I'm Now Coaching in 2 Leadership Masterminds

The Case for Both Tactical and Long-Term Leadership Learning Communities

tldr - I’m coaching weekly in a sales/growth Mastermind for agency owners, and monthly with the Timeless Leader Basecamp. The two combined represent a potent recipe for leadership development and creating impact short and long-term.

Read time: 5 minutes

Hi Timeless Leaders,

Over the past six weeks, I've had the privilege of facilitating leadership growth within two different but powerful Mastermind groups.

While I spend most of my time right now as a Fractional Chief of Staff for Edstruments¹, I’ve paired that with more “scalable” support for leaders. This includes this Substack, as well as working as a coach and facilitator in two different leadership groups - the AB Mastermind and the Timeless Leader Basecamp.

When run well and joined voluntarily, purposeful discussion groups are a uniquely human experience that aids in growth and transformation. Photo by Antenna on Unsplash

The unique combination of working in the AB Mastermind (a group focused on cold email and business growth) and the TL Basecamp has also reinforced a key lesson: every leader can benefit from at least two types of Mastermind groups:

1. A tactical group that focuses on achieving near term organizational goals, through daily practices and decisions unique to a specific role or industry

2. A strategic group that focuses on the longview, helping you refine your vision and values, perform in different roles, and build an impact portfolio.

This week, I want to introduce these two styles of Mastermind group to you, because I think all leaders can benefit from resources like this. It’s not just me saying it: research shows that peer learning communities don't just feel good—they get measurable results. For example, in one a meta-analysis by Vescio, Ross, and Adams (2008)² they found that professional learning communities had direct positive impacts on both practices and performance outcomes for teachers and students.

What I’ve found is that leaders love Mastermind groups because they offer multiple different mechanisms to efficiently work through a challenge, while picking up additional value (coaching practice, new case studies, peer connections) simultaneously.

Should you join either of these specific groups I’m writing about here? I can’t say for sure - but I can say that it’s worth the investment to make sure you have some sort of answer to both the tactical and strategic Mastermind.

Let’s take a look at the two examples I’m part of.

Tactical Masterminds: Your Weekly Problem-Solving Machine

Alex Berman³ is a well known “Cold Email” expert, who launched a private Mastermind last year to support agency owners master cold email and several other adjacent skills. After taking his online course called “The Baking Method” (about how to cold email prospects for up to a year and eventually win their business), I decided to give his Mastermind a try. After a few months I saw a need to help other members work through some of the foundational issues of their offer design, and I pitched Alex on adding new coaching call to the rotation - with me as the coach. Alex agreed.

Alex and his wife Kritika like to travel around with their young son and share their stories online, and it’s been fun to get to known them beyond Cold Email since we started working together last year.

So six weeks ago I started leading these calls, and have already helped 15 agency owners and GTM leaders through short- and medium-term business challenges like:

• How to differentiate services in a crowded market

• How to price and tier service offerings to balance revenue growth and profitability

• How to create offerings that build trust with people who have never heard of you

These tactical discussions get at the heart of the business, and provide members with actionable ideas to test and implement the same day. My weekly call combines with calls lead by a sales and marketing experts who help with other growth challenges - and I join these for myself and my clients whenever I need help (which I do, because I do a lot of cold email ⛄️).

What sort of daily challenges do you face in your work - and do you have a place you can routinely go to talk with peers and coaches without looking over your shoulder?

If you don’t, you might want to look for a Tactical Mastermind.

Strategic Masterminds: Building Your Legacy GPS

Meanwhile, the Timeless Leader Basecamp serves a completely different purpose.

In our second monthly session last week, members weren't debating conversion metrics—they were wrestling with questions like:

• "How do I build bridges across organizations that are all trying to mobilize around similar goals, but with different messages?"

• "How do I restructure my business to speak to the new priorities of large corporations that are floundering in the current tech, regulatory, and political climate?"

We grappled with these sorts of questions in breakouts, and as a whole group we workshopped one member’s specific challenge. We also discuss the Timeless Leader Oath, and each member selected a principle from the the list I published last week to focus on for the coming month.

As one member shared afterward, it “was so good. [I] really liked it… So much shared struggle and aspiration across the cohort.”

These conversations are monthly because our legacy is built over a long term. We pace things out, because we’re not trying to burn ourselves out… and we need to reserve space for the tactical work in between.

Ok, but what makes a good Mastermind, whether it’s Tactical or Strategic?

Good question…

Fundamentals of Good Peer Learning Groups

Parker, Hall, Kram, and Wasserman (2018)⁴ found that peer coaching creates "a focused relationship between equals who supportively learn from, actively listen to, and judiciously question each other," unlocking breakthroughs that might otherwise stay dormant.

Similarly, studies from higher education⁵ suggest peer leadership communities enhancing everything from communication skills to critical thinking to working with diverse perspectives. Adam Grant also talks about peer teaching (or the “Tutor Effect”) as a particularly effective way for learners to grow together.⁶

Grant introduces the Tutor Effect with the story of the “Golden 13” - the 13 African-American men who were the first of their race to be commissioned as officers in the United States Navy in 1944. They achieve this while overcoming intense training demands only because they worked together in a sort of Mastermind - they strategically divided up the work and taught, tutored, and coached each other to excellence.

For my part, I’ve found from years of experience with learning communities that the following components contribute significantly to participant’s success:

1. Regular rhythms - Calendared sessions that create accountability

2. Diverse yet focused participants - Different contexts, similar challenges, same buy-in

3. Structured, collaborative problem-solving - clear teaching and learning practices with an outcome orientation

4. Clear time horizons - intentional focus on specific deadlines, events, and cycles

If we’re lucky, we have many kinds of communities we’re part of that add value to our lives. From professional associations to alumni networks, religious groups to neighborhood gatherings, sports teams to parent-teacher organizations - we can get a lot done and have fun when we gather together. That said, nothing supports leadership growth like the right kind of Mastermind groups.

Do you have a good Mastermind story - that fits the pattern above, or breaks it?

This Week's Recommendation

Take a moment to reflect on your current group memberships and leadership development resources. Do you have Mastermind groups in the mix? In particular, ask yourself -

1. Where do I go to talk with peers and coaches about immediate, tactical execution of my work?

2. Where do I go to talk about my long-term impact, vision, and portfolio of commitments… and how that connects back to my daily leadership practice?

If the answers to either of these questions leaves you feeling unsatisfied, you might make a point to look into some new or improved Mastermind group options.

Finally, remember not to be a lone hero. The mark of leadership maturity isn't self-sufficiency—it's collaboration.

Mindfully yours,

-Joe

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PS. If you're in agency work or focusing on outbound sales, consider exploring the AB Mastermind led by Alex Berman. It's a powerhouse of GTM strategies and tactical problem-solving (and includes offer design coaching with yours-truly), but at $497/month it’s meant for folks who are serious about these topics.

PPS. If you're looking for a group that helps align your leadership practices with lasting impact and values, consider upgrading your subscription to this newsletter (for just $97/year!) and you’ll be added to the Timeless Leader Basecamp - we meet on the first Thursday of every month, and have a private chat group as well.

1. https://edstruments.com/

2. Meta-analysis of peer learning communities.

3. Alex Berman’s website.

4. Peer Coaching at Work.

5. 2012 New Directions for Higher Ed - Special Edition on Peer Leadership. (paywalled)

6. Adam Grant’s Hidden Potential.