Should anyone ask, on building strong teams

My thinking about building strong teams

My work goal is:

work with smart people,

on interesting problems,

that improve our lives.

So I started thinking about how I like to run teams.

No single contributors

I’ve had smart people on teams that I’ve run. I mean really smart, equipped with deep subject knowledge. These developers that were leagues ahead of others on the team. They wrote close to perfect code. They were also great at working directly with me and terrible at working with the rest of the team.

In one particular case, the individual contributor wasn’t able to, even after my working directly with him and my working with the rest of the team, to integrate.  And even though he was a star contributor, I had to let him go.

Teams are greater than the sum of their parts. It was sad to see him go. But also relieving for other members on the team who felt uncomfortable with the situation. Development work is the antithesis of working on a production like: we crave the interaction, the learning from other experts sitting next to us (and everyone is an expert in something). But someone unable to share their knowledge with others can only last so long in a team, and in this case was risking a team rift and the future of the project.

Developing a craft

None of this development stuff is rocket science. As technologists, we’re excited by the exotic, the new, the big “I deployed 1000 servers in 5 minutes” chest beating. But when you peer behind the curtain and stick around for long enough you notice the same patterns repeating again and again. The exotic was Java, then Ruby, Node, and now it’s Go. All great languages. All accompanied by the familiar aura of newness-hype.

Hype cycles come and go: it’s too easy to jump onto trends. Now it’s microservices. Next week there will be a new hype rocket leaving earth. We like the hype because it’s something to learn and the best people in IT are self-learners. The hyped-newness takes us deeper into our craft. The hype touches our curiosity-gland and new phrases make it sound exotic.

I’m not dissing container technology or a microservice approach, I am pointing out that there are always new trends on the technology event-horizon. We flirt with them (full disclaimer: I’m a huge new technology flirt). We kick the tires, try out a deployment or project with them.

A good team solves problems with great code and suns a smooth service. But our attraction to the new can blinker our vision: we serve our users not our tools and technology. Our users want solutions to their problems: “excite my ears with your streaming music” and “keep me happy with a mobile app that starts quickly”. That mobile app starts quickly because we were careful choosing our technology: sifting the value from the hype.

In the business world we see a similar things happening: insourcing is the new nearsourcing that once was outsourcing. Trends come and go.

When thinking about which trends to ride I imagine the selection to be somewhat similar to a hobo hopping trains to reach a destination. Hop the wrong train and your next stop is 80 miles down the track in the wrong direction. The observant hobo will discern which trains head out in the right direction and ride them until they veer off course.

So when we start feeling that our work is rocket science, it’s usually a sign to refocus and remember that even rocket scientists are practising a craft. And while we aren’t returning astronauts safely back to the earth, we are solving problems for our users who frankly don’t give a damn about tech hype.

I’m very much in favour of experimenting with the hyped-newness: it’s how we learn our craft, it’s how we experiment with new tools, and how we decide which technology trains to hop.


admire people who ask genuine questions about non-hyped technology stacks.

avoid people who claim their work is rocket science (unless they work at SpaceX) and therefore none of the existing tools will work.

Don’t make decisions, Then dive in.

I have a decision making system “gut-data-gut”:

What does my gut say about this?

What does my analytical/numerical side say (think: pro/con lists)?

What does my gut say after putting the gut and the data lists together?

Sometimes it takes a while to get a good/bad feeling about a decision. For example, imagine we’re a team thinking about what container system to use. This is a big decision that will impact the entire team. And yet, unless someone on the team has extensive experience, we need to hold off committing to something big until we can build up a strong team consensus.

But not making a decision will also slow us down. Or will it? Usually there’s another way: delay the decision until you really have all the gut-data, and the data-data. This sounds like a cop-out but if I can explain: In our example, not knowing what container format to use we can’t progress.

It turns out that this decision can be delayed while we look at some of the tooling options available for orchestrating the containers. And the decision can be delayed even further while we start building our new tooling (assuming that the orchestration system supports the different container types). All these other tasks touch on our container format decision and help to indirectly inform us.

Now we have our data-data and our gut-data and can make a strong decision and progress.

Humans: no API included

There’s a thousand books about running teams and setting goals each explaining a different way to work with people.

Mine’s pretty simple: be nice to eachother and good things will happen. Be nice means listening, questioning and treating each other’s egos with care / remembering that we all have insecurities. Shifting slightly to the right of the Kumbaya campfire, teams need to get stuff done: solving problems.

And that’s precisely how I like to run a team: frame the problem. When we know what the problem to be solved is, our engineering minds naturally start working toward a solution. The trick is asking the right question to discover the real problem. Using the previous example: is the real problem which container solution to use or is the real problem how to run a smooth service?

Without getting too meta, good teams come from hiring people smarter than myself. Usually much more so! Some of my best teams have been where I’ve felt like the stupidest person in the room. And yet I’ve felt valued because I had other skills to contribute. I wouldn’t be the deepest in the tech stack. I would feel comfortable that others knew what they were doing there. But I was able to clear the path so that the team could get stuff done without the organisation getting in the way. Some might call this managing up the organisation. And since the team knows what the problem is, they can now solve it without the weight of an organisation slowing them down.

This example of being the stupidest on the team (sure there’s a nicer way to say this but let’s press on), also illustrates the need for diversity in a team. There’s always going to be stronger candidates. And weaker candidates. But each has their role: I’ve seen strong candidates mentoring newer candidates. And I’ve seen newer candidates digging into documentation and meticulously fixing examples that would be missed by a flag-waving strong candidate. The trick is to develop a mutual respect in the team for everyone’s skills.

Should anyone ask, hiring a virtual assistant.

A few weeks ago I was hitting the admin wall: many small tasks that needed doing. Many small tasks that were turning into mountains. Many small tasks that were taking up space in my brain.

I admitted to myself:

  • I’m not good at this. 
  • I don’t need to be good at this. 
  • I don’t aspire to be good at this.
  • This has to be done.
  • I can hire someone to help me who will be excellent at this!

To solve this problem I started looking for a virtual assistant on Upwork.


I needed someone that could also help me while working both in English and in German. I received 5 applications from as far afield as Vancouver and Australia. One Applicant was Elisabeth. From Berlin too!


I dislike personnel administration: time zone differences from working with far off places would mean I’d be also sacrificing my nights to the beast. Vancouver and Australia were out and I hired Elisabeth. Having someone in Berlin with the option to potentially meetup seemed like a good option. I went ahead and arranged an initial Google Hangout call with Elisabeth. 

While I was waiting for the hangout call, I setup a Trello board and started dumping all my admin tasks onto a to-do list. And basked in the warm GTD feeling of getting things out of my head and onto a list.

This week started with my first session with Elisabeth. 9am and a strong coffee and knowing that I had support were powerful motivators for getting into the office! We powered through the tasks together: she doing some of them, me the rest: it was so much easier working this way. Yes, it took two hours, but that was a lot of build-up. I expect the next session to be about 30 minutes.

Without thinking too much about where this fear/hate/loathing of admin tasks comes from, I feel much better for knowing that a bunch of them are done. 

Perhaps not perfectly. But done!

Steps to slaying your own personal admin monster

Wanna do the same? Here’s the “I hate admin” summary plan if you want to setup a system like mine:

  • Create a task: Sign up to Upwork, create a task and estimate about how much time you will need from your assistant. On Upwork you can elect to pay hourly or by task. It seems only fair that for such a variable task to use hourly.
  • Find an applicant: Post your task and wait. I waited about 24 hours to get some applications. I also chatted with the applicants to find a good fit.
  • Hire your applicant: Simply hit the Hire button. This will let the other applicants know that, as nice as they are, you don’t need their services.
  • Setup an initial call: I wanted to get to know Elisabeth before working with her. Before setting up recurring events see if you can work well during one session.
  • Create a Trello Board: You could also use a shared email inbox. You could use an issue track. But both of you need to be able to action tasks: Trello works well for this.
  • Out of the brain-onto Trello: Create a Trello mail-in-email address so that you can forward tasks/bills/scary-emails from your inbox directly to the Trello board (and forget about them until the call).
  • Add the address to your contacts. I have a new contact called “Orga”. New tasks are emailed to Orga and land on my Trello board. 
  • The initial call: During the initial call talk about what you want to achieve.
  • Invite your applicant to the Trello board. We looked through the tasks and started nailing them.
  • Setup a recurring calendar event:  I waited until after the first session to decide on whether the new assistant was someone I felt comfortable committing to. Elisabeth was great and so we setup a call for every two weeks and dropped a reminder into the calendar.
  • Rinse-repeat: Keep dropping tasks onto Trello. Keep forgetting about Admin tasks until once a fortnight when you get a reminder for a call.

Do great things without admin hanging over you!

Should anyone ask, about rock climbing

I’m petrified of heights. I love rock climbing.

Being on the climbing wall wakes up primal fears. All I can focus on is staying on the wall. No work thoughts. No relationship thoughts. Just facing one fear. Slowly working up the wall to the top.

Climbing routes are marked out with a difficulty. For example one of the routes I climbed yesterday, marked as a 5+ difficulty, meant that I was only using the purple grips. The routes are cleverly designed: there’s always a way to the top. The routes gets increasingly more difficult as the numbers rise.

The grips on the wall are placed so that you’re solving a puzzle with a combination of two hands, two feet and your body weight. Half way up I’ll hit a patch that looks like there is no way forward. The grips above me are too high and the grip that I’m standing on is awkwardly placed. I’ll try and reach for the grip in front but it’s too far and I risk falling. Then I discover the grip I’d overlooked by my right foot because it’s out to the side. By shifting my weight to a new foothold I can better reach the grips above my head and suddenly a new route opens up and I can progress higher on the wall. 

Climbing shows us how different perspectives on a problem impact how we feel about it and solve it. For example, when watching a partner climb, we have a very different perspective and feeling. 

Perspective-wise, we can see a different route up the wall from our firmly-on-the-ground viewpoint. Feeling-wise, it’s easy to suggest “just reach for it” from below. And yet this is so different to being on the wall yourself. 

From below you see a different route up: different because you can see different footholds or grips that they can’t see. Different because your vision isn’t clouded by fear or the pain in your arms when getting around an overhang.

Hearing “there’s a grip to your left that might help” is useful. Being able to jump over our fear of falling in case we can’t reach the grip is hard. And needing to trust our climbing partner to be securing well in case of a fall, even harder.

Another thing I like about rock climbing: it teaches me the value of taking a break. Apart from good upper body strength, I imagine good climbers are intimately acquainted with their their own limits: how far they can reach, how long they can hang on in overhang or how long they can remain stretched out before the next push. Good climbers know when to take a break, when to hang on the wall with all your weight on the rope, resting the arms, recharging (and re-chalking). I’m not good at taking breaks. On the wall or in life. This year I have taken one week off (and stayed in the city). It’s a lousy way to progress and I’m not proud of it. I have a lovely break planned for the end of the year. If I can get there without falling from the wall. I’d like to change this approach in 2016. Know that I will need breaks and pre-plan them into the work year.

As a child I loved climbing trees. But I also had a healthy respect for the heights. Rock climbing reminds me of this flirting with fear and I love the “fear focus” that blocks out all the “brain noise” as you reach for the next grip.

If you are in Berlin and fancy learning, I think I’m a pretty good teacher.


Should anyone ask, now with 1% more gratitude.

I was 19 years old and walking from my London apartment on Gunterstone Road to Hyde Park. It was a sunny Saturday, there were many people on Kensington High Street. I had finished high school, was working at a publishing company during my gap year, and that day, walking along and thinking about how I wanted my future life to be (yes, even back then I was a personal-development geek). Living in a big city like London was something new to me. After growing up in a small suburb in South Africa, London was different. Very different.

In trying to make sense of these differences, I remember being concerned that the lowest common denominator seemed to win out in many city planning decisions. Looking around me I’d notice that the city didn’t work perfectly. Lights weren’t perfectly synchronised. Sometimes trains ran late. It seemed to me like things could be better, but good enough sufficed.

I’d grown up with the idea that “the UK was first-world and therefore got everything right, South Africa was third world and was imperfect”. This magical far off country wasn’t struggling with the violence, poverty and racial divide of South Africa. This tinted view was serenely delivered to darkest Africa on Sunday evenings via a radio in my father’s woodworking shop. Anthony Lejourn’s London Letter would paint a wistful picture of the perfect life in the “motherland” as my father showed me how to build things from wood. 

I was trying to make sense of my relationship with London: why was it that things didn’t work perfectly, especially if this was the perfect city? This was also the stage in my life where I’d put a new girlfriend on a pedestal and admire her perfection until friction exposed imperfection.

Today I can look back at that time and realise that labelling anything perfect, be it the admired girlfriend on the pedestal or the first world city, dooms me to disappointment. There is always a chink in the armour, always the moment when, perfect vanishes never to return. That moment when perfect is closer to really nice. I live in Berlin now. It’s really nice. Certainly not perfect. But right for the moment.

And so to the idea of gratitude: I’m asking myself why I’ve never been a fan of the gratitude. My gut immediately feels like it’s fake. I can see the value, but in the back of my mind there’s been a “yes, but”. The subtext being “Yes you can be grateful for that, but don’t you see this problem” or expanded even more “…but don’t you see the imperfection in that corner”. It’s a heavy load to carry.

And yet this is the same “she’s perfect”, “London’s perfect” thinking that never worked out in the past. The power to be grateful for the really nice or even the imperfect is a very powerful skill and echoes the vibrant positive personalities I see in many of my happiest friends.

Gratitude exercises can feel like checking off a list. Yeah, health, no war, warm clothes, roof above the head. Grateful, grateful, grateful, check check. And now? It sometimes feels like lowering my standards. Like not striving anymore. No more perfection. Here’s your mediocre served under a dry roof. And so we’re back to the perfect becoming the enemy of the really nice. And that didn’t work out so well in the past.

I have much to be grateful for. There are chinks of imperfection. And some chunks of major imperfection.

But my life is good. And should anyone ask, this is me dipping my toe in the gratitude waters: 

I’m grateful for the people and memories that have come into my life. And for the moments when I can smile. (Like this photo from back then. Boy I was young! And happy.)

Should anyone ask, if I did this again

This is a post for future-Simon.

Background: Admin kills me. It absolutely hammers me into the ground. I hate it, I don’t value it and it torments me until I find a way to get it done. So much hate. Server admin - love. ActualReality™ - not so much love.

Running your own company ramps up the admin immensely. Accounts, paying people (love that I can, hate the process), taxes, random paperwork. It’s horrible. 

This morning while cycling to work conversation went something like this: “Do you think $hero has to do this?” 

Answer: “No he has someone do it for him”.

Wow. I like that.

This is a note to future-Simon:

  • You don’t have to be good at this.
  • You can outsource it easily.
  • Outsourcing looks like “Make a checklist. Pay someone to work through the checklist once a month with you”
  • When $item arrives, put it on the stack and forget about it.
  • Hold the stack until the 3rd or 4th of the month (sometime not too early to miss end-of-month invoices, but early enough to make sure you get everyone paid nicely on time)
  • Have them work through the list with you.
  • Put this as a monthly, repeating calendar appointment so it just happens. 


  • Worry less about the things you don’t enjoy
  • Become better at asking for help
  • “Some people actually enjoy this stuff”
  • Live longer with less stress

That sounds pretty good to me.


Should anyone ask, reading about ABCs

Imagine some blind people describing an elephant. One might suggest that it feels like a tree. Another holding the tail would suggest it’s like rope. Each has a different perspective. And although they are all touching the elephant they end up arguing over whose perspective of the situation is correct.

This week I’m thinking about other ways of viewing thoughts. Too often I am not taking the time to be curious about the other person’s perspective or putting myself in other peoples’ shoes and getting their picture is a valuable exercise.

In cognitive therapy there’s the idea of ABCs: an Activating event, a Belief, and negative emotional Consequences. 

This ends up distorting our thinking and I know that I’m guilty of slotting events into categories based on beliefs that don’t serve me well. Some that I could think of as

  1. Black-and-White - Thinking or either / or thinking.
  2. Making Unfair Comparisons – usually in the negative
  3. Filtering – honing in on the negative, forgetting the positive.
  4. Personalizing - The Self-Blame Game
  5. Mind-Reading – thinking we know what others think (negatively)
  6. Catastrophising – imagining the worst case scenario
  7. Overgeneralising – “I always mess up…”
  8. Confusing Fact with Feeling – “If I think or feel this way then my thoughts/feelings must be correct’.
  9. Labelling – I’m  a loser vs. I made a mistake.
  10. “Can’t Standitis” – being unnecessarily intolerant

My theory on solving this is to change my inner voice. I heard someone describe it as “If we talked to our friends the way we talk to ourselves we wouldn’t have any good friends.”

Some of the through grooves in our brains are deeply worn. Noticing that some thoughts that aren’t so helpful for me, I’d like to work on developing more cognitive flexibility, more diversity in how I think and being more aware of when I’m falling into old thought patterns.

I think this should be possible by reducing the rushing, being more consequent and dare I say it, mindful (seems like it’s the phrase of the year).


Should anyone ask, interuptions

I recently received a replacement phone and have been systematically going through and disabling every single notification that vibrates or makes a sound.

It makes me feel like I’m clawing back some control over the interruptions that divert my attention. And sure it might only last for a second, but I come back to my mental bandwidth thinking: we only have so much time per day to think and communicate. An interruption that pulls me away from what I’m focusing on is the same as someone calling me. It takes a while to get back into the thought I was having. And I’d like my thoughts to be higher quality than interrupt driven “A friend of your’s in San Francisco checked into a place you don’t even know”.

And still they keep coming… just when I think I’ve found all apps that interrupt me there’s a new one.

I’ve also been taming Facebook: friend’s from pre-primary school are now unfollowed. “Friends” are unfollowed. Friends are followed. And that feels good.

Should anyone ask, I ran

I ran this morning. It was good.

Yesterday evening I chatted with a friend. She helped me put things into perspective. Perspective helps. There’s the Churchill quote (not exact) “when you walk through the valley of darkness, keep walking”. But knowing that you are in a valley with an ends helps. Moving forward always helps me.

I’ve been a big fan of Mixergy. Today I’m listening to Andrew Warner’s discussion about creating a mastermind group. And the power of turning over problems verbally as a way of getting stuff out of the countermind.

I tried creating a mastermind group when I lived in Munich. But after listening to this interview, good mastermind groups are made of up people who are at the same level. I’d like to create a new group. Some takeaways from the interview are:

  • meet every fortnight
  • meet for 90 minutes on a Hangout / in person doesn’t matter and commute time destroys productivity.
  • start with an inspiring quote.
  • then 10 minutes of general chit-chat.
  • jump into updates
  • two modes of feedback requesting: “gloves off” or “just feedback please”
  • set individual goals for the next meeting
  • A mastermind group needs a group leader to keep things on track.
  • The phrase “you are saying one thing, but your body language is saying something else” can help dig into things.

So I’d like to start a mastermind group with people working on SAAS products. Reach me on to see if you would be a good fit.


Should anyone ask, everything is a mountain.

What do you when you’re at work sitting in front of a computer trying and failing to concentrate on the code in front of you?

When even the most straightforward requirements seem like an impenetrable nests of complications and edge cases to your tired mind?

I find myself just staring into my computer, for hours. No movement, just staring.

11 weeks to go until the Christmas break.

At the same time I’m working on something that could potentially be really exciting and have a huge impact. But just want to walk away and curl up in a ball. And just want to go away next week. But I have no idea where to. Or who with. Or if I can justify it. Or even deal with the planning mountain.

Tomorrow I’m supposed to be excited and giving a talk in Hamburg. I want to stay in bed. 


  • Morning running. I need to get this back on track. Signed up for the Berlin half marathon in April.
  • Consulting. Feel better about finances. No point in worrying about this if I can fix it.
  • Ask for help. I have lovely friends. I have a hard time asking for help.
  • Connect with friends. Past depressions have been my mind overheating: stuck in a loop looking for an answer that isn’t there for the finding. 
  • Rock climbing. I want to start this again. I like it because of the intensity. I can’t think of anything else when I’m on the wall. And it’s nice to just think about one thing at a time. 

Should anyone ask, strategy

My thinking can often drift off into the details. A strategy talk will quickly become me latching onto a small problem and the conversation or thinking process stops being big picture. To avoid this I try to think through problems with someone. The process of talking about something, putting words to vague feeling and being nudged forward with good questions helps me create a plan of action.

Strategy builds on our fundamental beliefs: Jack Walsh is known for his “people first, strategy and everything else second”. I liked that. I believe that when you surround yourself with the right people, things can more easily fall into place and work becomes fun. I’ve been on both sides of this. Working with great people where the work flows. And working with people where I’ve been reincarnated as Sisyphus.

But knowing yourself isn’t always easy. We feel our fundamental beliefs but need to put them into words and communicate them. I find that hard. Recently I had the situation where I had to make a difficult decision. I ended up using a rather interesting decision making approach: gut, data, gut. “there’s no perfect data” and “there’s no perfect intuition”. The data looked great. The gut kinda looked good. But something was nagging me. And I walked away from the deal. I’ll never know if it was right or wrong. But had to trust my instinct. At a younger age, I’d probably have jumped in.

Summary: trying to know myself, and my weaknesses helps build a stronger strategy.


Should anyone ask, belief/optimism

I like being around people who believe. I find their optimism about an imagined better future because of what they are building is a huge motivator for me.

Optimism is power. I imagine some of the worst hardships - solitary confinement: optimistic people tend to succeed because they believe that everything will turn out right and the expectation of success makes them work harder. Great leaders also have an unusual ability to face up to stark reality, so creating a single powerful attribute: tough-minded optimism.

Should anyone ask, Passion

Should anyone ask, how does one sustain passion in work or in a relationship beyond the initial flurry of hormones beyond the initial excitement over a new project or relationship?

For me it’s about finding something that resonates with who I am. Then there’s the whole concept of finding out who I am discovering what works and what doesn’t work for me. But if I look back on times when I’ve been most engrossed in a project (I’d argue I was passionate about it), they were times when I was using all my skills to the right level. The “flow state” / “being in the zone” is when I feel  fully immersed and have amazing focus. Everything else blurs away.

This works because the project matches me. My skills are matching it. This is when the passion happens.

For me the passion is tested when a project hits hardships. How I deal with non-flow stuff/junk/bs is the true test of whether something is a work fling or a durable passion. It’s never going to be all easy. But being passionate about what I do carries me through and work becomes fun. And I can be myself.

And I really like that.


Should anyone ask, choose your own adventure

There is no rulebook.

No Celestial Compendium of Benevolent Knowledge.

There’s many a 10 step programme. An infinite supply of advisors. And our parents.

Ultimately we all want happiness. A steady stream of dopamine, oxytocin, serotonin and endorphins. Not too much all the time. Not too little ever.

How we get the right amount at the right rate is down to how we create our own rulebook. Get up. Make the bed. Shower. Eat healthy food. Be nice.

I once tried to write my life manifesto. And indeed still have a monthly “manifesto review” for the first Sunday of every month. In 2008 I read about 60 self-help books. And summarised the main points in each of them. From this I noticed that successful people have the following characteristics:

  • Passion
  • Belief
  • Strategy
  • Communication skills
  • Working hard
  • Being disciplined/creating good habits.

The other thing that came out of this was about belief in oneself: believe about yourself what you would like others to believe about you. The manifesto work was to make sure I was actively working on those 6 areas.

The other part was that there is a big gap between the knowledge or capacity and the acting on it. Be proactive.

In the next few posts I’ll dive into each of those areas.


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Should anyone ask, on building strong teams

My thinking about building strong teams My work goal is: work with smart people, on interesting problems, that improve our lives. So I start...