Key Takeaways/TLDR
- Respect the Mess Between Theory and Reality: Strategy is an intellectual exercise, but implementation is a human one. Most plans fail because leaders treat them like rigid blueprints rather than adaptable guides. To save your strategy, you must be willing to lead your team through the “messy middle” where plans meet the friction of real-world unknowns.
- Swap Rigid Rules for “Dynamic Incompletness”: A strategy that can’t bend will eventually break. Instead of micromanaging the “how,” focus on “dynamic incompleteness.” Be crystal clear about the destination (the outcome), but invite your team to co-create the path. This turns resistance into alignment and keeps the momentum moving forward when obstacles appear.
- Mine Resistance for Gold: Resistance isn’t a sign of rebellion; it’s clues to the map of reality. The best leaders proactively seek out disagreement to find the holes in their own “overconfidence bias.” If you can’t disprove the weaknesses in your strategy now, the market (or your own culture) will do it for you later.
Balance the Energy Ledger: Change makes an expensive withdrawal from your organization’s limited energy budget. You cannot add a major strategic shift to a 100% maintenance workload without hitting burnout. To ensure your strategy survives, you must curate focus—meaning to say “yes” to a new initiative, you must have the courage to say “no” to old ones.
Ready For A Fresh Start?
Happy New Year!
New year. New strategy. New…failure?
No one likes to start fresh thinking like that, but honestly, maybe we should plan for failure when it comes to strategic planning.
Consider that year after year, we see stats indicating that between 60 and 90% of major strategic efforts fail to deliver their promised boons.
Sometimes I wonder why I, and other business thought leaders, keep writing about a topic that seems so doomed. Then I remind myself: I write for the 10 to 40% who will succeed. My mission is to make their efforts more meaningful.
Since you’re likely to be one of the successful, let me ask you: why does strategy so often fail us? Because it was wrong?
Not always. Strategies fail because leaders so often do a poor job connecting their big ideas to the reality their stakeholders live in every day.
Strategy is a fundamentally intellectual activity. In this respect, it’s one step removed from reality. That’s what gives it the power to change reality. But when strategy gets close to implementation, it has to grapple with the messiness, confusion, and resistance of real people, processes, and unknowns.
Leaders who can see the strategy through to success then, must be equipped to guide it through that same mire of messiness and unknowns.
Here are three guidelines to help you survive the mire.
Three Keys To Keep Strategic Planning On Track
1. “They Be More Like Guidelines”: Replace Rigid Planning with Flexible Co-Creation
Rigid rules sink ships. The famous line suggesting that strategic guidelines are more powerful than rules and plans (delivered by actor Geoffrey Rush in Pirates of the Caribbean) continues to generate laughs in all kinds of contexts for good reason. If there’s one thing everyone knows, a good pirate doesn’t get bogged down by the rules; she wants to stay afloat.
I’m not suggesting that strategic planning should be an act of piracy, but there’s also a reason we secretly admire pirates; they get stuff done.
Focusing on the “get stuff done” energy (instead of the cutthroat vibes of true pirates), I’ve observed that good leaders navigating uncertainty are always willing to be curious when a plan meets resistance in reality. In the best of cases, this curiosity leads to an insight that helps the leader adjust the plan by improving it. In the worst cases, it leads to a clash of wills (see below) that diverts everyone’s energy from aligning on the strategy.
So how does a leader stay focused on the strategy while giving themselves and their team the room to be flexible? This is an aspect of leadership that’s more art than science, but I’ve seen it best described as framing a strategic vision with “dynamic incompleteness.” Perhaps paradoxically, part of what makes a strategy useful while being both dynamic and incomplete is a ruthless focus on the outcome. The military has an approach to this known as “commander’s intent.”
Here are the keys to strategic guidelines with the power to integrate a strategic plan with reality:
- Direction: Be crystal clear about what success looks like and ensure everyone stays aligned on the same outcome.
- Co-Creation: Invite everyone to find ways to improve the vision to address the reality they confront.
- Empowerment: Encourage, mentor, and coach people through the process, always staying on track. Never shame or blame, which shuts down learning and adaptation.
2. Seek Resistance: Confront “Overconfidence Bias” And Question Everything
When you read between the lines above, you realize that resistance to change is actually a key to success. Understanding resistance and adapting the strategy to reality improves both at the same time. The best leaders know this and actively seek resistance because it has the potential to make the strategic plan come to life in ways that work with reality instead of against it.
But leaders are humans and humans find it uncomfortable to invite disagreement. Even the best leaders can end up in change-induced disagreements that waste everyone’s energy. Even the best leaders can overvalue their own instincts, succumbing to overconfidence bias, in themselves and in the plan.
But the best of the best leaders have probably learned that lesson the hard way. Instead of indulging in overconfidence, they proactively seek resistance and cultivate skills that help them turn a potential fight into an act of alignment.
Here’s what the best of the best leaders do to move beyond overconfidence, seek resistance, and address reality:
- Welcome resistance: They don’t assume the worst. They understand that resistance flags ways the plan can be improved, and they assume positive intent on the part of the resisters for bringing this to their attention.
- Try to disprove their strategy: Knowing resistance is valuable, they support efforts to actively identify the weaknesses in their strategy. This surfaces more opportunities for improvement.
- Scenario-building: They play out the strategy in hypotheticals, both positive and negative, to determine the nature of the risk the strategy introduces. They align people around common risk tolerance levels, which eases the anxiety resistance generates.
3. Say Yes By Saying No: Crystalize Your Strategy By Curating Energy And Attention
A strategic direction, guideline, or plan creates many opportunities for success. One of the biggest opportunities for failure that comes along for the ride, however, is the creation of overwhelm.
Intuitively speaking, it’s good to assume that change takes twice as much energy from the energy budget as maintenance does. I’m talking about energy that people and the system itself have to give. Consider this basic example:
An established process takes an hour a day to execute. A new process–one designed to take 30 minutes less–takes two hours to learn for five days. So the investment of a 10-hour change training may yield 8,760.5 hours saved in a year.
We blow the energy budget when leaders and managers get so excited about the potential for savings that they pile on requirements to learn new approaches while simultaneously excelling at the old approach at the same time. If it was just once in a blue moon that we levied this demand, people would probably be happy to invest the 10 hours. They’d get the babysitters, give up their sports leagues for a week, and deal with a temporary lack of sleep. But a major change requires much more than 10 hours in one week. It demands extra alignment meetings for months preceding the change, the discomfort of learning during the change, and emotional churning if the change generates fear and anxiety. All of this taxes the system and threatens to defocus the effort.
And of course, we never levy just one change at a time. We overhaul as much as we can imagine.
Instead of temporarily dealing with discomfort, people exceed their energy budget in unsustainable ways, burning out.
So if maintenance requires 100-120% of the energy budget, you have to throttle maintenance back to 70-90% as you’re throttling change forward to 150%. Or, you have to invest in temporary duplication of resources.
Either way, you need to monitor, curate, and manage the energy budget by adding and removing things from the ledger in some kind of balance. Adding change without adjusting the energy budget is a recipe for burnout and failure. While this isn’t a tit for tat budgeting exercise, accounting for every investment by pruning a matching expense, some kind of balance must be maintained. In addition, for every “yes, we’ll take on a new strategy or activity,” there has to be alignment on what will receive less energy. Leaders can align on the future direction, but if they’re misaligned on what price will be paid, the effort will grind to a halt.
This process of managing the energy budget so people can focus on change also aligns with Michael Porter’s advice in the 90’s to honor strategic trade-offs, which create competitive advantage. Different rationale, similar advice.
Strategic Planning: What Will You Do Differently This Time?
As you embark on new initiatives in the months ahead, how can you apply the lessons above?
Make it a game. An experiment in leadership. Come up with a theory of how to evoke resistance and use it to improve your plan, how to curate the energy budget to accommodate the stress you’ll place on it, and how to level yourself up as a leader.
Try it. Make mistakes. Adjust before you achieve failure.
