What if your strategy could talk back?
Set and forget, put it on cruise control, we have always done that, it works, clear waters, full speed ahead.
How comforting it is for us as human beings to know that we have figured "it" out and can turn our attention elsewhere!
Yes, but...
The Titanic had a great first voyage until it ran into an iceberg and thousands of lives were lost.
Savings and loans prospered until high interest rates led to mortgage defaults and it cost the lenders more to get money to loan than borrowers would pay. (Younger readers may ask: What was a savings and loan? They were a type of bank that specialized in mortgage lending. Many failed. Some became regular commercial banks. Some linger as relics.)
We enjoyed the convenience of merchants giving us plastic bags to contain our purchases, until we figured out that the bags were befouling our environment and microplastics threatened our health.
Unassigned seating was a big differentiator for Southwest Airlines, until longer flights and carry-on delays eroded its turnaround-speed benefit, while customers actively avoided the stress and Southwest missed out on lucrative premium-seating revenue.
None of these strategies failed because the original answer was wrong. The Titanic's design, the savings and loan model, the plastic bag, unassigned seating, each was the right answer or at least a reasonable answer to the question in front of the organization at the time, and the results proved it was a great answer…at least for a while. That's why they're dangerous examples, not cautionary tales about bad ideas, but proof that success itself is what stops the questioning. The better an answer works, the more certain everyone becomes that it doesn't need to be asked again, and that's backwards. None of these strategies stopped being right all at once. The conditions around them changed, and nobody went back to ask (or at least they were slow to ask) whether the old answer still held. A strategy earns continued trust by surviving the question again and again, not by having survived it once.
The learning: Good strategic thinking needs more than answers. It needs good questions. Over time.
What are you assuming? What might you be missing? Does your strategy really address the goal? What would have to be true for this to work?
Many strategies never get questioned. They are written, approved, and then left alone, as if putting them down settled the matter. A strategy that could actually talk back, that continued to push on your assumptions instead of sitting quietly where you left it, would catch what a perfectly written plan never will: the moment it stopped being right.
Planning is a process, not an event
That's because strategic planning isn't an event. It's an ongoing process, and treating it like a one-time event is where the silence creeps in. The purpose of planning was never the plan itself. It's executing strategies that work, and adapting them so they keep working as conditions change.
Time is the piece planning often leaves out. Time represents change, and change means a strategy that was right when you wrote it may need to shift to keep driving the organization toward the vision. A strategy that can't talk back to new information isn't really a strategy anymore. It's a snapshot, aging the moment it's taken.
The trap of silent strategy
If planning is a process, why does it so often get treated like an event?
The mental traps and biases I catalogued in my book Big Decisions offer some reasons. Several traps and biases loom large here.
The commitment heuristic makes us believe a plan is still correct simply because we already committed to it, which is why revisiting it feels like second-guessing instead of due diligence. Status quo bias makes the current path feel like the safe one, so any deviation from it registers as risk, even when the deviation is the safer move. Confirmation bias means that once we believe the plan is sound, we notice the evidence that agrees with us and quietly discount the evidence that doesn't. And sunk cost lures us into pursuing our strategy long after that makes sense because we are trapped by our committment to the strategy, demonstrated by all the time, energy, cost, and attention we have devoted to it.
Underneath all four is the forever changeless trap: thinking that current conditions will never change. It's one of the most common reasons good strategies quietly go bad. Nothing dramatic happens. The world keeps moving while the plan stands still, and by the time the gap is visible, it's too wide to close quietly.
Kodak is the case I keep coming back to, because the company had every reason to know better. Its own engineer invented the digital camera. Kodak held the patent. And Kodak shelved it, because film and paper had ruled photography for 100 years, a familiarity heuristic so strong that it read as fact rather than habit. Confirmation bias was a big actor, discounting the mounting evidence that digital was catching on. Nothing in the organization was built to talk back to that assumption. The strategy just sat there, agreeing with itself, until the market answered the question Kodak never asked.
I don't want a cheerleader
I don't need someone telling me, "Lee, that's a great strategy." I can get that from anyone who wants to be agreeable, and agreeable people are easy to find. The more successful you get, the easier it becomes to surround yourself with agreeable people, and the more the illusion of control sets in, the belief that your influence over outcomes is larger than it actually is. Power doesn't make you immune to bad strategy. It just means that fewer people are willing to tell you that your strategy is not good.
I want people asking me: Are you sure? What are you assuming? What might you be missing? What would have to be true for this to work? And I want that question asked again in six months, not just at the start, because the answer might be different by then.
That's what talking back actually means. Not encouragement. Friction, the useful kind, the kind that makes a strategy stronger before it meets the real world instead of after.
What talking back actually sounds like
I coach the Third Friday Group, business owners and leaders who bring their challenges, opportunities, and decisions to the table every month, and to one-on-one conversations in between. We ask one other the kind of questions a silent strategy never asks itself. No one in the room has a reason to just tell you your plan is great. That's the point.
Confidentiality limits how much detail I can share, but the pattern is consistent enough to describe. In each case, someone's strategy got talked back to, and a decision changed because of it.
An innkeeper was buried in day-to-day tasks that a capable person on her team could handle. The question: What are you doing that someone else could do well, freeing you for what only you can do? She trained and promoted her housekeeper into a role with greater responsibility.
A photographer had built a body of work with nowhere to be seen or sold beyond the internet. The question: Where does this work actually belong, and what's stopping you from putting it there? He opened a gallery and found new customers
An attorney was generating referrals the same way he always had and the results were limited. The question: Is your process actually producing results, or is it just familiar and easy? He changed where and how he looked for clients, and client growth followed.
A financial advisor was trying to serve everyone. The question: You are assuming you need a broad client base. What might you gain by focusing on a niche? He found greater success by niching down and building a Center of Influence strategy around his niche.
A manufacturing company owner had never pursued the large suppliers he assumed were out of reach. The question: What relationships are you not pursuing because they feel too big to ask for? He pursued them, and, boom! Great growth followed.
Private school owners had one location, which meant that a constrained enrollment had to cover all the overhead of an education company. The question: How can you get greater enrollment to cover costs and deliver greater revenue and profits? They opened a second location which is now in the black and are on their way to a much larger enrollment and stronger results.
I'm reconstructing the questions behind each of these, not quoting them verbatim. The reconstructed questions show the shape of what talking back looks like: not a vague nudge to "think bigger," but a specific question aimed at a specific assumption nobody had examined in a while.
Building in scrutiny
A coach and a peer group are one way to get this perspective on your strategies. There are others:
A trusted advisor who is willing to push back.
A Board that actually challenges instead of rubber-stamping.
A standing practice of the team revisiting the plan on set calendar dates, not just when a crisis forces the conversation.
It's also the role we designed for Kai, the AI planning assistant in FastTrack™ 2.0, our complete system for developing and implementing strategy. Kai isn't the only way to get this kind of scrutiny, and it isn't a replacement for a good advisor or a group such as Third Friday. But it has value. It's a tool built to ask the hard questions consistently, at the start of plan development and as things unfold, proposing options, analyzing your work, challenging assumptions, spotting gaps and connections, and helping you think through the decisions that matter.
With our application of AI, you remain in control. You make the decisions. Kai offers options and questions them, but it doesn't choose for you.
Kai is one way to get that scrutiny. An advisor or a peer group are others. What matters isn't which one you use. It's that you have one, because a strategy doesn't question itself. Whatever does that job for you catches what needs to change before the market forces the question on you.
Southwest didn't get an early warning that unassigned boarding was costing it premium revenue and customer goodwill. The market surfaced that for them, slowly and expensively. That's what happens when nothing is asking the questions on your behalf: The world ends up asking them for you, on its timeline, not yours.
Don't wait for the market, a competitor, or a crisis to ask whether your strategy still holds. Build in something that asks first.
Take a look at FastTrack™ 2.0.
