Hey, it’s Aaron. I’m writing this from my study in Idaho, and we just started to experience our first signs of fall – a little rain, some fog, temps down in the 60s and 70s. I’m ready for it! It’s been a great summer.

We launched Season 2 of our podcast, Beyond the Meeting: The Moments and Decisions that Make Leaders. We were about a week out from launching the first episode, and my friend Jason Wenk went and sold his company for $4.6 billion dollars.

Soooo…we scrambled the fighters, and that became Season 2, Episode 1. It’s a great listen, and Jason shared some amazing perspectives about what it took to build over $4 billion in value.

Welcome again to all the new folks! I love hearing from you, so send back questions, thoughts, ideas, or just a hello any time by hitting reply.

Remember, most of the value gets created between meetings. Thanks for being here.

The Speed of Bad News

Years ago, I was an observer in a meeting between a leadership team and a CEO. I knew walking in that this was a bad-news meeting: the keystone customer had completely pulled out of the project.

People discussed progress, risks, and what might happen next. Everyone talked around the truth, but nobody said the sentence the CEO needed to hear: We lost the customer.

It was all I could do not to speak up, even though it wasn’t my place.

Afterward, I asked one of those leaders, “Why did nobody tell him?”

“That’s his signature initiative, and the last time somebody told him something bad about it, they had their head bitten off,” they told me. “We’ll scramble, replace the customer, and try to have good news to tell him next time.”

Of course, that CEO should have been able to help. He probably knew other customers who could step in. But nobody gave him the chance.

And it was his own fault — he’d built a culture that made bad news travel at the speed of molasses.

Bad news has a natural headwind

That CEO had created an extreme version of the problem. But even if you react wonderfully, people still don’t like being the bearer of bad news.

Sometimes the news reflects poorly on the person delivering it, their team, or a teammate they want to protect. Sometimes the facts are incomplete. Often, they simply hope one more day will let them fix the problem before you need to know.

Good news usually travels raw. Unfiltered. Sometimes even poorly sourced. People bring it to you while it’s still warm.

Bad news gets investigated, softened, repeated, nuanced, and packaged. By the time it reaches you, you have a small insight into a fraction of the original problem.

You can’t eliminate the human instinct to avoid delivering bad news. But you can make the incentives unmistakably clear.

Your first reaction writes the real policy

Cultures do not form from the values you state — they are trained like an AI model on the results they get.

Every leader says, “I hate surprises.” The trouble is that many leaders train their teams to surprise them—one bad reaction at a time.

If the first person who flags a problem gets blamed or treated as incompetent because they don’t have every answer, the organization hears the real rule: Don’t bring me trouble until you can explain and fix it.

The person in front of you learns that rule. Everyone else in the room learns it too. Then the story travels.

This is not an argument for lowering standards. Bad news can reveal poor judgment, a missed commitment, or outright negligence. Accountability still matters.

But the first conversation has a more urgent purpose: get the truth into the room while there is still time to act.

A signal is not a diagnosis, and a diagnosis is not a solution. People need to feel comfortable saying, “I think something is wrong. I don’t have the full answer yet, but I am working on it.”

Require a recovery plan with every signal, and your signal will go very dark.

Good news and bad news should travel at equal speeds

I’ve long told the leaders who work with me that I want good news and bad news to reach me at equal speeds. I want to be the first to know, not the last.

But saying that once is not enough. You have to explain the incentive plainly:

“This is going to get to me eventually. Bringing it later won’t make it smaller. I reward and appreciate people who are upfront with me because early truth gives us more time to solve the problem.”

Then your behavior has to prove it.

When someone brings bad news early, start with: “Thank you for telling me.” Establish what is known, what remains uncertain, and what needs to happen now. Save the full postmortem—and any necessary accountability—for later.

Appreciation is not absolution. You can value someone’s early candor and still hold them accountable for creating the problem. Separating those judgments shows your team that telling the truth quickly is always the right first move.

Another great tool is to not only celebrate heroic recoveries, but to celebrate even more the early warning that prevented one. If you recognize only people who arrive with a solved problem, you train everyone else to hide the glaring ones.

The Bottom Line

The next time someone brings you bad news, remember that your response is doing two things at once. You are reacting to today’s problem, and you are teaching the organization how quickly to bring you the next one.

The bad news is going to reach you eventually. The choice is whether it arrives early enough for you to change the ending, or late enough that all you can do is assign blame.

Great Reads / Listens of the Month

Every month I share a few great articles or podcasts I’ve loaded into my context window…and this month, it’s strangely all podcasts! Too much time in airports…

• The $4 Billion Dollar Man: Leadership Lessons from Jason Wenk. I had a blast having this conversation with my friend Jason, who sold his company to Vanguard for over $4 billion a day before this episode dropped.

• Senra on Lulu. David Senra is one of my favorite interviewers, and he got Lulu Cheng Meservey to spill the beans on how she became one of the world’s most trusted communications specialists.

• Ben Thompson on Big Tech, China, and the AI Boom Running Out of Money. Two of my favorite thinkers on one podcast — legendary tech analyst Ben Thompson and VC Patrick O’Shaughnessy. If you want a SWOT on where everything is going, this is a must-listen.

If you have a suggestion for a great read or listen of the month, hit reply and let me know — if I love it, I’ll give you credit in next month’s email!

Talent on the Prowl

I’ve got an action-packed Talent on the Prowl this month! If you want an intro to any of these people, hit reply and I’ll gladly make the connection.

• A friend of mine is a seasoned Client Success executive with 20+ years of leadership experience across FinTech and banking technology. She’s known for building strong executive relationships, leading complex client portfolios, developing high-performing teams, and driving retention, adoption, and measurable business value. She’s exploring senior Client Success, Customer Experience, or strategic leadership opportunities where she can help a growing company strengthen client relationships, scale effectively, and turn customer success into a real business advantage.

• Another friend is an experienced GTM and strategic partnerships executive

  with deep financial services, capital markets, wealth management and

  fintech experience. Most recently built GTM for an AI-enabled private

  lending marketplace startup and originated a strategic partnership that

  helped fund its continued development. Proven enterprise seller and

  relationship builder seeking a senior GTM, BD or strategic partnerships

  role with a fintech, financial services or adjacent technology company.

• And finally, another friend is in a career transition, pivoting from building startups toward small business acquisition, and is looking to connect with advisors who know the space. In the meantime, she is looking for projects and opportunities around operations, strategy, and AI implementation. She has a background spanning engineering and business, across tech, biomed, and CPG industries, and is equally comfortable talking to customers, executives, and engineering teams.

If this sounds like you, hit reply or send me a DM and I’ll connect you.

If I can help, let me know.

That’s it for this month! As a reminder, I am coaching five CEOs or leadership teams. That’s all I have time for, but I’m having fun doing it, and it’s allowing me not to pay myself a lot from the new company while we are in the build phase. 😉 

I don’t think I could have been nearly as effective for my team without the help of a CEO coach. There’s just something about having someone who has walked that journey before as a “safe” sounding board who you can speak freely to.

It looks like one of my coaching slots is opening up as a client has reached their strategic destination. If you want to discuss, click here to learn more about my approach, and hit reply if you’d like to talk about it.