Vanesa Castillo

Sometimes the problem isn't that you're giving leadership too much information. It's that they don't yet know what the information is supporting.

When you start with all of the background and analysis, the room can enter the conversation through any detail that catches someone's attention, and suddenly you're defending a number before you've even made the recommendation.

The shift isn't necessarily to remove information. It's to change the sequence so people understand the point, why it matters, and what you need from them before you take them deeper into the evidence.

The analysis is still there. It just isn't standing between the audience and the thing you need them to understand.

Registration is now open for Lead With the Point, my free masterclass on October 7 at 1 PM ET.

If this is a pattern you recognize in your own leadership conversations, you can register through the link in my bio.

I used to walk into leadership meetings with all the evidence for why I needed additional resources, and because I wanted to prove the case, I started with the evidence.

Sometimes the meeting would get completely pulled into one part of the analysis before I had even made the ask. I went in needing a decision and came out with homework.

What changed wasn't the quality of the analysis. It was the order in which I gave it to the room.

This week's newsletter goes deeper into that shift, and into the communication framework I now use when a complex recommendation needs to land clearly with senior leadership.

If you want the deeper weekly leadership pieces rather than just the social posts, the newsletter signup is in my bio.

I've been listening to Naomi Watts' book "𝗗𝗮𝗿𝗲 𝗜 𝗦𝗮𝗶𝗱 𝗜𝘁", about menopause and all the things she wishes she'd known before she got there.

And it has had me thinking about something we don't talk about nearly enough when we talk about women in senior leadership.

There can be a whole other layer happening underneath the pressure everyone sees.

The meeting is important.

The client is sitting across from you.

You're expected to be sharp, present, articulate and completely focused.

And meanwhile you can't remember a word you use all the time.

Or you suddenly feel like the temperature in the room has gone up 30 degrees, except apparently you're the only one experiencing it.

I remember a very senior Executive Director I worked with having to excuse herself from an important client dinner and go back to her room because the hot flashes were so intense she simply couldn't stay at the table.

This was an incredibly capable woman operating at a very high level.

And yet there she was trying to manage something her body had decided to do in the middle of an important professional moment.

I think about how much advice women receive about executive presence, confidence, visibility, communication, composure.

All useful things.

But sometimes there is a completely invisible layer underneath what it takes to maintain all of that.

I'm glad we're finally talking about this more openly.

Because knowing what's happening doesn't make the demands of the job disappear, but at least it means fewer women have to sit there wondering, “What on earth is happening to me?”

Anyone else finding themselves having conversations now that we probably should have been having years ago?

Ever start answering something in a meeting and realize halfway through that you're still figuring out what you actually think?

That doesn't always mean you need to “be more concise.”

Sometimes you need a little more space between 𝘁𝗵𝗶𝗻𝗸𝗶𝗻𝗴 and 𝘀𝗽𝗲𝗮𝗸𝗶𝗻𝗴.

This week's newsletter is about what to do when the meeting is moving faster than your analysis.

𝗣𝗮𝘂𝘀𝗲 → 𝗦𝘆𝗻𝘁𝗵𝗲𝘀𝗶𝘇𝗲 → 𝗥𝗲-𝗲𝗻𝘁𝗲𝗿.

Newsletter link in bio.

I've been talking about this all week because a reporting-line change can look operational on paper and still have a very real career consequence.

Your projects transfer. Your deadlines transfer. Your responsibilities transfer.

The context around your growth, readiness and direction may not.

And I don't think there is one universal right answer for when that conversation should happen.

But I do think there is a difference between being thoughtful about timing and unconsciously letting your own career go back to zero every time the organization changes.

I'm curious which of these you see happen most often when someone gets a new manager:

The conversation continues? Gets delayed? Restarts? Or quietly disappears?

A communication lesson while emailing a winemaking professor

I'm trying to learn as much as I can about grape growing and winemaking before we plant our vineyard in January, so I reached out to a professor at FAMU and asked about workshops and hands-on learning opportunities.

My first message gave him almost no background about me.

So naturally, one of the things he sent me was information about their bachelor's degree in grape and wine sciences.

And I realized... of course he did.

He had no idea I already had a molecular biology degree, had spent 25 years in pharma, already own the land we're planting, and am not looking for another four-year degree. I'm looking for practical experience.

So in my next email, I gave him just enough context to understand where I was coming from and what I wanted.

Not my CV. Not every detail of the vineyard. Not everything I'm experimenting with now.

Just the information that helped him place me correctly.

The result?

He invited me to volunteer when they process the grapes they just harvested so I can learn hands-on.

It was such a good reminder that clarity isn't always about saying more.

Sometimes it's deciding what someone actually needs to know first.

Your projects transfer to a new boss automatically.

Your career story doesn't.

They can look at your title, job description, team structure and current priorities and understand a lot about what you're responsible for.

What they won't automatically know is how much you've grown, what conversations you've already had about your next move, what you're increasingly being trusted to handle, or where you're trying to go next.

And if nobody gives them that context, they may only see the job you're doing now, not the trajectory you've been building.

I went deeper into this in this week's newsletter because I think this is one of those career dynamics that becomes especially important when organizations keep restructuring and leaders keep changing.

Every Tuesday I use the newsletter to go deeper than I can in a social post, usually with a real leadership situation, what I think is actually happening underneath it, and something practical you can apply in your own role.

If that's the kind of conversation you'd like in your inbox, you can subscribe through the link in my bio.

I needed this group before I ever thought about creating it.

Sixteen women business owners showed up for our first gathering this week, and watching the room fill with conversations, ideas, introductions, business opportunities and a lot of laughter was pretty incredible.

Porsha and I started it because we both wanted more women around us who understand what it feels like to build something of your own.

Sometimes exciting. Sometimes terrifying. Usually both in the same week. 😂

We don't know exactly what this group will become yet, and I think that's okay.

For now, I'm just really glad we made the first move.