Read time: 2 Minutes

When I was 22, I took my first real job at Open Systems Technologies in downtown Boston, working as a recruiter. We were a technical recruiting firm, placing Java developers, program managers, financial analysts, and a long list of other roles across different industries.

Open floor. No walls. No cubes. Just long rows of desks, each with a phone, a desktop, and a printed spreadsheet full of names. The air was filled with conversations. People pitching. People laughing. People getting shut down. People closing candidates.

The setup would give most people anxiety today. I loved it.

Was this newsletter forwarded to you?

If you picked up the phone, everyone could hear you. If you stumbled over your words, everyone could hear that too. If you landed a great call, the whole room knew. There was no way to hide behind Slack, or email, or “I will get back to them later.”

The most valuable asset in that room was the telephone. The second most valuable asset was your ability to adapt to whoever picked up on the other end.

I was given a simple role during my time there: call the people on the list, find out if they were open to a new role, pitch our opportunities, and see if there was a fit. These people were not inbound leads. They were not expecting my call. I had a few seconds to make enough sense to earn another ten seconds. And another ten.

At first, I was bad at it. Like really bad.

I rushed. I read from notes. I sounded like a script, not a person. You could feel people checking out mid-sentence. In an open office, there is no pretending it went better than it did. When someone hangs up on you after ten seconds, everyone around you hears the dead line.

It was uncomfortable. And it was also one of the best learning environments you can be in. 

Let’s dance.


Go from AI overwhelmed to AI savvy professional

AI will eliminate 300 million jobs in the next 5 years.

Yours doesn’t have to be one of them.

Here’s how to future-proof your career:

  • Join the Superhuman AI newsletter – read by 1M+ professionals

  • Learn AI skills in 3 mins a day

  • Become the AI expert on your team

Start learning AI now


Learning To Listen When Nobody Can See You

The people I worked with, people like David and Jason, were not just “good on the phone.” They were fluent and seasoned in their careers. They could move from talking about what the Celtics needed to do in the offseason, to joking about never dating anyone who was not a Red Sox fan, to diagnosing a hiring manager’s real problem in the span of a minute.

They taught me how to build a conversation from zero. It was part of teaching and mentoring me on how to build, how to structure, and what to say.

Practice, practice, practice.

There isn’t an overnight success, but you have to start somewhere and build on it.

Start with something human.
Ask a simple, clear question.
Listen to how they answer, not just what they say.
Find a small piece of common ground.
Then move into why you are actually calling.

Sometimes it was clumsy. Sometimes it clicked. Over time, I learned how to:

  • Hear when someone was actually curious versus being polite.

  • Tell the difference between “not now” and “not ever.”

  • Slow down for someone who sounded cautious.

  • Match the energy of someone who came in hot.

None of that came from a script. It came from reps. From listening more carefully than I talked. From adapting based on real-time information, I could only pick up through tone, pacing, and silence.

The phone did not change. The spreadsheet did not change. My environment did not change.

What changed was my ability to communicate and listen. And that changed everything.

If you want to check out other articles that I have written, you can check them out here:

The Importance of Executive-Level Sponsorship  

Stop Losing Deals to Ghosts: The New Stakeholder Intelligence 

Pivot or Perish: Seizing Your Advantage in the Wake of Policy Changes 


The Muscle You Cannot Let Waste

One of the most important things I built in that job was not a network. It was a muscle.

The muscle of being comfortable picking up a phone, dialing a number, and talking to someone I had never met, with no idea how they would respond. Not with fake confidence. With enough confidence to start, listen, and adapt.

That muscle matters everywhere.

If you work in recruiting, sales, or business development, it is obvious. But it also shows up when you:

  • Call a prime contractor to talk about teaming on a project.

  • Pick up the phone to negotiate a contract instead of hiding behind redlines.

  • Talk through a mistake with a client instead of sending a long apology email.

  • Have a hard conversation with your own team or your own family.

Phone calls force you to listen, adjust, and respond in real time. They build your ability to read situations, not just read words.

Those are not “old school” skills. They are the same soft skills every serious study now says are becoming more important as AI adoption accelerates.


Where AI Fits, And Where It Does Not

Fast forward to now. AI can absolutely make you better at parts of this job.

It can help you:

  • Draft outreach.

  • Craft a call outline.

  • Generate smart questions to ask.

  • Summarize a long conversation into key points.

If you are not using those capabilities, you are leaving efficiency on the table. Leaders and hiring managers already see AI literacy as a valuable skill.

But AI still has hard limits.

It cannot hear a long pause and know the person on the other end is struggling with something they have not said out loud yet.

It cannot feel when someone’s tone softens after you acknowledge a concern instead of plowing over it.

It cannot tell when the answer is technically “yes” but emotionally “no chance.”

Research and expert commentary keep landing on the same point. Soft skills like communication, empathy, and relationship building are not going away; they are becoming more important as AI takes over repetitive tasks. AI can support, but it cannot replace the human part of the interaction.

The muscle you built at 22 still matters in 2026.


The Risk No One Likes To Admit

Here is the quiet risk.

If someone starts their career today and never has to do the uncomfortable reps you did, they can get very good at interfacing with tools and very weak at interfacing with people.

On paper, they look smart.

They know how to:

  • Prompt an AI.

  • Use ten tools.

  • Build a dashboard.

But when you put them on a call with a client, or ask them to lead a live negotiation, or have them handle a tense internal conversation, you’ll see the gap.

  • They default to email when they should call.

  • They default to scripts when they should listen.

  • They default to what the AI suggested when the room is clearly telling them something else.

The danger is not that AI will replace them. 

The danger is that they will never build the resilience and judgment that come from actually doing the hard, human work.

AI will keep getting better. That part is guaranteed. Whether you keep getting better at the human side is not.


How To Keep The Basics Sharp In An AI-Heavy World

You do not need to recreate a 2000s Boston recruiting floor to keep this muscle strong. But you do need to be intentional.

Here are a few ways to do it.

  1. Use AI to prepare, not to hide.
    Let AI help you draft talking points, anticipate objections, or summarize background on a prospect. Then close the window and have the conversation yourself. When things go off script, do not reach for the model. Reach for your ears.

  2. Choose the phone on purpose.
    This week, take one situation where you would normally send a long, careful email and make a call instead. It might be a client update, a negotiation detail, or a tricky internal topic. Notice what you learn in that live conversation that the email would have buried.

  3. Debrief your calls like practice, not accidents.
    After an important conversation, take two minutes and ask yourself:

    • What did I hear in their tone.

    • Where did they speed up, slow down, or get quiet.

    • What would I do differently next time.
      This is the same feedback loop you get on an open floor. You are just running it for yourself.

  4. Let your team hear real reps.
    If you manage people, do some calls where others can listen in. Not to embarrass anyone, but to normalize the reality that live conversations are messy, and that is where the real skill is built. AI training should sit next to, not instead of, this.

  5. Treat communication as a core skill, not a soft one.
    When you think about your own development plan, or your team’s, put “live communication under pressure” right next to “AI tools mastery.” They are both leverage. One without the other is a liability.

Shout out to David, Jason, and the team for everything that they did. Might be a few years ago (more than a few), but even after those few years, definitely been very impactful across multiple jobs that I’ve had in everything that I’ve done, so thank you!


What the Internet Taught Me This Week

From new tools, recent trends, and market updates, here is what has been on my mind.

  1. Two Literal Crypto Bros Built a Real Estate Empire. Then the Homes Started to Fall Apart. Check it out here

  2. ‘Nobody Owns Us’: How Plans for a Google Data Center Divided an Oklahoma Town. Check it out here

  3. OpenAI founder Karpathy deletes viral AI job exposure map after ‘wild misinterpretation’. Check it out here


That open office in Boston started out uncomfortable. It was loud. It was unforgiving. But it worked and was a great skill-building and experience for me.

It also gave you something that is still paying dividends today. The ability to pick up a phone, talk to someone you do not know, listen hard, adapt on the fly, and help them solve a problem.

AI will keep getting better at everything except being you.

The more the tools evolve, the more valuable it will be to have actually built that human muscle instead of outsourcing it from the start.

If you are deep into AI adoption, keep going. Use it. Push it. Let it make you faster and sharper.

Just do not let it quietly erase the reps that taught you how to listen, how to read a situation, and how to show up when another human being is on the other end of the line.

Those are still the skills that close deals, build partnerships, and hold teams together.
And no model is coming for them, unless you stop practicing them yourself.

See you next week.


Whenever You’re Ready, Here are 4 Ways I Can Help You:

  1. Unlocking Hidden Potential – Reconnecting with Past Clients for Explosive Growth – Check out my free eBook on how you can find hidden gems in your past clients and help you crush your sales goals.

  2. AI for Business Development – Download our free eBook on how you can effectively leverage AI prompts to your advantage. From properly setting up your preferred AI tool, to how to shape your prompts, save time, and get the outputs you are looking for.

  3. Sales Resources at Your Fingertips – From tools, tips, demos, and how-tos, check out our Pages and content that can provide you with additional support, whether it be social selling, account management, or something else.

  4. Cribworks Advisor Program – Want more than just resources? Reach out to me and see if our Advisor Program can help you scale your business.