Stardate S03E30

Sean K. Gabriel
Captain’s Log: Supplemental
6 min readOct 26, 2022


Mood: 😞. Had the wind knocked out of my sails. The trick now is not to go adrift.

Overlooking the Regent’s canal from Hoxton 🍺

I alluded to it at the start of last week, but it’s been tough times at work lately. I feel the tension of being unable to be fully open about details here, but it shouldn’t stop me from reflecting altogether.

🌹 What am I grateful for this week?

Sharing in a difficult change can bring people together, and so in taking a posture of gratitude, I can see that my diary was full of coffee chats as a result (even one serendipitous encounter on a street corner waiting for breakfast!). I also spent time with my wider network and did my best to keep meets in that I could’ve cancelled* because I wasn’t in the mood.

I recently picked up a name for that posture, thanks to Andreas and his encouragement to apply for the PQ coaching program: the sage’s perspective. It’s one that sees all problems as a gift, and is endlessly curious, compassionate and empathetic. I’m still learning how best to channel it, but I can see how changes on the horizon might help me get to where I want to go faster. Or to find more fulfilment where it had started waning over time (or replaced by judgment, a mental saboteur I’m trying to identify as I put in more PQ reps). It’s strange that this coaching program fell into my lap, perhaps at just the moment I might need it most?

🌵 What do I wish could have gone differently?

I need to get better at asking for what I need. And not letting cognitive biases** dominate my thinking — that includes circumstantial happiness that’s been so up and down over the course of the week.

Sure, when you’re taken by surprise in a bad way, it erodes trust. But I know presiding over such surprises doesn’t bring anyone any joy. And you still have a job to do — as a manager and a leader, to look after people in good times and bad. That means avoiding making it about yourself and being the support others need, being candid with what you know, and preparing yourself and others for what’s to come.

💡 What do I need to remember?

We like to think we’re all extraordinary in our own way, right? That might mean buying into a narrative that we’ve somehow outfoxed the market (possible, but rare!). But Occam’s razor should remind us that the fundamental attribution error is more likely at play. And accepting we might not be able to see it clearly until we have hindsight — but that could make us more risk-averse at the critical moment, to avoid painful*** lessons down the line.

Check for a rising tide before you decide your boat is lifting the fastest.

Speaking of outfoxing the market, a recent talk from April Dunford broke down how to do this proactively. It starts with avoiding any temptation to trash the competition, and instead crafting a compelling narrative about the entire market. In effect, it means bending the worldview of a potential customer to use your rubric to evaluate the market, with you becoming the arbiter of pros and cons. It’s in your best interests to be honest, because you won’t outfox your customer — you need to believe your own worldview first! If the competition was actually that bad, why do they exist and still have customers? Instead, being the honest and clear-eyed guide is a path to building trust from the onset.

Be the guide to the entire market. But you need a compelling narrative to back it up.

📚 What did I discover?

Traditional jobs have well-worn inputs and outputs, with minimal risk of failure. But it’s easy to forget that the tradeoff is (usually) minimal impact. Working on the edges is a riskier proposition, but Seth puts it beautifully with his encouragement in this Q&A that “should it not work, you will not have failed, you will simply have found one more step forward on your way to making the difference that you seek to make.”

Any 2x2 with a “soul sucking” quadrant is worth resharing. Avoid depleting, non-urgent work the way you would trans fats! 😄

Can product leadership be distilled into five questions? I appreciate how Ellen’s laid them out across a variety of company growth phases, and that the ability to perform/execute/deliver is never zero.

Being less afraid of being wrong comes with practice. And with practice comes tacit knowledge. So why can’t we take the same approach with strategy definition?


One other gift from the week I didn’t want to miss was a working definition of allyship from the good folks at Stonewall. It’s more than a reactive stance (i.e. intervening**** when we see something wrong — necessary but not sufficient!) and it definitely can’t be passive. That means being proactive as well. I’ve got loads I could do better here, whether it’s lending privilege intentionally or being visible in celebrating diversity. I don’t think of myself as outspoken, but I also don’t buy into the narrative that proactive silence is complicity. There are non-performative signals that can make your acceptance clear without shouting from rooftops; take adding your pronouns to a Slack profile as a simple example. Not an end point, but part of a continuum of proactive behaviors to consider.

I also only just realized that my own workplace identity expresses itself most strongly through nationality (as well as age and class) and at least to me rarely registers on physical characteristics, gender identity, or a whole host of other dimensions that others may be acutely aware of. Usually it’s just being the lone American expat in most meetings I’m in, but I’ve gotten used to it over time.

*I would’ve robbed myself of friendly faces had I done so, but I have to admit that after so many back to backs, rehashing the narrative of the week, it was actually a welcome break to have a cancellation come to me. Guess I can only take so many doses of extraversion at once. 🙃

**In this case, I’m thinking of confirmation bias and loss aversion as the main illusions to see past. Whether that’s of a carefree culture, or belief in infallible planning, or innocence about business viability. I also need to remain grateful for all I’ve had and been privileged to enjoy up to this point.

***On that topic of pain, consider cells in an organism. Some die so others might live. When they do, who feels the pain? It probably depends on the sophistication of the organism’s nervous system, i.e. the network of feeling within that creature, and its ability to remember.

****I’ve felt ill-equipped in the past to deal with bad client behavior. But I know if identities are ever under attack, a single team member being uncomfortable for expressing their identity at work is one too many. But this is probably where organizations could benefit the most from role playing, or a similar type of practice that is contextualized to situations the team will actually find themselves in. And beyond the overt and obvious, how about the insidious under-the-radar behaviors that need to be brought to our collective attention? That’s where systemic change can start.



Sean K. Gabriel
Captain’s Log: Supplemental

Aloha (🤙。◕‿‿◕。)🤙 big on building teams & lean products. Author @ Thinking aloud with #weeknotes. Works best when caffeinated ☕️