• The October Group

When leadership changes, a deal closes, or growth stalls, your team either gets more aligned or quietly comes apart.

We help you make sure it's the first one. Executive alignment work for the specific moments that decide whether a strategy holds.

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Leaders from these companies trust us
• Who This Is For

The moments that actually matter

Most of our clients come to us at one of four specific moments — not because things are broadly bad, but because one of these is happening right now.

New Leadership

A new CEO, founder stepping into an enterprise role, or leader inheriting a team they didn't build.

M&A & Integration

A merger, acquisition, or private equity transition where two teams need to become one, fast.

Board-Mandated Reset

A board or investor demanding a new strategic direction, and a leadership team that has to move on it now.

Stalled Growth

Everyone's working harder, and the results still aren't compounding the way they should.

• Our Services

How we help, depending on where you are

Executive Experiences

Executive Experiences

For leadership teams navigating a high-stakes moment — a merger, a new CEO, a board-mandated pivot — we design offsites and facilitated sessions that surface the real disagreement in the room instead of letting it stay unspoken. You leave with actual decisions made, not just a good conversation.

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Executive Performance

Executive Performance

For leaders stepping into a role they didn't have a year ago — through promotion, acquisition, or succession — we work one-on-one or with the full team to close the specific gap between the authority they now hold and the credibility they haven't built yet.

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Strategic Planning

Strategic Planning

For teams facing real uncertainty — a market shift, a merger integration, a strategy that isn't translating into execution — we build a plan the team can actually run on. You'll walk away with a clear answer to what matters most, and clear ownership of who decides what.

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Start Here

The Executive Alignment Diagnostic

Five minutes, fifteen questions. See exactly where your leadership team has real momentum and where friction is quietly building — before it shows up in your numbers. I review every result personally.

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Your score
61/100
Friction building
Strategy clarity
Decision rights
Leadership alignment

Three steps, start to finish

1

Book a Consultation with Philipia

A direct conversation about what's actually driving the need right now. Complimentary, and focused entirely on your specific situation.

2

We Scope the Right Engagement

Based on that conversation, we recommend the service that fits, and build a plan sequenced around your specific trigger.

3

The Work Begins

Sequenced around the real event driving the need — a leadership change, a deal, a board mandate, a growth plateau.

Want a quick read before you talk with us? The Executive Alignment Diagnostic is a free five-minute assessment across five key areas — a helpful starting point, entirely optional.

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• Our Guiding Values

What we hold to in every engagement

Partnership

We believe in the power of our partnerships to bring out the best in our clients, colleagues, and communities.

Imagination

We believe in changing the questions to find the best answers.

Growth

We believe human flourishing comes from a growth mindset, inside and out.

Imperfection

We believe that embracing imperfection leads to freedom and creativity.

Joy

We bring the energy to spark joy in all we do.

• How It Works
• What Clients Say

Leaders who've done the work

Dr. Hillman and The October Group came in and equipped us with the skills that allowed us to grow as an organization, provided us with a very helpful strategy, and overall exceeded our expectations.

Romal Tune
Romal Tune
Vice President

I couldn't be more grateful to have had your partnership and thought leadership in developing leadership cultures and high performing teams! Congrats on building a thriving business valued by so many!

John Reing
John Reing
Strategic HR Executive

If you're a young leader trying to figure out how to grow that conversation of leadership in your team and trying to scale your business beyond what your wildest imaginations could be, The October Group will put that in perspective for you.

Alex Mwai
Alex Mwai
Director

At a critical growth moment, The October Group partnered with us to clarify our strategy, align our leadership team through quarterly sessions, and coach key executives. They helped us grow with purpose, coherence and confidence as we moved toward our collective North Star.

Sarah TeDesco
Sarah TeDesco
Chief Customer Officer
• Your Questions, Answered

From time constraints to ROI worries, we've heard the hesitation

How do I know this will deliver ROI?
Every engagement starts with the Executive Alignment Diagnostic, so we're working from real data about where your team actually stands, not assumptions. From there, we set specific outcomes together before any work begins, and measure progress against those, not just how the sessions felt.
We already do leadership training internally.
Good — that's not what this replaces. Internal training usually builds individual skill. We work on how your leadership team operates together, especially during a specific high-stakes moment like a merger, a leadership change, or a stalled growth period. Different problem, different fix.
I don't want coaching to make me look weak.
The leaders who come to us are usually the ones already performing well, who want to close a specific gap before it becomes visible to their board or their team. Asking a sharper question early is what strong leaders do. Waiting until it's a visible problem is the actual risk.
We've tried this before, and it didn't work.
Tell us what you tried. Most failed attempts we hear about were generic leadership development, not built around the specific transition the team was actually in. We start with a real diagnostic of your specific situation, not a standard program applied to a different problem.
Will this process take too long?
The Diagnostic takes five minutes. The first consultation is a single conversation. From there, the timeline depends on what we find, but we're not interested in a long engagement for its own sake. We move at the pace your actual situation requires.
What if my team resists?
That resistance is usually a signal, not a problem. A team that pushes back on a moment of real assessment is often the exact team quietly pulling in different directions once the meeting ends. We're not there to expose anyone. We're there to help everyone actually say what they think, instead of just agreeing out loud.
We need results, not therapy.
Agreed. This isn't a space for processing feelings — it's a space for making decisions your team can actually execute on. Every engagement ends with clear ownership: who decides what, and what happens next. That's the deliverable.
What makes The October Group different?
We work with leadership teams at the exact moment it matters most, not on a general leadership development calendar — a new CEO, a deal that just closed, a board demanding a reset, growth that's stalled. That specificity is the whole model.

Ready to take your business to the next level?

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