Insights from a mob learning Leadership meet-up

Recently I initiated a Leadership meet up in the Christchurch (NZ) area  and we had our first meet up couple of meetings ago. This meet up bore from my frustrations around not having a peer network of folks who want to get better at Leadership . Whether we consciously acknowledge or not , Leadership/Management has a tremendous impact on our work lives. And as with any other skill set if Leadership and Organisational management is exercised well, it can have such a positive influence on our peers, us and the wider community. So why not get better at it ?

Here are my summary notes on how the first meet-up went and things that I learnt from it
Format :: Mob-Learning “unconference” style

The format of the meet up was inspired from “Unconference”/Lean-Coffee and the central theme was that every participant brings atleast 1 Leadership/Management insight to share (“How did I achieve <x>”)  and atleast 1 Leadership/Management insight that they seek (“How can I solve <y>”) .

Everyone then pooled their insights (to share and seek) onto a whiteboard

And then we went around the group with each of the participants sharing what they achieved and what they seek guidance on ?

Simple !

A lean way to share your learning and harness mob wisdom

Insights from the “How did I ….?” theme

1. How did I gain respect as a Leader of a challenging group ?

One of the participants (before joining the IT domain) were a Team Leader in the concreting industry . The culture there was one of “us and them,them i.e. the management” . Engagement and well being of the staff was a major concern as there was lot of temp staff and attrition rate was high.

What this participant did to gain his Team’s trust was

  • Be hands on …walk the talk and get their hands dirty along with their staff
  • Empathize and connect informally ( not be the Boss) and “getting into their world” to relate with their problems

The key insight for me here was that the Leadership style ( one of many) that works in this kind of scenario is the (often cliched) lead by example style , where the Leader needs to prove her worth and be one of the Team to gain their trust .

2.  How did I support an Intern to re architecture all our Automated Checks ?

This participant shared a story around moving all their Team’s automated checks from running on local hardware to AWS. They lead this initiative , formed a student project out of it and supported an Uni grad to deliver it.

Here is how they did it

  • Get key stakeholders’ feedback and buy in … go around and understand the pain the consumers of your automated checks experience  and what they would like improved ?
  • Regularly check in with junior members and beginners. If they are not asking for help , does not mean that they do not need help or sometimes they dont even realize that they need help.
3.  How did my Team trail features in a controlled manner with our end-users ?

This story was from a Tester who work with a Kiwi household name in the Electronic appliances store space.

Their Team have been successfully trailing new application features for their in-store staff and here is what they shared about the process’ success

  • Be there in person to support,receive feedback and observe the in-store staff  using the new feature
  • Be there in person to manage their expectations on the use and scope of the new feature
  • Collate feedback and get together as a Team back at base to process it and shape upcoming features/enhancements
4.  How to identify an unhealthy company culture and apply those lessons in a new environment

Another fellow leader shared her experiences from working in a culture of blame , things they learnt and how is it helping them in their current organisation

  • Self reflect continuously , to assess whether the current culture is healthy or not ?
  • Seek support from peers in bringing issues out in the open
  • Dont put up with unhealthy culture,seek change
5. How to remember that as a Leader you are not a “know it all”

The last “how did I ” micro-talk was from one of the People Leaders who were leading a Team of professionals who were really senior from then. Their key challenge leading such a Team ,was dealing with a sense of pressure to be always in a position to have all the answers for their Team ,especially for the senior members

How did they do about dealing with that pressure

  • Openly put up your hand and admit that you dont have the answer
  • Never wing it !
  • Use the simple technique of “Can I get back to you on that?” and resist the urge to have the answers there and then
  • Dont feel ashamed of your vulnerability

Insights from the “How CAN I ….?” theme

Now the meet-up moved towards discourses to discuss the problem statements that participants had pooled in .

  1. How can I add value towards Team and company culture in a company that is still it’s infancy

    The backstory here was that the participant had just won a start-up event and formed a company ( with a winning business idea) as a result of that event . However they had not worked worked with any of the co-founders. So, their query was around how could build the kind of culture that they want without knowing anything about the co-founders working style & mindset .

Here was some of the solutions that the group offered

  • Build empathy using tools like “journey lines
  • Form a charter with your co-founders on what the company’s value system would look like ? Which behaviors would be encouraged/rewarded and which ones not so much . Achieve consensus on that charter
  • The litmus test of your company culture will be how you work through disagreements with your co-founders
  • What triumphs…. values or revenue ? These precedents are crucial in building a company culture
2. How can Leadership work in the DevOps space ?

The question came from a participant whose organisation were moving all their product Teams towards adopting the DevOps model . However current situation reflected limited success in adoption of the model and Teams were not sure whether they were going in right direction or not ? They were wondering how could Leadership be exercised in such a situation

Here is the wisdom that the group shared

  • Consider it less a DevOps problems but more a generic change management problem
  • Create objectivity around what Management wants to achieve from adopting of the DevOps model …..specifically what does DevOps’ adoption, it’s success  look like to them ?
  • Ensure that the Teams are communicated the above and build metrics around those success criteria
3. How can I create a balance between giving my time to those in need in the Team versus delivering on my own commitments  

This is a classic scenario around balancing your needs(not getting disrupted/derailed from current commitments) with selflessly helping/mentoring others.

The group’s suggestions were

  • Disruption is inevitable , you need tactics to manage them . Try not to jump immediately to help them , agree on a time later in the day if the need is not immediate
  • Use hand gestures ( if you got headphones on) to respectfully indicate that you will get back to them
  • Preempt disruption , by being in their physical vicinity to indicate that you are in for a check in ( and that you have time now) and see if they want your help or have any burning questions at that point

That’s it , I found it a very valuable session for a new experimental format

Already looking forward to more !


Want to Lead by example ? …. be “emotionally nimble”

The best Leadership experience comes from working for average Leaders

This experience is a close runner-up to, working for great Leaders

Fortunately I have had the experience with both kinds

The single biggest trait I have experienced in great Leaders is that they “lead by example”

I know that you are rolling your eyes now because this is such a girnormous cliche in Leadership folklore

But let me please put a twirl to it …

Leading by example is NOT

  •  walking on a bed of burning charcoals to single-handedly solve technical, business and strategic problems
  • or being perceived as the goto demigod expert who holds the key to delivering complex projects through chaos

It is rather simple and non-heroic and manifests itself as

someone, who ,  in the face of adversity and in the face of their own blunders , time and time again, demonstrates “emotional nimbleness”

“Emotional nimbleness” is defined as …

  1. Constant self reflection of your public and private organisational conduct
  2. Openly admitting and articulating your shortcomings and mistakes
  3. And then sweating on the minute details and emotional nuances , to demonstrate  measurable improvement in your organisational conduct and outcomes
  4. Doing all of 1-3 above before holding others accountable.

Leaders who don’t have or cultivate or grow , emotional nimbleness

,will often, be stuck in the bog of

  • Amplifying people’s shortcomings more than achievements( putting a facade of “the hard to please boss”, often resulting in distancing non-binary personalities (personality types very common in the Tech space)).
  • Falling back on lack of time or their personality type , as an excuse not to change their mindset/behavior
  • Blaming individuals for their lack of engagement rather than reflecting on whether they themselves have the skills to intrinsically motivate others ?
  • Not setting demonstrateable goals & measures on how are they holding themselves accountable

Smart leaders , are much more nimble,they have adaptive people and emotional skills with a cornerstone in brutal self reflection. They focuses on changing themselves and others’ working environments before trying to change the people in those environments

How to stay “emotionally nimble” ?

Here are some tactics and practices that I have been religiously employing over the past few years , to keep myself emotionally nimble

  • Make ,looking after your spiritual personality ,the same priority as your physical and business personality. Join a meet up , get a life coach or self learn using an app ( but make sure you put in a lot of proverbial blood and sweat into improving your spiritual side.
  • Demonstrate a linkage of a change in your behavior/mind set with a self reflection and learning incident . Maintain a public company blog to articulate how & what you learnt from your mistakes or use staff meetings  to broadcast what have you have actually done to not repeat your mistake(s). What ever the medium but you must ensure that you show demonstrable actions as a result of your self reflection . “Emotional nimbleness” is just MBA talk with out demonstrable and measurable change in you.
  • Have a framework to reflect and learn  . I use a simple checklist, that I go through mentally every day
a) Today,did I learn something new ?
b) Today,did I behave in a way that was not consistent with what I claim to be ?
c) Tomorrow, which are those 2 things that I will do to not repeat b) and ensure that answer to a) is yes

Stay nimble , stay leading from the front




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Don’t just be a “people person”, be a “people nerd”


Via Wikipedia – Nerd (adjective: nerdy) is a descriptive term, often used pejoratively, indicating a person that is overly intellectual, obsessive, or lacking social skills. Such a person may spend inordinate amounts of time on unpopular, little known, or non-mainstream activities, which are generally either highly technical, abstract, or relating to topics of fiction or fantasy, to the exclusion of more mainstream activities.

Mrs JJ Gill was my favorite middle school teacher and of the class’ too.

She was a nerd, not a stereotypical one (in appearance or in practice of her subject) but due to her obsession, attention to detail and extraordinary drive to understand her students. The drive was not just to connect with us, but to genuinely reach out to us with compassion, to learn –

  • What scared us ?
  • What confused us ?
  • Why were we sad that morning ?
  • Why did we withdrew from the singing competition at the last minute?
  • What did we do over the summer vacation ?
  • Why is our mum unwell ?
  • What are the frictional dynamics between the toppers of the class?
  • Why do the back benchers find it really hard to step up?
  • Why did we bunk classes and returned drunk to class ?

This drive was disproportionately large as compared to other teachers and manifested consistently in her actions. While other teachers focused on the bustle of achievements, exams and marks, Mrs. Gill’s focus was ‘us’.

Not that she was the most kind, congenial, friendly person (she was viciously candid when she used to give us feedback).Not that she was the most charismatic and influential teacher teaching the most critical subject ( she was an English Literature teacher).Not that she favored us unduly.

She just used to put in so much effort to “get” us.

In her nerdiness,she made us the center point of her teaching, rather than the books or the school reputation or grades.

Some folks are data visualization nerds, some are violent South Korean movies nerd, some are Indus valley civilization history nerds.

I am a people nerd

I am extremely curious about how people behave in organisations, how organisations influence their lives, how are they different from when they are in leadership positions versus at home,how do they react to authority,why do they shy away from taking initiative.

I work with discipline to study people’s achievements, what does success mean to them, what kind of work stokes their imagination, what kind of behavior stokes their fear, how do they like to be recognized, how my behavior affects them, why they shoot down my every idea,how do they negotiate, how do they put up resistance, why do they complain incessantly, how to influence them, why do they bitch behind their colleagues backs,why do they dont say good morning to everyone when they start….and so on …

People skills are useful but effective Leadership is not just limited to being nice and humorous or having the ability to get along with stakeholders or having a communal reputation of a leader.

It is the nerdiness of wanting to study people, wanting to understand people and putting them at the center of your sense of purpose and service.

This nerdiness is the nucleus of creating empathy and forging trust through people leadership. This nerdiness is what creates a sense of integrity about your leadership and travels much farther than charisma or people skills.

Someone asked Mrs Gill , as to why did she care about her students so much ?

Her answer….”I just like to”

Now that is a nerdy answer !


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A metric for the new year :: “Managing the boss” time

Does any organisation track this metric ?

Most likely not , primarily because we have almost given up on this being a norm.

As something that comes as part of being in the political cesspool of corporate organisations

As something that being in management roles brings, the unwritten charter of “getting things done around here”

You can not come wearing a Samurai armour to a Turkish bath……cry the conformists

But this mode of ,upwards management as a default, must be decried

In 2017 start tracking the time spent just on managing your boss.

On massaging their ego,

On working through their constant cynicism,

On feeding their biases to get the just outcome

On helping them cross the line

Now put that time against the time not spent

On making Team processes betters

On improving working conditions in the factory

On enhancing customer experience by paying off technical debt

On self-reflection and spiritual replenishment

How do we change this ?

Bosses must,

Start looking for reasons to say Yes more than No,

Start experimenting and embracing failures

Start harnessing their vulnerability instead of being ashamed of it (

Start seeking integrity feedback ( Ratio of …number of times your Team believes that you took a decision aligned with your touted values Vs. number of times you believe that you took a decision aligned with your touted values)

Start realizing that coaching does not necessarily have to come from someone more experienced and senior to you.
You must,

Stop feeding the monster, you are part responsible for making your boss a better leader ,take that oppurtunity

Stop reconciling that this is the only way to grow in this organisation

Stop having a parallel value system just to manage your relationship with your boss  (you are rendering the relationship flimsy rather than robust)

Stop not tracking this metric and stop not showing the ill-affects of managing your Boss to your Boss

The corporate world will be a better place, if we start and let be coached upwards rather than be managed upwards

Branding risks as personal impact, lessons in coaching # 2

Getting folks to pay heed to risks in time , is hard


I recently finished a coaching gig with a leading agriculture industry org here in Christchurch. My key responsibility was to coach their internal Test Lead to ,

a) frame a Test strategy for their multi year change management programme

b) provide on going coaching service as the strategy is delivered for initial phases of the programme.

The coachee were an extremely talented and knowledgeable business user and from an engineering+lab testing background , but were new to enterprise software Test management.

Yesterday, I had a catch up with them several weeks after I had finished the engagement . The focus of the discussion was on their experience of Test management so far and how could we as a “test strategy” Team have done better?

One of the things that they raised in the retro really captured my attention as something that I need to personally improve, here is how the conversation went

Coachee :: “Looking back at my first Test management project, one of the things I really I wish I could do better was to persistently advocate risks”

Coach :: “Fair point . However we did have a process to register all programme and project related risks in the risk register and had a process to discuss/escalate them on a regular basis . Didn’t that process work?”

Coachee :: ” Umm,the process was there  but I did not advocate testing risks as often I should have ”

Coach :: “Why was that ?”

Coachee :: “Because they were project related risks and part of the PM’s realm of responsibility”

Coach :: “Let us re-frame that….they are testing related risks that have a project impact , so are inherently your responsibility too?”

Coachee :: “Yes but over time they stopped feeling like testing risks to me”

Boom …pivot….this suddenly changed the whole dynamic in the conversation, I suddenly felt this rush of regret that I had missed a trick in coaching them on risk advocacy. And that I needed to get to the bottom of this !

Coach :: “Could you elaborate on what you mean by stopped feeling like testing risks over time ?”

Coachee :: “See, as you know this is my first software management project,while I could understand how the risks impacted the project I could not accurately gauge how  would those affect my ability to manage testing for the programme ! Due to this they did not bubble up often and high up enough on my list of things to worry about, hence I did not advocate them with senior leadership as often as I maybe should have? Over this long drawn programme I just left them as some-else’s job . However a lot of those risks materialized  and bit me  ”

Imagine these two articulation of risk ::

Example 1 :: We dont have a complete and good set of requirements . This is a critical risk to the project because if we dont have requirements we can not build and test the new features that the client is asking by this date . And that means that the project will slip it’s delivery date or would not be delivered at all

Example 2 :: I have reviewed the current set of requirements from a test-ability prescriptive. As per my analysis the requirements are neither complete nor can be reliably used as a basis for writing effective tests to critique what we are delivering . This will  hinder the ability of the test manager to estimate and the Team to complete design and execution phases of the project , which in turn puts the current delivery date at risk.

If I were a test manager reading the risk register with the above risk(s) in it or if I were a test manager hearing a tester articulating those risks

— am I more likely to advocate and bubble up the first or the second risk ?

Why ?

As throbbing sapient beings we all have a cognitive limit and biases towards what we let occupy our mental space (both for the good and the bad).

In complex , enterprise level projects this space gets filled very quickly.

And it is by no means selfish to admit that we worry more (and often) about things that affect us directly  , that are visceral to us ,that might impede execution of our personal roles.

Now revisiting the two examples again and comparing the text in red 

Example 1 :: We dont have a complete and good set of requirements . This is a critical risk to the project because if we dont have requirements we can not build and test the new features that the client is asking by this date . And that means that the project will slip it’s delivery date or would not be delivered at all

Example 2 :: I have reviewed the current set of requirements from a test-ability prescriptive. As per my analysis the requirements are neither complete nor can be reliably used as a basis for writing effective tests to critique what we are delivering . This will  hinder the ability of the test manager to estimate and the Team to complete design and execution phases of the project , which in turn puts the current delivery date at risk.

The message in red,in the second example is more personal. It answers the question , “how does the risk impact me/us?” , explicitly than example 1.

My mistake was to under-emphasize the importance of articulating how those risks could hamper the coachee’s (audience of the risk advocacy in this case) ability to execute their own role.

I was the victim of my own experience as I was seeing the so called bigger picture (of the impact on the project and the programme and beyond ) but missed the obvious, i.e. to start with how that risk impacts the coachee first .

This was a critical miss because I did not my advocate’s heart and mind on board.

Learning –

1.While coaching, always remember that I am serving the coachee first before their project /programme.

2.While advocating risk, in addition to articulating what the project/programme/commercial impact of the risk and articulate how that risk will impact the decision maker’s role and responsibilities that they are accountable for.

And if you do it well, irrespective of whether they are the Test Manager or the CEO , they will listen





Don’t await wizardry,lessons in coaching # 1


Close your eyes

Ask yourself to picture the word “Coach”

What are some of the images that come to your mind ?

Someone…. “grey haired” “knows all,full of wisdom” “motherly figure” “years of experience” “pointing to the north star”

Is it necessarily true that the best coaches are folks who have accomplished a lot, have had very long illustrious careers ,have all the answers,are “the non-playing captains” of their Teams ?

Not necessarily!

The best coaches that I have worked with , people who have changed some of my ingrained beliefs with their insights and experience , people who have taught me “how to fish” had these traits in common,

  1. They were not at the fag end of their careers or disseminating boardroom wisdom from an armchair
  2. They were selfless in giving time to others
  3. They were honest about not knowing everything
  4. They were not ashamed to speak about their vulnerabilities
  5. They did not hold back from coaching because they had lots to learn , still

These are the foundational principles and behaviors that I strive to model during my coaching gigs

I dont think we have to wait to achieve coaching nirvana to act as coaches.

I think we just need to show courage and be driven by our intellectual honesty,a desire to teach the process that has worked for us ,a desire to share knowledge and to improve others and ourselves.

And doing all this as a personal choice rather than a demand of the role.








Murdering empathy


Imagine the remotest tropical utopian island.

It is the island that is the coveted dream of every leader ,because on that island lies the formula to understand what success means…….?

What success means, to each of your Team members?

You yearn for that formula because if you have it ,you hold the key to authentically connecting with your team

Now imagine a raft. The raft will get you to that island, to the secret formula

That raft is empathy .

Now imagine sharks, yes great whites. Aka negative emotions and biases ,these are what the waters are full of.

They are trying to devour you or destroy your raft and then devour you.

An alternate term that I will use for those sharks is empathy killers.

Empathy killers are behaviors(fuelled by negative emotions and biases) that threaten your raft , the build of it , the existence of it.

The more you use or let these empathy killers exist in a working relationship the stronger will be the current of apathy that will take you away from the island , from making an authentic connection with someone in/outside your team.

Reflecting back on instances where I have been eaten by the sharks or I have fed someone to the sharks , I want to share the following empathy killers

Whenever as a leader you exercise any these behaviors ,empathy dies a little death.You drift away a little from that Team member who are struggling with their performance,from that peer with whom you are trying to mend fences, from that introverted person whom you can not convince about your strategy, from the business stakeholder who is failing to relate with the reasons why your Team can not keep their commitments.

This by no means is an exhaustive list , feel free to add your empathy killers to it .

  • Asserting that your problems or the company’s problems are bigger and more complex than theirs (just because you operate at a higher hierarchy level in the business)
  • Telling them that they don’t see the bigger picture (when they call out something which did not align with the company values charter pasted on the front door)
  • Taking it personally and giving back in the same coin (angry emails from them at 8 in the evening are responded by angry emails at 8:35 )
  • Raising things that they need to improve only when you are about to say no to something. 
  • Not being there due to lack of time. 
  • There but pretending to listen . 

[ Bonus material — What listening level are you at ? ]

  • Assessing their performance from a different lens than them. Especially without telling them which lens you are wearing and when?
  • Comparing. Yes ,comparing full stop. Comparing them with that high performing star in the Team as a means to justify your decision.
  • Quoting your (legitimately) vast (but invalid or unrelatable) experience to win the argument .

e.g. Because you have not worked at <x> you can not understand this.

  • Using glass half-empty as a motivation methodology .Corollary -> Also instilling fear of the glass being half empty, fear that it must not be broken, must not be filled with the wrong content or not being the type of vessel that you expected.

For a moment ,forgo metrics,forget numbers,forgo strategy,forget vision….just reflect on what your number one duty as a people leader is,

To create an emotionally safe environment where you can genuinely connect with your Team to understand what success means to them and where they can fearlessly connect with you to understand from where you are coming from.

Empathy, like charity begins at home . Start by being empathetic to your own emotions first, acknowledging them, questioning them, detecting patterns and then doing something about them.

I don’t claim to hold the secret formula from The Utopian island but I have started to know more about “my” great whites, learning to out maneuver them, learning to keep the raft safe.

Creativity , the heck ?

If you are failing to put your idea/thought/experience out there to be ridiculed as audacious

If you are failing to put your idea/thought/experience out there to be dismissed as infeasible

If you are failing to put your idea/thought/experience out there to be ignored as unoriginal

If you are failing to put your idea/thought/experience out there to be chided as nonconformist

then,you should seriously ask yourself why you are in the pursuit of anything creative ?

Creativity,starts by putting it out there ( to be ridiculed,dismissed,ignored and chided) and continuing to repeat it .




Going live


When there are no more bugs that need to triaged out as “no one will use it this way”

When there are no more end users who need convincing that “this is what it is and will be”

When there are no more apolitical voices to be ignored

When there are no more features left to turn into enhancement requests for future releases

When there are no more feasible workarounds left with the legacy product

Meet me there, because that is when, it will be time to “Go-Live”