Scaling Yourself as a Leader

Have you ever wondered what it takes to scale the career ladder as a technical leader? What skills and experiences do you need as you grow from Individual Contributor to Manager to Senior Manager to Executive roles? Or even what a typical day looks like? 

Last fall, SheTO had the opportunity to host two powerful women leaders who shared their perspectives and challenges as they navigated their career journeys – Avital Arora (Sr. Director of Engineering, Google Cloud) and Olubunmi ‘Boomie’  Odumade (Sr. Engineering Manager, DevSecOps, Omada Health).

Read on to learn from their experiences on how to navigate your career journey in technology leadership. 

On mapping out your career goal – moving to leadership

Both of them shared that their transition from Individual Contributor to Manager was organic; it was not something they were specifically seeking, but when the right opportunity showed up, they jumped in and learned what it takes.

Avital also shared that moving from Senior Manager to Director which is usually a big jump since it is an Executive level position came about by looking around at other directors and feeling confident that she could get it done and learn what it takes.

This is an important aspect – as we look to grow in our roles inside or outside of our current organization, it is partly down to just jumping in and being confident in our learning agility and resiliency.

What does a typical day look like? 

As you rise up the career ladder, a typical day involves context switching and handling many different items, some of which are short-term tactical items and others more towards the strategic end of the spectrum. Short term tactical items tend to lean towards keeping the train running, tending to any fires and longer term items could involve hiring plans, technical roadmap etc.

You will also spend some time on hiring and if you are new to the role, expect to spend a good amount of time learning about the players and the processes. Eventually, you will get to a place where you will know enough to make the right decisions. 

People and Product Strategy

As a leader, something to keep in mind is that work happens through others and our goal is not to micromanage, but to ask the right questions and bring the bigger picture perspective. Some of the questions to answer are around whether we have the right architecture for the next 3-5 years, what tech debt should we tackle and when, what refactoring we need to plan for and importantly, do we have the right leaders in place to help us execute on our strategy? 

Our goal should not be to be in constant firefighting mode but to make sure we have the right systems and people in place to spend the majority of our time on hiring, recruiting, architecture reviews, customer requirements,  program and timeline reviews. We should be watching people issues; if there is a conflict/situation that needs to be addressed, that takes top priority.

Staying connected as you rise up

Figure out what motivates people. Set up regular 1:1s, including skip level 1:1s to ask your direct and indirect reports how they are doing, what drives them and what concerns they may have. These conversations will also give you an insight into how you can support your people managers. 

Setting organization up for success 

Every team will over time transition from building the shiny new object to sustaining features. Avital shared her philosophy that the team implements the feature/service maintains it. This helps drive full accountability since they own the destiny of the product through its entire lifecycle. 

Measuring success and effectiveness 

When the team is meeting their goals and most team members are motivated and engaged, that is a great indicator of how well things are going. Another measure is how well the team can operate without you.

On the same topic, we have to be attuned to what the company measures – whether it is OKRs or cost metrics. It’s all about ownership and staying on top of things without having to explicitly telling our team members what to do, whether it is  customer escalations or hiring or any other operational tasks.

Effective survey strategies
Sometimes, companies send out a lot of surveys which can result in survey fatigue. One way to get around that is to set up working groups composed of engineers and managers to look at the survey results and collaborate on addressing the critical pain points. This serves to motivate engineers and drive up participation since they are involved in the decision making. 

It is also critical to have a feedback loop once the survey results are in and focus on what will be worked on and will not be worked on right away. The key takeaway is to explain why or why not we choose to focus on specific items vs others.

Evolving leadership style as the team grows and building trust

As your team grows, time management becomes all the more critical. You may have to restrict weekly 1:1s to new hires and have less frequent 1:1s with others. Also, look for dashboards, summary pages to get information across multiple projects more easily. 

One of the harder aspects of going up the career ladder is knowing when to let go and what aspects to let go of. One strategy is to hire people who are smarter than you and know enough to ask the non-obvious questions. As teams scale, it is a good strategy to hire the manager first and then grow the rest of the team. This gives your new managers accountability in the hiring process.

Staying on top of things 

In more operational roles such as in DevOps or DevSecOps, a lot of the work tends to be more reactive. It is critical to build in a buffer and put large requests in the sprint board so you can estimate the effort up front before committing.

Personal strategies to have a measure of control is to block time out for deep work. Sometimes, it is also effective to allocate the first 30 minutes and the last 30 minutes of each work day to mentally map out what issues need to be addressed that day or what issues need to be tackled the following workday.

Building relationships and communication

Even as you find yourself strapped for time, it is vital to establish a regular cadence of meeting with your leadership, your direct and indirect reports and crucially, your peer managers. Sideways communication channels with your peers are vital to make sure you have their support in solving organizational challenges.

With your leadership chain, it is important to highlight your team’s accomplishments, even if there are schedule slips or the expected outcome is not fully met. 

Learning to Unlearn

Yes, you read that right 😊. As you grow your career, you have to work at unlearning the desire to know all the details about the systems and the applications. You don’t want to be perceived as a micromanager, at the same time, learn to coach and delegate to your reports on how to achieve the outcome expected of you/your team. It is a fine balance between being completely hands-off and being a micromanager; developing a level of situational awareness and knowing when to jump in is critical to success. Also important is to learn to listen more and foster a team culture of coming up with ideas.  

Your success hinges on how well your team can understand and meet the business objectives of your organization and giving them ownership and accountability for ideas makes for a stronger team overall.