A conversation with Lee Caraher, communications strategist and founder of Double Forte, on why leaders are never one-and-done with a message, what the sandwich method is costing you, and the small habit that removes more workplace conflict than almost anything else.
The Communicator Leaders Don’t Know They Need
Lee Caraher has been in the business of communication longer than most people have been on LinkedIn. She founded her PR and communications firm Double Forte before Twitter existed, which means she’s watched every new channel, tool, and platform reshape how organizations talk to themselves and the world. What hasn’t changed, she’ll tell you, is the core problem. Leaders think they’ve communicated something when they’ve only said it once.
This is her third appearance on Transform Your Workplace, and I booked her back for the same reason I always do: she’s one of the sharpest, most grounded thinkers I know on how communication actually works inside organizations. Not the theory of it, but the messy, real-world version where people miss emails, nod along without understanding a word, and interpret a Friday deadline as 11:59 PM their time zone.
When I told her I’d recently sent a big internal update about launching Microsoft Copilot, spent weeks refining it, and then watched the questions roll in that I’d already answered, she didn’t miss a beat. “Everybody does this,” she said. “Raise your hand.”
The One-and-Done Trap
The most persistent mistake Lee sees leaders make is believing that communication is an event rather than a process. You’ve thought about the message for weeks. You’ve drafted it, revised it, maybe had someone build a deck around it. By the time you say it out loud, you’re bored of it. And that boredom, she argues, is exactly where things go wrong.
“You say it out loud, you have the presentation, and you’re like, okay, onto the next,” she told me. “And that is the biggest mistake leaders make day in, day out. You’re never one and done in leadership communication. Ever.”
The fix she recommends is less elegant than most leaders want to hear: say it again. Then say it again after that. For anything important, she suggests at minimum three drops over roughly ten days. The first is the original announcement. The second, a few days later, is framed around questions she says you can absolutely fabricate. “Hi everybody, I’ve gotten some questions. Here are the common ones.” Then you pull the key points out of the original message and present them differently, through the lens of what it means for specific teams or functions. Day ten gets a third drop, a brief recap that acknowledges people are busy and surfaces anything that still needs clarity.
The point isn’t to hammer people with the same email three times. It’s to meet them where they are, because not everyone was ready to receive the message the first time, and because something in their world may have changed since you sent it. “In that period of two weeks, maybe somebody new joined the company,” Lee said. “Something’s always changing. If you want something to stick, [say it] at least three times. And you can introduce it in different ways so it doesn’t look like you’re repeating yourself. You’re adding clarity.”
Mixed Messages and What They Actually Cost
The gap between what a leader thinks they communicated and what their team actually heard isn’t just a messaging problem. Over time, it erodes trust. And Lee is direct about the fact that most leaders don’t realize how many variables are working against them before they even open their mouths.
She walks through the layers: the words themselves, the timing of the message, the channel it travels through, and then the physical delivery, body language, eye contact, what you’re wearing, what’s behind you on the video call. She’s worked with clients who showed up to important video communications in bright green shirts, which, as she pointed out, turns into a floating head the moment anyone applies a green screen filter. “You have to surround yourself with people who will tell you the truth,” she said. “And will say, you cannot go out there. How about zipping up your fly? These are conversations I have had.”
For leaders who don’t have a communications specialist at their side, she’s a fan of AI tools used honestly. She mentioned Quillbot as a step beyond Grammarly, useful for humanizing text and catching things that read as artificially generated. She noted that at her firm, no final product goes to a client without human intervention, regardless of what tools were used to draft it. And she lit up when I mentioned using Claude to critique my own podcast transcripts. “Claude’s good at that,” she said. And then, characteristically: “Just don’t tell it to be nice to you.”
Who’s Actually in the Room
One of the most practical things Lee said in our entire conversation was also one of the simplest: before you try to communicate something, figure out who you’re talking to. Not in a demographic sense, but in a real, specific, present-tense sense. Who is actually in this meeting? Where are they from? What function do they work in? What’s their frame of reference for the thing you’re about to say?
“If you don’t know, ask some questions,” she told me. She’s seen leaders completely lose half a room because they pitched a message to one type of person and ignored everyone else. The engineering crowd on their phones. The first-generation college graduates who bring a different context to discussions of company vision. The regional teams whose day-to-day reality looks nothing like headquarters.
When you have a genuinely mixed audience and can’t tailor the message to everyone at once, she recommends building in a next step that does the tailoring for you. Ask each group to come back with what the announcement means for them specifically. What questions will their teams ask? What changes for their function? “You’re giving them the invitation to think about what you said in their own view,” she explained. “So you can go get that data again.” The communication doesn’t end when the meeting does. Instead, it starts there.
The Feedback You’re Not Getting
Nothing exposes this dynamic more than the way leaders collect, or don’t collect, genuine feedback. Lee described working with a client who delivered his new vision to his leadership team and called her afterward to report that everyone was on board. She was skeptical. He asked how she knew something was off. Her answer was simple: everyone was nodding.
“That’s how you know they didn’t get it,” she said. “Something big, you want to have a dialogue. No questions means no one wants to be the dumb person in the room. It means everyone’s thinking, what does this mean for me? And nobody wants to push back because of how you delivered it. You had a presentation, not a conversation.”
Her advice to him was to send a follow-up email reiterating the key points, but to frame the next meeting around questions rather than understanding. Give them a specific prompt: what questions do you expect from your team, and where do you still need clarity on how your department fits into this? “You’re not saying I don’t get it,” she explained. “You’re giving people the out.” And then, she added, the hardest part: stop talking. Ask the question and let the silence work.
The Deadline Problem Nobody Talks About
Beyond big announcements and vision rollouts, Lee is emphatic about one communication habit that she says eliminates more workplace conflict than almost any other: being ruthlessly specific about deadlines. Not just the day, but the date, the time, the time zone, and the format.
She traces this back to a story from years ago about asking a younger employee to send her a draft, and receiving a Google link to something unfinished. Both parties believed they’d done the right thing. Neither had been specific enough to prevent the confusion. The version of that story she tells now is the same problem, dressed differently for each new generation entering the workforce. “Send it to me Thursday” can mean 11:59 PM Hawaii time and be technically correct. “Send me the monthly report in Google by Thursday, March 26th at noon Central” has no ambiguity left in it.
“Whoever’s assigning something, you have to drive any ambiguity out of every assignment,” she said. “And you have to be relentless and vigilant about it.”
Throw Away the Sandwich
When I asked Lee what single piece of advice she’d leave leaders with, she surprised me a little. She didn’t go back to the three-drop communication rule or the specificity of deadlines. She went straight at one of the most persistent habits in workplace feedback: the sandwich method.
Most leaders know the formula. Positive feedback, critical feedback, positive feedback again. Wrap the hard thing in something nice on both ends. Lee is done with it. “No more sandwiches,” she said. “The research on that is clear. When you do that, people remember the two good things and the thing in the middle, which was actually the entire point of the conversation, gets lost.”
Instead, Lee recommends setting up the conversation before you start. Tell people what kind of feedback you’re about to give, whether it’s reinforcing something that’s working, addressing something that needs to change, or signaling that a significant shift in behavior is needed. Then deliver it clearly. “Say what you mean, mean what you say,” she told me. “Sometimes trying to be too nice is actually unfair. It’s not kind to someone to not explicitly tell them what they need to do to improve.”
That’s the thread running beneath everything Lee said in this conversation. Communication isn’t about making people comfortable in the moment. It’s about making sure the message actually lands, gets understood, and leads somewhere. Everything else, the repetition, the specificity, the feedback loops, the channel choices, is just the work of making that happen.
The Bottom Line
What Lee kept coming back to, in every example and every piece of advice, is that most leaders are further behind on communication than they realize. Not because they don’t care about it, but because they’ve mistaken delivery for completion. The announcement goes out, the meeting ends, the email gets sent, and the assumption is that the work is done. It rarely is.
The leaders who close the gap between what they said and what their people heard are the ones willing to do the unglamorous part: repeat themselves, ask honest questions, sit in uncomfortable silence, and trade the niceties for something with a little more backbone. None of it is complicated. Most of it just requires the willingness to accept that saying it once was never going to be enough.
Brandon Laws is a workplace culture and leadership enthusiast, host of the Transform Your Workplace podcast, and VP of Marketing and Product at Xenium HR.