Introverted Leadership Series: Influencing Gently and Genuinely

Making each other better

I had spent a large part of my life teaching and mentoring others. It has always been a theme in my life. Much of this is due to the help that my parents and I were given, which gave us the opportunities to build a life in America (I shared some of those personal details here). Here are some examples of how I taught and mentored through my early lift:

  • In elementary school, I helped teachers in the earlier grades by being a TA for math and science. I also taught students and teachers how to use computers.
  • During high school, I taught AP computer science for a few weeks while the school found a short-term teacher for the courses.
  • In college, I tutored students from non-technical majors so that they could pass their programming courses and graduate.
  • At this time I also started helping some of my friends through their decisions around navigating their academic careers and their college/summer jobs.

I realized through these experiences that I really loved helping people to become better versions of themselves, or gaining clarity into what their next steps for success were. When I first started my professional career, I wanted to learn how to do these things in an unstructured work environment. There was only one problem…

You’re not ready

Like many companies, mine had a policy that you needed to reach a certain career level before you could start managing people. It would likely take at least 4 years for me to reach that level. I totally understood that — you could cause some pretty serious damage to a lot of parts of an organization if you aren’t well-equipped to handle people management challenges and discussions. However, I really felt like I could grow those skills quickly and wanted to be given a shot to do so.

So I decided to be a little tricky about it. 2 or so years in, I started looking for engineers that were interested in helping me out with some of the projects that were on my backlog. Specifically, I wanted to find people interested in moving on from building apps with the XML-based inhouse language that my team created, and developing in C++ proper. I found an engineer who was both interested and who I knew was a hard worker. We asked our managers if we could work on this side project — creating a build and deployment system for the inhouse language — and they approved it as long as it didn’t affect our main work.

Over the next 6 months, I worked with the developer and we had weekly 1:1s, adhoc project meetings, and set up a few stakeholder project syncs. It took a lot of upfront teaching and mentoring, and a good amount of initial handholding, but she was a quick learner. Eventually we were able to deliver the new build system. The new system had far fewer incidents and rollbacks, and also allowed us to apply optimizations which allowed us to scale faster.

Thanks to the success of that project, that engineer was allowed to start branching out into C++ projects, and eventually leading her own C++ development team. For me, this 6-month project was enough evidence for my management chain to believe that I could be an effective manager. Just about 3 years in I was fast-tracked to take on my first two direct reports, which quickly grew into a team of 18-20.

So… What does this have to do with influencing?

This experience taught me a lot about how to convince someone to do something that seems high-risk, low-reward to them. Looking back at how I was able to do it, I think there were three main things that were important in helping to influence the outcome I was striving for:

  1. I brought them along on the journey from the very beginning: I started by telling them what I was looking to do, how I was thinking of doing it, and asked for them to help me to improve the plan and sign-off on it. This created alignment from the very beginning.
  2. I looked for the overlap between my incentives and their incentives: I made sure that I answered the WIIFM — What’s In It For Me — for everyone involved:
    • For our managers: They would be involved in shipping a “free” project that would have a big impact on the company’s success
    • For the engineer: She would be able to get her career to the next level and take on bigger roles in the company
    • For me: I can determine if I can manage people or not, and potentially make it happen faster
  3. I showed my work: We gave frequent updates to our managers and the stakeholders of the project to let them know how things were going. We built transparency into any pivots we were deciding on or making in the plan, and made sure that we were all continuously aligned on the success criteria. When the project was complete, we gained a lot of trust from our leadership team, which helped with future influence.

Find the overlap

In any situation, the easiest way to convince someone of anything is to find that overlap between what you want and what they want. If you want someone to be influenced, it’s less about making someone think like you do and more about helping them to see why your perspective makes sense. Pushing someone to think differently will often cause them to hold their ground — no one likes to have their values and opinions challenged. Instead, understand where they are coming from and how your decision/opinion/etc. aligns with that.

Although it took a bit of trickery, I was able to work within the system in order to become a manager sooner. If it weren’t for the support of my leaders and the talents of that engineer, my career might’ve taken longer to accelerate. I’ve used this system ever since to help to align entire organizations to common goals, and I hope it helps you out too!

Change the World,
DVT

Introverted Leadership Series: The Importance of Healthy Conflict

(Er, I don’t think that’s right…)

Many of us avoid direct conflict with others, especially in the workplace. We don’t want to come across as abrasive, and we certainly want to make sure that our colleagues recognize how much we respect them. However, sometimes by avoiding what we perceive will be a confrontation we are missing an opportunity to help make something better — an idea, a project, a person, or even an entire team.

There are very few examples of what healthy conflict looks like in mass media. Outside of some exceptional role-models like President Bartlet from “The West Wing” and President Obama from… real-life…, it’s actually difficult to think of someone who can present a conflicting value or perspective in a fully-authentic way without trying to turn the conversation into a black-and-white situation.

However, if you’re fortunate enough to have worked at an organization that had peers or leaders with this trait, you’ll have seen firsthand what it could look like. You’ll have seen how amazing they are at navigating the line between being too harsh or too subtle. It was always a skill that I admired, being someone who historically would rather find gentler ways to provide feedback that were honestly much less effective and timely.

Over the years, I took some time to analyze my difficulty in providing real-time feedback. I started noticing a few habits and self-confidence gaps that kept me from being more effective during meetings and conversations. Much of it came down to three main things:

  1. Not being 100% sure that I was right: This was something that really kept me from making a big impact early in my career. I was afraid to speak up unless I was completely certain that my point was valid and worth bringing up. If it had even the slightest chance of making me look dumb or uninformed, I chose to stay silent.
  2. Wanting everyone to like me: I worried that by not agreeing with someone or making them feel that I was on their side, I would lose them as a friend and advocate. The fewer people that liked me, the less likely I would have people I could learn from, ask questions to, and hang out with (I *really* liked my lunch group, okay?!).
  3. Being introverted and wanting to find the right time to speak up: I hated that one of the most common ways to contribute to group conversations was to cut other people off. I wanted to let people finish their thoughts before I shared mine. This often led to not finding any gaps in the conversation to take advantage of.

These three things were prevalent in nearly every single group meeting I had. I found that I was effective enough in 1:1s, but my ability to speak my mind almost completely vanished in group meetings. I knew that I had to figure out a way to address these problems if I wanted to have a bigger impact.

It’s easy to stand with the crowd. It takes courage to stand alone.
– Mahatma Gandhi

I addressed each of those three items individually:

  1. It’s rare to be 100% confident in anything in this world. However, that never stopped any of the effective leaders I worked with from challenging the team’s perspectives. I realized that instead of simply pushing a conflict idea or viewpoint, they often would frame it as an open question. “What if we used X instead of Y?” “How would things change if we did X instead?” “Why are we assuming X?” This would force a conversation that incorporated the idea, but didn’t assume that it was necessarily the right way to move forward.
  2. Wanting everyone to like me was a more subconscious thing, so it was harder for me to break this one. I had to ease my way into feeling okay with the fact that people didn’t have to like me. I only needed two things to preserve positive relationships: they had to respect me and feel that I was competent. I found that the best way to do this was to act as a genuine thought partner for everyone. I challenged their perspectives (with open questions!) but made sure to word everything in a way that showed that I wanted to help make them and their ideas better.
  3. This was by far, and still is, one of the hardest things for me to do. Being in a videoconference with other people who are remote is a bit easier, since we all have the same delay disadvantage. However, being in a room with everyone, or being remote with people who are in the room together meant that I had to confront the fact that there will be times where I need to talk over others. Not only that, but I would often have to keep talking over others, even if they kept going, so that I wouldn’t get steamrolled. This is still not easy for me, but we live in a world where people will talk over each other. As much as I want things to change, this is the reality we’re in and I need to adapt.

Healthy conflict is something that I continue to actively work on everyday. It’s still too easy for me to keep things to myself and avoid confrontations. However, more often than not, I now catch myself doing it and correct it. As a result, my impact has grown dramatically and I’m consulted frequently as an agent of change. With these improvements, I’ve become closer to the role models I looked up to over the years.

Change the World,
DVT

Introverted Leadership Series: Adjusting Humility For Quiet Voices

Going Against Best Practices

As managers, we’re taught that we should give away all of the credit and take all of the blame for our teams. However, as a minority and an introvert, I’ve found that this actually softened my leadership voice. The problem was finding the balance between being humble while still advocating for myself to not play down my achievements.

I’ve practiced a servant leadership style of management and leadership for quite some time. The problem is that this has lead to habits like me saying “we” instead of “I”, even when I might have been the sole driver of some projects or efforts. When combined with my natural tendency to be quiet during meetings or downplaying/not taking credit for my own work, it sometimes has the effect of people not realizing how much of influence I’ve had on our overall success.

It took me awhile to realize that this was happening. Fortunately I was taught a lesson very early in my career that I kept with me ever since. Back when I was still a junior engineer, I was tasked with building some large pieces of infrastructure to help us move off of a monolithic legacy system.

I spent months driving the project independently — meeting with various architects and senior engineers, planning out the new platform and a plan on how to migrate to it, and ultimately executing on it. I of course collaborated with a ton of other amazing engineers to build everything out, but I was coordinating it all in order to ensure that we’d have a successful implementation. At the end of the day, it was a major success and we were able to use it to migrate off of our old platform.

Given the project’s success, I was happy with the results and focused on the next set of projects and goals. However, later on I was hearing from various people and teams — especially from senior leaders and managers — referring to the projects and infrastructure as things being developed by my manager. In one meeting with my skip-level manager, I realized that they also thought that my manager had done a large majority of the work, when in practice they hadn’t contributed to the work at all. It took a bit of courage and I had to step out of character, but I corrected my skip-level manager on the spot, and they apologized. It was a very sobering experience for me.

Servant Leadership Doesn’t Mean Underselling Yourself

One of the things I learned through that experience was that I had to be much more thoughtful. This was not just about what my immediate team and engineers thought of me, but also people outside of the team. My accomplishments alone wouldn’t be enough to establish my worth and impact. I would have to make sure that I communicated them to the right people, in the right ways.

Immediately, I started making sure to take a more “public” stance on what I had built. I made sure that I was publishing new features and updates broadly throughout the company, not through others but directly. During cross-functional meetings, I would speak up with subject-matter expertise and acting as the representative for that platform. I also started taking more ownership over my work, but in ways that weren’t obnoxious. For example, I’d explain “an assumption I had made when building that feature” or I’d share some of the initial system diagrams that were clearly developed by me. Additionally, I kept an eye on how senior leaders were perceiving me and my role in the projects, and would make sure that I looked for opportunities to establish with them the role I had in developing those projects (again, in a non-obnoxious way).

Although I say that I tried to do this in non-obnoxious ways, I’m pretty sure that there were times when it came off as too boastful, but this was a risk that I was willing to take. I knew that it was better for me to be seen as proud than making less of an impact than I was actually making. Making this correction helped me to quickly establish transparency around my contributions. This also helped me to build my reputation quickly in the organization, which allowed me to stop having to advertise myself as frequently (which at times was super exhausting/stressful!).

I’ve applied these principles throughout my career since then, and continue to do so today in my current role as a CTO. Fortunately, I rarely need to exercise this skill nowadays, but I do notice opportunities for many of my engineers and leaders to do so. Although it’s important to exercise humility and empathy in everything that you do, it’s equally important to ensure that you are getting the appropriate level of credit for your achievements!

Change the World,
DVT

Another blog reboot

Every 5 or so years, I decide that it’s time to pick up blogging more regularly again. It usually takes me awhile to get it started up, mostly because I try to take the opportunity to learn a new platform or set of technologies. I do this so that I can get more insight into the new tech that’s come out since the last time, but also so that I can try to automate more of the process while preserving the level of customization that I want for my content. Last time, I used Hugo, which uses Go templates, and I hooked it to use a CI/CD platform so that I could submit my articles to a GitHub repo and they’d be published automatically to the live site. This time, I’m “cheating” and using WordPress, which is about as complicated and complex as any other platform that supports third-party plugins and allows for nearly unlimited customization (Jira, Salesforce, etc.) I totally get why some web developers can focus their entire careers around building and maintaining WordPress sites for people.

Anyway, I’ll post some more meaningful content in the near future. I have a few articles I’d like to write about leadership and management, and sharing random stories. More to come!

Change the World,
DVT