Structured 1:1 Best Boss Coaching

The program embodies the methodology I developed over the past 13 years for turning ordinary people into extraordinary leaders.

I’ll teach and coach you to effectively build trust and loyalty with your direct reports, and to effectively require (even demand) results, excellence and growth in the context of a highly trusting relationship.

26-Week Coaching Program Delivers Tailored Professional Development

Best Boss 26-Week 1:1 Structured Coaching is an intense, hands-on learning and growth experience that guides you through the steps of growing your leadership skills, abilities, and instincts. You’ll lead your team to achieve breakthrough results.


This coaching engagement takes you from where you are now to your next level, along the path toward Becoming a Best Boss. You become an ever more effective leader of yourself and your team — morale, performance, and capacity all increase. You’ll become increasingly able to show, teach and coach your own directs how to lead, cascading the improvements throughout your organization.

What is a Best Boss

Ask 100 people who their “best boss ever” was, and what that person did that was special. Their answers will all fall into two buckets: “kept me safe” and “made me grow.”

Safe means safe to admit a mistake, to try something new, to challenge the group, to ask for help.

Grow includes demanding their best, asking for rework when needed, and giving them stretch assignments during the ‘sweet spot’ period after they’ve developed a skill but before they feel comfortable with the skill.

Most managers can do one or the other. Some can do both for about 1/3 of their directs. Very few can do both — keep ’em safe and make ’em grow — with 100% of their directs 90% of the time.

Outcomes and Objectives

In our first week, we agree on goals for your coaching. We establish an ROI — this should be at least 5x the coaching fee. (See ROI section below.)

We’ll start any needed assessments or profiles of you during this week, including the Best Boss 360-Degree Assessment.

Each week we will review your results from last week, and set you up for your next area of growth and deliberate practice. By the end you will have been coached and guided to achieve whichever of these you most need:

Level 1: Know Thyself

  • Overcome your self-limiting beliefs, behaviors and patterns, and create and use systems for optimal time and self management. Includes any of the following as needed:
    • Time Management and Task Management
    • Self Management and Self Optimization
    • Block Clearing

Level 2: Grow Thyself

  • Show up as ever more calm, reslient, and unflappable, creating a zone of emotional safety that attracts others, and enables greater team trust. Includes any of the following as needed:
    • Emotional Intelligence training, practice and drills
    • Empathy exercises and Resiliance routines
    • The Language of Emotions

Level 3: Inspire Loyalty

  • Inspire ever greater levels of loyalty among your directs, boosting retention and making recruiting easy. Includes as-needed tools and training on:
    • How to inspire change and create a shared vision
    • How to tap the existing, unique internal motivations of each direct
    • How to create high psychological safety for your team
    • How to create a detailed map of your directs’ unique strengths, weaknesses, goals, needs, and growth path
    • How to grow your professional network like the best senior executives

Level 4: Demand Excellence

  • Require excellence from others and yourself in ways that make your directs want to give you their very best, and spurs them to grow and contribute at higher levels. Includes as-needed tools and training on:
    • Coaching your directs for performance and growth
    • Holding high performance meetings
    • Leading Kaizen improvement events
    • Engaging in positive conflict
    • Delegating effectively without micromanaging or abdicating


  • Role: You have direct reports, and thus you have positional power.
  • Values: You’re committed to mastering your craft as a leader and manager. You’re committed to self-improvement and lifelong learning. You feel a moral obligation to discharge your positional power with great responsibility. You resonate with the idea of “servant leadership.”
  • Technology: You have a phone. You have a computer or tablet that can run Skype or Google Hangouts, and you have an Internet connection.

Delivery Method

Phone or video conference calls between you and me. You’ll also receive all the Becoming a Best Boss systems, forms, templates, ebooks, sample protocols and workbooks for engaging with your followers day by day. You won’t get a data dump — each tool will be taught precisely when you need it, based on your unique leadership journey.

Price, how paid, terms

You pay $4,800 for 26 weeks (6 months), paid in advance (get a 5% discount) or two installments, half in advance and half within the first 45 days. I accept business checks in US dollars drawn on US banks, and major credit cards.


Duration, frequency

26 weekly 1:1 coaching calls, customized to your unique needs, 45 minutes each, plus check-ins as needed.

How It Works

We talk (on the phone or by video conference) each week at a scheduled date and time for 45 minutes:

  • You report on results since the last call;
  • we review your progress toward your goals; and
  • you get timely training on the next tool, or
  • we go deeper on the tool you’re currently mastering. Then,
  • we end with your next steps clearly laid out.

Since your leadership coaching assignments involve you working on your work (unlike MBA class that has you working on canned scenarios), your homework doesn’t take “extra” time. It takes about the same time you were going to take, doing the same work you were going to do anyway. Only now, you do it better, and soon you’ll do it better and faster.

Throughout the week we exchange emails, texts, Slack messages, etc. as needed. You reach out to me me any time for quick check-ins on anything urgent (a direct is melting down; a client is freaking out; your boss is on the warpath) where you want help getting centered and prepared.

Monthly, we do a progress check to ensure you’re on track with your bigger goals, including your coaching ROI target, and optionally you’ll report that progress to your boss, if that’s our arrangement.

My coaching arrangement is with you, the coachee. Even if your firm is paying, my accountability and confidentiality are with you — and you’re the one who remains answerable to your firm.

Return on Coaching Investment

How do we establish ROI for Coaching?

Simply, results flow from behaviors, and behaviors flow from motivation, skills, beliefs, and habits. You — like every leader — exert profound influence on the results of your directs individually, and on the whole team.  By establishing an ROI target up front, we force ourselves to hone in on the most important leadership behaviors, skills, beliefs and habits that you and I will target during your coaching.

I won’t engage with you unless we both agree that the realistic, measurable ROI of successful coaching is at least 5x the fee you pay.

Ready to Act?

Call me directly right now: dial 503-516-3886 and say you want to discuss the ROI of Best Boss Coaching.

Or, take your own Best Boss self-assessment here, or read more about the Becoming a Best Boss System here.