Take a cold hard look

In my 20 years of strategic planning and execution, it’s extremely rare to see when organizations look back at the previous strategic initiatives to ask what worked and what did not work.

The strategy review is very important because if you don’t properly evaluate how things are working you have a risk of continuing to do the things that aren’t working. Even worse, you may not be putting enough resources into the things that are working.

We don’t always have to do something new, if we have found the formula, and there’s proof it is actually time to double down on those actions. 

So, today I’m going to spend some time reflecting on what has worked for us in the past year and what did not work as well.

First, let’s discuss what the most elite companies in the world do.

How to evaluate whether you’ve done well or not

If you study strategy, you recognize that the greatest leaders will evaluate, look very carefully at what did work and what did not work. You have to address the brutal facts, what was the decision that worked, and what were the decisions that didn’t work.

Many other elite forces, such as the Navy SEALs, are known for doing what’s called an after action reports (AAR). These reports look at the brutal facts. What were all the right decisions? What were all the wrong decisions? And who should take full responsibility for those particular decisions?

The problem in most corporate board rooms is that we want to hide the fact we have made decisions that did not work.

If we actually allow the fact that we made a mistake with larger companies, and especially the government, you’re at risk of not getting your funding. So if your job is tied towards that resource, you are very unlikely to admit it.

But the beauty of being a closely held organization is that you should and can have the courage to say what is working and what didn’t work. The reality is, it’s your money so why are you continuing to spend good money if it’s not working? Because it's difficult. There are good people behind those decisions. Trust me, I am guilty as charged.

However, we have this tendency to turn our eyes away, so we can avoid difficult conversations, even if it costs my own bank account.

Keep, Start, Stop

If you recall last week’s blog, we spent a fair amount of time saying how we accomplished these amazing things. We did, and it was an amazing year. However, the internal sausage factory, here at 40 Strategy, where I made several mistakes, which cost me tens of thousands of dollars, ouch!

Many years ago, I learned from a great mentor named Dan Meub, the concept of Keep, Start, Stop for strategic planning review. 

Keep: Continue doing the things that are working

Start: Initiate new projects to reach new goals

Stop: Kill the things that are wasting you time and resources

What is Working 

Reflecting back on 2025, here are the activities that we know worked:

• Speaking authentically

• Pricing presentation

• 40 Strategy Growth Workshop

• Meeting with clients weekly

Before finishing this blog, I actually reached out to my team to get their input on this, so I didn’t have blind spots. Frankly, as owners, we tend to have blind spots, so I reached out to them to help me out with this exercise. We’ll share their results in next week’s blog. 

My Pre-Survey Thoughts

OK, here is my pre-survey idea of the things that were working and the things that were not working, etc.

What we KEEP doing:

• Exceeding client expectations 

• Growing significantly 

• Speaking authentically

• Pricing presentation

• Meeting with Strategy clients weekly (40x per year) to maximize results

• 40 Strategy Growth Workshop™

• Measure success podcast

• Keep using AI as a tool

• Blog

What we START doing:

• Develop 200 raving fans

• Write sequel to lost at CEO

• Start using AI is an operating system

• Launch first cohort

• Develop integrated system to grow leads pressure leads

• Standardize pricing for 40 Strategy and 40 accounting

• Hire tax manager and get them fully integrated with all our clients for tax season

• Start connecting deeper on the right social platforms

• Sell products and services online

• Create an online training system

• Create more consistency and themes with online outreach

• Develop a decision making matrix for growing team

• Meet with team more frequently to mentor and guide culture 

• Take two courses on AI

• Do multiple workshops in 2026

What we STOP doing:

• Producing content that is not relevant, nor is it connecting us with clients/prospects

• Producing one off pricing to clients

• Learn when to say no when we can’t properly serve potential clients

• Spending on marketing companions with little or no ROI

• Being late to meetings

• Overbooking

• Stop having unscheduled weeks in terms of be more clear in terms of what I’m trying to accomplish

• Stop meeting with just anyone, make sure there is a clear purpose and the value correction

• Stop meeting with associations and organizations that I cannot commit time properly to

• Stop hesitating on decisions - it should be a heck yeah or a simple no