The Weekly Hagakure #27

"Don’t settle, and don’t struggle. Life is what flows in between." -- Naval Ravikant

Having wrapped up my first week working at Sharpist, I regularly remind myself of how important self-care is. Mostly due to lack of experience, I haven’t really thought in these terms going into my previous jobs at tech startups and I paid the price for it. In both my last two companies, I approached (or even crossed at times) the burnout threshold.

This time around, while incredibly excited and energized going in, I’m also doing all I can to increase self-awareness of my own physical and mental states. I mentioned a regular meditation practice last week, and I’ve also got into regular intermittent fasting. I believe only a clearer mind can help us notice and understand what may be interfering with our well being.

That said, I am not immune to burnout. No one is. The scariest thing is that we’re by definition the worst judges of our own burnout. Therefore, we must enlist the help of others who care about us and whom we care about. Proactively asking them to give us blunt feedback when we’re “not ourselves” in some interaction can make a big, big difference. And, again, it’s a leader’s job to make sure the people in their charge are not slowly sliding into a dark place. Nothing justifies it.

With this, let’s dive right into this week’s picks. ✍️💈📚

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3 Articles

✍️ Less status updates, more coaching

Rather than being that dull manager who just asks what’s going on on all of the time, you can be that manager who has a magical way of getting their direct reports to continually level up themselves and their team without them even knowing that you’re doing it.

Many managers don't get past the status update one-to-ones because they simply don't know any better. But it doesn't have to (and shouldn't) be that way. James Stanier (whom I interviewed recently) gives actionable guidance here on how to unlock the coaching mode in you along with the real potential of your direct reports.

✍️ Preventing process deadlock

We need this thinking about unblocking to be a consistent frame of mind so that we can identify new blockers quickly and address them. To do this we need to emphasize team deliverables over individual deliverables. Get your team used to asking: how am I blocking someone else from achieving their goals?

Great write-up by Victor Vu, Senior Engineer at Credit Karma, on how critical a mindset of team over individual is to truly agile teams — what he calls a "culture of unblocking". Love it.

✍️ Communicating Organizational Changes

In smaller, rapidly growing environments, information flows much more fluidly by design and it is particularly important to have communication done well, to prevent organizational fatigue. Neglecting communication leads to thrash, lack of alignment and a rapid erosion of trust. Think of communication as part of your organization’s DNA.

In any growing org with more than a handful of people, communication won't sort itself out -- there's only the illusion that it does. This short post by Uma Chingunde, Engineering Manager at Stripe, makes the case for how important articulating and giving context to changes is, along with a thoughtful template to make it actionable.

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2 Twitter Threads

💈 Lovely reminder by Claire Lew of a management skill with high demand yet in such short supply. I like to call this "guided self-discovery" -- helping your direct reports continuously self-reflect while focusing on 1-2 areas of improvement instead of 10. So much value here.

💈 Interesting meditation from Dragan Stepanović on how psychological safety impacts batch size. Not the angle you usually see in agile discussions, yet another solid reason why building an environment of trust and positive collaboration is so important.


1 Book

📚 Good To Great, by Jim Collins

What is greatness? That’s a big question that I won’t even attempt to answer in this space. But when it comes to greatness in companies, this week’s book is probably the best recommendation I can think of to explore the topic.

When I first read Jim Collins’ Good To Great I remember being mesmerized by how a so-called “business book” could be a page-turner. But somehow Collins’ writing has a way of doing just that. The topic obviously helps — I’m obsessed with what makes world-class team and individual performance, probably the reason I love podcasts like The Tim Ferriss Show and The Knowledge Project.

Similarly to the fantastic (and much more recent) Accelerate, Good To Great is also research-driven by design. Collins and his team set out to pour into the data and try to figure out what makes companies go from being merely good to becoming great. What they found is equal parts not surprising, fascinating, and fully applicable to running any team within a company itself.

I won’t go here into what those drivers because I fundamentally believe anyone working in tech startups, in any role, should read this book. Suffice it to say that, as I wrote about before, simple things that never go out of fashion applied consistently are the key to business and team success. The data says so.

Good To Great is a landmark of business writing, the antithesis of all the crap out there giving the genre a bad rep. More than that, and perhaps less obviously so, it’s an excellent book on Leadership. I turn to its findings and teachings often, and can’t recommend it enough.


🙌🏽 Thank you for reading! Enjoyed this week’s edition? Have feedback on how I can make this more valuable to you? I’d love to hear it — my DMs are open on Twitter or just write a comment below.

✍️ Find some of my own ramblings on tech and org stuff over at The Evolutionary Manager.

👉 You can also follow me on Twitter @prla