BUILD CAPABILITY, NOT DEPENDENCY
Leading One-to-One
Give managers practical tools for delegating effectively, adapting to different work styles, coaching others, and developing people who can solve problems—independently and collaboratively.
Leading One-to-One is an intensive, practice-based workshop that helps managers get better results through others. Building on Leadership and the Middle Path, it helps managers move beyond being the go-to problem-solvers and become more effective at developing the judgment, confidence, and independence of the people they lead.
The result: more capable employees, stronger working relationships, and managers who can focus their attention where it adds the most value.
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.
You may see it when:
-
Managers become the answer source for every problem.
-
Delegation involves either too much direction or too little support.
-
Managers use the same approach with everyone, regardless of their experience or needs.
-
Difficult feedback gets postponed or avoided.
-
Managers solve problems their people could be learning to solve themselves.
The result? Work rolls back uphill, employees remain unnecessarily dependent on their managers, and senior leaders get pulled into problems that could reasonably be solved elsewhere.
Leading One-to-One helps managers 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 on availability
match the task, the person, and the degree of freedom they provide
giving too much or too little direction
adjust their approach to the person's capability and the demands of the work
communicating the same way with everyone
adapt to different work styles
solving other people's problems
help people develop their own solutions
treating feedback as a verdict
examine what happened and agree on a way forward
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
Building on Leadership and the Middle Path, this workshop gives managers practical approaches to four essential responsibilities: delegation, coaching, adapting to different work styles, and providing feedback that builds capability.
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.
“As a result of working with Russ, our leadership skills have tangibly improved. We've achieved a stronger team dynamic and a more effective approach to problem-solving.”
–John LaGue, COO
trainwell
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:
-
Two full days when delivered in person; four half-days when delivered virtually
-
Between-session application in the virtual format
-
Each manager participates in two small-group Mastery Sessions, with the first held four to six weeks after the workshop
The second step in the Collaborative Leadership System
Leading One-to-One builds on the foundation established in Leadership and the Middle Path, where managers learn a shared approach to solving problems, making decisions, reaching agreements, and navigating difficult conversations.
Here, managers learn to apply those same principles when coaching, delegating, providing feedback, and developing others.
Leading Teams, the third workshop, extends these skills to managing groups and teams.
Prerequisite: Participants must complete Leadership and the Middle Path before attending Leading One-to-One.
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.
“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
For groups of six or more, 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.
Upcoming in-person workshop
March 17-18, 2027
8:30 a.m.–5:30 p.m. (Pacific)
San Rafael, CA
Next virtual workshop
Nov 9, 10, 16 and 17, 2027
8:30 a.m.–1:00 p.m. (Pacific) each day • Live via Zoom
Tuition for either format
Register 60+ days in advance
Register 30-59 days in advance
Standard tuition within 30 days
Leading One-to-One (in-person, two full days)
Leading One-to-One (virtual, four half days)
$1,950 USD
$2,100 USD
$2,250 USD
$1,950 USD
$2,100 USD
$2,250 USD
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.
How it works: Register early and save. Contact Russ for discount codes and/or questions.
Help managers bring out more of the capability around them
Leading One-to-One helps managers delegate more effectively, develop more capable and independent employees, and spend less time solving problems others can learn to solve.
If that would help your managers—and your organization—let's talk.