About Roger
Leadership problems are usually human problems first.
A missed deadline may look like an accountability problem. A struggling manager may look like a performance problem. Turnover may look like a hiring problem.
But underneath those problems are often people trying to communicate, make decisions, manage emotions, navigate conflict, understand expectations, and figure out whether they can trust one another.
That’s where Roger Wolkoff does his best work.
Roger helps leaders understand the human problems underneath leadership problems, and gives them practical ways to change what they do.
His work focuses on the everyday behaviors that shape trust, communication, accountability, confidence, and retention: how leaders respond when someone makes a mistake, how they set expectations, how they handle difficult conversations, whether their actions match their words, and what their teams learn from them every day.
More than 30 years of seeing leadership from different sides
Roger didn’t come to leadership development through one traditional path.
He has worked as a project manager, technology support lead, facilitator, network administrator, software trainer, programmer, sales representative, and competitive intelligence analyst.
Those experiences gave him a front-row seat to what happens when communication works—and when it doesn’t.
He has seen talented people struggle because expectations were unclear. He has watched leaders create unnecessary friction despite having good intentions. He has worked with teams where trust made difficult conversations possible and others where people avoided saying what needed to be said.
Those experiences shaped the work he does today.
Roger believes strong leadership begins with self-awareness: understanding your behavior, recognizing your impact on other people, and being willing to adjust when your intentions aren’t producing the results you want.
That is emotional intelligence in practice.
Practical leadership development for the real world
Roger works with executives, business owners, managers, emerging leaders, HR professionals, and leadership teams through speaking, workshops, facilitation, and coaching.
His work explores topics including:
- Leadership trust and the signals leaders send every day
- Intent versus impact
- Communication and expectations
- Accountability and follow-through
- Difficult conversations and conflict
- Emotional intelligence
- Leadership transitions and new managers
- Team trust and collaboration
Roger is also an Authorized Partner for Everything DiSC® and The Five Behaviors®, using both tools to help people better understand themselves, communicate across differences, and work more effectively together.
His style is conversational, practical, and grounded in real workplace situations. Expect stories, questions, humor, and ideas people can actually use, not leadership theory that disappears when everyone gets back to work.
Why this work matters to Roger
Roger started All About Authenticity because he had experienced firsthand what poor leadership, weak communication, and a lack of self-awareness can do to people.
He also saw the opposite.
A leader who listens differently can change a conversation.
A clearer expectation can prevent weeks of frustration.
A thoughtful response to a mistake can determine whether someone speaks up the next time.
A difficult conversation handled well can strengthen rather than damage a relationship.
Small leadership behaviors create signals. Those signals teach people what is safe, what matters, what gets rewarded, and whether they can trust the person leading them.
Roger’s goal is to help leaders become more intentional about those signals and build workplaces where people can do good work, have honest conversations, and want to stay.
A little more about Roger
Roger earned his undergraduate degree in political science from the University of Rochester, a certificate in project management from the University of Wisconsin–Madison, and his MBA from Edgewood College.
He has lived in New York, Atlanta, Birmingham, Chicago, and Madison.
Outside of work, Roger is a devoted science-fiction fan, particularly stories involving time travel and alternate realities. He loves traveling, swimming, and sushi, and will happily have a conversation about any of them.
Want to work with Roger?
If you’re trying to strengthen leadership, improve communication, build trust, or address the people problems getting in the way of performance, Roger would welcome the conversation.