Quick Hits

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2. 😩Decline in Small Business Confidence: The National Federation of Independent Business (NFIB) reported a significant drop in its Small Business Optimism Index for March 2025, marking the third consecutive monthly decline.

3. 🌦️Impact of Tariffs on Small Businesses: Small business owners expressed significant concerns over new tariffs imposed by the Trump administration.

Deep Dive: The Meetings Are Too Damn Long

Why You're Wasting Time in Planning Hell

Let's be honest about something: Most business planning methodologies are bloated, inefficient time-sucks that make you want to cancel your next quarterly.

Two full days for annual planning? A full day every quarter? Come on.

I'm a fan of business planning. Really, I am. But the current approach is like saying your workout needs to be three hours long to be effective. What happens?

You never go to the gym.

The Coaching Business Model Problem

Part of this is just the business model of coaching. More hours equals more pay. While coaches don’t always charge by the hour, it’s hard to charge a lot for a meeting that doesn’t last that long.

Even if that’s the optimal solution.

I don't want to be completely cynical here, but there's definitely an element of that.

The bigger problem, though, is that these marathon sessions create a massive barrier to actually doing any planning at all.

So instead of imperfect planning, you get no planning. Instead of a shorter session, you get nothing.

I also find that the quality of the planning suffers the longer the session goes on. All of us know that feeling when you are finally planning your yearly or quarterly initiatives at the end of day-long or two-day session. You’re exhausted and it’s guaranteed the team isn’t operating with its A-game at that point.

AI Pre-Work Is Your Secret Weapon

Here's my approach:

Much of what happens in those mind-numbing planning sessions can be done before anyone walks into the room. That was always true but AI has now super powered that process and made it much easier.

Here are five things you can do to prepare for a quarterly or annual meeting with your AI of choice:

• Upload your weekly meeting transcripts. You should record your weekly meetings and use an AI note taker. Most of these now offer transcripts. Simply copy and paste them into ChatGPT, Gemini, or Claude.

• Load in all KPI and financial results. Give the AI as much of the data as you can get. If you have customer feedback forms or results, include that too.

• Include information from publicly traded companies in your space. If you have a few companies that have to make quarterly disclosures, you can include those and have the AI extract any generic market insights that might apply to your company.

• Ask the AI what insights it gleans from the meetings and data you provide. You can have it develop an analysis of progress throughout the quarter and suggest issues that should be on the table for your next quarterly meeting.

• Have it analyze the data from the perspective of different legendary business leaders. Ask the AI to provide feedback as if it were Steve Jobs, Jeff Bezos, Frank Slootman (lesser known but awesome on execution), or whoever you want as long as they have a record of discussing business.

For an annual planning session I would also have the AI:

• Do a “deep research” report on your industry and the trends that are shaping it. Most AIs now have a deep research function that will comb the web for any information about your industry. You can tailor the project to any specific issues or questions you have.

• Conduct a SWOT on your company based on all the data it has. The AI can do your basic Strengths, Weaknesses, Opportunities, and Threats analysis better than your team can.

Now take the results and ask each team member to review and reflect on how it impacts their function or job. Have them write up some quick thoughts for a quarterly or a 2-3 page memo for an annual meeting. The memo should cover:

• Last year's results and highlights

• Market changes and trends

• Key recommendations for the coming year

Guess what? They can use ChatGPT to help write it. I don't care. Just get it done.

Now you're walking into your planning session with 80-90% of the analysis already done. You're not starting from zero and it probably took an hour at most to put the information together. If you document the process, an admin can do it for you.

The Two-Hour Quarterly Meeting

You can now condense your quarterly meeting from 8 down to 2 hours.

Here’s my recommended agenda:

• What are you most proud of, what was the biggest fail, and what did you learn? This is your time to process as a team. (30 minutes)

• What did we take away from the analysis of the last quarter? (30 minutes)

  • Are the yearly goals we picked still the most important things to focus on? If not, why not?

• Based on that discussion, what are the 3-4 most important things we team should focus on for the next 90 days? (30 minutes)

  • I like to have each person develop their list on their own so you can avoid groupthink.

  • Put each list up on the white board.

  • Now vote on the most essential thing that has to get done no matter what and then work your way down until you have 3-4.

• Plan out the first milestones the lead on each initiative needs to get done coming out of the meeting.

  • DO NOT LEAVE THE MEETING WITHOUT THESE MILESTONES.

  • You have to hit the ground running and I’ve seen too many teams waste a month before those milestones are in place.

You get extra credit if you use AI to record each section of the meeting. Then feed the transcript into the same chat as all your analysis and ask it to inform how to approach the next section of the meeting.

Studies have shown that a team working with an AI performs at a higher level than teams on their own. Take advantage of it.

You can also have the AI keep certain things in mind like:

• Always focus on the most important things that will make a real difference.

• Make sure we are conscious of the tradeoffs between choices.

• Make sure we develop SMART initiatives and goals.

• Etc.

The Four-Hour Annual Meeting

For your annual meeting we’re simply opening up a bit more time for each section. The idea is to have a deeper conversation about each subject and to bring more data and analysis to each section.

Add the deep research report on your industry, any annual filings you have from public companies in your space, and the memos each key leader writes up.

You also now have a year of financial and KPI data to add and, you guessed it, all the transcripts from your monthly and quarterly meetings!

Here’s a sample meeting agenda:

• Reflect on the last year personally and professionally (30-60 minutes)

• Discuss what you’ve learned from all the analysis we’ve done from the last year (60-90 minutes)

• Goals: Identify the 3-4 most important things we need to get done this year (60 minutes)

• Initiatives: Identify the 3-4 most important things we need to do this quarter in support of those annual goals (30 minutes)

• Milestones: Plan the first month’s milestones for each initiative (30 minutes)

One thing I would not do before the meeting is ask the AI to identify the top goals or initiatives for your business. Your team needs to do this and it’s easy for them to cede too much to the AI and not think for themselves. I would ask the AI to identify other candidate goals and initiatives after you have a draft list but never before.

The Planning Session Diet

If you follow this approach, your planning commitment gets a lot easier and more effective:

• Annual planning: 4 hours (not 2 days)

• Quarterly planning: 2 hours (not 1 day)

• Monthly reviews: 90 minutes

• Weekly leadership meetings: 1 hour

That's a planning approach people will actually stick with. It's focused on the highest-value activities and cuts out the fluff.

And if you want team bonding? Great.

Do a dinner afterward. Take the team bowling. Go on a retreat. Just don't pretend that eight hours of being trapped in a conference room is "team building."

Business owners don't have time to go away for a full day four times a year, plus two days for annual planning. It's unreasonable, and the quality suffers.

Who's planning good initiatives after talking for seven straight hours?

Try this leaner approach. Use the tools we now have at our disposal. Get the planning done so you can focus on the part that actually matters: execution.

Want to see how your company stacks up on planning and the other key business functions?

Take our Free Assessment and get a personalized report that let’s you know.

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