Leadership Learnings of 2021 

Jakob Reiter
Jakob Reiter, Partner & Head of IT at TheVentury, shares his most valuable #leadership lessons from the past year. Personal, intimate and straight from the heart. Have a read and see if something resonates with you or even inspires you to dig deeper about your own learnings.

2021 was the second year of the COVID-19 pandemic, which means, that we can now look back on two years and start to see the emerging patterns (remember one is never a pattern, you need at least two). Those new patterns force us to change our behaviour and rethink our style of leadership.

Personally, my role at TheVentury changed quite heavily as well. I moved – in my operational role – even further away from programming machines towards working with humans. And before you ask: I love it. That is why I felt the urge over the holidays to reflect and write down the ten most impactful leadership learnings from the past year. And then I thought: why not share them with others to spread the word? So here they are. My main personal learnings from 2021: 

  1. Thinking in times of turbulence
  2. Wholeheartedly listening to people
  3. Reinterpreting discipline
  4. Not knowing is the most intimate
  5. Cultivate pronoia
  6. Do repeat yourself
  7. Engineering serendipity
  8. Everything has it’s time
  9. How you move authority to the information
  10. The most beautiful organ in my body

1. Thinking in times of turbulence 

The greatest danger in times of turbulence is not the turbulence. 
It is to act with yesterday’s logic.  

Peter Drucker

The further along we are into the pandemic the more we see that the rules of the game have changed. Not just with remote/hybrid work but also with how much we value agility and autonomy in an organization. We are starting to see that central planning beyond a certain time span just becomes immoderately clouded and unpredictable. That’s why we need to stay agile and embrace the change.

In the team

For me, that meant that I tried to bring the team closer together in a remote setup and to foster understanding of what is going on. We started a Standup Communication Channel in MS Teams and everyone started posting their standup as they started their day. We came up with this solution, since the time people start their day was varying quite heavily. Programmers generally prefer to start later in the day, whereas project managers prefer a head start. To bring everyone on the same page however we introduced the following topics:

  • Leftover -> Are there things that are unfinished and cause potential problems or delays?
  • Focus -> What will I focus on today, where is my mind?
  • Impediments -> Is there anything that is already blocking me (so we can help each other)?
  • General Mood -> How am I feeling, what is my energy level?
  • Special Answer -> Everyday someone is allowed to prompt a question of their choosing (completely free, often funny, sometimes deep, always different)

This was new thinking. Now everyone was responsible for communicating their needs and updates and in turn, other members were responsible to coordinate with everyone. Through the special questions, we started to learn even more about our colleagues’ hobbies, what everyone’s favourite Harry Potter book is and what dinosaur we identified most with.

In the company

On a company-wide level, we doubled down on OKRs as our leading change tool – with the goal to adjust the organization in quicker iterations. So, every trimester we ask the entire company what they think we should change – basically asking for objectives. Those proposals are then refined by the leadership process and again presented to the entire company.

Now everyone is challenged to propose key results and people are encouraged to take ownership. Those who do will report directly to the CEO who in turn empowers them to influence the KR. This way everyone can get engaged and improve the company. And we have already discovered a lot of blind spots this way that we would otherwise not have spotted.

In summary, I took out of this to start valuing agility even more – may it be in Agile/Scrum/Standups or in OKRs. Empower people around you and make them a part of the journey. Because in this fast-moving environment of times of turbulence, everyone is challenged to make decisions (big or small), and it’s always better if people are aligned.

2. Wholeheartedly listening to people

Chinese characters are one of the oldest systems of writing in the world, dating back almost 5,000 years. There are tens of thousands of characters, each with its own special meaning.  

But the one I got fascinated with this year is the Chinese character for listening: 聽 TING 

And since those characters evolved from pictograms or symbols they are very often composed out of other characters. Much like words are composed of letters, Chinese characters are composed out of other characters with more “primitive” but connected meanings.  
In the case of TING, it can be disassembled into six parts (see if you can spot them):   

–  ěr, means ear 
wáng, means king 
shí, means ten, or also complete 
mù, means eyes  
yī, means one, or undivided 
xīn, means heart 

Now – what do I take out of this as meaning: 

Listening comprises of giving complete and undivided attention, with your ears (what is said), eyes (what you observe), and heart (what you feel) like your counterpart is a king or queen

This means I visualize TING as my mantra going into every meeting, especially 1-on-1s. I remind myself to listen carefully, observe what I see and feel the topics discussed. I feel that this little change in how I approach meetings and my counterparts in them change a lot of tones and vibes within the meeting. People started to mirror that behaviour and meetings that would have otherwise escalated, turned into fruitful discussions.

3. Reinterpreting discipline 

When I heard about discipline I very often thought of hardship, pain, and exhaustion. But this year, a different interpretation opened up for me:

What if discipline just means: I have an agreement with myself to act in a certain way. And by doing so I show respect to the counterpart I have the contract with – which is myself. This means that by practising discipline I am also practising an act of self-love. Of course, if the circumstances change, I can then renegotiate the agreement, but I have to be careful that both sides have an advantage from that – similar to the real world – otherwise, it’s not advisable to change.

This way of looking at discipline has helped me a lot last year. Whenever I had to control time logs or write yet another funding proposal, I reminded myself that I made an agreement with me (and others) to finish on time – to show up on time – to go through with it. The outcome was that I started to be more punctual, honour more deadlines and people noticed it.

4. Not knowing is most intimate 

Here is another leadership lesson that I learned from getting in touch with Zen Philosophy: 

From the Book of Equanimity, Koan Case 20: 

The monk Fayan was going on a pilgrimage.   
Master Dizang asked, “Where are you going?” 
Fayan said, “On a pilgrimage.” 
Dizang inquired, “Why?” 
Fayan responded: “I don’t know.” 
Dizang said, “Ah! Not knowing is most intimate.” 

Not knowing is most intimate? How can not knowing be more intimate than actual knowing?   

What I discovered these last years, is that the answer to this lies in the inquiry and inwards looking view that we take when we don’t know. When we believe we know, then we hurry along, giving halfhearted answers. It is only in the state of not knowing do we really look there and try to see, feel, and experience with an open mind what is missing. We start that journey of discovering way more, way deeper, more honestly what we are truly looking for, why we truly do things, and what truly heals us. And what could be more intimate than that? 

For me, this meant figuring out this year what my next development step is. Am I an IT developer with good management skills, a manager with an IT development background or just a manager – or even just a developer? I was struggling with that question for quite some time but looking inwards showed me the answer: nothing of all that – neither a manager, nor a developer, but something very much on my own. I can’t yet fully put it in words, but I touched upon something that will hopefully blossom fully in 2022 – and it’s going to be spectacular. It will involve leadership, tech but also other parts that I have mostly ignored previously. Let’s see…

5. Cultivate pronoia 

If you don’t know the term pronoia, it’s the opposite of paranoia. Whereas a person suffering from paranoia feels that people or entities are conspiring against them, a person experiencing pronoia feels that the world around them conspires to do them good

Pronoia is also a recurring theme in the 1988 (my birth year) novel “The Alchemist”, by Paulo Coelho. In it, the protagonist, a young boy, is told by an older man to pursue his dreams. He tells the boy: 

“When you want something, all the universe conspires in helping you to achieve it.” 

But this feels too good to be true, right? Well, I made the experience this year that if you focus on the paranoid part of the world, all you will see is the conspiracy and all the hurdles in your way. But if you focus on pronoia you will start to see teamwork and support everywhere. It ties into the learning that what goes around, comes around. 

So last year I really tried to choose pronoia. I reminded myself that every piece of criticism or thing thrown at me was to my own benefit and that the universe wanted to do something good with that. I am not going to lie: It was a difficult challenge, and I am still struggling with it, but I also have to say: I see this working. Coincidences were coming together, opportunities opened, and you start to see the silver lining more often. And maybe it’s just perception, but being constantly open for those good things also seems to shift your creative energy on how to use situations to your advantage. So maybe it’s just that. But for me and for 2022 I want to double down on pronoia.

6. Do repeat yourself

In IT development there is the mantra of “DRY – Don’t Repeat Yourself”. With that, we remind ourselves that if we repeat part of the source code it should be abstracted and not repeated. We do this because we hope that by that we later have a central place to change things in case something happens. We want to reduce redundancy.

But when you transition from working with code to working with humans, “don’t repeat yourself” becomes a real problem. We humans need repetition to learn and understand. If you want to communicate a lot of changes in the organization, it’s not just enough to say it once and then don’t repeat yourself. You must constantly recapitulate the message. Even if you feel like “everyone got it”.

The art of that lies in not just saying the same thing over and over again but planning to repeat the message in different ways. Therefore, if I wanted to communicate a change in role responsibility, I would plan in my head at least 3 different ways to repeat the message:

  • Say it in an announcement – no brainer
  • Repeat the message in the summary with other words
  • Showcase the change in an update session

Or to say it with the DRY analogy: DRY is great for coding, terrible for humans! 

7. Engineering serendipity 

Shaping and building an organization of any kind is hard – especially so if you want to build a modern organization that takes care to prevent a lot of the mistakes of the past. What mistakes you ask? Take this still relevant quote from 2017: 

“…we have put ourselves to work in organizations so badly put together as to militate against our working together effectively. Thus, we have too many layers, undefined cross-functional working relationships, false concepts of leadership, unclear managerial accountability and authority, chaotic compensation systems, phoney performance systems, false notions of capability and its growth, poor career development processes, and on and on. It is these systems that have to be mended. The art is to mend them in such a way as to elicit the behaviours we want in the process.” 

– Dr. Elliott Jaques  

At TheVentury, we realized this year that we needed to build an organism that allows us to support each other and operate in an ever-changing environment. And there are many ways to do so. Frederic Laloux gave a great overview of certain paradigms of structure that we see out there in his book Reinventing Organisations. From the tribal (wolf pack, red) through the traditional (military, amber) and the modern (machine, orange) all the way to the post-modern (family, green) and beyond to teal (self-organizing organism). 

Most of the companies we see around us are currently still in the orange pattern – the machine. But as the saying goes:

If the only mental model you have to work with comes from the industrial age, then everything looks like a factory. 

Especially in our business of fostering innovation and challenging the status quo, the mindset of the factory or machine is sometimes is very detrimental. Therefore, we needed a new thinking model – one that at its best helps us engineer serendipity (the occurrence and development of beneficial events by happy accident). We also need a way to allow us to focus even more on the customers’ needs and adjust ourselves around that. 

What we discovered – unsurprisingly – is that achieving this is very hard. On the one hand, you want to control and measure and on the other hand, you want people to evolve and live out their potential. Letting go of control too much can also be dangerous to a business endeavour or a client project on a tight budget. In the end, we opted for designing certain parts of the company (everything around client projects) in an orange pattern, and the rest (which is the majority) around a green pattern. This means allowing quite a lot of freedom, fostering a learning culture, and introducing a meaningful mentorship model into the mix.

The main leadership takeaway of this was that now more than ever we need to rethink organizations and what they do, how they function, and how, considering all of this, how they are designed by their leadership team. We are all just starting on this journey and there is way more to come! 

8. Everything has it’s time 

You can’t push the River

Random Zen monk 

As you can see, Zen philosophy had quite an impact on my thinking this year. It gave me new ways to think about existing things and challenged me to rethink or better – not think and just live the thing. 

In the case of the quoted “river”, the realization is plain, simple but powerful. Everything needs its time. Nothing can be done before its time has come. And everything flows in its natural way. Don’t even try to push it. You can’t push the river. 

This came to me in so many sales talks that I had. Trying to push the client to make a decision or convincing a partner to cooperate with us, was almost every time in vain. Surely you can signal your willingness to go ahead and push, but if there is no reaction, I learned it’s just not worth forcing it. Because if you succeed by forcing it, there will be another element that will hunt you later. May it be a stakeholder that was not involved, or some information that got lost.

And just to be clear here: This also does not mean giving up too early or letting others control your agenda. It simply means to accept the natural flow of processes and trust that they will lead to an overall good outcome – even though you can maybe sometimes successfully motivate the river.

9. How you move authority to the information. 

One book that I read this year that was very influential was “Turn the ship around” by David Marquet. In the book he describes a principle: 

Don’t move information to authority, move authority to the information. 

You might have heard something like this already. It’s the idea that people should be empowered to be “leader-leaders” (read the book, it’s great) and act on their own. Something an agile organization is striving for.

That idea was familiar to me already and we worked on that at TheVentury quite hard the last few years. However, what came next was even more interesting and is usually left out by many people.  

“Passing on control, we discovered, only works with a competent workforce that understands the organization’s purpose. Hence, as control is divested, both technical competence and organizational clarity need to be strengthened” 

And with that sentence, one of the most important jobs of a “manager” was described. Especially in an Agile Setting which is inherently dynamic and empowers the individual – the general organisational goal becomes a core support function that “management” needs to provide.

Technical competence and organizational clarity

Provide guidance in technical competencies – meaning where, what, and how to do things properly. Education is still the core of what managers can provide and foster. They should provide information on what is needed in the future and what projects or competencies are expected to come in so that people can prepare themselves and the organization for the challenges. For us this was manifested in building up a competence database so we can share, assess, and improve on our technical competencies on all levels may it be IT, growth marketing or innovation management.

The other essential is guidance on organizational clarity. Even if you know how to properly do a thing and are empowered to make a decision, you still need to know in which direction you take the decision. This is where clarity comes in. As a manager you need to provide that service of a clear framework that everyone can actually make the decision – not only theoretically, but also practically. For us, at TheVentury this is clearly embedded in the OKR framework that gives us a clear focus for a trimester or a clear measurement to improve a key result. And then there is also always the yearly overall strategy, our mission, our vision and as ultima ratio even the company values (read about them here).

To summarize, if you want to divest control and give more responsibility to the people around you, you must build up their competence and strengthen organizational clarity so everything can still function properly.

10. The most beautiful organ in my body 

The joke that best starts this lesson goes like this: 

I used to think that the brain was the most wonderful organ in my body. Then I realized who was telling me this.  

– Emo Philips 

For quite a long time I proudly considered myself a “brain person”, meaning I was proud of the knowledge and brainpower I aggregated over the years. I also very much identified with my brain. This came mainly because interacting with my brain was the easiest for me. I could have discussions, thoughts, arguments, and all kinds of interactions with my brain and I am very fluent to understand its language. 

But one day my mindfulness trainer gave me radical feedback: “You are basically a brain on a stick, don’t you think you have a body too!?”.  

This question caused a long inwards journey for me last year. I started to increasingly get more familiar with the other languages of my being – e.g., my heart and my gut – standing for my emotions and my intuition. And just to be clear: I am not saying that they were not there before of course. But nevertheless, my intuition and my feelings for example were always second-grade decision-makers, because they speak a different language. Learning your “entire body‘s language” (this includes the brain of course), was – and is – a demanding work.  

The body’s language

Thus the journey started to listen more to the little itches my body was communicating with, like the fluffy feeling in my gut that my intuition places there to warn me of something I should be suspicious of. Actually, if you think about it, our body’s intelligence has always been the most effective warning system (it would tell us when to eat or drink, when to fight or flight, etc.) and is crucial for our survival as humankind.

The learning that stuck with me here was to embrace myself more wholeheartedly (appreciation pause for the nice wording here).

And this also needs some practice. Some invaluable tools that I found for me: yoga, mindfulness, meditation, long walks in the woods, sports (running, swimming, does not matter), reflection – lots and lots of reflection. Best done with a coach, mentor, therapist, whatever works for you. And if you are sceptical about the last point (as so many still are), think about this: 

If you want to learn a new sport, don’t you seek the support of a coach? It’s still you that must perform all the action, but it helps if someone points to certain things, and makes you aware of them.

Thoughts going forward: Live the questions instead 

So how do I feel about 2021? Grateful and humbled.  

I learned so much last year, and so many people allowed me to have great lessons that I can now take away and spread. To those people I wanna say: Thank you and Namaste – or, the light within me honours the light within you!    

And, to conclude this intense and intimate post, and to state my wishes for 2022 I think there is barely a better way than to do it with a poem from Rainer Maria Rilke that I found last year and that easily became my most beloved: 

Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms or books that are written in a very foreign tongue. Do not now seek the answers, which cannot be given to you, because you would not be able to live them.  
And the point is, to live everything.  
Live the questions instead.  
Perhaps you will then gradually one day, without even noticing it, live into the answer. 

Rainer Maria Rilke 

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