I have been thinking lately about how fast I can decide something is not working.
We try a new approach for a week. The results are not what I expected. And almost immediately I start questioning the strategy. Maybe the messaging is wrong. Maybe the marketing is not going to produce the opportunities we thought it would. Maybe a new process is taking the team longer than the old one did, and that is evidence we picked the wrong process.
Sometimes those concerns are right. Plenty of strategies deserve to be killed, and killing them early is cheaper than killing them late.
But sometimes I am judging something before I have given us a real chance to make it work. The discomfort is real, and I am treating the discomfort as the verdict.
That is the question I keep coming back to. Am I looking at a genuine problem, or am I reacting to something that is simply unfamiliar?
Having a strategy and executing it are two different things
Writing a strategy feels productive. There is something to show at the end of it. A plan, a document, a decision everyone agreed to in a meeting.
Implementation is a different activity, and it is much less interesting.
Building a new marketing strategy is not the same as running it consistently for six months. Writing a sales process is not the same as getting the team to use it when they are busy. Buying new technology is not the same as changing the workflows underneath it. Deciding to specialize in a market is not the same as reorganizing the agency around that market.
Each of those second halves takes repetition, correction, training, accountability, and patience. None of it produces anything you can hold up.
A strategy does not become part of a business because leadership approved it. It becomes part of the business when it changes what people do on a Tuesday.
I know that. I still underestimate it, and I underestimate it most when the plan was mine.
When different feels like something is not working
We are in the middle of a significant transition right now, moving the agency to new management and operational software. The platform is built around artificial intelligence and better connected processes, and adopting it means reconsidering how we handle information and how we serve clients.
Here is the honest part. It does not always feel more efficient yet.
We have spent years learning how to work inside the systems we are leaving. We know where everything lives. We know the shortcuts. A long list of routine tasks had become automatic, the kind of thing nobody thinks about because the thinking was done years ago.
Now we are learning software built on a different set of assumptions. Things that were easy have temporarily become harder. People have to learn new ways to find information and finish tasks they could already finish. Habits that worked have to change. There have been moments where going back to the old system would obviously be the easier afternoon.
The comparison I keep catching myself making is not a fair one. We are measuring something we spent years learning and refining against something we are still figuring out. Of course the familiar one feels easier. That does not make it better.
What we are after is not a different place to type the same information. It is a chance to rethink the work itself: less unnecessary administrative effort, information that is accessible when someone needs it, better support for the people doing the work, and a better experience for the client on the other end.
I want to be careful here. That is what we are trying to achieve. I am not going to tell you we have achieved it. The technology still has to prove itself, and it does not get unlimited time or money because it promised to be an improvement. I have written about why insurance software was built for a world where people did all the work, and about the point being to fix the friction rather than deploy the tool. Both still apply to us. The test is whether real problems get solved, not whether the software is new.
But abandoning it because the first stretch was uncomfortable would also be a decision made on bad evidence.
The temptation to go back to what we know
The pull toward the familiar is not weakness. It comes from real obligations.
Clients still need service while you are changing systems. Employees still have to finish their work. Renewals do not move because the agency is in a transition. There is genuine pressure to protect productivity, and protecting productivity matters. An owner who ignores that in the name of transformation is not being disciplined. He is being careless with the people who depend on the business running.
So I understand the instinct. What I try to watch for is reverting only because reverting is easier. The old way may have worked well for years. That is not the same as it being the best way to operate from here.
It also helps to remember that change is not all or nothing. Some of our existing processes are good and should survive this untouched. The work is figuring out which ones those are, not replacing everything because we are replacing something.
Sometimes the strategy really is wrong
I do not want to leave the impression that persistence is always the answer, because that is its own trap.
Sometimes the assumptions were wrong from the start. Sometimes the market moved after the decision was made. Sometimes the technology does not solve the problem you bought it to solve. Sometimes implementation costs more than the value it creates. Sometimes the strategy was right two years ago and no longer fits what the business is trying to be.
Those are real possibilities, and an owner has to be willing to say them out loud.
Continuing with something indefinitely because of the money and hours already in it is not discipline. It is a different mistake wearing discipline’s clothes. Knowing when a direction no longer fits is part of the job, which is why the profitability of saying no applies to your own past decisions as much as to new ones.
The distinction I am after is this. There is a difference between giving a strategy enough time to work and holding onto something the evidence says is not working. Both look like commitment from the outside.
Alignment is more than believing in the plan
When an initiative struggles, the easy explanation is that the team is not bought in.
Sometimes that is true. More often, in my experience, the team believes in the plan and the business is not built to deliver it.
Alignment is operational. It means the resources, the priorities, the capabilities, the systems, and the expectations all support the thing you said you were doing. A leadership team can agree completely and still lack the capacity to execute.
The failures tend to look like this. New technology introduced without creating any time for training. Changed sales expectations without a defined process to meet them. New marketing work with no clear owner. People asked to become more efficient while administrative tasks keep getting added to their week.
In every one of those, the strategy is fine and the environment makes it impossible.
That puts the first question on me rather than on the team. If we want people to work differently, we have to build conditions where working differently can succeed.
The owner has to be willing to look in the mirror
I am drawn to ideas. I see an opportunity and I want to move on it. That instinct has been useful to this business and I am not going to pretend otherwise.
It also creates a specific risk. I can introduce the next initiative before the last one is actually running, and then wonder why none of them took hold. Adding faster than an organization can absorb is exactly the complexity tax I have written about, and owners are usually the ones charging it.
So before I conclude that something is not working, I try to get through a short list of questions.
Have I explained what we are trying to accomplish, or just what we are doing? Have I given the team the time and resources to make the change? Are our priorities realistic, or did I add this to an already full week? Have we defined success specifically enough to recognize it? And am I judging results against the goal rather than against how it feels?
This is not about assigning blame. It is about accepting that execution is a shared responsibility and the owner holds most of the levers.
What I am trying to do differently
I am trying to be more deliberate before I change direction. A few things I am working on.
Define the improvement first. Before we start, what specifically should be better if this works? If I cannot answer that, I have no way to evaluate it later and I will end up judging on feel.
Separate learning curve from structural flaw. Is this hard because it is new, or hard because the process is broken? Those two problems feel identical in week three and need opposite responses.
Measure against outcomes that matter. Not how smooth the unfamiliar process feels, but whether the work is getting better, faster, or more accurate for the client.
Adjust without abandoning. Most of the time the strategy is sound and the implementation needs correcting. Changing how we are doing something is not the same as deciding not to do it.
Know when the evidence says stop. Patience is a virtue right up until it turns into stubbornness, and the line between them is evidence rather than time.
Before you change the strategy
One of the harder parts of running a business is telling the difference between something that needs to change and something that needs more time.
We should not hold onto a bad strategy because we have already paid for it. We also should not walk away from a good one because the first few weeks were uncomfortable.
If you are in the middle of this right now, I would ask yourself one thing before you reverse course. Have you actually given it a real chance to work, or have you given it long enough to feel awkward?
Sometimes progress takes a new direction. Other times it takes the patience to keep walking in the one you already chose.