ADAPTING TO THE PERSON AND THE SITUATION
Leading One-to-One
Give managers a practical system for delegating clearly, adapting to different work styles, and helping others solve problems without taking over.
Growth changes what managers must be able to do through others
As a company grows, capable individual contributors become responsible for other people's work and development. Their technical judgment may be strong, but managing through others requires a different set of skills.
Without those skills, managers often become the answer source for every problem. They delegate too much or too little detail, use the same approach with everyone, postpone difficult feedback, or solve problems their people need to learn to solve. Work rolls back uphill—and senior leaders remain more involved than they should be.
Leading One-to-One helps managers make the shift from solving problems themselves to building the judgment, confidence, and capability of the people they lead.
How the workshop changes the way managers work
The workshop is designed to change how managers respond when another person needs direction, support, feedback, or room to work.
Instead of...
Managers learn to...
delegating based mainly on who is available
match the task, the person, and the degree of freedom they provide
giving either too much direction or too little support
adjust their approach to the person's capability and the demands of the work
communicating with everyone in the way that comes most naturally to them
recognize work-style differences and adapt without becoming inauthentic
answering questions and solving problems for others
help people examine situations, think more clearly, and develop their own solutions
treating feedback as a verdict
examine what happened, agree on what needs to change, and build future capability
Over time, these practices can reduce the problems that roll upward, improve performance and follow-through, and free managers to focus on the work that most needs their attention.
A practical system for the one-to-one work of management
Leading One-to-One builds on the collaborative problem-solving foundation established in Leadership and the Middle Path. It gives managers a practical set of approaches for delegation, coaching, feedback, and development—so they can respond to the person and the situation rather than rely on a single default style.
Delegate with clarity and judgment
Managers learn to clarify the desired outcome—including what “goodness” looks like—and consider both what the work requires and who is best prepared to take it on. They then establish the right level of authority, support and follow-up.
Coach and support development without taking over
Managers learn to move intentionally along a helping continuum—from giving direction and teaching to asking questions and listening. They help people make sense of immediate problems, develop their own solutions and take greater ownership of their longer-term growth.
Adapt to the person and the situation
Using the DiSC work-style framework, managers become more aware of their own preferences and those of others. They learn to adjust their pace, emphasis, and communication while remaining clear about the work.
Give feedback that builds capability
Managers learn a structured process for examining what happened, separating observations from assumptions, understanding differing interpretations, and agreeing on what to do next. The approach helps them address concerns directly while involving the other person in making sense of the situation and shaping the way forward.
Managers build fluency through application and feedback
The workshop alternates between focused instruction and active application. Managers use each framework to work through realistic delegation, feedback, coaching, and development situations. They compare interpretations, test responses, rehearse important conversations, and receive direct feedback.
That cycle—learn, apply, reflect, and refine—continues throughout the workshop. For company cohorts, two small-group Mastery Sessions extend the cycle into work in the field, helping managers use the methods with greater judgment and fluency day to day.
The format supports that progression:
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Two full days when delivered in person; four half-days when delivered virtually
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Between-session application in the virtual format
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Each manager participates in two small-group Mastery Sessions, with the first held four to six weeks after the workshop​
Russ speaking about DiSC styles in San Francisco, CA
The second step in the Collaborative Leadership System
Leading One-to-One is the second workshop in the three-part Middle Path learning pathway. Russ Powell Consulting incorporates that pathway into the broader Collaborative Leadership System (CLS), which adds organizational alignment, workplace application, and follow-up Mastery Sessions.
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Leadership and the Middle Path establishes a shared approach to collaborative problem-solving, decision-making, agreements, and difficult conversations.
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Leading One-to-One applies that foundation to delegation, coaching, feedback, work-style differences, and individual development.
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Leading Teams extends the work to the dynamics and disciplines required to lead groups effectively.
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Leadership and the Middle Path is a prerequisite. Managers first learn to recognize their own assumptions and solve problems collaboratively; they then learn to help another person do the same. That progression prepares them for the more complex work of developing teams.
Within the full CLS engagement, workplace application and follow-up Mastery Sessions help managers continue developing the practices after each workshop.
Built for real management work
Leading One-to-One is part of the Middle Path curriculum, designed by Chris Holmberg of Middle Path Consulting and delivered by Russ Powell under license. The curriculum has been used with management teams in more than 160 technical startups and other organizations, including Fortune 100 companies, across 15 countries.
Russ Powell brings more than three decades of experience helping managers and teams improve how they work together and solve problems. He has facilitated this kind of work with hundreds of managers in dozens of technical startups and global organizations.
“I am a business owner who is growing my team, and I decided to hire Russ to help me sharpen my leadership skills. Working with Russ, I learned how to better manage my team, listen more actively, and be a better leader.”​
–Ashley Gomez, Founder
Digital Twinners
“If you get nothing else out of it, you're going to find out that there's a lot more going on in a person's conversation than what you might be hearing at that top level. And just building the awareness of what's going on in a conversation is gold.”
–Mary Anne Rasmussen, President
Rasmussen Consulting Group
Bring Leading One-to-One to your management team
The workshop can be delivered virtually or in person for managers who have completed Leadership and the Middle Path. Exercises can draw on the group's real delegation challenges, coaching opportunities, performance conversations, and work-style differences—building individual skill and a more consistent, effective way of leading people across the company.
Join an upcoming public workshop​
Individuals who have completed Leadership and the Middle Path can join selected public cohorts. The public workshops cover the same core curriculum for people whose organizations are not yet ready to bring the workshop to a full management team.
Next virtual workshop
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October 7, 8, 14, and 15, 2026 8:30 a.m.–1:00 p.m. (Pacific) each day • Live via Zoom
Upcoming in-person workshop
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Coming soon
8:30 a.m.–5:30 p.m. (Pacific)
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Check back soon and/or contact Russ regarding your interest.
Tuition: $2,250. A $500 deposit reserves your seat. Tuition includes a DiSC assessment and personalized profile, workshop materials, and one small-group Mastery Session four to six weeks later.
Early registration: $1,900 at least 60 days ahead; $2,050 at least 30 days ahead. Contact Russ for the applicable registration code.​​