Technical leadership at scale

I do have experience in the software industry for more than 18 years. And from that 18 years , more than 15 years I do work as a some kind of leader starting from a small software team leader and now a global leader who is having the technical leadership role in a multi national company as a CTO. This article is about how effective you can be as a technical leader and I got some input from few great books that I refered at the end of the article.

Being effective in leadership is not something that always can be promised. However, when the scale is involved, or leadership is required to manage a team of teams, the complexity is always needed to be welcomed willingly or unwillingly — complexity with leading at scale results from the larger and abstract nature of the scope of the problems. The problems are now strategic and broad. Therefore, a leader’s impact is more immense than an individual contributor or even a leader of one team. The effectiveness relies more on general intuition than expertise in technical knowledge. Yet, Basics of the leadership are valid and have to be understood as the best practices of leadership still apply when the leadership scale evolves.

Then you may realize how to tackle this puzzle of scaling leadership across teams and what it takes to be effective in leading at scale. There you have “Three Always of Leadership”:

  • Always Be Deciding
  • Always Be Leaving
  • Always Be Scaling.

Always be deciding

This time you may not have hands-on solutions for the strategic type, high-level, difficult, ambiguous problems you are facing now as you were having when you were leading your teams’ technical problems. You probably have been the export of knowing what and how of the technical stuff. The strategic problems do not necessarily have one perfect solution but a bunch of trade-offs you have to select from. By ambiguous, we mean that the problem has no obvious solution and might even be unsolvable. The problem needs to be explored, navigated, wrestled into a state in which it’s under control. Three steps will help you with that:

  • Identify the Blinders.
  • Identify the Key Trade-Offs.
  • Decide, Then Iterate”.

You may come across whacky problems that have become the status quo, and you’ll discover bizarre coping mechanisms or rationalizations that have evolved to justify the status quo. As the leader, you have to see with fresh eyes to identify the blinders. Further, dig deep into the problem by asking questions.

Making trade-offs in one direction or another is the best solution you have right now. As the leader, you have to call out the trade-offs, explain them to everyone, and then help decide how to balance them.

After the trade-off is decided, we need to re-evaluate and rebalance the trade-offs again; it’s an iterative process. So, it is Always be Deciding as a process of continuous rebalancing of trade-offs. Because your team may fall into “analysis paralysis,” which is trap of searching for the perfect solution. The team has to be comfortable with iteration.

Always be leaving

The leader has to avid the team completely depending on him/her. If not, it will be a single point of failure (SPOF). The goal is a “self-driving team,” even in the absence of the leader. Success is not leader often interfering but building an organization that can solve the difficult problem by itself.

Self- driving organization needs a strong set of leaders, healthy engineering processes, and a positive, self-perpetuating culture that persists over time. The leader is the one organizing people. Constructing this sort of self-sufficient group involves:

  • Dividing the problem space:

The best way to tackle this is to put a team in charge of each subproblem; the subproblems can change over time. The idea is to avoid rigid team boundaries where subteams can change the size, individuals can migrate between subteams, and the problems assigned to subteams can morph over time.

  • Delegating subproblems:

Coach them on the work if need be. They need to learn to “level up.” Do that nobody else on my team can do. Making sure your management chain understands what your group is doing and staying connected to the company at large.

  • Iterating:

The freedom to tackle a new, adjacent problem, or perhaps you could even move yourself to a whole new department and problem space, making room for the careers of the leaders you’ve trained.

Always be Scaling

Our recipe for growth and success is a self-driving organization with strong leaders. Leaders’ limited pool of time, attention, and energy are their most precious resource. Therefore, a leader has to be more careful to protect your personal sanity.

Effectively scale yourself through this process require you to go through the cycle of success — the standard pattern to tackle difficult problems.

  • Analysis: Identify the blinders, find all the trade-offs, and build consensus about managing them. “Need to start wrestling with the problem.”
  • Struggle: As you as the leader, encourage your leaders and experts on the ground to form opinions and then listen carefully and devise an overall strategy. Prepare for failures, retries, and iteration.
  • Traction: Eventually, you iterating on trade-offs, staring to make smarter decisions, real progress is made. Morale improves. “Real progress”.
  • Reward: You’ll get rewarded for your success. “More work…and more responsibility!.”
  • Compression stage: You’re taking everything you’ve been doing and compressing it down to half the size.

This is how your organization is scaling by tackling new problems and then figuring out how to compress them so that it can take on new, parallel struggles.

The act of compressing a problem isn’t just about figuring out how to maximize your team’s efficiency but also about learning to scale your own time and attention to match the new breadth of responsibility.

In fact, it was US President Dwight D. Eisenhower who popularized this idea in a famous 1954 quote:

I have two kinds of problems, the urgent and the important. The urgent are not important, and the important are never urgent.

Back in the time, you, as a carefree individual contributor, would methodically work down your list, writing code and debugging problems. Prioritizing, planning, and executing your work was straightforward.

The higher up in leadership you go, the more escalations you receive. Your job became less proactive and more reactive. In fact, if you’re not mindful, you end up spending 100% of your time in reactive mode. Here are a few key techniques to avoid falling into the trap of urgent over important:

  • Delegate:
  • Schedule dedicated time:
  • Find a tracking system that works:

Managing time is a big part of the equation. But as a leader of leaders, your time and attention are under constant attack. As an engineer, you pay attention to detail; you make lists, you check things off lists, you’re precise, and you finish what you start. You get overwhelmed with balls throwing at you constantly. If dropping some number of balls is inevitable, isn’t it better to drop certain balls deliberately rather than accidentally?

Most people declutter their lives incorrectly: they spend time tossing the bottom 20% in the garbage, but the remaining 80% still feels too cluttered. She argues that the true work of decluttering is about identifying the top 20%, not the bottom 20%. If you can identify only the critical things, you should then toss out the other 80%. Divide your pile of balls into three groups: the bottom 20% are probably neither urgent nor important and very easy to delete or ignore. There’s a middle 60%, which might contain some bits of urgency or importance, but it’s a mixed bag. At the top, there’s 20% of things that are absolutely, critically important. And so now, as you work through your tasks, do not try to tackle the top 80% — you’ll still end up overwhelmed and mostly working on urgent but not important tasks. Instead, mindfully identify the balls that strictly fall in the top 20% — critical things that only you can do — and focus strictly on them. Give yourself explicit permission to drop the other 80%.

Scaling is exhausting and draining leaders’ energy out. Leaders need to stay charged and optimistic to save personal energy as it is important as time and attention.

The stamina builds up over time is helping. Your brain and body build up larger reserves of stamina over time. The key part is leaders gradually learn to manage their energy more intelligently.

CTO @ ZorroSign | Seasoned Software Architect | Expertise in AI/ML , Blockchain , Distributed Systems and IoT | Lecturer | Speaker | Blogger