How will this end?

 I'm constantly amazed by how much emphasis people place on starting things - a new hobby, a new career, getting married, starting up a new company, initiating a new war, but how little thought they put into how things might end.  Starting new activities, companies, even wars, is relatively easy.  Unless a lot of thought is put into how things might end, getting out can be very difficult.  It's a lesson that seems we must constantly relearn, to our detriment.

The enthusiasm of the beginning

In the beginning of the execution of any new idea, the energy and passion seems to virtually guarantee success.  You've found the perfect mate, or spotted an emerging market to address, or found a tin pot tyrant to take out.  As Bill Murray says in Stripes, when they have to take the armed RV into what was then Czechoslovakia, "We go in, we get out, it's like going to Wisconsin".  Oh, the unwilling led by the unready.

But, and there is a big "but" here, few people at the august beginning appreciates the opposing voice asking "what if this doesn't go well" at the beginning of any significant endeavor.  What if that perfect spouse isn't quite right, what if that market is more difficult to enter and has more competition than you expect, what if attacking a country that controls oil flows and has proxies across the middle east will react violently?

In most instances such as these, the enthusiasm and certainty of the decision will override the questioning perspective.  Worse, the energy behind a new opportunity will call the individual who raises the issues into question.  It's difficult to be a "doubting Thomas" when everyone wants the new activity to succeed.  But in the early going of any significant activity, this is exactly what you need.  Someone to ask the tough questions, such as:

• Why is this a good idea?  Why is it necessary?  Why now?
• Why us?  Why do we have the "right to win"?
• What happens if things don't go so well?  How do we unwind this if the outcome isn't what we expected?
• What is our main purpose or goal?
• And, one of my favorites:  is the juice worth the squeeze?  Do we get more benefit than we invest in effort?

Unless you can answer these questions with honesty and care before you enter significant engagements, you may want to reconsider.  Getting out is almost always more difficult than getting in.

After the shock and awe

As the Gartner hype cycle curve demonstrates, there's almost always a significant ramp up of enthusiasm after launch of a new activity or technology.  People will get behind something that has momentum, in the hopes of being part of something that is successful.  It's when the curve reaches its peak and starts to come down, the point after the shock and awe wasn't quite the killer app you hoped for, that you'd better have milestones and checkpoints.

As Eisenhower said, plans are nothing and planning is everything.  You can plan for both wildly successful initial engagements AND gameplan for alternative scenarios without casting doubt on your work.  If the shock and awe doesn't fully win the day, what's the next action?  What adjacent activities or pivots should you consider?  What's the investment in time and treasure versus the return, and does continuing on in the same manner make sense?  

How will you know without clear end goals and plans?  No plan needs to be fixed in stone, but by exploring alternatives before you engage, you can more quickly pivot to a better path.  Without timelines, milestones and clear goals, you become subject to the whims of the environment, external forces, competitors and other bystanders.

Shock and awe works well in some instances, but not every instance.  Making a big splash, capturing a lot of the market share, eloping to Las Vegas are all immediate actions that have effect quickly.  Once you've reached the end of shock and awe, however, and haven't achieved what you'd hoped for, what's next?  Plans and/or planning should provide direction. 

This is where a lack of planning becomes evident, and people who joined the bandwagon will say - "now what" and there won't be a great single answer, but a multitude of possibilities.

Getting unwound

Once things become a bit difficult or dicey, or it becomes clear that the spouse you married wasn't quite who you thought they were, or the business opportunity isn't unfolding quite the way you thought it would, or.. you get the picture, what's next?  Without good planning and forethought, getting unwound is typically far more difficult than getting started.  Why?

• Lack of agreement.  Not everyone will have the same opinion about the timing and need to unwind.  If there is a lack of agreement about when, why and how to end, it's difficult to end anything
• Legal issues.  Most of the activities I've described come with contracts - a marriage contract, a business contract.  Contracts define how parties should work together and typically impose penalties if the parties disagree.  Once you start unwinding, there will be legal and contractual obligations, which will delay or distract from unwinding.
• The Pottery Barn rule.  This is what Colin Powell, who was George W. Bush's chief of staff called the responsibility to leave things at least as you found them.  He was referring to Iraq and used the "you break it, you bought it" concept.  Basically, saying that if you attack Iraq, you'll upset the norms in that country and others around it, and will own the responsibility for putting it back together.  Turns out that was a 20-year effort, if we are even complete yet.
• Monetary issues.  You may decide that a specific initiative is no longer worth the effort and can't be won, but the individuals who invested in your efforts may not feel the same way, or may demand their money back.  When things don't go quite so well, you'll find out who your "friends" are and who is in it strictly for the money.
• No one steps in the same river twice.  The reality is, once you've stirred the pot, it is exceptionally difficult to unstir it.  Your actions have ripple effects in secondary and tertiary locations far beyond what you are likely to expect.  The US is still viewed with suspicion in Central America for actions we took during the global battle against communism, and some of the regimes we propped up or toppled in the 1950s.  This isn't to say that those decisions were "right" or "wrong", just that there are knock on effects decades later.
• Your prospects just can't see the vision.  There are plenty of examples where what appeared to be good ideas just didn't align to market expectations or needs, but the founders felt that customers just weren't informed enough or smart enough to see the benefits.

Who plays the bad guy?

If I've convinced you that thinking about the unwinding, or at least the end state, is important at the beginning, who plays that role?  There are often people with different points of view, glass half-full or glass half-empty kind of people, and they quickly get pigeonholed and their opinions discounted.  Their natural inclination does not make them wrong, but in a group of people who are highly energized, the person asking for end states and alternative scenarios can be put in a corner.

What leadership teams ought to do is use a time-tested approach along the line of De Bono's Six Thinking Hats.  The different "hats" are used to designate people to play different roles or perspectives.  Unfortunately, the black hat was designated as the risks and concerns "hat", black hat having a sometimes negative connotation.  But the idea is right - we need to explore any new venture from different perspectives and points of view to ensure we have 1) the best chance for success 2) understand opportunities and adjacencies 3) milestones and 4) what the risks and end goals are.

With De Bono's approach, you can trade off who plays which role.  In some instances, it may make sense for the biggest advocate to put on the black hat, to fully explore and question the downsides of their proposals, rather than simply shoot down other's concerns.

Speed without foresight

What we are faced with is the need for commitment and speed, in order to win new opportunities and get deeply engaged before other competitors, but that does not negate the need for foresight and consideration of alternatives and end states.  As I've noted before, it's very easy to get into something, and AI and vibe coding and new technologies will make it easier to get into new businesses, but will consume time and attention (which is the real limiting factor) that could be deployed elsewhere.

The fact that you CAN go faster does not convey the insight required to win faster.