in all forms of communication, and be a relentless advocate for the mission.
Lesson 1 - Have a Point of View
When you elevate into leadership, your job is no longer just to spot problems. Your job is to come with solutions, to think long-term, and to operate at the enterprise level. Youve been hired for your point of view, so give it.
For example: you are asked to present to the board about volunteer engagement. You put together a 20-slide deck, pack it with data, and reveal your conclusion: engagement is declining because of XYZ reason. Then, you open the floor for ideas on what to do. The CEO offers a few ideas, turns to you, and asks for your opinion. You shrug and say, ‘I’m not sure yet’ or maybe you speculate a little. The topic falls off the agenda, even though it’s critical. Welp… you just signaled you are an operator, not a strategist.
As an exec and board member, I don’t want just your data and facts, followed by a ‘what do you think we should do?’. This kills me. No. What do YOU think? That’s why you were hired. Presenting a complex issue without a recommended path forward simply pushes the analytical and strategic heavy lifting onto the executive above you.
💡The Lesson: Adopt a ‘Point of View First’ approach to communicating. Make sure every time you bring forward a problem or presentation, you clearly articulate your position or recommendation. Stop saying ‘I think’… followed by your speculation, and instead say ‘I recommend’ and definitively why. Even if the executive chooses a different route, demonstrate the ability to architect a path forward. This will get you more respect.
Lesson 2 - Lead with the Headlines, Save the Context
You are asked for a recommendation on a new vendor. You spend ten minutes walking the CEO through the 15 you evaluated, the scoring, and the opinions of others. By the time you get to your recommendation, your exec is probably thinking: ‘just tell me who we are going with and why.’
Unfortunately, a lot of leaders experience imposter syndrome, and explain their entire thinking process behind a decision in order to try and demonstrate competence: Heres all the data and context, here’s my thinking process, step by step, here are my conclusions, and here is what we should do.
While I’m glad you have a point of view…(Lesson 1), I didn’t need the 10 minute walk to it. This type of bottom-up thinking is how mid-levels report to their supervisors. But executives and boards are busy. If you try to walk them through your entire thought process, you will lose their attention. Worse, you signal that you are incapable of synthesizing complex information into actionable insights.
💡The lesson: Learn top-down, Pyramid Principle thinking. Lead with the answer. Speak in headlines and critical metrics. Keep the altitude, and avoid the weeds. If there is a lot of support data, use appendices that participants can reference as they desire, and allow people to ask questions if they need more context.
Lesson 3 - Ditch the Jargon
Speaking of imposter syndrome, over-reliance on corporate jargon is almost always driven by insecurity. People try to ‘sound smart’ by using complex language and buzzwords… but instead, it obscures your message and signals you don’t understand the problem well enough to explain it plain. Exceptional leaders are exceptional at simplifying complexity so that decisions can get made.
💡The lesson: I’m lifting two, actually, from the book Smart Brevity: “Brevity is confidence. Length is fear.” And: “Complexity confuses. Abstraction alienates. Length loses.” Keep your language simple, precise, and direct. Strip out the filler. If a layperson can’t understand what you are saying, keep working at it.
Lesson 4 - Say it, and Say it Again
Executives are the key advocates for the organization’s strategy. A common mistake is assuming that because you said something once in the boardroom or an all-staff meeting, the org absorbed it. Nope. People are busy, distracted, or overloaded with information or their own interests. They need to hear your priorities repeated and reinforced, otherwise they will forget or drift off course. I’ve had many execs come to me with frustrations that their board seem scattered on priorities. But, without your consistency, that’s exactly the reality you’re enabling.
💡The lesson: Repeat yourself on the things that matter. Champion the mission and strategic plan. Don’t assume people will remember. Bring the strategy into every leadership meeting and board report; Use it to frame your agendas and major decisions. The only way for it to become the default mindset is if you repeat, repeat, repeat.
Show Up Like You Belong There (Because You Do!).
tend to how your words land, and show uplike you belong at the table.
Lesson 5 - Fix your Nonverbals & Delivery
People love to push back on this feedback. They think their ideas speak for themselves and that delivery should be superficial. But at the executive level, public speaking is king. How you say something is as, if not more, important as what you say. Using too many filler words (e.g. like, um, ah), having poor posture, relying heavily on notes instead of speaking up to the room, talking too fast, failing to project your voice …all of these unconsciously signal a lack of command and undermine your executive presence.
💡The lesson: Practice. Practice. Practice. It’s the only way forward. You need to learn how to slow down, project, articulate clearly, use pauses to give weight, and so on. Filler words can be trained out. Slide design can be learned. Your material can be memorized and recited in a natural fashion. Posture can be fixed. … all with practice. I recently have been enjoying videos from Vinh Giang (youtube: @askvinh), but there are plenty of other ways to learn. You can even just record yourself talking and you’re likely to find a lot to work on.
Lesson 6 - Think Before You Speak
Here’s a mistake I’ve made: You are in a meeting with your team and start brainstorming. ‘I’ve been thinking, what if we sunset the youth mentorship program next year and pivot all those resources to this xyz other thing?’ Well, it might have been a passing thought experiment to you but your team? Off they go, spending the following weeks stressed out thinking through the details of what a transition might look like.
The higher up you move in your organization, the more your words carry weight. There is now an assumption that you know more than the average person on staff, and that you have the power to make it happen. So while you might not have changed as a person, the way your audience perceives you have, even if you’ve been working with your team for years. For this reason, sharing unfiltered or half-baked thoughts in a broad forum can trigger panic or send teams off in the wrong direction.
💡The lesson: You need to distinguish between a casual brainstorm and a formal directive. Save the unfiltered ideation for your trusted inner circle. This might be inside the org, or it might be with peers or a coach outside. When you are brainstorming, verbally label it at the outstart. If you find that you’ve already floated an idea that’s caused some panic, close the loop before the thing gets legs.
Lesson 7 - Don’t Hide Behind Email
This might seem overly basic compared to other things in my list, but frankly, email is one of the quickest ways leaders create problems for themselves. I know email feels safer, where you can draft and redraft and avoid the direct emotion. But the truth is, what you gain in comfort you’ll lose in credibility.
Knowing when to put something in writing and when to have a conversation is an executive judgment skill, and calls for ongoing calibration. Written comms are great for documentation or clarity on decisions, but terrible for working through disagreement, problem solving, and nuance.
💡The lesson: Email is a tool for information, not trust-building. If you find yourself going back and forth over email, or writing paragraph after paragraph to explain something, pick up the phone or book a meeting. Reserve email for facts and decisions made. Remember: there are very few circumstances where you should be delivering bad news, feedback, or apologies via text.
💡The bonus lesson: Be thoughtful in who you CC (do they really need the visibility?), proofread before sending, calibrate your writing to your audience (formal vs informal—and play it conservative if you’re unsure), and never hit send if you’re in a rush. I’ve seen some terrible, reputation-damaging ‘woops’s in my career.
Manage (and Protect) Your Reputation.
Have the hard conversations, keep solidarity with your leadership team, and make your impact visible.
Lesson 8 - Have the Hard Conversation
As you move up, hard conversations are going to be more frequent and higher stakes. You’ll have to give negative feedback to peers, push back on a board idea, or deliver bad news of a staff reduction or program cut, etc. Under-skilled leaders make the mistake of staying vague or talking around the issue, or they avoid the conflict entirely, hoping it resolves itself.
Yet, in this case, your problems are more likely to compound. Eventually, people around you, especially seasoned leaders, will see the avoidance. It will erode trust in your ability and create a lot of work for you (and others) down the line.
💡 The lesson: Clarity is kindness, even if the news is hard. If you have a staff member who wants to grow, but there is no path for career advancement, tell them directly, so they can make informed choices about their future. If a peer on your team is consistently missing deadlines that impact your work, address it head on one-on-one. Don’t let your fear of an uncomfortable conversation get in the way of your effectiveness.
Lesson 9 - Show Leadership Solidarity
When a CEO comes in with a new direction, inevitably there’ll be people in leadership who don’t agree with where things are going. Maybe they openly express this disagreement, or maybe they nod along and then go back to their teams and signal their skepticism.
Leadership can only be effective when it’s united. You can absolutely debate behind closed doors about the why and how (I’d say that’s your job), but ‘disagree and commit’ needs to be the mindset. Once the decision is made and the direction pointed, you need to get on board. If you can’t, this coaching is simple: it’s time to move on. What you absolutely shouldn’t do is undermine the team by complaining across and down.
💡The lesson: When you join a leadership team, you join the vision and direction. You have a seat at the table and opportunity to disagree and debate in the room, but once the decision is made and the door closes, you need to show true solidarity. This means, being able to advocate even if it wasn’t your position. If not? Like I said, transition might be the better route.
Lesson 10 - Stop Performing Busyness
Many leaders fall into the trap of performing their dedication by talking about how busy or how late they’re going to work, or by behaving in a stressed out and overwhelmed manner. But this type of behavior backfires. At this point in your career, you are expected to manage your workload, delegate, and advocate for the resources you need. Constantly signaling overload suggests you are at the limits (or beyond them) of your ability. It also will undermine the trust you’re trying to build with your team and board, and people may start passing you over for opportunities, thinking they’re doing you a favor by keeping work off your plate.
💡 The lesson: This isn’t a lesson for those in legitimate overwhelm. Rather, it’s a prompt to reflect on whether you might be dramatizing the load, wearing exhaustion as a status symbol, or failing to exercise the power you have to make your work manageable. Executive leaders that command the confidence of their seniors and board manage both their work and their energy. Block your calendar in for work, aggressively prioritize, and advocate for reprioritization when needed. When you’re feeling overwhelmed, get to the root of the issue and ask for the supports you need before it bleeds over.
Bonus Lesson 11 - Advertise Your Impact
I am ending on this lesson because it is one of the most painful ones to learn the hard way, and the one that can cause the most harm to your career.
There is this myth that if you just do great work, leadership or the board will notice. Sorry, they won’t. They are busy and focused on their own priorities. When you fail to advertise your victories, you might think you’re being humble… but you’re actually being invisible. And invisibility is a career-killer. The people making promotion and opportunity decisions don't have time to figure out your impact. You need to serve it to them, clearly and consistently.
💡The lesson: Say what you’re going to do, do what you’re going to say, and, most importantly, advertise! This was the stickiest takeaway from the book Speed of Trust. It radically changed how others perceived my efficacy, and bought me trust far faster than what I was doing before. The leaders who will go the farthest are those not necessarily doing the most work, but those who are exceptional at storytelling their impact. Communicate your wins and connect it back to your mission. Don’t shy from ‘I’ statements when describing work you owned.
The TL;DR?
🚩Bottom Line 1: Your board (or your boss) doesn’t need you to recite the weather. They need you to tell them whether to bring an umbrella, and why.
🚩Bottom Line 2: Your ideas don’t speak for themselves. You do. How you show up, in the room, on the page, and in the hard moments, will be the message.
🚩Bottom Line 3: If you don’t tell the story of your impact, someone else will tell it for you, or no one will tell it at all.
Remember the internal candidate I mentioned at the start? She wasn’t short on talent, results, or relationships. She was missing a way to communicate like the leader she already was. But the good news is that none of these lessons require you to become a different person. They’re skills, and skills can be built.
Don’t try to tackle all eleven at once. Pick the one that stung a little when you read it, and start there this week. :)