Isaac Sacolick offers Heller Report readers an exclusive excerpt from his new book, Digital Trailblazer.

My anxiety increases as I arrive at the office. Today is a big day for me. It’s my fiftieth day at this business, and I am halfway into my 100-day plan, a ceremonious time when C-levels are expected to articulate their plans and roadmaps. The tactical parts of this plan aren’t the issue, and I’m confident the technical aspects of the roadmap will get done.

Getting a leadership team together and turning around the culture is the greater challenge.

When you accept a new leadership role, you’ll be asked this wonderful question from your mentors. They’ll ask about your team, your direct reports, your lieutenants. They’ll say, “Make sure you focus on your leadership team and get the right people working for you.” Or something like that.

And the first time you hear it, you might scratch your head as to the exact meaning of the statement or question. Who are the right people? What does it mean to focus in this context? Then you’ll get to the heart of the matter. How should I go about forming a leadership team?

Digital-Trailblazer-CoverIt’s not easy, even for those of us who have done it several times before. Every organization is different. Every situation where you are fifty days into the job is different. It starts with hundreds of questions about who is already on this team, and then determining whether and to what extent you can make changes.

I do this on day 50, but also day 100, 150, and again and again. I still look at leading organizations and grooming leaders aligned to an agile cadence, though the sprints are not fixed in duration. As a leader, there are times when I can only listen and can make a few tweaks, while at other times I can grab the bull by its horns and drive significant changes.

Today is one of those days, and today is the start of the next fifty days I use to develop my leadership team. In my first fifty days, one leader elected to leave, and the other one – well, let’s just say the person wasn’t going to work out. I fought to get one additional open position, so now I’m in a race to find the right people.

What is the right type of leader?

I am not just seeking leaders to take on responsibilities. These leaders will be closer to the agile teams. They must echo the company’s strategy and my vision and have their own voice with their teams and with me. I seek leaders who are great listeners and are ready to make data-driven decisions. They must be collaborators and handle the pressures of driving change. I want drivers, but not bulldozers, because they must seek feedback and contributions from everyone. Of course, they need some of the skills I am seeking, but I must pick which skills are critical and which they can learn during the journey.

Hiring and nurturing diverse teams, creating an inclusive culture, and driving empathy are ongoing needs and essential to transformations. The mix of backgrounds, skills, drivers, and interests all play into how well teams collaborate and manage conflicts. Even when you have the right people, you must constantly adjust to whether they’re in the right seats with optimal responsibilities and agreed upon collaboration principles. Organizations transforming and managing shifting priorities must make reviews of leader and team dynamics an ongoing process.

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