This is Part 2 of a two-part series on executive storytelling. In Part 1, we covered knowing your audience and cutting the noise. Now let’s talk about directness and clarity of purpose.
I’ve talked about the importance of knowing your audience and cutting through the noise when communicating with executives. These are foundational skills. But even if you’ve nailed those, you can still lose the room. You lose it by hedging instead of being direct. You lose it by being unclear about what you’re actually asking for.
Let’s dig into the final two principles that separate good executive communicators from great ones.
Say what you mean.
Executives don’t have time for subtext. If you’re dancing around your message because you’re worried about how it will land, you’ve already lost them.
I get it. It’s tempting to soften the blow, hedge your language, craft your message in a way that feels more palatable. But here’s what that can signal: you’re not confident in your own recommendation. And if you’re not confident, why should they be?
Directness means clarity and respect. Saying the hard thing in a way that’s grounded, honest, and constructive. Research backs this up too. According to the Interaction Design Foundation, when delivering bad news to leadership, you ought to “deliver bad news directly and calmly. Don’t soften the message so much that it sounds unclear or evasive.” It’s less about who caused the issue and more about what mitigation looks like.
Compare the difference:
Instead of:
“We’ve encountered some challenges in the current sprint that may impact our ability to meet the original timeline, though we’re exploring options to mitigate.”
Try:
“We’re going to miss the deadline by two weeks. Here’s why, and here’s what we’re doing about it.”
The second version feels scarier to say, however it’s infinitely more useful to hear. It gives leadership the information they need to make decisions, reallocate resources, adjust expectations. Obfuscation doesn’t protect anyone, it just delays the inevitable and erodes trust. Poor communication has material impact too. As Harvard Business School research shows, poor communication can lead to low morale, missed performance goals, and lost sales. Companies lose an average of $64.2 million per year due to inadequate communication.
One of the best pieces of advice I ever received: If you’re asking for something, ask for it. If you’re recommending something, recommend it. Don’t hide your agenda or make them guess what you want, the best leaders can spot that a mile away.
Name your North Star.
This is the move most people miss. You walk into the room with a problem, a proposal, a plan. But have you told them what you’re optimizing for?
Every conversation with leadership is a negotiation of priorities. If you don’t name yours explicitly, they’ll fill in the gap themselves. And they’ll probably guess wrong. Worse, they’ll wonder if you even know. So be explicit about your objective!
Are you optimizing for speed? Quality? Team stability? Sscalability? For a win-win partnership? For managing risk?
Here’s what that looks like:
“I’m recommending we extend the delivery timeline by a month. I know speed matters, but right now I am optimizing for quality and team sustainability. If we push too hard, we’ll ship something brittle and burn out the team doing it.”
Or this:
“I know you’re evaluating three vendors. Here’s why I think we should go with Vendor B. I’m optimizing for long-term partnership and flexibility over lowest cost upfront.”
Naming your objective does two things.
- It shows you’ve thought beyond the immediate ask to the why behind it, and
- It invites leadership to engage with your reasoning, beyond just your conclusion. Maybe they agree with your priority. Maybe they don’t. Either way, you’ve created space for a real conversation.
And here’s the thing: Executives respect those who are transparent about what they’re optimizing for, even when that priority differs from what leadership would choose. Research from Ideals Board shows that authenticity and transparency are critical for building trust and credibility among stakeholders. What they don’t respect? People who present recommendations without owning the tradeoffs.
Storytelling to Executive Leadership
Storytelling to executive leadership means making it easy for them to understand the situation, trust your judgment, and make a decision. That means knowing your audience, cutting the noise, saying what you mean, and naming your North Star.
The best communicators I know can read a room, adapt on the fly, and make it obvious what matters. If you can do that, you’ll earn trust, influence decisions, and get better results. That’s the whole point!