Greg Crossan Coaching

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Greg Crossan Coaching I help people reduce stress and find the energy and skills they need to live at their peak.

Programs include 1x1and group coaching, leadership development, team workshops and trainings, individual and group assessments, keynotes.

10/04/2026

Early in my career I was afraid to hire people who knew more than me. Part of me didn't want to get shown up.

That fear held me back. A leader's job is to surround yourself with people stronger than you in their area, then connect their work to what the business needs. When I finally started hiring that way, the work got better and so did I.

Took me too long to learn it.

This is a clip from a conversation I had with Zara Muradali on the Unbillable podcast, out of the Uncommon Collective. More clips coming, full episode in October.

Looking to grow your business and build stronger referral relationships?Our BNI Biz Builders chapter is hosting a Networ...
09/08/2026

Looking to grow your business and build stronger referral relationships?

Our BNI Biz Builders chapter is hosting a Networking Happy Hour on Tuesday, September 22 from 5:00 to 8:00 PM at Hopothecary Ales in North Reading.

It’s a relaxed opportunity to meet local business professionals, and make some meaningful connections.

All business owners and professionals are welcome.

If you are looking to expand your network, or simply want to meet some great local professionals, I’d love to see you there.

📍 Hopothecary Ales Brewery and Kitchen, North Reading
📅 Tuesday, September 22
🕔 5:00 to 8:00 PM

Feel free to message me with any questions, or use the QR code on the flyer to RSVP.

06/18/2026

Congratulations Blaine Evans on your BNI Biz Builders Scholarship win! All of us at BNI Biz Builders wish you nothing but success as you begin your journey at UMass Amherst

05/04/2026

There is a moment in every senior tax career when the work changes.

You stop being the person who knows the answer and start being the person who decides which answers matter.

It is a quieter shift than most people expect. No promotion announces it. No training prepares you for it. One day you realize the team is looking at you for a decision, not for a memo.

This is the part nobody warned me about when I was coming up.

Technical mastery got me to the table. But once I was at the table, the questions changed. Should we wait on this position, or push? How do I tell the CFO something he does not want to hear without losing his trust? Why is the project I asked for sitting in someone else's queue, and what do I do about it?

None of those are tax questions. They are leadership questions, and they show up whether you have practiced them or not.

The leaders I know who navigate this well share one habit: they stopped trying to figure it out alone. They found a small circle of peers who understood the specific pressures of the role. Not mentors. Not bosses. Peers.

Because the work at this level is not lonely by accident. It is lonely by design. Most of us were promoted because we could carry it. So we keep carrying it.

You do not have to.

What changed for you when you stepped from being the expert to being the leader?

Frodo didn't carry the ring to Mordor alone… he had the Fellowship.But here's what makes that story so powerful:Frodo di...
04/21/2026

Frodo didn't carry the ring to Mordor alone… he had the Fellowship.
But here's what makes that story so powerful:
Frodo didn't need people who had all the answers.

He needed people who were willing to walk with him into uncertainty.

That's what tax and accounting leadership feels like right now.

The regulatory changes. The talent crisis. The pressure to always know what's next.

Fear-based leadership says: "I should have this figured out by now."

But the leaders who are actually thriving? They've stopped trying to carry it alone.

They've built their fellowship, a trusted circle where they can:
• Admit what they don't know
• Test decisions before making them
• Lead with confidence because they're not isolated

That's the Meridian Leadership Collective.

Because leadership should not be lonely.

If you're ready to stop going it alone, let's talk.
Comment "Meridian" or DM me to book a 20-minute discovery call.

A lot of people avoid asking for clarity because they do not want to sound difficult.But if your manager is not communic...
02/06/2026

A lot of people avoid asking for clarity because they do not want to sound difficult.
But if your manager is not communicating expectations, waiting does not create clarity. It creates guessing.

Here is a script you can use that stays calm and professional:
“I want to make sure I’m operating at the right level and focusing on the right outcomes. I drafted a one-page role charter so we can confirm priorities, decision rights, and escalation criteria. Can we spend 20 minutes aligning on it?”

That one conversation can change a lot.

I explain the full role charter and give examples in this article:
https://gregcrossan.com/blog/role-charter-when-your-boss-is-unclear

Quick test.If you cannot answer these clearly, you are probably operating without role clarity:* What outcomes do I own?...
02/05/2026

Quick test.
If you cannot answer these clearly, you are probably operating without role clarity:
* What outcomes do I own?
* What decisions can I make versus recommend versus escalate?
* What does good look like in my lane?

When those answers are unclear, you end up guessing. And guessing creates stress, rework, and decision pileups.

A role charter is not a job description. It is a one-page working agreement that makes expectations visible.

In today’s article, I share a simple structure you can use right away:
1. Outcomes I Own
2. Decision Rights
3. What good looks like
4. Communication cadence
5. What I need from my manager

Read the full article here: https://gregcrossan.com/blog/role-charter-when-your-boss-is-unclear

How many work days feel like this?Not because you can't handle the work. Not because you're not capable.But because the ...
02/03/2026

How many work days feel like this?

Not because you can't handle the work.
Not because you're not capable.
But because the cart keeps getting heavier while expectations stay unclear.

When roles expand and standards are high, most people respond the same way. They step in. They over-check. They stay close to decisions so nothing breaks.
It looks like ownership. It often gets praised. And it quietly turns into overload.

A simple reset is a one-page role charter:
- What you own
- What decisions you can make versus recommend versus escalate
- What good looks like
- How you will stay aligned with your manager

If you want the structure and the script, I wrote it up here:
https://gregcrossan.com/blog/role-charter-when-your-boss-is-unclear

If it feels like everything is landing on your desk, you are not imagining it.Decisions route to you. Drafts come back t...
02/03/2026

If it feels like everything is landing on your desk, you are not imagining it.
Decisions route to you. Drafts come back to you. Risk gets parked with you. People wait for you to interpret what leadership really wants.

This is rarely just a workload problem.

Most of the time, it is a clarity problem.

When expectations are unclear, high performers do what they have always done. They step in, over-check, and stay close to every decision to protect quality. It looks like ownership. It often gets praised. And it quietly turns you into the default decision maker.

If this sounds familiar, I wrote a Crossan’s Corner edition on a simple fix: a one-page role charter that defines what you own, how decisions get made, and what gets escalated.

Read it here: https://gregcrossan.com/blog/role-charter-when-your-boss-is-unclear

Imposter syndrome gets stronger in isolation.It gets weaker in collaboration.Small business owners feel this because the...
01/31/2026

Imposter syndrome gets stronger in isolation.
It gets weaker in collaboration.

Small business owners feel this because they have to make a lot of decisions alone.
CPAs feel this because the profession can reward people who look like they know everything, even when no one can.

The result is predictable. People overwork, over research, hesitate, and carry stress quietly.

Real confidence is not pretending you know.
It is knowing how to handle uncertainty with professionalism.

I wrote this newsletter to help you do that with a simple diagnostic and practical language you can use right away.

Read it here: https://www.linkedin.com/newsletters/crossan-s-corner-7317527723461992448/

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