What does the word consigliere mean to you?

Clever, criminal, culture appropriation?

Quick question for you today.

I was in a small group talking about personal positioning (see below in my section about what we’re up to with Optionality to learn more). I was describing a consulting gig I have right now that I think takes perfect advantage of my Expertise+Lived Experience+Empathy.

I described myself as acting like “a consigliere.” A trusted advisor across a range of topics…someone whose brain they can pick, with whom they can bounce ideas, and who can, when warranted, make a few quality connections too. This happens to be an early-stage start-up, and without fail, every week, they have something to discuss that makes for a rich and rewarding hour-long session. I don’t think it would be that different if they were a later-stage start-up, a non-profit, a solopreneur, or really any size organization…running a business, organization, or P&L is a dynamic job. At the end of every weekly session the client says much the same thing…that the conversation was highly valuable.

Most on the group call had a positive reaction to the word “consigliere.” It felt accurate and also unique. It felt evocative. Like shorthand. But here’s the but: These were all people demographically pretty similar to me, namely I think most of them are somewhere within a decade of my age and are familiar with the word via, first, the Godfather movies and then seeing it applied (as Merriam-Webster’s does) to other situations, often political.

So, here’s my quick poll for you. (Note: It might be relevant to say that I’m not Italian given option #3.)

Tell me more thoughts, if you have them :)

What else is going on?

Optionality

Here’s the latest we’ve been up to with Optionality:

• I recorded a brief but focused personal podcast episode inviting you all to join Optionality. Because I realized I had never really, you know, MADE THE ASK!!! Listen here: It’s part origin story and part a “what’s in it for me?” explanation.

• We’ve had some great “In the Trenches” podcast guests, including chef, author, and TV host Carla Hall and Shelley Paxton, author of the book with the intriguing portmanteau, Soulbbatical. We’ve also introduced guests into our shorter, more informal “Conversationality” audio posts, including Cathy Brooks confessing how she realized that *she* was the asshole, and Joanna Bloor interviewing Libby Rodney and John Gerzema from The Harris Poll about generational shifts in perspective on power and purpose in the workplace.

• I’ve written two Optionality newsletters in the past month that I’m particularly fond of. One takes a different perspective on choosing family over career, wondering how this is still a choice that too many people have to make. One inspired by the conversation with Libby and John and predicting that it will be both the most senior and the newest, most junior employees who bring the radical change to the workplace that Jory and I think is inevitable (and is why we started Optionality in the first place).

• We’ve held two super-useful webinars in the past month or so, the first about how to use Generative AI effectively and ethically, and the second…just this past Wednesday…about managing the anxiety of an optionality-driven life. Our next member webinar is on June 18th and will zoom in, no pun intended, on the Creator Economy.

All that, plus we’ve been focusing on curating programming for our Premium members based on what they’re talking about in the Slack community. That’s why we’re wrapping up our first “working group” where a dozen of us workshopped upgrading our personal positioning. I mean, if you’re going to say you’re great at helping other people do such work, but suck at doing it for yourself, I’m 100% going to suggest we convene and help one another! We also did an ad hoc screen-share show & tell where we showed off how we’re using AI tools today…I always love sharing my go-to time-savers. So, one more time with the pitch: We’re planning to end our early adopter Premium Membership price at the end of this quarter, so if you’ve been toying with the idea of upgrading or subscribing for all the benefits of premium membership at the low low price of $299/year, now’s the time. We have our monthly live Office Hours for premium members coming in three weeks on June 12, so it’s perfect timing to join and get introduced to people live right away!

Here’s a clip from Wednesday’s webinar for your edification! You don’t have to wait until your anxiety is debilitating to do something about it!!

Out in the World

I’ve done two podcast appearances lately that were super fun and in both cases the interviewer asked questions outside the typical top ten questions I get asked. These are for you, especially if you enjoy me in soapbox mode 😹 Coincidentally they both released on the same day, although they were recorded literally months apart:

• Me, solo, speaking with Becky Mollenkamp on her Feminist Founders podcast. Two F-words I am proud to call myself!!

• Jory and I both spoke with Kelly Meerbott for her Hidden Human podcast. I almost never talk about my childhood, but Kelly got me doing it.

That’s it for today. Until next time, please leave a comment and let me know your thoughts on any or all of the above. This is basically my blog now! And as always, I appreciate a share of this newsletter or my podcast.

If I can help you break through the things that keep you stuck (or if you are intrigued by the idea of securing my fractional leadership for your initiative), set up your first introductory 30-minute consult for free by booking it in my Calendly. And you can always check out my new LinkedIn Learning Course, Telling Stories That Stick, a 57-minute course on crafting your stories for different audiences (media, investors, prospects, hiring managers) and ensuring those stories stick…and convey exactly what you hope to convey.

Thanks for reading!

-E