Tuesday, November 03, 2026
You've run the numbers four times and still haven't decided. It's not the decision that's the problem — it's that you're making it with no one to pressure-test your thinking.
The decision's been sitting in your head for two weeks. Hire the second person, or hold. Take the lease, or wait another quarter. Say yes to the big client, or protect the team you've already got. You've run the numbers four times. You still haven't said the real version of how stuck you feel on it to anyone.
If you're wondering why a strategic decision in a small business can drag on for weeks when a similar call at a big company gets made in a single meeting, this is usually why. It's not the decision itself. It's that you're making it with no one in the room to push back on your thinking.
There's a quiet myth in small business that strategic thinking is a solo skill — that a good owner should simply be able to weigh the options and know. But no leader in a business of any real size makes the big calls alone. There's a board, an exec team, a creative director down the hall who says "that won't work and here's why." In a five-person business, you're often the only person in that room.
It costs more than it looks like. In the United States in 2026, 43% of small business owners admitted they'd hidden business stress from a partner or family member — not because the stress wasn't real, but because saying it out loud felt like admitting they couldn't handle it (Xero Emotional Tax Return 2026, via CPA Practice Advisor). Carrying the decision alone and hiding how heavy it feels tend to be the same habit.
After more than 30 years building and running businesses, I hired my own Icehouse coach — not because I didn't know what I was doing, but because every decision gets sharper when someone outside it is allowed to ask the annoying question. That's the whole value. Not answers. A second mind in the room that isn't attached to being right.
You don't need a coach by 9am tomorrow to get some of that benefit. Here's where to start:
"Talking with Kevin the first time was so valuable and we were learning so much. Within an hour Kevin had us thinking about our business and our goals in a totally different way. In fact we were supposed to be catching a flight but we decided it was more important that we continued the meeting with Kevin."
— Angus and Cameron, Flatpack Co
Most owners already suspect a second opinion would help. They don't ask for one, because asking can feel like admitting they can't handle the business they built. It's the opposite. A coach's entire job is to be the person in the room your business doesn't currently have — the one who's allowed to say "walk me through why" without an agenda of their own.
This isn't for you if you've already got a strong board, a trusted CFO or a leadership team who argue with you properly. If that's you, you've solved this. If it isn't, that's the gap worth closing.
You don't need to become braver to make this decision well. You need someone in the room. That's the whole fix — and it's available to you this week, not someday.
Be the owner who makes the biggest calls with someone in the room who will ask the annoying question.
If the last three decisions you made alone took twice as long as they should have, that's the first thing Kevin will work on with you.
Thursday, October 22, 2026
Roughly one in four founders report loneliness and isolation running their business. Here's what a coach actually does differently, and why the first session is rarely about strategy.
Thursday, October 22, 2026
NZ small business sales rose 8.6 percent this quarter, but growth ranged from 2.9 to 16.3 percent by industry. Here's the three-number check that tells you whether your growth is actually yours.
Thursday, October 22, 2026
Only 30 percent of business change efforts fully succeed. Here's the three-part diagnosis, borrowed from strategy academic Richard Rumelt, most owners skip before fixing anything.
Thursday, October 22, 2026
Close to six in ten of this year's US holiday shoppers are already buying, in October or year-round. Here are three sales moves to make this week before Black Friday arrives.
Thursday, October 22, 2026
77.6 percent of US consumers used AI to help with a purchase decision in the past six months. Here are three moves that make your small business visible when customers ask AI about you.
Thursday, October 22, 2026
54 percent of US business owners have no real plan, and only 11 percent have anything detailed. Here's the one-afternoon exercise that gives your business a sharper three-year direction than any spreadsheet.
Wednesday, October 21, 2026
Before you spend another dollar on ads, staff or software, find the one step that limits your growth. Here is a one-hour spend-gate test you can run this week.
Wednesday, October 21, 2026
ActionCOACH began in Brisbane, Australia. What does its story tell US owners about where good growth ideas come from, and how to test an outside idea in your own business?
Wednesday, October 21, 2026
SME owner confidence is climbing, but for most, revenue isn't following. Here's why time isn't your real constraint, and the three-step framework that finds the one that is.
Wednesday, October 21, 2026
49% of business owners question monthly whether running the business is worth it, a US survey found. Here's what changes when someone else is asking that question with you.
Wednesday, October 21, 2026
Nearly half of NZ SME owners are planning Christmas trading changes, MYOB research found, and most of it is a discount. Here's how to build memory before you build the offer.
Wednesday, October 21, 2026
46% of New Zealand business owners aren't paying themselves, Xero research found. Here's the Profit First fix that changes the order money moves through your business, not the hours you work.
Wednesday, October 21, 2026
The share of businesses reporting serious dead stock has doubled since 2024, new research found. Here's why rising revenue can still mean tightening cash, and the three numbers that catch it early.
Wednesday, October 21, 2026
42% of business owners named efficiency their top 2026 priority, a US survey found. Here's Michalowicz's Clockwork system for building a business that doesn't need you in every decision.
Wednesday, October 21, 2026
B2B win rates fell to 19-21% in 2025. Here's why a quiet Q4 pipeline is usually a budget deadline in disguise, and the three moves that use it instead of waiting for January.