Don't Pick Brains with a Shovel
The best advice comes after you've done your own research
Welcome back to The Workaround. I’m Bob 👋
You’re in good company with thousands of fellow entrepreneurs and innovators who follow my stories from a career in tech startups and corporate innovation.
I’m here to make you think, smile, and discover a shortcut to success or a trap to avoid.
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In 2024, I had meetings in person or on video with 304 people.
That was down a bit from 420 meetings in 2023, but still a lot!
Many of these meetings involved requests for advice from people about switching careers, launching a company, or dealing with the countless challenges in work and life.
No matter what the topic is or who the person is, I enjoy these discussions. They offer me the chance to pay it forward and learn something new.
I’ve noticed across thousands of requests for advice that the more specific people are in the questions they ask, the better the perspective I can provide.
It’s a lesson that crystallized for me last month when I met my new friend, Jodi. And I think her example can serve as a lesson for the rest of us.
Is this business sellable?
My business partner Ross introduced me to Jodi, the owner of a small service business in the HR space. In their discussion, Jodi shared that she was thinking long-term and looking into the potential to sell her business someday. Based on my experience doing this a few times, Ross suggested we chat. I was happy to accept the intro and make time.
[Note: Click my Office Hours link if you’d like to do the same!]
Shortly before our meeting, I boot up Zoom and resurface a little script in my head about the basics of selling a company. I had some set questions in mind to help Jodi understand what buyers are looking for. Knowing that her business was still on the smaller side, I prepared to warn her that these deals can be harder to put together.
Jodi enters my screen, and we spend a few minutes in the dance of getting to know each other. It’s obvious that she’s smart and built a successful company by hand. She admits she has never spoken to anyone who has sold a business.
I take that as my cue to share my Selling Your Company 101 talking points. After all, most people interested in picking my brain on this topic haven’t spent much time thinking about it beforehand.
As I speak, I see her nodding her head vigorously. But it’s not the nods of “This is gold, I’m taking lots of notes!” It’s more of a “Yeah, yeah, I already know all this stuff.”
Soon Jodi gently interrupts me and says:
“I’ve already done a lot of research using ChatGPT, so I know a lot about the standard pricing models, what buyers are looking for, and what turns them off.”
I was taken aback, yet felt compelled to lean in. This was suddenly getting more interesting…
I returned the steering wheel of the conversation to Jodi, and she began to ask me a series of very specific, probing questions. Her inquiries enabled me to delve into topics I rarely explore in conversations or writing.
I learned more about Jodi’s personal history, mindset, and preferences through her questions. The more I got to know her, the more personalized my advice became.
As we wrapped up, it was clear that she got human validation of her AI research and took away insights that would be difficult to pull from any flavor of typed query.
Pick Brains with a Scalpel
I kind of love the analogy of picking brains with a scalpel rather than a shovel.
[Side note: You should be glad I didn’t use an AI image generator for my cover photo above. I tried. It’s gross.]
A shovel is just a big dump of information that may or may not be helpful. There are plenty of places where you can get a shovelful of data. Google, ChatGPT, podcasts, and books are all easily available and don’t require requesting an intro or finding a calendar opening.
And when we only have a half-hour meeting slot with someone, the shovel of information they throw at us is pretty messy. We struggle to understand, can’t take notes well, and aren’t sure which follow-up questions to ask. It’s a waste of time for both sides.
However, a scalpel approach unearths more personalized and very specific data because it comes from the deeper perspective of the person you’re meeting. And it leads to a much more useful and enjoyable conversation for both parties.
I like Jodi’s model: Do your research first, then come into meetings with more advanced approaches like the following:
What doesn’t add up for you?—Ask about what you don’t understand or what is unclear. Or—What emotionally troubles you?
What’s your biggest risk?—In startups, for example, you might be betting on one big thing. Find the people that have faced this specific bet and pry that perspective out of them.
Go deeper than the research—Last week, someone who heard my Built to Sell podcast episode asked me some specific follow-up questions about picking an investment banker between two finalists. This decision requires a human perspective and led me to share information no one has asked.
Ask them to tell their story—Personal stories address the emotional challenges missing from regular research. Humans often give you killer advice when they can look back and analyze what they would do the same or differently.
Invite them into your shoes—Transparently share as much as possible about your situation and ask, “Knowing your experience and what I’ve shared, what would you do if you were me?” AI can’t do that, but our fellow human beings excel here.
Unearth the dark side—AI tends to paint a rosy picture of the future. Humans often do too, until and unless you ask them to get real. Ask about the biggest risks and worst-case scenarios.
Human+AI FTW
I haven’t been honest enough about something…
When Jodi mentioned she had used ChatGPT to research selling her company, a chorus of voices shouted words of doubt and dislike in my head. It was a real internal struggle for a few moments there…
“What could it know?”
“I’m sure it’s just remixing standard stuff.”
“I’m smarter and more experienced than any AI.”
I’m on the record as more of a doubter of the hype around AI, but, thankfully, I held back these ego voices and opened myself to listening and learning.
Now, I think Jodi’s example might be my favorite ChatGPT use case of the year.
We are compelled to seek advice because we know that many people have been there and done that before us. Thanks to the world wide web and our web of personal networks, there is tantalizing potential to get the ideal information to aid critical decision-making.
But people are busy, emails go to spam, the good stuff is behind paywalls, and the rest seems packed with content marketing tie-ins.
The information we need is already here—it’s just not evenly distributed. (Nod to William Gibson)
OR: The information we need is already here—it’s just hidden in a crappy business model.
BUT: Free and low-cost AI subscriptions might be the solution we need.
Go to ChatGPT for the basic understanding, then have deep conversations with human beings with details to share and stories to tell.
This could be the right path forward between AI Boosters and Doomers.
It’s also why I’m more confident that sharing my perspective here, usually in storytelling form, will be of greater value in the years ahead. Thank you for being a part of this ride.
If you like my writing, feel free to click the ❤️ or 🔄 button on this post so more people can discover it on Substack 🙏
How we might work together…
Fleet is our holding company for services businesses. We invest in leaders who are ready to start their own companies (we also do some M&A). If this might be you, Hit my Office Hours link.
A2 Influence is our content development agency that helps some of the biggest brands and retailers create and distribute authentic content at scale, including social+influencer. CEO Rob Reinfeld would love to share our approach.
Revelin is our consulting practice that helps with revenue alignment, growth management, and other RevOps functions. CEO Jess Shuman is standing by to share a no-cost assessment of your business.
Shipwright Studio is our software development agency led by Ross Lewellyn, a CTO who has led multiple successful startups. He loves helping turn your dreams into reality, and our clients trust us for software built to last.
Hearty is our boutique recruiting service. Our difference is that you get C-level partners—including me!—to source and screen, resulting in killer talent in less time. When you’re ready, let’s chat.
Feel free to schedule a chat during my Office Hours to discuss questions, feedback, networking, or any other topic. Seriously, any topic! You can also reach me on LinkedIn or by email.
BONUS: Cool Content of the Week
A little something I found meaningful. You might agree…
Alien Chess
Whether you’re on the entrepreneur or corporate path, the times we’re working in are a-changin’ rapidly. Chaos reigns and career stability was something our parents had. But here we are, and we’ve got to try on new perspectives and strategies to survive.
In my search for such answers, I ran across a post by Mark Rabkin, who survived 13 years of changes as an employee at Facebook. He writes of the mindset he developed during this time in “The Resilience of Alien Chess.”
With constant re-orgs, wicked growth, and shuffling reporting relationships, Rabkin eventually realized his career wasn’t like a chess match of carefully plotting moves, but instead:
“You sit at a table with a chess board, making your fancy chess moves. Then suddenly, a little green Alien swoops in. The Alien takes your board away and swaps in a new one -- where stuff is changed. Sometimes, you become the opposite color pieces. Sometimes, it’s all the same but your single most key piece is missing (argh). Sometimes, it’s just a totally new board. So you hunker down and play that one for a while, and then the Alien whisks it away and gives you a new board again.”
It’s a pretty great analogy for work (and life?) today. Even better are his suggestions to Accept, Detect, and Adapt. Check out the full post, and maybe you’ll agree that “the Alien’s visits give us an opportunity to become great leaders.”