Category: Thinking Clearly — Archive of past newsletters

3 minute read

Hello Amazing!

I really believe that we can all benefit from practicing more vulnerability in all aspects of our lives. But there’s one domain that I’m extra interested in: vulnerability in leadership.

What does it mean?

For starters, I hope we can all agree that it’s potent stuff. We all look to leaders—both the formal leaders with rank and the informal leaders—to be role models. What they do, what they say, and especially how they do it, gets amplified. For better and for worse. Let’s explore why and how.

Here’s the thing I’ve noticed when looking at vulnerability in leadership: The vulnerability sweet spot is a much narrower window. Under pressure, with lots of people around, things moving quickly, the space between ‘too soon’ and ‘too late’ is small. You can’t plan and rehearse too far in advance, then it just feels forced. But too raw and spontaneous can be confusing and uncomfortable for everyone. You really need to learn to recognize when the moment is just right and at the same time hit the right dosage.

Within that narrow sweet spot, you have an opportunity to do something for the benefit of the whole. Let me give you two examples:

1/ Setting a warm tone in the beginning of a meeting and opening up the space for others to bring more of themselves into the conversation. I’ve seen a leader who would enter every meeting telling a small story (not a 7 minute “small story” but literally 30-40 seconds) about some little mistake or issue she had that morning. Not in an angry or frustrated way, but in a light and fun and self deprecating way, laughing warmly at her own silliness. Nothing that required a follow up or risked derailing the meeting agenda in any way. But everyone’s shoulders came down and the meeting started from that tone. That was an example of frequent small doses that served a shared purpose: disarming tension in meetings, efficiently and reliably.

2/ On the grand scale, it can be an explicit ask. During the pandemic, I saw a CEO ask all employees to take a voluntary, temporary pay cut in order to preserve liquidity in a worst case scenario, avoiding immediate layoffs (with a promise to pay it back in case the worst case could be averted). That’s a pretty big ask to make, and there’s no guarantee that people will accept. It could have truly backfired. But it was so genuine—the whole company and everyone’s jobs were on the line—and you could feel how humbling it was to make that ask. It was also an appeal to think about the whole and not just oneself. That’s why it’s so powerful. The individual sacrifice serves a shared purpose, and everyone gets to feel that their actions are meaningful and contributing. The genuine ask allows the recipient to become part of a shared narrative and play an active role in the outcome.

It’s such a fine balance because if your vulnerable approach seems the least bit calculated, it will have the exact opposite effect. If it feels performative (“Just look at the tears in my eyes as proof of how touched I am by my own story”) or even competitive (“There is no way you can top my bravery now”) people will likely feel alienated, manipulated and in the worst cases emotionally violated. When it’s bad, it’s bad!

However, I’ve seen first hand how some leaders do it so well that they can melt away cynicism and fear within minutes.

Much love

Mathias

This is part 3 of 3.

• Part 1: Why vulnerability matters for social connection
• Part 2: Finding your own vulnerability sweet spot
• Part 3: Using vulnerability as a leader

4 minute read

Hello Amazing!

In the previous post we looked at why vulnerability and openness is so important for social connection. But how do you actually share with vulnerability?

Remember, the goal is to share something in a way that builds human connection. If we only share our success and when we are on top, the projection can make others feel inferior and hold back with sharing what is actually going on for them. The relationship becomes superficial. But the solution isn’t to share all things right away, making it all completely raw and unfiltered. This isn’t vulnerability. It’s just oversharing, and it has all its own issues: in extreme cases it feels completely inappropriate, and the recipient can feel violated (and yes, I’ve done it too!). It can also be triggering for others, who may have had similar experiences.

Let’s take an example of something I’ve tried a few times now: getting laid off from a job. I’ve been laid off due to restructuring, where my work would be chunked up and given to freelancers. I’ve also been asked to think about a “transition plan” which was code for “you are not delivering to the expectation.” Technically speaking it was me who quit, but it wasn’t exactly voluntarily or on my own timeline.

On the day it happens and immediately after, it’s been so raw. I’ve been in a bit of a shock, not sure what was up and down. This isn’t a good time to share, except with our closest friends and family. The people who for better or worse will have to endure us in that state.

When it comes to sharing more widely, for example on social media, I find that a useful way to look at this, is not to think so much about how to share vulnerably, but to focus on when. Then the how will follow.

If you think of it as a timeline, there is a window of opportunity somewhere in between that initial shock and being back in full safety (You’ve seen those Instagram posts: “First day at my new job. So excited about all my smart new colleagues. Btw. the communal lunch is incredible.” ).

What we are looking for is the vulnerability sweet spot. It has to be recent enough that you are still affected by it. It still matters. But not so recent that it’s too raw. Let’s take a closer look.

To find out if you are sharing too late: if you are already ‘safe’ again (new job, new wife, etc.) and really just telling others what you went through, even if it was hell and absolutely terrible, it probably isn’t vulnerability that you are showing. It’s more likely showing off what you’ve overcome. There’s nothing in it for the recipient. If all they can do is give you a toast and say ‘wow, congratulations’, you are ‘proving’ not ‘sharing’. Yes, I’m guilty of this too.

So what’s too soon? Imagine that you share online what you are going through and someone leaves a comment. If it’s too raw, you are still feeling a need to be seen and feel validated, for example through supportive comments. Thus, when it turns out that the comment is not really about you and what you posted, it’s the other person sharing their own struggle, you get frustrated. I’ve been there too. In those moments, keep sharing with trusted friends, whom you can count on for that kind of support.

If, however, in this thought experiment, you feel grounded enough that you could appreciate others’ stories and experiences as a positive thing and not be counting on them to validate your experience, you’re in the sweet spot. When you do vulnerability well, people will reciprocate and share a bit of themselves. You are helping people be more vulnerable and share a bit more of themselves because they are following your example.

So it’s a ‘when’ to share more than a ‘how’. But how long time are we talking about? Days, weeks, months? It depends on what happened. And it depends on you!

The first time I got laid off, I didn’t tell the full story until 10 months later, where I felt I had enough solid ground under my feet, but still had it fresh enough in my memory to share the emotional part as well. Check out my annual report from 2016 and judge for yourself. Does it feel too early or too late or does it land somewhere in the sweet spot?

Last but not least: we can’t get it right every time. Many times we won’t know if we are too early or too late until it’s too late. Be patient with yourself. Know what you are aiming for and notice whenever you are a little bit off.

In the next issue we will take this theme of vulnerability one step further and look at how you can also use it as a leadership advantage.

Until then

Much love

Mathias

This is part 2 of 3.

• Part 1: Why vulnerability matters for social connection
• Part 2: Finding your own vulnerability sweet spot
• Part 3: Using vulnerability as a leader

2 minute read

Hello Amazing!

This is the first of three newsletters diving into the topic of vulnerability and openness: why it matters so much, when to do it and how to use it effectively as a leader.

The story begins back in January (remember January?). My wife and I were getting ready to leave NYC, and everyone was asking “Do you have a job lined up?” I hated that question because the answer was ‘no’, and whenever I had to answer the question I felt exposed.

On January 20th, just 10 days before we left, I got offered a job at Implement Consulting Group. I was so happy. Finally I could put that pesky question to rest and update my LinkedIn: look at how successful I am! My God I loved that.

Fast forward through a pandemic, life crisis and being let go again from the job, I’ve been reaching out to old friends, sharing my struggle and asking for help.

One person wrote back: “I’m surprised to hear from you. I thought you had it all figured out.”

This comment hit me. I’ve been working intentionally with vulnerability and openness for more than nine years, so I thought I was as open as one could be. However, to him, and maybe others, I had still seemed unapproachable. He told me that he too had been struggling lately, something I probably wouldn’t have heard about if I hadn’t shared my own struggle first.

From being unapproachable it can quickly get worse. The more successful you appear, the more likely it is that others will feel inferior around you. That can turn into insecurity and even envy. All of which makes it harder to have a strong relationship. More success projection means less human connection.

The solution obviously isn’t to replace all your success stories with negative stories of misery and self pity. But what then? In the next issue, we will dive into some very tangible ways, you can practice sharing more vulnerability without falling into the trap of oversharing.

Until then

Much love

Mathias

This is part 1 of 3.

• Part 1: Why vulnerability matters for social connection
• Part 2: Finding your own vulnerability sweet spot
• Part 3: Using vulnerability as a leader

Hello Amazing!

Even before Covid-19 closed down most of the world, our work and lives in general are increasingly mediated through technology. I spend as much time looking at my friends’ lives on Instagram or sending text messages or talking over FaceTime as I spend in company of my friends physically, it’s just chopped up into many little moments of scrolling and liking and replying. The same was also close to true for my work: even while working in an office, many client meetings were held virtually as well as meetings between offices on different costs. The Covid-19 pandemic has further accelerated this trend.

I’m finding that one of the most important things for me is to really double down on the deeply human qualities:

1/ I have enjoyed going for extended walks outside with a new friend and coworker in my ears, having what we at Implement call REAL conversations.
2/ I also enjoy not doing screen sharing and instead opting for fewer and simpler slides that I draw by hand and hold up to the camera. It makes it feel so much more intuitive for me to present virtually and I can feel the audience much better.
3/ And lastly I enjoy facilitating reflection, especially when I manage to get a group of people together like I did recently with Janus Boye. There is something so beautiful and simple about a group of strangers coming together to process and share their experiences in life.

As always, if there is any way I can help you get started (or go further) with REAL conversations, drawing slides by hand or facilitating reflection, I would be honored help you. Just get in touch via WhatsApp on +4522212355 (my e-mail is a mess). It’s my humble attempt to share what has helped me the most.

With much love

— Mathias

Hello amazing!

The Corona-pandemic has upended lives everywhere. At first I felt a great loss and sense of disappointment. We just moved to Copenhagen to be closer to family, not to be isolated at home. Then adjusting to work from home with kids running around. 

It’s still a major challenge, and I’m not here to peddle a quick-fix or “seven magic tricks.” However, there’s one thing I’ve kept returning to and that’s the shift I’ve tried to illustrate below in the Cynefin framework.

Before the crisis a large part of our world seemed to behave in ways that were complicated. This meant that with the right expertise, analysis and planning we could reasonably predict the relationship between cause and effect.

But now we are in a completely new territory: it’s complex. There are feedback loops which behave in unpredictable ways. And what the Cynefin framework teaches us is that to succeed in the complex domain we need to probe the system with intent and observe the reaction before we probe again. 

For me, the single most helpful thing I’ve done throughout the past decade, especially when navigating new territory, is reflection with pen and paper. It helps me process my experiences and emotions and surface insights that I can use. It’s not a magic quick-fix and it requires effort. But it helps in small and important ways. 

If you would like to get started with reflection and begin building a habit, I would be honored help you. Just get in touch via WhatsApp on +4522212355 (my e-mail is a mess). It’s my humble attempt to share freely what has helped me the most. I also plan to record a few guided reflections (like a guided meditation) and share as a podcast. 

I hope you’ll mostly keep up the good spirits (and be kind and gently with yourself when you can’t) 

With much love  

— Mathias

Hello amazing!
It’s been a while since I last wrote a new Think Clearly newsletter. One month ago we moved from Brooklyn to Copenhagen and I’ve started a new job with Implement Consulting Group which is very exciting. Yesterday I was in my first delivery, in a workshop with a leadership team and we talked about the matrix above. In a changing world, incumbent companies are at great risk of drifting gradually from the top left towards the top right: you keep on doing what you do well, even if it’s less relevant. It’s also easy for incumbent firms to dismiss a startup, since many successful startups initially obsess over being in the left column, even if they are in the bottom left. Chances are that they will learn and move upward. Lastly, I thought about it on an individual level, as I am new in this job. I’m trying to remind myself that if I want to do the right things well, I need to first be open to what the right things are, instead of sticking with my experience and just doing what I do well. 

What insights does this 2×2 give you in your current situation? Where are you? Which direction are you trying to move? 

Also, if you are in or near Copenhagen and would like to grab coffee, please let me know. 

With much love  

— Mathias

Hello amazing!
I love reminding other people how real learning can be quite hard while I tend to believe that this somehow doesn’t apply to me, only to be shocked when it’s suddenly my turn. Alas, the past months have been challenging. This is what I’ve learned about myself: for most of the past decade I have shown up in life as an artist, meaning: regardless of the situation or moment I’ve generally done whatever I wanted to do. It’s a bit like going to class, pretending that all classes are art classes, but lately I’ve found myself in situations where the expectations of me are different. Now I gotta figure out what each moment is actually about ahead of time, and make sure I do the right homework for it. 

How do you know what your ‘homework’ is in each moment? 

With much love  

— Mathias

Hello Amazing!
Two weeks ago I wrote about ‘being dangerous’—a topic that is still swirling around my head. One reader pointed out that it might actually not be about intent, but also if someone perceives your interest to be aligned or unaligned to their own. For example, if you have good intent, for example when creating change in the world, but your interests go against someone else’s (the people who want to preserve what is) then they will still view you as dangerous. Thanks for pushing my thinking.
—
For today I’ve been further exploring what dangerous actually looks like under different circumstances. For example, in a lawful society most physical violence and threats of violence are forbidden, and it’s hard to get away with, at least in the long run. For most of us it’s an effective deterrence. But lawful society doesn’t cover all aspects. What about the small slights? Someone taking credit for your work or trying to plant harmful rumors about you in the workplace? The little things that are hard to catch, and that someone might be able to get away with?
—
I struggle to write about this because it goes against my desire to believe deeply in the goodness and generosity of every person. Is this belief deeply naive? If you have built a strong and trusted network through generosity, and these people watch your back, I wonder if that is actually as good a deterrence as one can get. Or maybe I’m just suffering from pronoia—the delusion that other people are plotting my wellbeing being my back.
—
Please, share your thoughts on the above with me. It might take me a moment to get back to you, but I will.
—
With much love

— Mathias

Hello Amazing!
She said “You are dangerous! This man is dangerous!” I could see the terror in her eyes. She was afraid of me. She wasn’t kidding. She was a participant in one of the Digital Acceleration Master Classes I used to facilitate when I worked at Hyper Island, and something I had said had frightened her. I didn’t know exactly what it was that I had said that had upset her so much. My guess is that it was in the way I was advocating for more openness and transparency. Never before had I experienced someone reacting this way. In her eyes I saw myself reflected as a dangerous monster—not a pleasant sight for someone who is used to seeing a friendly, warm and gentle man in the mirror. Someone with his heart in the right place. It had not occurred to me that anyone could perceive me as being dangerous. And it has taken me nearly four years to come around to this idea and I’m still only beginning to see how it fits with my worldview and sense of self. that’s why this issue is a bit longer and more open ended than usual.
—
The way I see it currently is that there are two fundamental choices. The first choice is if you intend to do good or evil. The second choice is how much power you seek to have. Becoming powerful, however, is not an instant choice. You have to keep at it consistently over time. Every day you can choose to try to become more powerful or less powerful. Once you become powerful it seems to stick. Once you learn to shoot a gun, to yield a sword, to speak persuasively or to hack into a secret database, your skills won’t just go away. The trouble is that your first choice is less stable. Today you might intend to be good. But what happens if someone harms you or your family? Can you be sure that you won’t suddenly decide to use your accumulated power to seek revenge? You can’t be competent without also being dangerous. But with such capacity for evil, might it be better to avoid power and remain harmless? I don’t think so, yet I wonder if there is an upper limit on how powerful one should become.
—
What do you think? Are you willing to be dangerous?
—
With much love

— Mathias

Hello Amazing!
In the past few years I’ve felt my social influence to be waning. I get less likes on Instagram than ever before. On LinkedIn and Facebook it’s near zero, so I’ve just stopped using these. My newsletter audience has been stagnant for years. I don’t like to admit it, but this stuff bothers me.
However, a few weeks ago the danish-american author Lars AP, known for his creation of the ‘Fucking Friendly’ movement came to visit. And as we talked it occurred to me that I find it so much more satisfying to have a single mutually inspiring conversation, than any number of likes or clicks. It also made me re-think how I consider my actual ‘reach’—if I can be a source of inspiration for people who reach millions, perhaps that’s enough. How do you think about reach and influence? And what’s most important to you?
With much love

— Mathias

p.s. if you are in Europe, I’ll be speaking at the Digital Leadership Conference in Aarhus, Denmark (my hometown)—and let me know if you’re interested in attending

Hello Amazing!
I’ve been fascinated with feedback for a long time. Why most people (incl. myself) do it so rarely, how it works, how it feels, and how it might be better. Most recently it occurred to me that as I listen to someone giving me valuable feedback, I’m constantly worried about what they might say next, while secretly hoping to hear something super positive. In preparation for a feedback session I tried to write these things down in advance: 

1) What I was hoping to hear (I was in a tough moment, unsure of myself and my contribution and was really hoping to hear some positive validation)
2) What I realistically could expect to hear (I know I haven’t been very proactive lately, so I could easily expect to hear that, which made it less scary) 
3) What I was trying to understand. 

How do you prepare yourself to give and get feedback? 

With much love  — Mathias

Hello Amazing!
I’m not against smartphones or technology in general, but I find the habit-making trigger—action—reward feedback loop to be much too powerful to control. My willpower just isn’t strong enough to resist the constant temptation of quickly checking my phone, and thus I found myself looking at it for hours every day. Until I had enough. I added a 35-digit password to unlock my phone. This is a huge obstacle! Whenever I’m triggered to look at my phone and see the prompt I usually just give up and put it away again. It’s annoying. And that’s the point. The effect is that I’ve broken habit that I found undesirable. What habits do you have, that are undesirable to you, and how might you interject an obstacle to help break it? 
With much love  

— Mathias

Hello Amazing!
I used to worry about finding the right idea, so that I wouldn’t waste effort on executing the wrong thing. Then I learned that I could minimize the risk of going with the wrong idea by executing really fast (many of my projects were birthed this way). But in my work at SYPartners I’m learning a third path: we pick the best idea that we have (even it it might not be perfect) and then we execute it really really really well. When we show it to our client, new ideas inevitably come up, but it turns out the execution isn’t wasted. A surprisingly large amount of it can be re-used, because it was executed well. I’m trying to apply the same method to my book writing as I’m working with my editor Helen. The book we have agreed to write together right now might not be right. But writing it well will (hopefully) help in the same way.  
With much love  

— Mathias

Hello Amazing!
I am a huge believer in personal projects (this newsletter is my favorite example of one of my own). I’ve gotten a lot of constructive feedback on my work, which has helped me improve the quality. Feedback is seen mostly as a universal good. However, when it comes to personal projects I have also found that feedback can have a significant cost in terms of depressing my motivation, which is the only energy that drives the project forward. For example I recently asked for constructive feedback on my podcast from someone and while their points were all valid, the most immediate effect was that I stopped recording altogether. My motivation was already fragile and I think asking for feedback in that moment was a mistake because it took out the last bit of motivation. I beleive this is a general point when it comes to asking for feedback on your personal projects: no matter how valuable the feedback is it won’t matter if it it kills the energy that moved your project forward. So when someone suggests that you should ask for more feedback, first take stock at your motivation and ask yourself: can I afford the associated loss of motivation or will it kill the project entirely? 
With much love  

— Mathias

Hello Amazing!
The world I live in is always trying to sell me something that promises to make my life more convenient. However, I think there’s wisdom in inconvenience. I’ve noticed that all the things that are really meaningful and important in my life involve lots of inconvenience. From the deliberate act of ironing my own shirts and baking bread (which dictates most of my schedule in my free time) to the raising three kids (with all their eye infections, broken bones and bad dreams) to name just a few of the things I’ve willingly chosen to bring into my life. What are your favorite inconveniences and what have they taught you? 
With much love  

— Mathias

Hello Amazing!
Throughout my life I have had many mentors who have believed in me, supported me, challenged me and inspired me.* From an uncle who was willing to attempt an explanation of molecular structures when I was a very young child, to leaders who have guided me through major life transitions. I am eternally grateful. However, I recently realized that I have also been holding on emotionally to some of the relationships of the past, with a negative attachment. A mix of mourning and guilt related to the way the mentoringrelationship seemed to just gradually fade out. I think this is unnecessary. In Robert Greene’s book Mastery he writes about how it’s inevitable that you will grow apart. Perhaps it’s a good thing.  
With much love  

— Mathias

(*) My mentors, both past and present: Thomas V., Mike J., Klaus M., Jakob L., Annemette U., Carsten W., Rasmus V., Michael K., Susan K., Fabian P., Nico L., Kane S., Nilofer M., Dave G., Tom K., Dev A., Lisa M., Marcus G., Thomas P., Sarah G.

Hello Amazing!
While writing about facilitation and teaching I’ve been interviewing people I admire for their teaching skills. One of them is Mattan Griffel, who currently teaches programming at Columbia Business School. One of his brilliant insights was to give his students challenges that required knowledge that he hadn’t taught yet. Some groups figured it out anyway because they began searching for an answer on their own. And those who didn’t, had at least experienced the problem, so when he introduced the solution later, they understood how it would help them. And either way it builds their stamina for being in the frustration. I think this can be applied far beyond programming. 
With much love  

— Mathias

Hello Amazing!
As an airplane nerd I have been following the recent 737 Max 8 crashes, trying to figure out my own point of view on the tragedies. As details emerged I sketched out this diagram of two interlocking and reinforcing feedback loops, one showing how investing in ever more sophisticated technology makes it more useful, and another showing how more useful technology allows us to delegate more authority to technology. However, as technology gradually gains more authority, and become harder to understand, the invisible risk of fatal failure also gradually increases. 
My point here is not that technology is bad. But I do think it’s useful to be aware of feedback loops that consistently push a system in one direction. ROI is always visible. Risk is not as visible until after it goes wrong. You can apply the same thinking to self-driving cars and the Nasdaq flash crash. 
With much love  

— Mathias

Hello Amazing!
I’m constantly checking myself, maintaining awareness of how I feel in each moment. I find that this is useful in many situations, but not always. When, on a rare occasion, I am having a not-so-great day, this constant attention to myself isn’t helpful, so I’ve been trying instead to think of someone else, and focus on showing up to be helpful to them. I explained all this to a colleague. “Ah!” she said, “You are adulting!” 
I guess that sums it up 🙂 
With much love  

— Mathias

Hello Amazing!
A lot of people have asked my about my teaching practice both at Parsons and in my own workshops. One of my principles, is to avoid relying too much on 1:1 feedback with each student, and instead focus on first building a very safe but also ambitious space amongst the students, where they learn from each other. This can build a self-reinforcing mechanism. That way, once I do give some more direct insight to one person, there’s a chance that these ideas will spread amongst them and be amplified. This idea, and many more of my ideas and principles around facilitation and learning, I’m trying to put together into a coherent whole (aka. a book). If you want to help me by giving feedback on super early book drafts, please share your contact info here. 
With much love  

— Mathias