Leadership Skills You Must Master When Moving to Digital Transformation Roles

I recently visited my alma mater, The University of Arizona, where I received my Master’s in electrical engineering and studied neural networks, computer vision, and medical imaging. It reminded me of the key lessons I learned in grad school; asking questions, reviewing research, developing hypotheses, collecting data, analyzing results, and repeating.

Transitioning to Digital Transformation Leadership Roles - Isaac Sacolick

I learned plenty of lessons in my first roles out of grad school, especially around developing commercial software, tuning algorithms, and collaborating with business leaders. I tell many of my stories and lessons learned in my new book, Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leaders. You can learn more about the book and pre-order it here.

One of the key lessons I learned and continue to experience throughout my career is a cornerstone lesson in Chapter 1 of the book: Reflect on the skills that got you here won’t get you there.

Reflect on the digital transformation skills

Digital Trailblazer has many of my stories, and there are 50+ lessons to learn about leading digital transformations. IMHO, driving transformation requires humble leaders who are lifelong learners who challenge the status quo and deliver meaningful results. More businesses must develop their leadership talent because business disruptions, technology evolutions, and best practices continuously evolve.   

That means individual contributors have more opportunities to accelerate their careers and take on transformation leadership roles. I know from experience, having been a CTO in my 20s and a CIO in my 30s.

Here’s a preview of what to expect from the book. In thinking about the transition from roles where you are an individual contributor on a team to leadership roles where you have responsibilities guiding one or more teams, I’ve identified two skills you must master.

1. Facilitate collaborative decision-making and meaningful communications

Leaders must develop the skills to make decisions with incomplete information and then learn to adjust, course correct, or pivot as new information becomes available. Leaders should seek data-driven decision-making but must acknowledge that aiming for perfectly clean data, complete information, and conclusive evidence is unusual and unlikely. The art of decision-making requires having confidence and conviction – knowing what decisions are needed and when – and then using active listening and analytical skills to make course corrections.

Digital Trailblazer by Isaac Sacolick

When making decisions, we need inclusive discussions, collaborative thinking, and debate with people on our teams, stakeholders, and partners. We must encourage people to ask questions and challenge the status quo. But businesses can ill afford to debate indefinitely, long meetings that yield few conclusions, or cultures of kicking the can down the road decision making – a topic I discuss at length in Digital Trailblazer.

Even worse are top-down command-and-control decision-making behaviors. Adopting a “what I say goes” attitude rarely achieves the true buy-in required to drive transformative change.

Collaborative decision-making is a skill every aspiring leader must learn. It requires mastering the transition from (1) agreeing on the problem statement, (2) collaborative and collegial debate, (3) making decisions, (4) communicating direction, and (5) reviewing the latest feedback and information to course correct.   

The secret to doing this well lies in developing communication skills. A key area where individual contributors (and frankly longtime leaders) can hone this skill includes the way they run meetings – from start to finish:

  • When calling a meeting, how are you communicating the agenda so that people know what decisions you’re looking to make? 
  • Who are the key people that should contribute to the discussion and debate?
  • How are you facilitating an open dialog during the meeting? 
  • When should you end the discussion and shift to ratifying a decision? 
  • Where are decisions documented, and how are they communicated? 
  • What recourse can people take to escalate concerns? 
  • What data should be collected to follow up on key decisions?
  • When should the team review data, new information, and feedback around decisions?

These aren’t skills you easily learn in a classroom and are critical when shifting to transformation leadership roles. Mastering these skills requires stepping out of your comfort zone and learning from mistakes.

2. Develop relationships and market your best ideas

Transformation leaders aren’t order takers – they are members of the leadership team who articulate the vision, commit to a strategy, and collaborate on roadmaps. Want a seat at this table? Better be ready to share your ideas and market the ones that require organizational commitments.

Marketing your ideas requires more effort and conviction than presenting a business case. Businesses have choices on what, when, and where to invest, so you better be ready to market and sell these ideas for them to rise to the top of the priority list.

But as every salesperson will tell you, cold-calling is a tough hill to climb when trying to close a sale. The art of selling starts with developing meaningful relationships with decision-makers, influencers, and stakeholders.

What does developing relationships mean in this context? It requires

  • Understanding the leader’s business goals, incentives, opportunities, and challenges
  • Collaborating and providing service to the leader ahead of your needs and asks
  • Getting to know them personally – and for them to know you personally

Digital transformation leaders that develop meaningful relationships with their peers and other executives are more likely to see them listening and supporting their ideas.

Watch this week’s episode of 5 Minutes with @NYIke to learn more, and please review my stories and lessons in Digital Trailblazer.

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