Discussing the Merits of Digital Leadership with Toni Townes-Whitley

Post Date: 06/25/2019
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Note: The following is a recap of Toni Townes-Whitley’s session at Shift Happens Conference 2019. Check out the other session recaps below: 

The digital landscape is continually making business owners reconsider the way they think about how to lead their organizations. These strides in technology also mean that employees need to start rethinking how best to interact with each other and improve their workflows. These shifts in perspective were at the core of Toni Townes-Whitley’s session “Digital Leadership: Insights from the Trenches.”

As President of US Regulated Industries at Microsoft, Toni has had significant experience driving digital transformation in various types of organizations. She’s spoken publicly on the benefits of using AI to empower employees and the importance of digital privacy in an age where privacy is becoming increasingly difficult to maintain.

In terms of her ShiftHappens talk, she broke down digital leadership into three core sections: knowing what you’re digitally transforming, how it’s being transformed, and who is being affected by the change.


It’s important to take a look at your environment and determine what needs to be migrated over. You need to ask yourself questions such as:

  • What emerging technology do we have?
  • What technology do we have with cognitive and predictive capabilities?
  • Which bits of data can we use in ways that’re current and that resonate with our users?
  • In terms of security, how much data is safe to move and when should it be moved?
  • How do we carry out the migration, and what’ll the data logic be behind it?


The “How will we transform this data?” conversation is just as important. What’s the leader’s role in “how” that digital transformation occurs? And not just in the obvious ways of assuring compliance and accountability, but also in terms of transparency. How do you build trust into your transformation?

Toni emphasized those last two questions. Being highly transparent with your team about the entire transformation process is a must if you want to facilitate a smoother user adoption period. You should be clear about:

  • What’s transforming
  • Where that data sits
  • What the principles are around privacy and security
  • How these changes will affect the end user

How you transform is ultimately going to be the brand that you represent and the legacy you leave behind. How you facilitate it with your users–whether it be from the top-down or by using a grassroots method–will play a major role in this, as will making sure that your stakeholders understand your vision.

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Just as we touched on in the “How” section, it’s key to consider who you’ll be impacting by digitally transforming your business. Ask yourself:

  • How will your users adapt?
  • How many users will these changes be affecting?
  • How drastic a change will your new processes be from that which your users are used to?
  • Have you laid out a clear adoption roadmap?

Looking Towards the Future

After going over these three considerations, Toni proceeded to discuss the future of the modern workplace. She noted that most of us grew up in “crystal structures;” structures that offered a very clear sense of mission, vision, and objectives. The new benefit of working within the digital economy is the ability to move to where the problems are with greater agility.

We now have an environment where we have three generations in the workforce for the first time. The youngest group, “phygitals,” cannot (or sometimes choose not to) see the difference between the physical and digital world.

Desired skill sets in this world are different from what we learned coming up. The expectation of citizens, patients, soldiers in the field, frontline workers, etc., will be that they’ll know how to access real-time data at any time without being in a fully connected environment. Your workforce will eventually expect interoperability from you.

So, how can you lead your team/colleagues to accomplish tasks efficiently and be more open-minded in your approach to working in this digital space?

1. Have tangible empathy. Be aware of how you translate how you feel into what you do, hold yourself accountable for your actions, and try to gauge what your team does when you’re not around.

2. Work on mastering the 10 inclusive behaviors. These include:

  1. Examining your assumptions.
  2. Making a habit of asking questions.
  3. Ensuring all voices are heard.
  4. Listening carefully to the person speaking until they feel understood.
  5. Addressing misunderstandings and resolve disagreements.
  6. If you have a strong reaction to someone, ask yourself why.
  7. Including and seeking input from people with a wide variety of backgrounds.
  8. Taking action to reduce stressful situations.
  9. Understanding each person’s contribution.
  10. Being brave.

3. Understand the process of technology adoption. There’s a good deal that goes into carrying out a successful migration, so familiarizing yourself with those steps is a must.

Want to hear everything we’ve discussed here in full? Enjoy the recording below!

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As the former Content Marketing Specialist for AvePoint, Brent led the strategy and direction of all AvePoint's blog properties.

View all post by Brent Middleton

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