What Goldman Sachs Taught Me About Practice.
The skill most people overlook.
Last week I posted a video about 10 lessons from Goldman Sachs.
The video is cooking.
When I watched it again, I realized I left out the most important lesson.
The lesson is this: I used to think I was good at pitching when I really just showed up and winged it.
Most salespeople operate the same way.
They believe being good with people means they can walk into a room and figure it out in real time. That works until the deal matters, and then they lose to someone who practiced.
Here’s why winging it fails: when something unexpected happens (and it always does), you have no mental space left to handle it. Your brain is too busy trying to remember what comes next, how to transition smoothly, or what your opening was supposed to be. So when the client randomly interrupts you and asks about fees, it’s easy to fumble.
What rehearsal actually looked like at Goldman
My first pitch at Goldman started multiple days before the client showed up.
My managing partner and I rehearsed the entire meeting three times over several days. We did not practice the morning of the meeting or two hours before the client walked in. We practiced for multiple days.
In fact, we worked on these specific parts:
We decided who would speak first and what exact words we would use to position ourselves
We scripted the exact sentence that would transition us from conversation to presentation
We divided the content so he would explain market context and I would explain deal structure
We wrote the exact sentence bridges we would use to connect each page to the next
Then we walked into the room.
As you can imagine, just 4 minutes in, the CFO stopped us with a question about our fees. This happened way earlier than we expected. However, since everything else was practiced to the point of automation, I could stop, answer his concern without fumbling, and bring us back to the agenda we had planned.
The meeting went almost exactly as we practiced. This happened not because clients are predictable, but because we had rehearsed the highest probability path to winning.
If you’re reading this and thinking “I can’t rehearse every meeting, I have too many,” you’re right.
You can’t rehearse every meeting. You rehearse the ones that matter, like the big deal, the quarterly review with your board, or the pitch to a partner who could change your business.
But then the right question to ask is: what exactly do you practice?
The three things I practice before anything important
I have done over 100 investments, had 5 exits, built 2 billion dollar companies, and bought more than 3,500 units of real estate. Today we manage a portfolio of businesses that bring in over $250M in revenue.
When we meet with top executives or pitch potential partners, we role play every single time.
Here’s the process:
1. Act like you have zero natural ability
You need to practice like this is a completely foreign skill and you cannot trust your instincts.
For example: Write out your first 90 seconds word for word. Say it out loud three times before the meeting. Say it out loud, not in your head. If you skip this step, you will start the meeting searching for the right words instead of listening to what the other person actually cares about.
Also, rehearse your transitions. Know the exact sentence that shifts you from small talk to the pitch. Know the exact sentence that takes you from slide 3 to slide 4. If you don’t script these transitions, you will fill them with filler words and feel sloppy.
2. Write down every question they might ask, then answer the scariest ones before they bring them up
Before every meeting, write 8 to 10 questions the other person might ask. Do not try to answer all of them in your presentation.
For example: Turn 2 or 3 of the most likely questions into rhetorical questions you pose and answer during your pitch. “Can we actually handle the workload if you sign today? We can, and here’s why.” When you answer before they ask, you look prepared instead of defensive.
Keep the rest of the questions in your head so you are ready when they come up.
If someone asks about pricing and you have already thought through three different ways to answer depending on their tone, you will sound confident, which in essence gives them safety. If you haven’t thought it through, you will sound like you are making it up (because you probably are).
3. What are the three biggest objections, and what proof are you bringing?
If you had to bet money, what are the three biggest objections or questions? For those three, do not just prepare answers. Bring proof.
For example:
If you know they will ask about your track record with companies their size, bring a one page case study.
If you know they will ask whether your team can handle the workload, bring a capacity chart.
If you know they will question your pricing, bring a comparison model that shows where you land relative to alternatives.
The proof matters more than the answer.
When you show up with a document that proves you saw their concern coming and did the work, it tells them something about how you operate. It separates you from everyone else who just talks.
The single biggest lessons I learned through this process
There is no such thing as natural ability in high stakes conversations.
Every conversation that looks natural was practiced until it became automatic. The person across from you cannot tell the difference between someone who is naturally smooth and someone who rehearsed 47 times because they only see the outcome.
Wild, right?
That’s why practice is the entire game.
Everyone else is winging it and hoping their charisma carries them, which means you can win by just showing up a little bit more prepared.
Because how you prepare shows just how much you care.
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I am going to steep this article inside a glass of water and drink until this practice becomes one of my defaults. This was the thought in my mind as I was reading this article. It sounds smoother in my native language... Thanks for sharing as always.
I do this in my sleep, literally dream rehearsal