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Time To Lead #2 | Leading in a Fight House


Hello Reader!

What a week. That meeting dominated the headlines, and while I won't turn this into a political newsletter, I do think it's a fascinating case study in leadership. Especially when it comes to conflict and communication, which you'll find are the key themes in this update. I have no doubt that business schools will be dissecting this moment for years to come.

One thing I found interesting was the real time example of what happens when leaders who communicate with emotion and control meet those who rely on logic and facts. We need to adjust our style to the other party to win them over, else we're just throwing words at them that don't land.

It also became apparent just how hard it is to stay in an 'adult mindset' when the conversation pulls us towards the parent and child mindset (hello Transactional Analysis). When the other party starts to 'parent' us, you're easily pulled towards defensiveness, submission, or even combativeness.

In the heat of the moment (and it was hot), it's hard to keep control of the conversation - we get caught reacting, defending, debating instead of leading the conversation back to our vision. Even in moments like this, the most influential communicators use storytelling to inspire, not just to the people in the room, but to the global audience watching (and rewatching) the conversation.

I hope the below snippets give you a few practical takeaways. Just scroll through and see what catches your eye. Make sure you save this message so that next time you're navigating conflict or facing a tough stakeholder that requires you to communicate sharper, you know where to find your guidance.

Let's do this!

Anna

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INSIDE LEADERSHIP

What I'm working on, thinking about, and talking about with leaders around me.


CROSS-CULTURAL COLLABORATION

Last week, I co-hosted a session on Cross-Cultural Collaboration for DutchCham with Dr. Catherine Wu (not the one making headlines in Singapore!). It was an informal, very Dutch-style discussion where Dr. Catherine showed us that storytelling done well is truly a superpower and where she inspired us that cultural intelligence is something we should actively develop in others.

I then grabbed a flipchart and sketched some of my favorite frameworks - Adam Grant's Rethinking Cycle, Dunning Kruger's Mount Stupid, the Confident Humility matrix and the 3 Types of Mistakes. The last one is critical to encourage a growth mindset in your team. Just saying 'make more mistakes' won't get you there. We don't need more preventable mistakes; we need more intelligent mistakes.

COMMUNICATION STILL LEADS

Last Wednesday, I worked with 50 leaders from a major Singaporean enterprise on leadership communication. We started with the essentials—know your audience, set realistic goals for each interaction, and plan for real impact.

We then practiced Barbara Minto’s SCQA Framework and the Pyramid Principle, the foundation of top-down communication. I also shared my “Could this have been an email?” thoughts and my strong belief that update meetings shouldn’t exist. And of course there were slides; we explored how to transform appendix-style data dumps into insight-driven visuals that actually tell a story.

UNLOCKING GENDER PARITY AT WORK

Just yesterday I joined a panel about gender parity at PropertyGuru Group. Skillfully moderated by their Director of Talent Acquisition Amanda Dew, we spoke about the need to double down on diversity, especially now. I loved listening to the stories of my fellow panelists Phan Thuc Anh, Director of Technology Strategy at PropertyGuru and Norman Chua, HR leader.

I shared my views on mentorship versus sponsorship and the paradox of skill, which argues that in situations where skill levels are high, and relative skill differences are low, luck not skill is the defining factor.

One of the questions from the audience built on that: How as an ally can you make sure you are a sponsor instead of mentor. My answer, which I hope you all put in practice: When you walk out of a conversation with a talented individual that you'd like to see advance, make sure the To Do's are added to your list, not to theirs.

LEAD BY NUMBERS

A data point that caught my attention - curious to hear your take.


of workplace conflict is caused by poor communication.

Communication keeps proving to be the root of many problems at work, and here are a few reasons why. First, we assume we're clearer than we actually are - because something makes perfect sense in our heads, we expect others to just 'get it'. But the knowledge bias is real: as a sender you know all the context, but we often forget that the receiver is hearing it for the first time.

Second, we need to repeat things far more than we think before they stick. Our marketing friends know that it takes at least seven repetitions for a message to fully land, and psychology tells us that without reinforcement, new information fades fast (aka the Forgetting Curve). Yet people still say: "I wrote this in an email two weeks ago - why don't you know this?"

Third, in multilingual and multicultural workplaces (like many of us in a globalizing work environment), communication gaps widen even more. What's obvious in one culture or language can be indirect or unclear in another.

So, just remember that the responsibility for a message to land always lies with the sender, not the receiver. Reiterate. Rephrase. Repeat.

QUOTED WISDOM

Words that shifted my perspective and thoughts worth keeping close.


There is always somebody who knows better than you what you meant with your message.
Professor Osmo Wiio

Professor Osmo Wiio’s legendary laws of communication (1978) are as relevant today as ever. It’s hard to pick just one, but the one above always sticks with me. Another thing he famously said is that if a message can be misinterpreted, it will be - often in the way that maximizes damage.

The real insight is that this goes both ways: sending and receiving. Are you reacting to what was actually meant, or just to how it landed on you? Are you frustrated because they don’t understand you - or because you feel misunderstood?

Next time you realize that a message triggers you, try to pause. Squeeze in a quick question to yourself: “What’s another way they could have meant this?” Or better yet, ask the other person. Most miscommunication isn’t meant wrong - it’s just delivered in a bit of a clumsy way.

LEAD WITHIN

Questions I ask myself, reflect on, and sit with to keep growing as a leader.


For the longest time I believed that being triggered is an automatic, instinctive reaction - like a reptile brain response we can't control. We would teach our clients about the Amygdala hijack. Only in the more recent years I realized there are a lot of flaws in this theory, after diving into the work of Dr. Lisa Feldman Barrett, neuroscientist, psychologist and world expert on the psychology of emotions.

She explains that when we react to a situation, our brain isn't going into an auto-response mode. It's predicting. Our response is our brain's prediction of what is most appropriate as behavior in this specific situation. Based on what we've learned from parents, teachers, early managers and authority figures in our life, especially during our forming years, our brain anticipates what is appropriate and decides on a reaction accordingly. And this is way more in our control than we realize.

So next time you feel triggered, pause and ask: Is this reaction really mine, or is it a script I have inherited? And: does this reaction serve me and my objective? Being intentional about our responses is about making sure we are leading in a way that aligns with our values. The real question isn't just what do I want to do in this moment? but what kind of leader do I want to be? It's not just about achieving your objective, it's about doing so without losing yourself in the process.

When you feel triggered, ask yourself: If I were the leader I aspire to be, how would I handle this differently?

SUPERCHARGE

A tool, habit or trick I picked up that's been making things easier for me.


A central theme to this update is communication, and as leaders, top-down communication is critical. But it's easier said than done. The general idea is that you need to start with the main message - or in internet slang the TL;DR. In consulting we called it the synthesis or the So What? We would say: "You have to push the thinking" and then that would get you the synthesis.

Then I reread Barbara Minto's The Pyramid Principle and I realized she doesn't talk about pushing the thinking. She calls it complete the thinking. Because until you have the clear takeaway, the essence of everything, your thinking isn't done. Pushing the thinking sound like "Ah, it's 85% there, try a bit more". A nice to have. Completing the thinking makes you realize, you aren't done yet.

A simple way to practice this, any day of the week, for any topic professional or personal, is my 20-10-5-2 exercise. State your point in exactly 20 words, where word #1 is the subject (I, we, you, the organization, the product, etc). Then, review that sentence and rewrite the message in 10 words, starting with the same subject. This is a summary. Now complete the thinking: write a message with the same meaning in only 5 words. You're getting close to the synthesis. One more level: two words only. Now you found the core of what you want to say. From here, add on essential words for understanding, but keep it between 5 - 10 words maximum. Here, you just completed your thinking!

LEARN TO LEAD

Resources I created or came across that I found valuable.


How to master conflict resolution

A great HBR article by Amy Gallo with the foundational approach to resolving conflict at work. If you're new to conflict resolution, this is a great place to start. Read it here.

Culture eats mineral deals for breakfast

I've found it quite challenging to find articles about that meeting in the White House that go beyond the polarized views in politics and instead analyse and reflect the leadership communication principles we saw at work. While this article isn't conclusive and doesn't attempt to be a complete view, I did find that it offers perspectives that made me think and reflect. Read it here.

You have more control over your emotions than you think

The first time I learned about the work of Dr. Lisa Feldman Barrett was when I listened to this podcast with Adam Grant. She's been a guest to many other podcasts, but this is a good, shorter one to start with. Listen here.

MARK THE MOMENT

In-person and online events, conversations, talks I'm looking forward to.


TOMORROW | Living Fully: How We Prioritize Wellbeing While Building Success

In-person, Singapore

7 March | 9:00am

A bit last minute but pushing this out one more time: Come join me for this morning session on wellbeing in the workplace. Living fully is about purpose-driven work, personal growth, autonomy and flexibility. I'll be joining a panel with Clarissa Choo from Huggs Coffee, Sophia Ng from Kidztropic, Tulika Tripathi from Snaphunt and Trasy Lou Walsh from Fluid, moderated by Sharon Li from CHOYS.

Sign up here.

ON THE HORIZON

A sneak peek of ideas, projects and launches I'm working on before they go public.


Affiliated Facilitators

I’m building a network of affiliated facilitators to help deliver leadership programs and workshops in local languages. Through recommendations from my network, I’ve already found some fantastic facilitators, but I’d love to connect with a few more. If you are (or know) a facilitator based in Thailand, Malaysia, China, Vietnam, Indonesia or the Philippines - especially the first three countries - and can deliver leadership programs proficiently in the local language, please reach out! I’d love to get to know you.

Custom GPTs and AI Agents for Leaders

Coming in April 2025

Last year, I raised over USD 20,000 to support my 33-year-old caregiver through her surprise advanced kidney disease diagnosis by running masterclasses on using GenAI as a thought partner. Fast forward, she is preparing for her kidney transplant surgery and soon, I’ll be launching a second initiative to raise more funds for her upcoming medical bills. This time, I’ll focus on AI Agents and Custom GPTs—how to tailor them to amplify your leadership effectiveness. If there’s anything specific you’d like covered, now’s the time to let me know as I finalize the masterclasses. Please do spread the word and let me know if you're interested to join, sign up will start soon.

In The Lead Podcast

I’m preparing to launch a podcast with CEOs and executives who are ‘in the lead.’ We’ll explore what it’s like to sit in their chair, make high-stakes decisions, and navigate rapid change. I’ve already got my first guest confirmations and will start recording Season 1 soon. If you have suggestions for guests I should invite or topics I should address, let me know—I’d love to hear your thoughts.

Online Learning Offerings

The first few months of this year have been all about experimenting with online learning formats. Now, I’m taking what I’ve learned, refining the approach, and putting together online learning programs that fit my unique style participants know from my in-person sessions. The plan is to launch in April and May, so stay tuned! If there’s a specific leadership challenge you’d like to see covered, let me know—I’m shaping these courses with real needs in mind.


Hey, I'm Anna. I'm a leadership expert based in Singapore, helping leaders worldwide get ready to lead next. Over the past six years, I've worked with thousands of leaders across tech giants, MNCs, and hypergrowth startups. Glad to have you here. Let's figure this out together!

The world needs better leaders. Leaders who are ready to rise up in the moments that matter. Leaders like you.

If you're looking to level up leadership—whether for yourself, your team, or your organization—let’s talk.

Bring me in for your next offsite, keynote, or online webinar. I also work with executive teams and can help you design and deliver a flagship manager or leadership development program. Plus, with my network of affiliate coaches and facilitators, we can scale impact across your organization, wherever you are in the world.

It's time to lead.

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