Image credit: Coffee People Stock photos by Vecteezy

I recently met a woman who is interested in changing careers and wanted to hear about the various shifts I’ve made over the years from law, to politics, to technology, to real estate and back to technology. She was anticipating a big change from having had her own company for many years and now wanting to go back to working in a tech company, something she’d last done over 15 years ago.

When I told her about my jumps between tech companies, she asked how I had done it — how did I go from Intuit, to Netflix, to theBoardlist…


Photo credit: “Tokyo — Baseball on Television” by roger4336 is licensed under CC BY-SA 2.0

Growing up, I never understood why the person in charge of running a Major League Baseball team was called a “manager” instead of a “coach.” They seemed to do all the things a coach in any another sport would do . . . they would come up with the plan, inspire the team, push the team to correct mistakes when they messed up — all things that looked a lot like “coaching” to me.

I recently learned that in baseball, the title of manager came about because in the early days of the game, the manager was usually a player…


I started mentoring a young product manager who’s super talented: a great communicator, strategic and resourceful. She works at one of those big name tech companies whose products everyone uses — the kind of company that only hires the creme de la creme (and would never hire me because I look totally wrong on paper).

And yet, she feels like she’s not quite adequate. Why? Because she’s not a “technical” PM. She doesn’t have a computer science degree, and she’s not an engineer, so she feels like she’s not “technical.”

My response to this was: who cares? You’re a PM…


Your kids’ schools are closed indefinitely. Your work has gone fully remote. Now that you’re all in the house, how will you manage to keep it all together?

This is a challenging and unprecedented situation to be sure. But many homeschool parents have balanced working from home and have developed some basic coping mechanisms to help — I’m one of them. …


You might not have known this, but my father spoke Spanish fluently. This was always surprising to people when I was growing up, like when he’d go to Taqueria San Jose in San Francisco to order our favorite steak tacos. He’d walk up to the counter, pause for a second, and then unleash his order in rapid-fire Spanish, leaving the workers’ jaws agape.

I tell this story by way of context. As a Spanish speaker, he loved the work of Spanish writers including the Chilean poet Pablo Neruda. …


Imagine this: you’re trying to solve an incredibly complex, thorny problem for your customers. They’ve told you the solution is to give them A, which is something that you can build pretty easily right now. And they want their problem solved now.

But (there’s always a “but,” right?) … you’ve shown some of your customers what A would look like in practice, and their response was, “That doesn’t make any sense.”

Do you give them A anyway?

Or do you wait until you find B — something that works better to solve their need, even if only in theory or…


I mentor a woman who has great instincts, judgment and ideas. She’s recently been given some feedback that she needs to speak up more in meetings — to assert herself more.

The funny thing is, I’ve been in lots of those meetings and have always seen her speak up. What I notice is that other people don’t listen.

At a presentation she was giving recently, she asked the audience to speak to each other for a few minutes. When she was ready to bring the group back together, she started talking, continuing with her presentation. But the audience didn’t hear…


I spend a lot of time talking to people who have ideas. It’s part of my job, but it’s also something I do just as a hobby. I like riffing and expanding, clarifying and strategizing. I also like giving away my ideas.

A friend and I were talking through a business idea she had. It was a really good one, something that would solve a huge need in a way that it seems no one else is solving it.

“It seems so duh, no brainer,” she said. “Maybe I should stop telling people about it.”

Nope, wrong answer. And the…


An amazing thing happened this week. My beloved Golden State Warriors played in the NBA Finals for the first time in 40 years (and they happened to win game 1 in OT). The accomplishment is even more notable because they were led to the best record in the league this season by a rookie head coach, Steve Kerr. Sounds like an overnight success, right? Beginner’s luck?

Not quite. Before becoming a head coach, Kerr did something remarkable: he started doing his job before anyone hired him. Sports Illustrated’s Chris Ballard explains:

Kerr always planned on coaching, but it wasn’t until…


Lately, I’ve been spending a lot of time networking and meeting people for informational interviews. A couple of the people I’ve talked to recently have been in similar situations; they’re in careers that they don’t really like and want to do something different, but since they’re so entrenched in their current field, they have no idea how or where to start thinking about what they should be doing instead of what they’re doing now.

“I’m just so done being a lawyer,” one told me. “I think I want to do marketing. Or something. I don’t know.”

This is a conversation…

Lesley Grossblatt

I'm a product innovator and mama to 2 awesome kids.

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