👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, driving growth, and standing out as a high-performing leader.

In this week’s newsletter, you’ll learn how to respond when stakeholders question your decisions or misunderstand you. We’ll cover:

• Defending your thinking is normal. Embrace it.

• Your response will either diminish or build your credibility

• Case study #1: A colleague from another team questions your decision

• Case study #2: Your CEO questions your strategy

Read time: 7 minutes

I have a friend who trains horses. She’s been doing it for twenty years.

I asked her, “Are you afraid of getting thrown off a horse?”

She said, “If you ride long enough, eventually you get thrown off.”

There’s a business lesson here: If you build and lead for long enough, eventually someone will question what you’re doing.

It will feel frustrating, unjustified, and lame that they’re doubting decisions that you’ve put a lot more thought into than they have. It will feel like they don’t understand your work—and maybe they don’t.

Which is precisely why you need to take these moments of skepticism seriously.

People will misunderstand and disagree with you. It’s not nefarious. It’s normal. You have two objectives: First, learn to explain your ideas better. Second, stay calm and share your thought process in the most objective way possible.

I’ve written a lot about explaining your ideas and getting buy-in through the lens of playing offense. Today, I want to talk about playing defense. What’s the difference?

• Playing offense: Proposing an idea, making a recommendation, getting buy-in for your suggestion

• Playing defense: Defending your decision, explaining your point, answering questions, correcting misunderstandings

The lines aren’t clearly defined, and there’s an ebb and flow between the two. Ideally, you play offense well, so you reduce the need to play defense.

Let’s get into it.

⛑️ Welcome and thanks for reading! If you’re looking for a sparring partner, work with me 1:1 for executive coaching. I typically work with tech leaders on: managing up to a CEO, communicating with executive presence, and delegating to a team of junior ICs while maintaining high standards. If you’re interested in how I can support you, learn more about my coaching approach.

Defending your thinking is normal. Embrace it.

When I say you should “defend your thinking,” I don’t mean you should be argumentative. I mean you should share logic, evidence, and rationale that explains why you believe your conclusion is the right one.

Being defensive and defending your ideas are not the same thing:

• Being defensive is digging your heels in the ground when you shouldn’t, trying to protect your ego by refusing to acknowledge a good argument, and being delusional about the strength of your claim. 

• Defending your ideas is a normal part of working with others and having a point of view. It’s a normal part of discussing problems with non-obvious solutions. It allows you and your colleagues to evaluate ideas with more precision.

Your goal is to get to the truth of a matter. When you defend your assertions, you’re serving your audience by putting effort into fleshing out an idea so you can identify the right path together.

If, through rigorous discussion and debate, it turns out you should improve your idea or abandon it altogether, those are equally good outcomes. 

But what isn’t a good outcome?

Rolling over at the first sign of skepticism.

Your response will either diminish or build your credibility

It’s important to learn how to defend your ideas for another simple reason:

Your credibility is at stake.

If someone asks, “Why did you do X?” and you don’t have a good reason, they will assume you did X randomly. Any success you had will be deemed random. And any failure was due to your lack of rigor.

This makes you look bad and diminishes trust in your abilities.

On the other hand, if you explain yourself well, you actually build MORE trust. They think, “You have thought about this in more depth than I have. Those are good insights—I’m glad you are in charge of this decision.”

They feel safer knowing you are leading. You seem strategic, logical, and grounded.

Many people underestimate the daily moments where your credibility can either be reinforced or eroded. This might sound dramatic, but it’s quite banal: Every interaction folks have with you gets added to their subconscious cumulative repository of data points about you.

Here’s how to those interactions count:

• Try to anticipate questions. This will prevent you from feeling caught off guard. If you pause for a few moments, you can probably think of what folks are most likely to ask. Anticipating questions is a skill that keeps on giving.

• Embrace “show, not tell.” Telling is saying “Look, I’m so competent. I have a title that implies functional expertise. Just trust me.” Showing is having a point of view, explaining your decisions, and engaging in productive debate about what to do.

• React positively, or at least be neutral. Don’t act shocked and horrified when you’re questioned. Part of your role is to educate others and build alignment—this becomes even more important as you get more senior.

• Consider the question behind the question. If your initial answer isn’t landing, don’t blindly engage in a never-ending back-and-forth. Step back and identify what their true concern might be.

• Be happy that the person asked this question. They were skeptical anyway, and at least now you have a chance to correct their assumptions and show the depth of your thinking.

Let’s see what this looks like in action.

Case study #1: A colleague from another team questions your decision

My client is head of product at a NYC-based tech company. He finished presenting at a cross-functional meeting, when a colleague known for being snarky asked, 

“Why are you building X? Doesn’t the customer want Y from us?”

My client had been working on this feature for months, so he rightfully felt a little riled up about being publicly challenged by someone who wasn’t as close to the problem.

He answered:

“Thanks for that suggestion. We thought about it a lot and eventually landed on X, but I appreciate you for chiming in.” 

That was not a satisfying answer.

When you answer without sharing your logic, you’re basically saying: “This is it. Take my word for it.”

People don't want to take your word for it. You have to try a little harder than that.

You must give them actual reasons to believe you.

The problem is my client was “telling” instead of “showing.” In my opinion, it would be much more satisfying if he shared his thought process and showed more.

Here’s a better response:

“Great question. I thought that too when the team and I started working on this a few months ago. But after digging in, we realized A, B, and C. This made Y a much less attractive option. Meanwhile, X was [reasons why you chose X]. I'm keeping [the end goal] in mind, so will make sure that’s front and center. Thanks for bringing this up.”

Notice how much more convincing and thoughtful this response is. Even if folks aren’t persuaded yet, which is totally possible, you gave them enough specifics to allow for a productive debate.

Note: The quality of your logic for A, B, and C matters a lot here. It’s the crux of your argument. Make sure your reasons make sense.

Case study #2: Your CEO questions your strategy

Let’s say you’re a CMO. You’re generally aligned with your CEO on strategy. But one day, they swoop in 5 feet above the ground and post this in Slack:

“I noticed our marketing guidance mainly tells customers to post on social. That doesn’t seem like enough. We should do more.”

You could say:

“Yes, great idea. We share other tactics too, but will definitely keep this in mind.”

That’s a decent response, but it misses an opportunity to educate the broader organization on your strategy. A marketing leader has many responsibilities, but one of the most important is selling marketing internally in your organization.

Here’s a better response that explains your logic:

“Yes, great idea. We share other tactics too, but will definitely keep this in mind.

For context, social is one tactic and distribution channel among many that we teach instrutors about. We recommend it to new instructors because it’s free, doable yourself (fewer dependencies on others), more accessible than paid, has fewer logistics than coordinating partnerships, etc.

In short, it’s a practical channel for instructors to get some reps in with relatively low stakes. Many instructors are new to marketing, so this seemed like a good place to start. But it’s by no means the only path.

The underlying premise we teach instructors about course marketing is:

• A premium course is an investment for most prospective students. It’s not an impulse purchase.

• Therefore, people are unlikely to hand you $750 the first time they hear from you.

• Marketing is simply a way to build trust with your target student, which usually happens over time and across multiple touchpoints. Every individual/company is trying to shorten this sales cycle so they can close students faster.

• As an instructor, you get to decide what those touchpoints are, where to appear (podcasts, email, social, ads, communities, etc), what you want to say, and how you want to show up.

The high-level strategy helps instructors keep the big picture in mind, and the repository of tactics gives them inspiration to draw from.”

The “after” response sets a new frame. It corrects the record of what your team is doing and why.

It’s common to overestimate how much other people think about—much less understand—what you and your team are doing. If you answer a question like this poorly, it’s reasonable for folks to come to the wrong conclusion:

Hmm, the marketing team doesn’t seem to have a strong strategy. I hope they’re not being overly tactical, and are actually focused on driving the business. Honestly, I’m not so sure.

This is a shame.

You put too much effort into the work for it to be wrongfully labeled as “just X.” It isn’t accurate, doesn’t do your team justice, and erodes confidence in your judgment as a leader.

A quick one-line response might take 15 seconds, and a thoughtful response like the one above only takes 15 minutes. It takes a bit more time upfront, but consider it an investment in proactively removing friction and gaining more support for your approach.

I believe that’s time well spent.

Have you experienced stakeholders questioning your decisions, and what was your response? 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

PS If you found this valuable, here are more ways I can help:

1. Follow me on Twitter or LinkedIn for insights during the week (free).

2. Check my availability to do a keynote talk for your team.

3. Work with me for 1:1 executive coaching.