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Shoulda, Coulda, Woulda: 3 Things to Avoid

Business, Strategy, Management, HR

I’ve heard the term “shoulda, coulda, woulda” as an episode title of a TV comedy, as part of an NFL kicker’s interview where a game winning field goal was missed, and even during a political news conference!

We can all think back on our lives and remember a time when things may have turned out differently if we prepared, responded, or delivered differently.  We all have a “shoulda, coulda, woulda” experience.

Mistakes and missteps are inevitable. They are just part of life, and part of business.  But have too many “shoulda, coulda, wouldas”, and you may find yourself saying one of the following in your next leadership meeting:

  • “We should have enforced our work-from-home policy, then overtime would be under control.”
  • “If we properly trained our employees on the use of this machine, numerous injuries could have been avoided”.
  • “I would have consulted our attorney had I known this employment issue would end up in court.”

Smart organizations, and strong leaders, are not only skilled at minimizing mistakes, but also looking at the outcome of a plan or project to avoid the “shoulda, coulda, woulda” scenarios.

Before you, or your team, make the next big decision, consider these 3 things to avoid the regret of “shoulda, coulda, woulda”:

1. Take a Time Out. We are all going in so many directions we sometimes feel we don’t have the time to stop and think through a decision or choice.  But you do!  In all areas of life, you make time for the things that are important to you.  Sacrificing accuracy for speed, or quality for quantity is just not worth it. Use your head.  Yes, there are deadlines and circumstances that call for an immediate response, but there must be balance.  The time you take today may save you time, money, and resources tomorrow.  Pause, take a breath, talk to your people.  You will be glad you did.

2. Run the Traps. When faced with a decision, I like to “run all the traps”.  By this, I mean going through an intentional “if this / then that” analysis.  Think through scenarios, risks, rewards, potential outcomes and the associated resulting consequences.  Process through known information, then step back and ask, “What am I missing?”  The time for surprises is early in the process, not after the fact.

3. Consider the Dominos. Even minor decisions have a domino effect, so always expand your perspective. Discuss decisions with your team, consult other stakeholders, think about business operations, ask questions. Consider the downstream impact before you finalize a decision. If you don’t zoom out and consider all perspectives, you risk missing something important.

Honest reflection on your “shoulda, coulda, woulda” experiences can help you avoid making the same mistake twice. I’ll leave you with a real-life example.

A large, growing medical practice decided an employee survey was a good idea. The physician owners and management group wanted insight on the employee perspective. In a few weeks, a culture survey was pulled together, administered and the results came in.  The Docs and Leadership were expecting glowing comments and results, but instead they got raked over the coals and received a big wake-up call.

Why? They didn’t pay attention to the signals employees were already sending.

They “shoulda” paid attention to the work environment and thought through the survey idea. If they adequately ran the traps and anticipated the results, the team would’ve been better prepared for the inevitable outcome. When turnover is high, employee morale is low and patient demand is up, what do you expect? Of course, survey results were harsh!

Leadership “coulda” paid attention to metrics, performed a market study on compensation or created opportunities to show employees appreciation. If these things happened, they “woulda” realized pay was well below market due to a recent industry shift, and employee engagement was lacking due to an overstretched, understaffed clinic model.

The survey was beneficial because it did give leaders what they were looking for…the employee perspective. It also prompted conversation around the “shoulda, coulda, woulda” lessons they learned and how to adjust going forward. Hard lesson, but well done.


Is your organization bogged down in the “shoulda, coulda, wouldas?” How does your culture ensure strategic decision making is part of your business operating norm?


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