Business Justification for Chief of Staff Mastermind Groups

Here’s a draft letter to your executive sponsor, with some suggested talking points and ROI verbiage (just add your own math!), for you to edit and make your own.

Dear <Executive Sponsor>,

As part of my development in the chief of staff role, I have an opportunity to participate in a chief of staff Mastermind Group, a year-long learning cohort (3 in-person workshops, bi-weekly video calls) that combines the power of chief of staff-specific training, group and 1:1 coaching, and peer advisory to take my performance and career to the next level.

It’s hosted by the world’s leading researcher on the chief of staff role, Tyler Parris, an executive coach, author, and former corporate chief of staff who’s been featured in MSNBC, The Washington Post, Chief Executive Magazine, SHRM’s HR Magazine, the One Accord Partners newsletter, and other outlets.

The Chief of Staff Mastermind Group will connect me to tools, frameworks, models, resources, and experts that will help us excel as a chief of staff-executive tandem. And, it’s extended by personalized coaching that enables me to craft experiments, learn, and iterate.

The price is $5,250, but I can attend for $4,600 if I can get your approval for the expenditure by <date>. I expect this investment will more than pay for itself in short order because my participation in this community will help:

  • Achieve/accelerate $X revenue by… <pick and choose sample verbiage below>
  • Achieve/accelerate $Y opex savings by…<pick and choose sample verbiage below>
  • Improve the culture or employee engagement by…<pick and choose sample verbiage below>


I await your approval of this expenditure by <date>.


<Your Name>


From the sample value prop/ROI statements below, do the math for your organization to show the return if you fixed these problems/took your/your exec’s game to the next level, then copy/paste it above:

If you’re struggling with role clarity:

  • 9 months is the average time to chief of staff role clarity. That’s a long time for confusion among staff about who’s doing what, and it diminishes the principal exec’s credibility. What if we could shorten that to 3 months? What is the cost (in terms of time, $, or your exec’s reputation) of any ambiguity about the CoS role and how the leadership team interact with me?
  • The Mastermind Group will help us revisit key assumptions about my role and highlight additional areas where I can add value, and equip us with tools for communicating about the role, setting expectations, and enforcing boundaries.

If you’re struggling with misalignment:

  • What is the opex savings of having better alignment of working teams to high level strategic priorities (vertical alignment) and to each other (horizontal alignment) in your organization?
  • The Mastermind Group will explore best practices and tools for starting with and maintaining alignment vertically from highest-level strategic priorities to tactical projects that drive them and horizontally across departments.

If you’re struggling with conflict among the leadership team (including you, your executive, staff):

  • 4 hours/week is the average # of hours chiefs of staff report dealing with conflict at the LT level (the average American worker spends 2.8 hours/week). How much time do your leadership team or key influencers in the organization spend in conflict?
  • “That’s a lot of time spent gossiping, protecting turf, retaliating, recruiting people to one side or the other, planning defenses and navigating the drama. More importantly, that’s time not spent answering customer questions, filling orders or doing the job employees were hired to do.” – Jennifer Lawler, “The Real Cost of Workplace Conflict,”
  • The Mastermind Group provides a framework for managing conflict before it starts, but also once it’s already in play. If you could reduce the amount of time in unhealthy conflict (in terms of LT time, their estimated hourly pay, or reduced turnover due to conflict), how much is it worth to your organization?

If you’re struggling with people spending too much time in wasteful meetings:

  • Have you found what Satya Nadella recently discovered –  that when he set up a review meeting, there were at least 5 pre-meeting review meetings among various people in the organization before he saw anything? Or do your LT meetings consist of round robin info-sharing updates? What is the cost to your organization every time you meet? In direct costs (even a guestimate avg hourly pay of those in the room)? Opportunity costs?
  • The Mastermind Group provides a framework for better managing meetings by starting with an effective rhythm of business that intentionally and systematically determines the kinds of meetings needed to drive key outcomes, and looks in depth at those kinds of meetings and how they affect preparation, materials, the running of the meeting, and follow up. Using LT meetings to wrestle through obstacles, challenges, or conflict about issues that are keeping initiatives from moving forward – and sharing status and general information elsewhere – translates into opex savings or revenue generated from programs delivered on time and on budget or reaching customers more quickly.

If you’re struggling with resistance to your executive’s agenda or vision, or your executive’s resistance to good grassroots ideas from within the organization:

  • How much more could you and your exec get done if you were a masterful change agent? You can save months getting buy-in from key leaders up front rather than someone dictating or requesting a change only to have people resist, then having to reverse-engineer why they’re resisting, etc.
  • The Mastermind Group will up-level your skills in influencing, intentionally building strategic relationships, and getting the team (or you, the executive) past resistance faster to needed changes.

If you’re struggling with negative surprises that you or your exec didn’t see coming:

  • One study showed that 38% of CEOs reported being blindsided by a negative surprise in the past 90 days. CEO dismissals are at a near-historic high, and “I didn’t know this was going on in my organization, or I can’t know everything” isn’t a great defense.
  • The Mastermind Group will explore ways to systematically set up early warning systems, through dashboards, triggers, and relationships. Don’t lose your job or credibility. Be prepared!

If you’re struggling to keep up with real-time events or technological disruption:

  • There might not be best practices for certain things because everyone’s just realizing the consequences (intentional or unintended) of the latest development.
  • The Mastermind Group provides space to create responses, test, iterate, and apply back at the office with others in similar situations.



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