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  • Writer's pictureJeremy Willets

Leadership Lesson: Repeating Your Message


I’ve been an Agile leader for more than a decade. One of the lessons that I wish I would have learned sooner was the frequency with which leaders must repeat their message. In this post, we’ll examine why this is true, share some examples, and look at some strategies for making your message resonate.

Start with Why?

Simon Sinek has made a career out of this concept. And I agree with him. As leaders, this is a critical practice.

Why do you want this group of people to do this thing? Is it just because you’re the boss and you’re on a power trip? Or is there some underlying mission to what you’re asking?

The typical pattern we fall into is articulating “why?” the first time we deliver the message. But we rarely come back to it. We assume that everyone heard it the first time. As leaders, we fail to realize that saying it once is never enough.

The story we tell ourselves when we have to repeat the message is something like, “I’m not going to repeat myself. They’ve heard it already. Let’s get down to business. Repeating myself makes it seem like I’m just running my mouth. It’s duplicative. And I’m sick of saying the same thing.” Ego also plays a huge part. “The thing I’ve told them is such an important thing, of course they’re going to remember it.” This perspective shortchanges the obvious litany of other things that happen outside of your particular purview. We all have things going on in our lives competing for our attention on a daily basis. Whether they’re bona fide distractions, or just “life” — they can impede your message’s ability to sink in.

An Example — How Your Message Degrades Over Time

Let’s say you’re leading a company that’s launching a new product to get some traction in an industry that you’ve never historically been involved in. The first time you announce this to the company, you’re going to probably start with something like, “We have a huge business opportunity in front of us in this new industry. And that’s why we’re going to build this new product.” Perhaps you follow-up the announcement with some sort of e-mail message that repeats the message that you delivered verbally. The nature of new product development can be lengthy, though. Weeks become months and months sometimes become years. Throughout the time it takes your company to create this new product, employees come and go. Employees don’t seem as energized as they did when you made the initial announcement. With the passing of time and employee turnover, the message that was so galvanizing has degraded; almost to the point of being forgotten.

Forgetting is Part of the Human Experience

Over the years, there’s been endless amounts of research on how often people need to see or hear something in order to retain knowledge and act. Advertisers and marketers know that they have to engage with potential customers multiple times before they get traction. Why do we neglect this well-known fact in our profession?

Think about the last new product you tried. How many times did you hear about it before you pulled the trigger and purchased it? Where did you hear about? How was the message delivered? Who delivered the message? And why did you ultimately buy it?

An Example — How Many Times?

Here’s a personal example. I’m an avid maker of music on my iPad. Over the past few years, I’ve become somewhat of an “appoholic.” A multitude of incredible musical instruments, effects, and tools can be purchased via the App Store for the price of a cup of coffee. This is very different from the world of desktop computer recording, or studio recording, where similar items can cost hundreds or thousands of dollars. The iOS version, in all cases, costs exponentially less.

This leads to a recent purchase — a boutique reverb application called MagicVerb. When this app was released, I was downright shocked at the sticker price of $25. The sticker shock was due to the price point of other reverb effects that I own. Less than $10 is the typical price of an iOS reverb. I was content to pass on MagicVerb, until I learned more about it. I learned that:

  • The UI looked very cool (Monty Python-meets-Mellon Collie-era Smashing Pumpkins).

  • It’s unique in that it uses samples of echo chambers to produce the reverb (which isn’t something that many other reverb apps do).

  • It’s made by a well-respected developer who has a reputation for high quality applications (some of which I own).

  • The reviews on the AudioBus forum were glowing.

  • The video demos of it were great.

In this example, I needed to hear about this app multiple times — from multiple different sources — before I finally hit the “Buy” button. I was exposed to the MagicVerb message enough that I pulled the trigger.

What’s in it for…?

In the Agile space, the message we’re often tasked with “selling” is that of something new. Whether it’s a new process to follow, a tool to adopt, or a change we’re making to a product, this new-ness is at the heart of what we do. The status quo is often the enemy. Let’s examine what’s in the delivery of this new message for us, as leaders, as well as the people we serve.


Ask any leader how they’d like to spend their day, and they’ll probably respond with something about how they want to make an impact on the company they work for and the people they lead. They’re probably not going to say, “today’s a Wednesday, so I’ll probably have to repeat my message on three different conference calls this afternoon.” Repeating one’s self can seem like a waste of our time to leaders. In fact, we think that we save ourselves time by skipping the repeat of the message. I’d submit that we lose more ground when we don’t repeat the message, which causes whatever change we’re trying to make to become elongated. Each time you repeat the message, you check for understanding. If you’re met with quizzical looks and lots of questions, then it’s clear that your audience isn’t aligned and understanding the message you’re trying to deliver.

In the example above that discusses how a message can degrade over time, to the point that it’s nearly forgotten, imagine how much more effective the development cycle of this product could’ve been had the leader reiterated the message behind the development of the product to every new employee. Now imagine how effective it could’ve been had this leader reiterated the message every single week during the company all hands meeting.

The People We Serve

Ask any employee how they’d like to spend their day, and they’ll probably respond with something about how they want to make an impact on the company they work for and do something meaningful with their career. They’re probably not going to say, “I want to put my headphones on for 8 hours every day for 35 years and then retire.” Working for a company is a job, yes, but let’s examine the reason we work in companies. Jim Benson once said, “we work in companies to be kept company.” And if you think about the idea of work from a meta-perspective, he’s absolutely correct. Humans are social creatures and the only way we can do hugely impactful things is by working together in groups — whether your group is a team, a department, or an entire Fortune 500 company. Working together to produce something meaningful translates fairly directly to the idea of each individual employee doing something meaningful with their career. It’s the sense of purpose that Daniel Pink talks about in Drive. People do meaningful things when they know why they’re going something. And that’s where reiterating messaging comes in.

Think about the example above again. Imagine how much more engaged and energized the employees would be if their leaders were reiterating the message to them with some level of frequency.


Repeating yourself requires deliberate practice. The more you repeat the message, the better you get at articulating it. You hone it. And it becomes, as Eric Reis is fond of saying, “sticky.” People remember it. And they start to almost sing along with the message each time they hear it. They also start to repeat your message to other people. That’s one way to know you’ve done an effective job at articulating your message.

So how do you go about doing it? Here are some strategies to employ:

  • K.I.S.S.

    • No, this is not a reference to the famous rock band. It stands for “Keep It Simple, Stupid.” Think about your message before you deliver it the first time. Distill it into a few bullet points. Use the same words every time you repeat the message. Consider using verbal tricks, like alliteration, to make things stickier.

  • Each interaction is an opportunity to reinforce your message.

    • Leaders often fall into the trap of using the big stage as their default position for delivering their message, but the small stage matters just as much. Yeah, you’ll reach more people if you get up in front of the department at the monthly meeting and deliver your message, but you’ll also make a lot of traction by showing up at each team’s monthly team meeting to speak to the smaller group and address concerns that they just aren’t comfortable raising in the large room.

  • Trust, but verify.

    • Give your audience the benefit of the doubt when it comes to understanding your message. Assume they’ve heard your message once, and then verify their understanding.

    • “Agile Conversations” includes a lovely metaphor that we can use to check understanding — it’s a “ladder.” Keep this in mind when delivering a message. Make sure you check the audience’s understanding before you climb to the next proverbial rung.

  • Different communication channels

    • Employ different communication channels to spread your message. Sending a “high importance” e-mail might make you feel very comfortable about the words you chose to articulate your message, but not everyone will read that communication in the same way. Some folks we interact with might not always always stay “up to date” with e-mail. Mix different types of communication for maximum message saturation.

Examples — Strategies for Stickiness

Let’s examine the behavior of two CEOs and see which one’s message is likely “stickier”:

  • CEO A gets up at the annual company meeting and talks about how the company is going to undertake a huge effort to modernize their software, so that the company can continue to be competitive for new customers. It’s a simple enough message to deliver. After the initial message is delivered, the CEO shifts their attention to other initiatives and rarely mentions the modernization effort.

  • CEO B announces a major new product development effort at the beginning of the fiscal year. It’s going to take multiple years to complete, but the company expects to reap huge profits from it. Each month, the CEO releases a new video to employees describing how customers plan to use the new product and the value proposition of the new thing being created.

In this example, CEO A may have delivered an effective message initially, but didn’t continuously reinforce the message. In this kind of scenario, it’s highly likely that the people doing the work will forget the initial purpose of the work being done. Particularly if the effort is lengthy and employee turnover happens. CEO B, on the other hand, does a great job continually reinforcing the initial message. Monthly videos seems like a great strategy to employee to reinforce messaging.


Someone once said that the first mistake of communication is the illusion that it actually happened. Our lives are full of interactions where someone said something that was misconstrued, or taken in a way that was never intended. Whether it happens in our personal lives or professional lives, it’s bound to occur more frequently than we’d all like to admit. Repeating your message might seem redundant, but it’s actually one of the most valuable things that you can do as a leader — both for you, but also the people you serve. It’ll give you the piece of mind that your message is sinking in. It’ll also give the people you serve the energy, guidance, motivation to go out and execute on the thing you’re asking them to do.

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