CHAPTER 25
Leader Profile: Lisa Kavanaugh

Path to Leadership

The profile of Lisa Kavanaugh, who has dedicated her career to coaching others, helping technology leaders to become the leaders of their companies.

I first met Lisa in 2010 when she was the VP Engineering at Ask.com.

Lisa studied computer science at UC Santa Barbara, and began a long career in technology, initially as an engineer at HP, but soon she joined a young ask.com (do you remember “Ask Jeeves”?).

Over the next 12 years, Lisa earned her way through the engineering ranks to eventually becoming the CTO of what by then was a very large, global engineering organization.

What has always defined Lisa, however, was her passion for coaching, and for continuously improving both herself and those who worked for her.

For the past several years, she has dedicated her career to coaching others, helping technology leaders to become the leaders their companies need them to be.

Leadership in Action

I asked Lisa how she generally goes about helping technology leaders to become skilled leaders of empowered teams and organizations.

Here's Lisa in her own words:

Different leaders have different motivations for seeking coaching. Some desire a major promotion, some are facing an obstacle standing in the way of their goals, and others want to establish a better working relationship with their team or peers. They all desire an outcome that feels out of reach.

Whatever the case, transforming to a strong, confident, inspiring leader can take effort and personal courage.

These are four key skills that each leader needs to complete that transformation.

Self‐Awareness

It begins with being honest with yourself and understanding what behaviors or traits might be getting in your own way, or in your team's way. Ask yourself, what are the behaviors that may have served you well earlier in your career, but now are no longer advantages?

Here's a remarkably common example of that. I often meet technology executives that have built a reputation for absolutely dependable execution. They have consistently put in the effort and delivered what they had promised. In many cases, they have had to move mountains to deliver, but they did. They are known for their reliable execution and that is a large part of their identity.

But now the leader has been promoted to the level where her personal effort can't scale, and her teams feel like they are being micromanaged. The self‐awareness that is needed here is to realize that the skills that got her to this level won't get her to the next level.

Courage

When you have built a career and identity out of one set of behaviors and you realize you need to change, especially in ways that now depend on other people, this can take real courage.

It takes courage to make space for teams to learn and make mistakes. It takes courage to give meaningful and honest feedback. It takes courage to take this leap of faith that trusting your team will have better results than just trusting in yourself. It takes courage to leave your tactical skills behind and move into the world of strategy. It takes courage to be vulnerable.

As an example, I had a technology executive that was struggling to truly partner with a particular peer, because an earlier project they had worked on had not gone well. She was convinced that this peer thought poorly of her and her response was to avoid this peer. But she knew she needed this relationship, and she mustered up the courage to reach out and have a truly difficult conversation. She confessed that she had been avoiding him, the reason why, and what she wished for their partnership going forward. It took bravery and vulnerability to put herself out there like this, and it proved to be the turning point in their relationship.

Courageous leadership is going forward despite the discomfort.

Rules of Engagement

For many leaders, learning to trust their teams can take a very big leap of faith. Especially because they know they are still ultimately responsible for successful outcomes.

Rules of engagement are simply an agreement with the teams on what type of visibility the leader needs in order to give the teams the space they need to work. What information does the leader need in order to trust? What context does the team need to understand to be successful? What does the team need to feel safe in surfacing risks and problems early or asking for help?

It's important to emphasize that these rules of engagement typically evolve as the trust and learning is built over time, but establishing some agreement around what information to communicate when, can help both the leader and the teams to work out effective ways for each party to get their needs met.

Disrupting Yourself

Even if the leader is self‐aware, has the personal courage to make the necessary changes, and has agreed to rules of engagement, it's no secret that long‐held habits can be very hard to break. Especially habits and behaviors that get to the very core of someone's identity and feelings of self‐worth.

Effectively, we're asking the leader to disrupt herself. We're asking her to commit to change. We acknowledge that there will be mistakes and regressions, but each time that happens we'll identify the triggers and look at better ways to respond. We acknowledge that the first days and weeks will be the most difficult. But every day that goes by, the leader will be able to access the new behaviors more easily.

Every leader's journey is different, but I have found over the years that if a leader truly wants to improve, and has the courage to take the leap of faith necessary to learn to trust others, that they can indeed disrupt themselves and become the leader their company needs, and that their employees deserve.

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