When Senior Leadership Gets It Wrong: Speaking Truth to Power

When I was 27 years old, I was a junior member of the marketing team at a large newspaper company. The VP of Marketing wanted to promote reading our Sunday paper as a “slow, relaxing, weekend experience.” He was in his 50s. So was the head of the boutique advertising firm he hired to create the ad campaign. They were golfing buddies or something.

The campaign slogan was “Spread Out Sunday”. It featured people with the newspaper dissected into its multiple sections, spread out across a kitchen table, a coffee table, an outdoor patio table. And then there was the fourth ad. It featured a young woman, lying on her stomach across her bed, newspaper before her, with the slogan “Spread Out Sunday” above her.

Yikes!

I knew immediately that ad was highly, and I mean highly problematic. And yet, there I was in a room full of middle-aged men. They loved it. The Publisher loved it. The Executive Editor loved it. The VP Marketing loved it. So, I had to decide – do I say something? How would I say it? It was embarrassing. I didn’t want them to think I had a dirty mind. Who was I to object anyway? Maybe they would think I was being difficult. So, I said nothing.

Later that week, the campaign was presented at an all-hands meeting of about 500 people. That meant there were journalists in the room. Lots of journalists. And they have no issues speaking up when something’s amiss. There was a rumble in the room. And then a young woman, probably the same age as me, stood up. And she just said it, “That fourth ad seems to be sexually suggestive and is very inappropriate.” Just like that, the ad was killed.

That woman taught me a lot that day.

I bet you've been in a similar situation. The executive team announces a strategic direction and something in your gut quietly screams this is going to cost us.

Maybe it's a restructuring that ignores the operational realities you see every day. Maybe it's a resource decision that sounds bold in a slide deck and disastrous in practice. Maybe it's a DEI rollback dressed up as "refocusing on performance."

Whatever it is, you're sitting there running the math, and the math doesn't work.

So, what do you do?

If you're a woman you already know this isn't a simple question. Research from Victoria Brescoll at Yale found that when female CEOs spoke often, their leadership ratings took a significant dive compared to when they were described as quiet. In contrast, male CEOs received a boost in ratings for being talkative rather than quiet. The same dynamic plays out at every level below the C-suite. A man who speaks up is demonstrating leadership. A woman who does the same is risking her reputation for being "difficult."

None of that means you should stay silent. It means you need to be strategic about when and how you use your voice. Let's talk about how to do it.

First: Know What Kind of Wrong You're Dealing With

Not all bad decisions deserve the same response. Before you do anything, get clear on the nature of the problem.

Is this a values violation? Decisions that cross ethical lines, put people at risk, or compromise your integrity need to be addressed, full stop. This is non-negotiable territory.

Is this a strategic error? A direction you believe will fail based on your analysis, market knowledge, or operational expertise. This is worth raising, thoughtfully.

Is this just not how you'd do it? Different approaches, competing priorities, a style mismatch between your instincts and the leadership team's. Unless you have data to suggest real harm, this one usually falls into "make peace with it" territory.

The mistake many directors make is treating category three like category one. That's how you build a reputation for being inflexible rather than for having good strategic judgment.

When to Speak Up

Research suggests that groups and organizations perform better when employees share their ideas and concerns, and that performance suffers when there is a high level of silence.

Dissenting opinions can lead to more informed decisions.

You know this. The problem is that knowing it and feeling safe enough to act on it are two different things.

Here's when speaking up is worth the risk:

When you have something specific to add, not just a general objection. "I'm concerned about this" is not enough. "I'm concerned because our enterprise clients have contractually required a 99.9% uptime SLA and this migration plan doesn't account for the maintenance window" is a contribution.

When the window is still open. If a decision has been finalized, the budget signed, the press release drafted, your moment has passed. Raising concerns after the fact reads as sour grapes. Raise them during the decision-making process, before the commitment is made.

When you're speaking from data, not intuition alone. Intuition matters and it's often right, but in male-dominated environments especially, you'll be taken more seriously when you can anchor your concerns in numbers, precedent, or documented risk.

When your relationship with the decision-maker gives you standing. You don't need to be best friends with the VP, but you do need to have established enough credibility that your concern will be received as expertise rather than interference.

The likelihood that information is taken seriously and acted upon is greater if one is able to present it in a way that is less directly threatening to the recipient, and to provide a potential solution rather than just information about a problem. This is the key strategic move: come with an alternative, not just a critique.

How to Present Alternatives Without Torching the Relationship

This is the part they don't teach you in leadership development programs. You know the what (the problem); the hard part is the how (raising it in a way that lands).

A few principles that work:

Lead with alignment, then introduce the tension. Start by acknowledging what the decision is trying to accomplish. "I know we're prioritizing speed to market here, and I want to make sure we hit that goal. I've been looking at the Q3 data and I'm seeing a risk to that timeline that I think we should factor in." You're not opposing the goal; you're protecting it and communicating that you’re all on the same side.

Frame your concern in terms of organizational risk, not personal disagreement. "I disagree with this" positions you as an obstacle. "Here's what I'm seeing as a potential risk and here are two options for how we might address it" positions you as a strategic asset.

Make your ask specific. Don't just flag the problem and leave it floating. Tell them what you want. Do you need a 30-minute conversation before the decision is final? A delay on implementation to allow for a pilot? A small adjustment to the rollout plan? Know what you're asking for before you walk into the room.

Use writing when the stakes are high. A concise email summarizing your concern before a meeting serves two purposes: it gives the decision-maker time to consider your point without the pressure of a live audience, and it creates a record of your analysis. More on documentation shortly.

Research on workplace voice also points to something counterintuitive for women navigating this: when women's assertive or take-charge initiatives are in the service of a team, they are not only accepted but make a greater impression than similar endeavors by men. Frame your dissent as being on behalf of the team, the clients, or the organization's mission, and you're less likely to trigger the "she's being difficult" response.

The Double Standard Is Real. Plan for It.

You know it and I know it: women are held to a different standard when they push back.

Women are burdened with the additional assumption that they will conform to cultural stereotypes that typecast women as caring and nurturing. Speaking forcefully violates these cultural norms and women experience a more punishing backlash than men.

A study by Brescoll and Uhlmann documented that observers attribute women's anger to internal characteristics ("she is an angry person," "she is out of control") while attributing men's anger to external circumstances ("he was under a lot of stress," "things were out of control so someone had to take charge").

This is maddening. It's also the reality of the environment you're operating in. Given this, a few tactical adjustments:

Regulate your approach, not your content. You don't need to soften what you're saying. Regulate how you're saying it. Calm, measured delivery paired with pointed analysis is harder to dismiss and harder to label as emotional.

Enlist an ally when possible. Peer support can help women report without career repercussions. The same principle applies to raising strategic concerns. It becomes "several people on the team see this risk" rather than "she's being difficult again."

Watch your hedging language. Phrases like "I might be wrong but..." or "This is probably nothing, but..." undercut your credibility before you've made your point. You don't need to be aggressive. You do need to own your analysis.

When to Document and Move On

Sometimes you do everything right and it doesn't matter. The decision stands. The leadership team has made its choice, and your concern has been heard, acknowledged, and set aside.

This is not a defeat. This is information.

Document your analysis. Not in a dramatic "I told you so" way, but in a clear, factual record of your assessment, the risk you identified, and the date you raised it. Keep it in your own files. If the risk materializes, that documentation demonstrates your strategic thinking. If it doesn't materialize, you delete the file and move on.

Then actually move on. The director who raises a concern once, is heard, and then commits fully to implementing the decision is a strategic leader. The director who raises the same concern repeatedly, visibly sulks, or lobbies others against the decision is a liability. Know the difference.

There's one exception to this rule: if the decision crosses ethical lines, your documentation takes on a different character. Keep records, know your organization's escalation paths, and understand what protections exist for internal dissent. That's a different conversation, and one worth having with HR or legal counsel if you find yourself there.

The Bigger Picture

Speaking truth to power is not about winning arguments or being right. It's about being the kind of leader whose analysis is trusted, whose concerns get taken seriously, and whose contributions to strategic decision-making are genuinely valued.

That kind of credibility takes time to build and very little time to spend. Use it thoughtfully.

Your silence costs the organization something real. Voice behavior, which focuses on voicing constructive challenges to improve processes rather than just delivering criticism, is a crucial component of extra-role behavior that contributes to organizational growth and success. That's not just a nice theory. That's what you bring to the table.

The system that makes speaking up harder for you than for your male peers is real and it's broken. Working within it doesn't mean accepting it. It means being strategic enough to stay in the room and influential enough to keep pushing.

You've made it this far without backing down. Don't start now.

Well hellooooooo there!

If you read this and recognized yourself — maybe you've been sitting on a concern for weeks and can't figure out how to raise it, or you keep raising concerns that go nowhere, or you just quietly implement whatever comes down from above because it feels safer — the FREE Stuck Director Assessment can help you get specific about what's keeping you stuck.

Three profiles in particular tend to show up in situations like this one:

The Invisible Expert has the analysis and the instincts, but hasn't built the visibility or the standing to get her voice heard at the level where decisions actually get made.

The Uncertain Leader sees the problem clearly but second-guesses whether it's her place to say something — and by the time she's decided, the window has closed.

The Capable Executor is excellent at delivering results, which is exactly why she's learned to keep her head down and implement, even when she knows something is off.

If any of those sound familiar, take the assessment here.

It's free, it takes about five minutes, and it comes with a free 30-page workbook tailored to your profile — so you walk away with something concrete, not just a label.