We are often described as the right hand to our executive—supporting, anticipating, and smoothing the way. But what happens when the executive is wrong? Whether it’s a factual inaccuracy in a board report, a mis-handled personnel issue, or a strategic decision that overlooks a key detail, we are uniquely positioned to spot the problem—and sometimes uniquely burdened with the question: Do I say something?
The answer, more often than not, is yes. But how you do it—and what happens if you’re ignored—is where true professionalism comes into play. This week’s Extra Wrap explores how to challenge upward with tact, when to escalate, and how to protect the relationship in the process.
Why It Matters
Challenging a senior leader isn’t about being difficult or proving someone wrong. It’s about safeguarding the business, supporting ethical decision-making and, ultimately, helping your executive succeed. It’s ultimately your right to speak up, as an employee of the business.
When done well, speaking up:
Prevents costly mistakes
Builds mutual respect
Demonstrates your strategic value
Protects both your reputation and theirs
You are not “just the assistant.” You are a partner—and with partnership comes the responsibility to speak up when something isn’t right.
Start by Checking Yourself
Not every disagreement needs a red flag. Before saying anything, ask yourself:
Is the issue factually wrong, ethically questionable, or likely to lead to negative consequences?
Am I reacting emotionally, or do I have clear, reasoned grounds to intervene?
Is this the right time and place to raise it?
There’s a difference between your boss mis-quoting a statistic in an internal meeting (fixable, minor) and giving misinformation to a client (potentially damaging). Knowing the difference is part of what makes you great at your job.
Professional shorthand for “pick your battles”:
“Not every issue warrants escalation, but those that do deserve clarity, care and courage.”
Raising the Red Flag—Without Setting Off Alarm Bells
1 | Use Evidence, Not Emotion
Swap “I don’t think that’s right” for specifics:
“The latest sales report shows £1.3 million, not £1.8 million.”
“I’ve re-checked the supplier’s timeline; the delay was four days rather than two.”
Being precise, factual and calm keeps the discussion objective. Having data or evidence to support your correction will help.
2 | Lead with Agreement – Steven Bartlett’s “Never Disagree” Law
In The Diary of a CEO: The 33 Laws of Business and Life, entrepreneur Steven Bartlett writes:
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