👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, executive communication, and standing out as a higher performer. For more, check out my new intensive course on Executive Communication & Influence.

Read time: 7 minutes

Today’s newsletter is sponsored by Uptempo. Planning season hits hard—with months of meetings, data dives, and presentations. Yet results often fail to tie back to corporate strategy and revenue. That's why Uptempo created the Marketing Planning Blueprint to help you streamline the process and drive impact. Get the guide today.

I got this question from a student in my October course cohort:

I’d love to hear any advice on helping people more senior than me recognize patterns of behavior that are stopping them from getting the results they want. 

A few examples: 

• Not giving clear guidance during a process--then being disappointed with the results

• Not setting priorities--then being disappointed their team isn’t working on the right things

• Not training new hires--then being disappointed when they take longer to ramp up

Ah, this is a dilemma.

How can you help a senior leader see they’re making life harder for themselves and their team?

If you don’t speak up, you’re robbing your organization of your good insights.

If you do speak up, you might put your employment and well-being at risk.

This puts you in a tough spot.

Today I want to share some ways you can share feedback with senior leaders, or anyone more powerful than you—while being respectful, helpful, and protecting yourself from their wrath.

Giving feedback to someone more powerful than you is a pattern break

Traditionally, the more powerful person gives feedback to the less powerful person.

So if you want to give feedback to a more senior person, it’s an inversion of norms. This causes a moment of potential chaos, which is why you want to control the energy and channel it in a positive direction.

Feeling nervous about giving your senior leader feedback is a good thing. It means you have survival instincts that help with self-preservation.

This will alert you to proceed with the appropriate level of caution.

You may want to adjust tactics based on your specific leader, their idiosyncrasies, worldview, your relationship, etc. 

Or, you might realize your relationship or credibility isn’t strong enough for you to give them feedback--that’s an equally appropriate conclusion.

The only path I’d advise against:

Going in with guns blazing, assuming you have moral high ground simply because you are right.

If you’re wondering how to be thoughtful about giving your senior leader feedback, this probably means you’re a grounded person who wants to do right by your leader and organization.

If that’s the case, here’s what I do that might be useful for you too. 

1. “Even more” technique

I’ve taught this framework to my clients, and they love it. I’m going to share it with you.

The framing of “even more” works so well because you’re speaking from a place of generosity and giving the benefit of the doubt.

You’re assuming they’re doing X--and that they should do it even more. You are assuming they are great--and you want to make them even stronger. 

🚫

You: “We might need to give guidance to new hires.”

Senior leader: “You think I don’t know that I need to give new hires guidance? I obviously gave them guidance. GTFO.”

✅

You: “We may need to give even more guidance to new hires.”

Senior leader: “Hmm yeah. I gave them some guidance, but that probably wasn’t enough.”

Why this works:

The “before” scenario is binary—the senior leader either did or didn’t give guidance. And if they didn’t, well, they messed up. They feel threatened that you noticed.

The “after” is a spectrum: You are generous in assuming that they did give guidance. You’re suggesting they may want to amp this up even more. This is much easier for them to accept.

This isn’t simply an issue of semantics or phrasing. This is about positioning to increase the chances they change their behavior.

Getting anyone to listen and change their behavior, especially someone more senior? That’s a huge win.

[The “even more” technique works with giving feedback to direct reports too. It’s super versatile.]

2. Use yourself as an example

Talk about yourself so it doesn’t seem like you’re pointing fingers. I do this whenever I want to say something the person might find insulting.

🚫 “You should try X.”

✅ “I used to struggle with this, and when I tried X, it really helped.” 

By the way, saying “you should try X” is fine--there’s nothing inherently wrong about it. The reason I would avoid it is because of the power dynamic and CONTENT of what I’m saying. 

If there’s a power dynamic and/or the content of what I’m saying might be sensitive for the person, that’s when I share about my own experience. 

I’m not saying YOU are struggling with X, I’m saying I used to and what I did. And if that lesson applies to what you’re dealing with, that’s cool, but no pressure.

3. Adopt diplomatic, curiosity-forward language

Most people are extreme in one of two ways:

1. They think “respecting the person’s power” means being 100% supplicant. They do everything the powerful person says, and never push back even when they have reason to. → These people are spineless.

2. They share their POV in the most blunt, low-finesse way without any regard for their recipient’s person’s ego. They think, “Well, I’m right, so I should just say the thing with zero framing.” → These people are insubordinate.

Both are bad. Both lack judgment.

What you want to do is: Share your POV in a way that doesn’t threaten the senior person, and gets them to listen.

One simple way you can achieve this is by using diplomatic, curiosity-forward language. 

These phrases help you ease into the suggestion in a way that feels non-threatening:

• "We might want to try…”

• “I wonder if...”

• "Perhaps we could...”

• “What are your thoughts on...”

• “One approach might be...”

You adopt the vibe of a helpful team member who has your leader’s best interest in mind and wants to serve your organization. 

You are forward-looking. Instead of focusing on what went wrong (which risks making your leader feel defensive), you’re focused on what to potentially do going forward.

4. Bring data and examples to support your point

If you've been reading this newsletter for a minute, you know I bang on the drum of sharing your logic. I believe most people do not share their rationale enough.

Don’t just make a high-level, hand-waving statement.

Instead, share examples of what worked well in the past because it helps your feedback land. Supporting your claims makes you more persuasive and objective--and increases the chances your senior leader will take your recommendation.

Example 1: Guidance during projects 

🚫 “We need to give more feedback during projects.”

✅ “I noticed when we reviewed the design mockups weekly with the client, they loved the final result. For this project, early check-ins could help us make sure we’re aligned before going too far down a certain direction and could prevent rework.”

Example 2: Setting priorities 

🚫 “The team needs clearer priorities.”

✅ “The team made amazing progress when we all focused on the website update last month. It might help to have one or two clear priorities for the team this month that everyone can rally behind.”

Example 3: Training new hires 

🚫 “We should spend more time training new people.”

✅ “When we were able to dedicate that first week to training Steve, he got up to speed pretty quickly. The bit of upfront time seemed to have paid off, and taking a similar training approach for our next hire could help them ramp up just as fast. What do you think?”

Why this works:

• Ends with a clear, actionable suggestion

• Shows the upside of updating their approach

• Keeps it simple, logical, and positive

Personally, I think phrasing a recommendation as a statement reduces cognitive load. You can follow up with an open-ended question, like “what do you think?”

Notice how the examples above are concrete AND concise. Avoid long diatribes and over-explaining—use your judgment to share just enough context.

And for goodness sake, do not have a “well actually…” vibe when you share logic and data. This is obnoxious and will probably backfire. Notice how in the examples above, I’m sharing rationale, and doing it in a collaborative way.

To recap, here are the points:

1. Deploy the “even more” technique

2. Use yourself as an example

3. Adopt a diplomatic, curiosity-forward language

4. Bring data and examples to support your point

Which principle above do you want to try? Which do you think will work best with the senior leader you have in mind and why? Hit reply because I’d love to hear from you.

Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

Executive Communication & Influence course

The February 2025 cohort of my course is now open. I’m thrilled to see the testimonials from alumni continue to roll in too. Here’s what students are saying:

“I decided to join Wes’ course because I've been a huge fan of her newsletter for a long time. It's always easy to get stuck in your own head or to be verbose in your writing when people are constantly asking for something from you and there's no time to think about your audience. I found the frameworks and perspective Wes shared really valuable, especially in a world where concise and clear written communication is critical. I would recommend this class for anyone who needs to align a large group of stakeholders or bring a valuable recommendation to executives.”

- Angela Santurbano, Principal Product Manager, Square

“Highly, highly recommended. This is the rare communication course I’ve taken that focuses on how I actually get things done at work: Slacks, emails, last minute cross-functional meetings, and constantly managing up. It’s also the rare virtual course where the activities are challenging, actually mirror real life scenarios, and provide a valuable opportunity to practice skills. On top of all that, Wes is giving real-time constructive feedback to her students. Sign up!”

- Fred Geyer, Manager, Employee Onboarding Experience, HelloFresh

“This course was filled with clear, actionable insights to improve communication habits and practices in my everyday work. I'm excited to implement the strategies Wes covered.”

- Jess Mordo, Senior Manager, Senior Manager (Acquisition Marketing), Grammarly

“This course provides a practical set of tools and tactics to apply immediately to your writing. It sparked valuable discussions within my team, who also attended, and I highly recommend it to anyone frequently operating in a ‘debate and commit’ environment. Wes’s approach to clear, kind, and persuasive writing is especially relevant if you rely on channels like Slack or Teams.”

- Morgan King, Director of Client Support, Stitch Fix

“This was an excellent course. I appreciated the real-world examples, appropriate level and complexity of coursework, and the ask-me-anything Q&A sessions. Very well done!”

- Eric Livingston, Senior Director of Product Management, Salesforce

In the past week, operators from Adobe, Meta, Shopify, Autodesk, Grammarly, Klayvio, Chick-fil-A, eBay, Square, Equifax, Roblox, etc have signed up. Check out the course page to learn more and see if it’s a fit for you.

Connect with Wes

• Are you new to the newsletter? Subscribe for free

• Follow me on LinkedIn for more insights

• Check my availability to do a keynote for your team

• Work with me for 1:1 executive coaching

• Check out my 2-day intensive course. Join us: → Executive Communication & Influence for Senior ICs and Managers