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Macromanaging

The CEO of Shopify recently sent a memo on AI, which included the mandate: “ Using AI effectively is now a fundamental expectation of everyone at Shopify. ” Reading the piece, I was reminded how rarely leaders give clear guidance on working methods. Too many view this as a taboo subject – the realm of micromanagers. But I think it’s critical for building productive teams, especially when facing…

Open-ended questions

One day, I aspire to ask a question without layering on caveats and trying to guess the answer. It hasn’t happened yet. But I remain an optimist.

Who’s the customer?

The rules for a decent conference badge are simple: Two-sided. Attendee name in large bold lettering. Company name in large bold lettering. This is obvious to any conference attendee. So why do most badges fall short of this – crammed with logos, small text, and other irritations? The answer is simple. Attendees are not the primary customers of this product. Our opinions don’t drive revenue.…

Reframing

I usually view work travel as mundane and exhausting. It disrupts my body clock, keeps me from my family, and triggers a pile of expenses. Instead, on the way to the airport today, I decided to enjoy this trip. I reframed the flight as relaxation. When do I get seven hours to watch films in peace? Never! I reminded myself of the luxuries. I’ve flown enough to hold airline status, so I can relax in…

The last moments

I like to take lunch walks past my son’s primary school. The roar of sound hits me five minutes before I reach the school fence, and as I walk the perimeter, I smile at the unabashed joy within. Kids are crazy, in all the right ways. If I’m lucky, I’ll see my son. Like any parent, I can spot him at a great distance. Something about his posture and gait marks him as my boy as clearly as if he stood…

Old habits

I used to meditate for twenty minutes every day. So, when I started again recently, I decided to ease in with ten-minute sessions. I was surprised at how painful it was. More than once, I sneaked a peek at the timer because I was convinced it had stopped. I was losing my mojo, and it was only the first week. Then I remembered the golden rule – if you’re not having fun, make it easier. I cut the…

In praise of boredom

In Craig Mod’s recent podcast interview with Tim Ferriss, he described his regular practice of taking long, multiple-week walks through the Japanese countryside. One of his goals on these walks is to get very bored, so as to reset his mind and gain more attachment to the present moment. It reminded me how rarely I experience boredom, quick as I am to fill the gaps in my life with reading,…

Rinsing the rice

I bought a rice cooker in the January sales. The instructions told me to rinse the rice for the best results, so I did. And it was a bloody nightmare: clogged sieves, rice on the floor, and water everywhere. One brave day, I skipped the rinsing and cooked the rice straight from the packet. Guess what? There was no difference. At all. It made me think – where else am I metaphorically rinsing the…

And what should I stop?

Another benefit of documenting your priorities is you can share the list with others. When they ask you to do something new, you can point to your list and ask them which item gets bumped. Your priority list is also your opportunity cost list.

Two-way management

The path to management is not a one-way door. If helping others brings you joy, you should stick with it. But if you feel hollow, as though your job has lost its sparkle, then perhaps you were a specialist all along. And that’s just fine. You can’t predict this in advance, so you must try both. But if you don’t sense the joy, you should walk straight back through the door.

Birthday directions

I’m writing this on my birthday, which is a great moment to reflect and plan. Rather than concrete goals, I prefer defining directions of travel. This year, there are three: Finding a groove with meditation. Buying fewer items. Striking a balance between improvement and contentment. Each represents an identity I cling to without merit. Having meditated in the past, I see myself as somewhat Zen.…

Brainstorming

Free-form brainstorming is great, provided you only want ideas from confident people. Unfortunately, it leaves many good ideas unspoken. To involve everyone, structure is needed. Here are two fantastic approaches you can leverage. Brainwriting gathers ideas through writing. Everyone spends five minutes silently writing ideas on an index card. When the timer rings, cards are circulated to the left.…

Trust your people

Last week, a fire crippled Heathrow’s power supply, and every flight was cancelled. Passengers were rebooked for the next day, doubling the foot traffic at Europe’s busiest airport. This was a disaster for my friend, who had assumed his Saturday travel plans would be calm and quiet. He struggles with crowds even at the best of times, and now everywhere he turned there were hundreds of people. His…

Five minutes

Outlook has a neat feature that automatically shortens all your meetings by five minutes. Five minutes to head to the toilet, grab a coffee, or stare out the window and decompress. In the post-pandemic flurry of back-to-back Zoom meetings, five minutes makes a big difference. Try it by following these instructions .

It’s not a bug

When you eat in a Wagamama restaurant, the food arrives when it’s ready, rather than all at once. This disrupts the dining experience. Starters often arrive after the main courses. You might sit for five minutes with no food while everyone around you eats ramen. Somehow, Wagamama turned a bug into a feature. They’re unashamed to operate this way – it’s positioned as trendy and kooky. I try to…

Process

I’m writing this on a flight to Copenhagen. Everything about my experience today has been automatic. All airports feel identical. All flights board in the same way. The attendants say the same script before every take-off. No fuss. No mistakes. No thinking. This is the power of processes. They make everything easier and faster. Where can you add processes to your life to achieve that same…

When do you need this by?

We assume tasks are urgent when they arrive without a deadline. Rarely is this true. Next time, avoid assumptions and discover the facts. Clarifying deadlines also reveals their true nature. Sometimes, you get a crisp answer: “I need this before my meeting on Wednesday.” More often, you get a vague answer: “Uh, how about Friday?” This is your moment to renegotiate.

Needles

With a small team, every activity has to move the needle, otherwise you waste scant resources. The phrase is clichéd, but oddly effective. When you challenge someone with, “ But will this move the needle? ”, they know exactly what you mean and immediately know the answer.

The trap

Setting priorities is important but it’s less than half the battle. Let’s say you’ve picked your top five priorities. Of the thousands of things you could focus on, these five are the most impactful. Just behind those top five are items six through ten. You may not have written them down, but they exist, nonetheless. Now, imagine that someone asks you to tackle priority number seven. It will be…

Out of orders

One of my favourite leadership quotes is hidden within Frank Herbert’s Dune : “Give as few orders as possible," his father had told him once long ago. “Once you’ve given orders on a subject, you must always give orders on that subject.” Said differently, if you always tell your team what to do, they become reliant on your instructions, and you become the bottleneck for all progress. I…

Short on strategy

Earlier in my career, I thought a strategy was a presentation with forty slides. I worried nobody would believe me unless my deck looked well-researched. I needed mission statements, revenue projections, market trends, etc. (Note: I worked with several former Bain consultants when I started making strategy decks.) In truth, I was hiding behind the data. A good strategy can be expressed in a…

Annual priorities

Setting work priorities can feel like a chore. An annual activity to appease the higher-ups. I used to feel this way. But several years ago, I realised my calmest moments were when I knew exactly what needed to be done – when my priorities were clearest. The extreme version of this is a crisis. When everything’s on fire, your priorities drop into sharp focus. You abandon the trivial and focus on…

Who is selling?

A familiar scene unfolded in the boardroom today. My team met another company, and we discovered we were both trying to sell to each other. It wasn’t a good meeting. In a company, the people who sell things are rarely the people who buy things. The result was like pushing two opposing magnets together – an awkward hour that failed to generate meaningful actions. Why does this keep happening? It…

We need more PAs

When I joined my current company, I was assigned a personal assistant. I had never worked with a PA before. And frankly, I found the idea antiquated. Didn’t we throw out PAs with the fax machines? Hadn’t these people heard of Calendly? But as the weeks passed and I fell into a rhythm with my new PA, I got it. And I’m now a total convert. In fact, it’s crazy we don’t have ten times as many PAs. A…

Frequently assumed questions

If you’re launching a product or service and you’re tempted to write an FAQ, stop. At this stage, you don’t know what your users will struggle with, so your FAQ would be a list of assumed questions. This is the curse of knowledge in action. Even if you could predict the questions, wouldn’t it be better to improve the user interface or manual, so the user is no longer confused? An FAQ should be a…

Escalators

Two years ago, I started walking up escalators. More specifically, I decided to become the kind of guy who walks up escalators. I embraced it as an identity change, not a behavioural change, and it stuck Now, when I approach an escalator, I get a thrill. I charge up the left-hand-side and emerge victorious at the top. Nobody applauds. They probably think I’m crazy. But I don’t care. I love it.…