Walking with Tech Leaders: Personal Takeaways on Leadership (Part 2)
This is the next part of the first list of lessons I shared a couple of weeks ago. Really appreciate the lovely comments and feedback from the first part!!!
For the next part, will hone in a little bit on my experience from leaders in terms of executing initiatives and making plans into reality, but also building relationships and trust.
TL/DR — My Part 2 List: A Summary
11. Leaders walk through Initiatives with Space for Questions.
12. Leaders value Initiative Kick Offs.
13. Leaders have Great Relationships with Tech Leaders outside the Organisation.
14. Leaders ‘may be up there’, but will always be with the teams during ‘tough times’.
15. Leaders recognises and heroes all voices.
16. Leaders establishes Trust and Good Working Relationships, and is patient in doing so.
17. Leaders deliver bad news early.
18. Leaders understand and provide space for One-Way and Two-Way Door Decisions.
19. Leaders sees beyond the Hype and Buzzwords, but also are excited to try new things whenever appropriate.
20. Leaders are excited by change and the opportunity it brings.
11. Leaders Walk Through Initiatives by Providing Space for Questions
Let’s resume the list by looking at how I noticed the great leaders I worked with approach the beginning any big initiatives (whether tech transformation initiatives or big product features) — assuring Clarity.
Instead of immediately asking the teams for a roadmap & estimates, or a plan for implementation, they begin first by setting the stage by providing context, framing the initiative within the broader, overall company strategy and clearly articulating the value. Again, the leaders understand that Repetition is key to make things stick.
At the beginning of it all, a ‘kick off’ session is established, but this session is not just as a one-way information dump, but an interactive discussion. The leader provides structure, but they don’t dominate the conversation. Instead, they leave ample space for questions and dialogue.
I find this is where the conversation is valuable because of a couple of reasons:
- Surfaces assumptions from the teams (and from the leaders as well, of course) and corrects any incorrect assumptions early;
- Identifies Key Unknowns and surfaces things that needed to be validated or researched first, before actually starting on an initiative;
- Strengthens the team’s buy in to the initiative and connects to the team the value of the planned work; and
- Excites the team for the upcoming initiative however big or small it is in terms of impact.
A personal experience — Moving to the Cloud: Some key memories I’ve had related to this — moving to a cloud provider from on prem. Naturally, a move like this came with loads of excitement — new tech, modern frameworks, and fresh approach to infrastructure. But it wasn’t the main driver for the conversation — but why it mattered to the company (and the session ultimately dictated a potential rollout path on ‘lift and shift’ vs ‘start from the beginning’ — and depending on context, both are viable options, to be perfectly honest).
12. Leaders value and facilitate Initiative Kick Offs — and pushes the team to do the same moving forward
Just wanted to hone in on Initiative Kick Off sessions and why I’ve come to appreciate this as key parts of any initiatives. As mentioned earlier, these sessions are where teams get really excited about delivering and discovering the many new challenges and opportunities within an initiative.
Great leaders facilitate these sessions plenty of times in the beginning, but what’s even more empowering is when — after going through a big initiative kick offs — the teams themselves begin leading the sessions. This change, from being walked through to taking ownership, is a major milestone in how a team becomes even more productive.
Over the course of the many initiatives being considered, we refined and iterated on the structure of these kick offs (another iterating improvement moment, actually!), but some of the most valuable frameworks or approaches we’ve used include:
- We’ve loosely used the Business Model Canvas (we usually didn’t follow this by the book (soz)), but we get key parts of it to set the context of the Initiative. It surfaces value that are Customer-centric, key resources required (and dependencies), and which Customer Segments it impacts (funnily enough, this part is actually what makes defining impact on incidents easier!). The canvas was so useful we put it in the team’s wiki as a reminder / reference.
- Surfacing the RAID matrix really early on, and constantly revisiting it as the initiative progresses during check points and see if things have changed.
- Identifying the initiative’s RASCI table and clarifying key roles. One practical insight we had: when there are so many roles in here, we have a firm look at it and see — which ones are really Consulted vs Informed and a reality check to streamline communications.
13. Leaders have good relationships with Tech Leaders outside the Organisation
Another one of the most valuable lessons I’ve learned from leaders is that there’s a strong tech leadership network out there and they provide a vast, great wealth of knowledge and experience.
A quote that someone told me that really stuck with me (can’t remember the exact words, but…)
‘Most of the time, we all solve the same big problems and challenges, we don’t always have to reinvent the wheel.’
This is why I see great leaders proactively builds their networks and connects with peers outside the organisation. Exchanges and Meet Ups — not just during conferences, but even during monthly informal gatherings with key topics to discuss every month — are a great way to connect to peers. Seeing my own leaders engage in these conversations was amazing. They weren’t just leading within the teams; they were continuously learning and exchanging ideas externally.
Side note: Having said that, I have not been able to since moving to Europe — but need to do this year!!
One of my most memorable experiences in 1–1s was when a leader asked me: ‘Thoughts on having a mentor?’
At first, it really took me aback that it was actually an option, and proceeded to give me names I could be interested in chatting to, and getting some valuable learnings. That moment not only reinforced the value of external connections, but also tying it back to my very first learning (‘Leaders are Great Connectors’) and extending this even outside the organisation.
14. Leaders ‘may be up there’, but will always be with the teams during ‘tough times’
An upcoming Band of Brothers reference again, sorry.
“If you are a leader, you lead the way, not just in the easy ones, but on the tough ones, too. The key to being a successful combat leader is to earn respect, not because of rank, but because you are a (hu)man.”
― Cole C. Kingseed, Conversations with Major Dick Winters: Life Lessons from the Commander of the Band of Brothers
This is an easy learning to relate to but hard to embody. I’ve seen great leaders really visible during high-pressure moments — not by taking over, but by providing the right kind of support.
This is particularly evident during major incidents. Instead of simply observing or requesting for constant updates, they provide the support the teams need in order to resolve and go back to stability. They ask guiding and coaching questions, rather than prescribing solutions all the time (some times it is needed, but I notice they ‘ask the right questions’ depending on the severity), they help the team think critically and how to prioritise to tackle the problem.
And it is always about improvements for the future when the incidents settle — how might we put things in place to not let this happen again? What are the gaps in our processes and systems? What things that are missing for us to not have the same incident? Not to blame, but to recognise & remind that things will go wrong and there’s always room for improvement.
Here’s the key part of it after an incident: Gets ideas from the team, and prioritises them & provides the team to balance this improvement with other business initiatives.
15. Leaders recognises and heroes all voices — not just the loudest
One of the key things I learned is that not all people like to present, or to share the things they do — but that doesn’t make their contributions any less valuable. The tough part of it though, is it makes things less visible compared to others — thus shaping some Perceptions.
I am definitely not going to talk about Introverts vs Extroverts here, but more on how leaders hero everyone’s contribution in one way or another. They look beyond surface-level perceptions and actively work on elevating those who might otherwise go unnoticed.
“Perception precedes reality”
- Andy Warhol
One lesson I learned from a great leader related to this: organisational perceptions of individuals can be slow to counter or change, but that doesn’t mean it is not doable and they can’t be shifted.
I’ve seen leaders work with the individual contributors to balance this at the same time giving them the space to thrive and share in ways the team member is comfortable with (on occasions nudge them that sometimes, it is needed to showcase and share for personal growth).
16. Leaders establish Trust and Good Working Relationships, and is Patient in Doing So
When joining a new organisation, I’ve learned one of the priorities I need to do as a newbie as part of my 30–60–90 day plan was to establish trust. This crucial lesson I’ve learned from a great leader I worked with. The key parts of our 1–1s in the first couple of months was — on top of the establishing connections (again, point 1) was to make sure I establish myself as a tech lead that they can trust and work with collaboratively.
At times, I found myself frustrated that trust wasn’t forming as quickly as I hoped. But I was reminded by the leader: trust takes time. It isn’t built within a sprint or two — it’s built through consistent actions, walking the talk, follow-through, and patience.
I’ve also seen this play out many times when new leaders join an organisation. The great leaders don’t rush in with drastic changes (ahem, current political climate, ahem); instead, they take time to understand the people, their priorities, and their ways of working. They listen, connect, collaborate & co-innovate — creating the much important space for trust to develop organically.
17. Leaders Deliver Bad News early
In one of the leadership workshops I attended in the past, one quote really resonated with me:
“Bad news doesn’t get any better with age.”
This principle isn’t just about delivering news about incidents or technical failures — it also very much so applies to managing expectations, in particular, when it comes to individual performances.
I’ve learned (the hard way, mind you) that one of the most challenging moments for any leader is when an individual gets their performance review at the end of the year and is completely off guard by the feedback due to their lack of awareness from it during the whole year. They didn’t realise they are not ‘meeting expectations’ earlier. A great leader once told me, “if you’ve done your task right as a leader, the end-of-the-year review should feel like a regular 1–1”.
This is where I find that great leaders align expectations constantly and early — so the leader and the individual have something tangible to talk about every catch up and course correct or pivot whenever needed.
18. Leaders Understand and Provide Space for One-Way and Two-Way Door Decisions
The idea of what are One-way and Two-way Door Decisions is brilliantly explained in the linked article, so I don’t think I will attempt to expound on it any further than it does. However, some key takeaways from my humble experience:
- The question on whether a decision is ‘hard or easy to reverse’ sometimes need critical thought — sometimes we as engineers strive for perfection and we plan & want to do things perfectly, but sometimes we need to make decisions geared towards experimentation and iteration, making it easy to reverse (e.g. put toggles! use A/B tests! :))
- I really appreciated it when leaders were explaining the concept to us in the past — and gave us the space & autonomy to act and make these types of decisions without always asking for a ‘yes’. This approach made us feel less like just initiative implementers, but more like accountable initiative owners.
Might have said it multiple times, but I find the core of leadership is to empower, not to act as bottle necks in the decision-making process.
19. Leaders Sees Beyond the Hype and Buzzwords, but also are excited to try new things whenever appropriate
I wouldn’t say some of the great leaders are cautious when an emerging technology arises, but I’ve noticed that the first thing they ask is if it is a right fit for a situation. It is when they evaluate things critically, tap on their network for any similar stories or experiences, and position it as part of the strategic plan for the organisation.
Being innovative is always a very hard thing to get right, especially for well established applications / technologies, but I’ve seen organisations do it well outside of hackathons.
Being too conservative not only means missing out potentially on a next big opportunity, but it could make the engineers get less inspired and innovative in the longer run. The leaders avoid chasing the fleeting trends that don’t align with the overall strategic goals, but makes sure teams are open to experimentation, almost R&D-type that connects (sometimes it can be a two-way door decision!) to product initiatives.
Somehow, Gartner’s hype cycle comes to mind here.
Speaking of change, the last lesson I’d like to close of this article:
20. Leaders are Excited by Change and the Opportunity it Brings
Like in software engineering, everything in leadership is iterative and change is a key ingredient for progress. Leaders understand that nothing is static, and bringing in change is something to embrace (rather than to shy away from). They will come up with effective Business Cases to justify and sell an idea, and see the shifts — whether technology, organisational, or process — as a way to improve on the status quo.
I’ve seen great leaders really looking at places for improvement, and doesn’t shy away from asking the fundamental questions (e.g. I remember a leader asking in a meeting of managers — ‘are our teams actually organised as effectively or do we need to reorganise the teams?’) I felt the question was not a critique of the organisation — but a genuine curiosity and a desire to make things better. Change is viewed not as a threat (or a very big laborious task to do again), but as a positive force.
And so — if you’ve gotten this far, thanks!! I hope my key takeaways I’ve gathered over the years working with leaders offer some value. They may not be new or revolutionary, but I hope looking at it as a collection might spark great memories from working with your leaders as well (like how lucky I have been working with some really, really inspiring leaders). May your 2025 so far has been really productive!