Halloween is approaching and, for some, this observance can be a scary time.

The notion of witches, ghosts and goblins haunting the living on Halloween is hundreds of years old.

While some folklorists believe Halloween has its origins in the Roman feast of Pomona (the goddess of fruits and seeds) or in the festival of the dead (called Parentalia), others trace Halloween to the ancient Celtic festival of Samhain celebrating “summer’s end.”  This Irish festival was the first and most important of the four “quarter days” of the medieval Gaelic calendar and marked the end of the harvest season, the beginning of the “darker half” of the year, and a time when spirits could more easily come into the world of the living.

These spirits were both respected and feared, prompting individuals to invoke God’s protection when approaching their dwellings. During the festival of Samhain, food and drink and even portions of the annual crop were offered to spirits to ensure that people and livestock would survive the winter.  Souls of the dead were also believed to revisit their homes, so places were set at the dinner table or by the fire to welcome them.

Today, this once-scary time has been transformed into an occasion to don costumes, patrol for candy, attend parties and have fun.

And yet, in some organizations, the month of October is still a scary time.

With only 58 business days left between now and year-end, some leaders are rightfully concerned about their organization’s ability to achieve their objectives.

Other leaders are gathering their direct reports to begin the strategic planning process and may fear the process will not yield any meaningful outcome.

Can We Talk?

Let’s address the second issue – the traps to avoid during strategic planning – first.

To get the most from your planning session, avoid at all costs four traps that I examine in a recent issue of Forbes magazine:Why Most Company Strategic Plans Fail”

The greatest danger in the strategic process is the failure to discuss meaty issues that are hindering individual and organizational performance.

It’s not always easy to talk about the tough stuff, and doing so may not be comfortable for many in the room, but these discussions must occur if you expect to make necessary changes and move to the next level of success.

In a recent planning session I asked six company leaders a simple question:  What’s one principle you wished the people in this room practiced more consistently?

It was a scary question for that group because the answers that emerged indicated that trust was absent with one of the executives.

At the time, the discussion felt like surgery without anesthesia.  The CEO told me after the session how uncomfortable he had been during the discussion, and wondered if the issue could have been handled differently.

Were you aware this situation existed? I asked.  Yes, replied the CEO, but I was hoping it would fix itself.  How long, I asked, have you known this situation existed?  Months, the CEO replied.  Then what, I asked, causes you to believe the situation would fix itself without the conversation we had this afternoon?  No answer.

Just 60 days later, the executive who was the source of the trust issues had been dismissed from the company. Morale rose. Results improved.

Lesson:  Don’t be scared of talking honestly and respectfully about the real issues in your organization that are holding you back.  The ability of a senior leadership team to handle conflict is predictive of the size of problems the team can address on its way to becoming a high-performing organization.

More Scary Questions for Leaders

I’ve led nearly 200 strategic planning sessions in dozens of industries, and my book Lead The Way outlines the process for an effective session.  I keep the process simple and straightforward.  It’s the questions that deliver the value.

So whether you’re concerned about finishing 2014 strong, or you’re worried that a planning session will be a waste of time, consider these questions to coax out the ghosts in your machine:

• What’s our promise to our customer?  How are we doing delivering on our promise?
• If a new leader took over today, what’s one change the leader would make to improve our performance?
• In what areas are we not doing the best that we can do?  How will we respond?
• What factors does our industry take for granted that we can eliminate?
• Does our organization’s mission give our people something to cheer for?
• Do we have the people on our team we need to succeed?  Who’s missing? What will it take to attract the people we need to win?
• Are we committed to winning? How can we tell?

My third book That’s a Great Question includes more than 500 questions like the ones above that are organized around 18 topics, such as “Talent,” “Trust,” “Accountability,” “Change,” and “Results.”

The only thing scarier than asking the questions, is not asking them.