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Picard Day

By In IT Culture, Leadership

There have been many great and memorable fictional leaders in my life: Kathryn Janeway, Kermit the Frog, and Jedediah Bartlett are instantly called to my mind. People (and frogs) like these are figures I can look to for inspiration. Their character, values, and managerial styles all contain qualities to which we can all aspire. But one mythical leader towers above all others in my admiration: Jean-Luc Picard.

I am not alone in my love of this nerd icon. Blog posts abound with the tales of his heroic deeds, suave manner, and gleaming, sexy head.The giants of the business publishing world fill column inches with click-baity “top ten” lists about Picard’s management philosophies. There is also some pretty strange fanfiction out there. 

So there’s no reason for me not to jump on the bandwagon in celebrating June 16th as Picard Day! I will do this in the great Internet tradition of writing a list (because it’s easy), and telling you six things about Captain Jean-Luc; three things you should know and three things that are entirely unnecessary. 

1. What is Picard Day?

In Star Trek: The Next Generation (TNG for short), Season 7, Episode 12 (S07E12) titled “The Pegasus,” all the children on the Enterprise (the USS Enterprise NCC-1701-D to be specific, and Enterprise-D for short) throw a celebration in honor of the captain. Deanna Troi explains that this is because the children look up to him as a role model. Fair enough. 

I believe that the teachers do this because they know it annoys Picard, and they know that one of his few faults is his distaste for children. Picard is an idealized figure and must come across as fairly uptight to those not under his direct supervision. I’m surprised that there are not more events like this in the show, where there are subtle attempts to force cracks in the steely veneer of principles and high cheekbones. 

Picard Day in the show is written as a cute, humanizing scene before the episode plunges into a story about espionage, death, disloyalty, and how creepy the dad from That 70’s Show can be… but that’s another blog. 

Outside of the show, Picard Day is when TNG fans celebrate the greatest fictional commander in all of literary history (yeah, I said it!) at  least in this sector of the galaxy. 

2. Picard’s Power Base

Star Trek TNG was written to be set in a more utopian human future than its predecessor. That means less curse words like “dammit” and “hell,” and the addition of even loftier ideals. That put a lot of pressure on the captain character to be an exemplary human being who still ran a tight ship. Fortunately, the writers of TNG knew a thing or two about power bases. Picard leads through both referent power and expert power. Referent power comes from being trusted and respected, whereas expert power comes from skills or knowledge. Leaders who are able to display both can be extremely effective. Jean-Luc clearly has the respect of the crew due to fairness and consistency, but we sometimes forget how well he understands the technical details of his ship. In “Disaster” (S05E05), we get to watch Jean-Luc save a group of children, stranded in a turbo-life, using his intimate knowledge of the wiring schematics of minor ship subsystems. We are also reminded of how much he dislikes children. 

3. The Picard Maneuver

Many nerds will talk of the Picard Maneuver being a tactic where you aim your ship directly at another ship and then engage your highest level of warp so that it briefly appears that you are in two places at once. The real Picard Maneuver, however, is the motion of adjusting your shirt after you stand up so that it’s not all bunchy on the bottom.

4. He leads through trust

“You have the bridge” might be used second only to “Tea, Earl Grey, hot” in Captain Picard’s dialog. Jean-Luc hands over command to his crew frequently and with absolute confidence. He has built an amazing culture of trust among his officers. Trust is something very difficult to articulate, but there are two dimensions of trust that TNG gets right. 

The first dimension is “Trust in Principles.” The crew of the Enterprise-D are on the same page when it comes to their mission and their intentions. Captain Picard has modeled how to show respect to his fellow officers, how to engage in task conflict, how to praise and reward members of his crew, and how to stand up for what is right. In one of my favorite scenes in all of Star Trek (S07E04 – Gambit, Part 1), Data is temporarily made captain while Worf becomes his first officer. Tensions rise and Data and Worf argue about how to settle disagreements on the bridge. However, the dispute is rapidly resolved when they both agree how Picard and Riker would handle the same situation, modeled for them hundreds of times by experienced leaders. 

“Performance Trust” is the second pillar of trust. This is the concept that you need to be able to know that your team will be able to accomplish the actual tasks they are given. Performance trust is probably much simpler in a world of standardized starship equipment, promotions and ranks, and Starfleet academy testing. That said, Picard encourages mutual and ongoing performance trust among his crew by being consistent and fair in his praise and feedback of their duties. He keeps an open door policy to his ready room, and actually makes changes when his staff come to him with concerns. 

5. The Picard Facepalm

The facepalm that spawned a thousand memes comes from TNG S03E13, “Déjà Q.” The facepalm in the actual footage is as fleeting as the movement of Muhammad Ali’s fist over Sonny Liston’s semiconcious body. In both situations, the image has become massively more powerful than the video. In the episode, Picard is simply exasperated and a little annoyed that Q, a godlike being and constant annoyance, has been made human and sent to the Enterprise-D. That’s pretty much it.

6. Leadership Through Clarity

Picard and his writers understood the most important thing about leadership: Clarity. Patrick Lencioni’s “The Five Temptations of a CEO” is required reading for anyone in a position of power, and the book’s arguably most important “temptation” is “Clarity over Certainty.” This describes the tendency of executives to focus on being sure about a decision, rather than clearly understanding and articulating why they are making a decision. Captain Picard is a leader with an almost superhuman reservoir of clarity. He is able to passionately articulate the reasons WHY any command has been given at any point. He can speak to the philosophy behind a value that led to the mission that informed the decision that enabled the command just given. His clear understanding of his own convictions and values, as well as those of The Federation in general, make him the leader that he is. Just watch the Captain (in “The First Duty“ S05E19) explain to the eternally annoying Wesley Crusher how the first duty of an officer is always to the truth.

Star Trek can be very silly sometimes. Fans can be even sillier when they idolize the show and its characters to an unhealthy degree. But we should still remember that Star Trek TNG at its core is not a science fiction show; it’s a morality drama. Jean-Luc Picard sits at the head of this modern morality play as a vessel for the most aspirational ideals of not just leadership, but almost every type of human value the writers could pour into him. Star Trek is nerdy and silly, sure —  but from an inspirational perspective, Gene Roddenberry can outwrite Peter Drucker any day.
Finally, if anyone out there is inspired by this post to watch the show Star Trek: Picard on Paramount+, please, please, please don’t. It is a sloppy, meaningless, morally bankrupt mess, and is mainly about explosions and ninjas (yes, I’m serious). I would rewatch a thousand episodes of Star Trek: Enterprise while being forced to say, “I see five lights” when I can clearly see four, before I ever subject myself to one more minute of Star Trek: Picard.

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I help companies turn their technical ideas into reality.

CEO @Sourcetoad and @OnDeck

Founder of Thankscrate and Data and Sons

Author of Herding Cats and Coders

Fan of judo, squash, whiskey, aggressive inline, and temperamental British sports cars.

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Things I Wish I Knew Before Selling My Company

In Entrepreneurship, Leadership

…or, how to survive due diligence without screaming into a pillow (too often)

On January 1st, 2026, Sourcetoad was acquired by Thompson Holdings. That part’s public now, and I can say, I couldn’t have hoped for a better outcome. We landed inside an employee-owned ESOP structure, surrounded by genuinely kind, sharp, and values-aligned humans. The strategy, culture, and incentive structures are everything I had hoped to build, and now get to be part of.

But even when you end up in a great place, the road there can feel like trying to run your company during the day while being interrogated by a team of lawyers at night. In a language you don’t speak. Using documents you didn’t know existed.

There are things I’d do differently if I ever had to go through it again. And since I’d prefer you not learn these the hard way, here’s the post I wish someone had handed me before I started.

1. Learn What Working Capital Really Is

You may think working capital is just “the money in the bank to make payroll.” I did. But in M&A, working capital becomes a financial and legal Rubik’s cube, and it directly impacts your final payout.

Here’s the short version as I understand it: your acquirer wants to make sure they’re buying a business that can operate normally on day one. So they’ll calculate how much short-term capital (cash, AR, prepaid expenses) needs to be in the business at closing, and they’ll negotiate that as a target.

That number is ESTIMATED. It’s also normalized and adjusted. And if you miss the target, you may be writing a check post-close.

Working capital trues up after the deal, and it gets shaped by your business model. Services companies, SaaS companies, project-based revenue, each one complicates the math. And everyone else at the table knows this well, but even in our deal our CFO understood subtleties that NO ONE else did. So you need to know more than the basics on this one.

Takeaway:

Working capital isn’t intuitive, but it’s important. Study it, model it, and don’t assume your gut will guide you right.

2. Trust, But Verify, Every Time

You’re surrounded by experts: bankers, lawyers, accountants. This is their job. They’ve done hundreds of these. But even experts miss things. Especially when they assume you’re a typical deal.

Like Simon Sinek always says, “Ask the stupid question”. Stop the meeting and go back to that thing on page 73.

In our deal, the biggest potential errors we caught came from small misunderstandings or unclear phrasing. We were almost too embarrassed to bring them up. But those awkward questions (asked by my amazing CTO) saved real money, and avoided some serious cleanup work later.

Takeaway:

If something doesn’t make sense, say so. You might be the last person who catches it. Also, have an amazing partner if possible who is more diligent than you are.

3. Track Due Diligence Like a Real Project

If your deal is mid-size or larger, you’ll probably have a junior banker acting as project manager. If it’s smaller, congrats, you are the project manager now.

You’ll be asked for contracts from 2018, explanations of deferred revenue, SOC 2 policies, lists of vendors, screenshots of your HR system, and a notarized blood sample from your head of finance.

I think that you should treat this like a set of software dev sprints: set up a simple spreadsheet, assign owners, and check in weekly. Otherwise you’ll lose track or lose your mind.

Takeaway:

Diligence is a second full-time job. Manage it like one.

4. M&A Lawyers Are Insane (In a Good Way)

They don’t seem to sleep. They respond to 1:00 a.m. emails. And they will happily work through weekends like it’s a sport.

This is great, because if you’re running a company during the day, you’ll be doing your deal work at night. Prepare for that rhythm. Use it. And then take them out to a really nice dinner when all is said and done.

Yes, the billable hours can be terrifying. But the best lawyers are worth it, and not just for paperwork. They’re your coaches in how to behave when the stakes are high.

Takeaway:

If you find a lawyer who texts back at 11:30 p.m. with bullet points, think of nicer and nicer places to take them for dinner.

5. Get Comfortable Being Talked About While You’re in the Room

There’s a moment (probably more than one) when someone on a call will say something like:

“Let’s review the comp structure for the founder if he dies.”

And you’ll be sitting right there.

At some point in the process, you stop being the protagonist and become a line item. That’s good. It means the business can live beyond you. But it can be weird. No one tells you how surreal it is to hear strangers talking about your salary, your severance, or what happens if you vanish.

Takeaway:

You’re not the business anymore. And that’s the goal.

6. Talk Less. Prep More. Don’t Negotiate

This might be the hardest lesson for most founders, especially if they’re used to wearing all the newest hats: you are not the negotiator.

You are not there to show how clever you are, or explain how smart your team was for choosing that customer billing cadence. You are there to answer questions, briefly, and let the professionals work.

The deal room is not your turf. Your team, your advisors, trained for this game. Hopefully you’re good at running a company… which is COMPLETELY FREAKING DIFFERENT.

Takeaway:

Channel your inner witness stand. Brief answers. Don’t ramble like I did. Let the pros handle the rest.

7. You Get to Watch Pros Be Amazing

One of the unexpected joys of going through this process was simply watching people who are really good at their jobs work together.

Bankers who know the exact number of turns in your industry. Lawyers who can dissect a 200-page agreement in an hour. The team on the other side of the table who’s been through five acquisitions and knows what to look for.

As operators, we’re often too deep in the weeds to step back and admire professional excellence. This process gives you that chance if you’re not too sleep-deprived to notice. Hopefully you can apply that feeling to your customers and clients. They should feel as deeply impressed by you if you’re doing things right.

Takeaway:

Sometimes, it’s okay to just watch and be impressed.

Final Thought

Selling your company is intense and humbling. It’ll test your patience, your understanding of finance, and your ability to stay quiet on Microsoft Teams calls (even when you are begging for a Google Meet or a Zoom). But if you’ve built something real, and you surround yourself with people who know what they’re doing, it can also be one of the most meaningful transitions of your life.

And if you’re lucky, you’ll end up where I did: not just with a great outcome, but with a future you’re excited to help build.

Just don’t forget to sleep after it closes.