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One of the things that never fails to surprise me is how often you have to repeat information for people to really internalize it.

This applies pretty much at all levels, even when folks are earnest and trying their best to pay attention. It applies when you’re managing up, down, and laterally.

Today I want to share an example of why you have to repeat key information (especially potential trade-offs) and remind senior leaders of your strategy not once, not twice, but throughout the life of a project.

Tell me if this sounds familiar:

You: Hey senior leader, I want to give you a heads up about X risk. Do we feel comfortable with this?

Executive: Yes, that sounds like a reasonable risk. Thanks for surfacing. Let’s do it.

[One month later]

Executive: How did X risk happen? Did we know about this?? Why didn’t we prevent this???

This happens surprisingly often.

Every day, good operators get blamed for stuff that isn’t their fault because they haven’t set expectations properly.

Here’s how to ensure the enthusiastic yes you started with actually lasts throughout your project.

Why might your leader be surprised by something they already agreed to?

First, because they have a lot going on and might not remember the details of your project. Senior leaders typically oversee multiple direct reports, multiple teams, and multiple functions—each with projects, updates, decisions, risks, trade-offs, and evolving circumstances.

Second, because even if you mentioned a risk proactively, most humans secretly hope the downside situation won’t actually happen. Even if it’s an acceptable risk, we still hope for the best case scenario. Even if your leader admits you did mention that X issue might happen, they might still be surprised when it actually happens.

Both elements above—your leader being busy/having a lot going on in their world and understanding downside but hoping for upside—these are structural issues. These are big issues to fight against.

Which is why mentioning a risk once isn’t enough.

One of my coaching clients is a PM pitching their CEO on a new product launch. It took months of convincing, but eventually the CEO agreed. The PM was clear about the biggest risk: potential cannibalization.

PM: “If we launch this new product, our existing product will likely be cannibalized. We’re not sure for how long, but perhaps 6 months. I want to make sure we’re okay with this.”

CEO: “Okay, this makes sense. I agree with moving forward.”

Later that year, the product went live. The sales numbers started rolling in, and, lo and behold, the existing product took a hit:

CEO: “Wait, why is our existing product being cannibalized here?? This is really bad.”

PM: “Umm we discussed this when kicking off this initiative that our existing product would be cannibalized, at least for a bit until both business lines stabilized.”

CEO: “I don’t know why we didn’t prevent this more. I might have agreed, but didn’t realize our business would take this big of a hit. I’m not sure this new launch was worth it. Honestly I don’t even know why we decided to do it in the first place.”

Unfortunately, despite the work that went into the launch and its success in hitting targets, the project felt like a disappointment.

What could the PM have done to prevent this?

Reinforce expectations at the beginning, middle, and end

Most operators get buy-in at the beginning of a project—this is what allows you to move forward in the first place.

Some operators will close the loop with a recap at the end of a project.

But in my experience, very few operators reinforce expectations in the middle.

This is leaving a lot of proverbial money on the table because “the middle” is actually the MAJORITY of how the project exists.

If you don’t continue to “sell” during this phase, you risk losing the momentum you started with—or risk losing support for finishing the project at all.

Let’s continue with the PM and CEO example above.

The PM should have built alignment throughout the launch process.

You can do this by reminding your audience of your strategy at multiple touchpoints:

• Beginning: Get initial buy-in for the strategy and trade-offs.

• Middle: Remind the team of the strategy, including setting expectations about trade-offs, what you’re doing to minimize the impact of these trade-offs, and why the upside is worth pursuing.

• End: Proactively share context as you share metrics. Instead of expecting the numbers to speak for themselves, you’re adding narrative to numbers. You’re contextualizing what these numbers mean so your audience knows what’s “good” or “bad.”

“Selling” in the middle phase might look like sharing reminders for anything that might come as a surprise. For example, in a bi-weekly update, you could include a line like, “We’ve accounted for temporary cannibalization for the first 6 months of the new product. I’ve built this into our sales forecast and are aware this will likely happen.”

We must reduce cognitive load as much as possible for our recipients.

We cannot expect others to read our minds, connect dots, or keep our projects top of mind.

Remember: Buy-in is not binary. For projects with a longer time horizon, you need to get buy-in on a continual basis to remind your leaders and team about your strategy.

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Have you ever had a leader act surprised by something they previously agreed to? What was your response? What’s one situation where you could reinforce buy-in throughout the project?

Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

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