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The goal of a leader is to ensure that your team finds a solution to their problem.

To do that, they have to know what the problem is. You must know how to ask open-ended leadership questions to ensure successful conversations. Open-ended questions are essential for any leadership strategy because they allow you to understand your employee’s wishes and needs with subtlety.

What Is an Open-Ended Leadership Question?

An open-ended question is not one with a simple answer. When understanding an employee’s motivations and goals, you don’t want curt “yes” or “no” answers; you want them to deliberate and talk at length.

You want to know their point of view, and open-ended questions make that happen. The more the employee says in response to the first question, the more details you have to ask further questions.

The clearest example of an open-ended versus a closed-ended question is “Do you have any questions?” versus “What questions can I answer?”. The first could prompt a simple “no,” and then there is a lull in the conversation. The second, however, starts your listener to deliberate longer and ask several questions they may not have thought of.

Questions usually asked by leaders include fact-gathering questions, goal-oriented questions, and rapport-building questions. All of these are good and useful to the leadership process, but each needs to allow for an open-ended answer and tie in with the larger goals and needs of the employee.

Benefits of Open-Ended Question

Many things asking open-ended questions equips you with better leadership skills. For example:

• It allows you to build trust and rapport with the employee, as it demonstrates your interest.
• You can learn more about the employee wants and preferences and define needs, goals, challenges, and other data.
• It places you as the expert in the discussion, presenting the value you bring to the table. 

Open-Ended Rapport-Building Questions

Rapport-building questions start the conversation, get your employee talking, and help you understand the person you’re working with. It can also make you both more comfortable with a more personal connection and allow you to begin gathering the necessary information.

Examples:

• • Can you tell me about your priorities for this meeting?
  • What is your background?
  • How is business going?
  • Please tell me about your upcoming plans for the year.
  • What would you like to see improve?
  • What is your biggest challenge right now?
  • Could you list your concerns in this area?

 Open-Ended Qualifying Questions

These questions can help determine the interest level of your employee in how you’ve approached the conversation. It can also let you know how to proceed. Not every employee will buy what you’re selling, and it’s essential to figure out how much an employee is committed.

Examples:

• • What is your timeline for this to be resolved?
  • What do you see as the next steps moving forward?
  • How do you decide this?
  • When should you assess these solutions?
  • How should we move forward after this?

Open-Ended Priority Questions

These questions help discover and address your employees’ roadblocks or concerns and further understand their priorities and needs. These questions should be carefully constructed not to steer the conversation toward something that can’t be fixed. Be sure to treat each employee individually, and don’t assume you know their priorities based only on similar customers.

Examples:

• What would you like to achieve in the upcoming year?
• How is that problem changing how you operate?
• What isn’t working in the current setup?
• What improvements are you hoping to gain from this?
• What would prevent you from making this change right now?

 Open-Ended Discovery Questions

A discovery question should be clarifying and probing, provoking thought and deliberation in your employee. The better you understand the employee’s wishes, the better you can tailor a solution to their needs.

Examples:

• • What are your intentions for the future?
  • Can you elaborate on that?
  • What are your reservations?
  • What needs to be fixed with the current process?
  • What have I not covered that you’d like to hear more about?

 Open-Ended Goal-Based Questions

These help you discover the wishes and wants of your employee if you listen closely. When you know what’s holding them back from achieving their goals, you can better assist them with a solution. Focusing on the benefits of your product and how they attune to the purposes of the employee can also help close a deal.

Examples:

• • Why do you think this solution isn’t working?
  • How is the problem affecting your work?
  • What do you want this meeting to achieve?
  • How should we assess the success of this?
  • What could we do to avoid similar problems?

 Responding to the Answers to Open-Ended Questions

Be sure to ask your questions without rushing into them or being pushy. Show your genuine interest. Your questions should, fundamentally, make your employee talk for as long as they want, and you must be sure to listen to them and provide helpful conversation. Be patient and don’t interrupt; everything you hear can benefit a sale.

Learning How to Ask the Right Questions

Increasing your experience with leadership discussions will allow you to keep a better ear out for helpful information.

When you know what to look for, you will find that subsequent conversations will go easier.

You are not your 2 AM conversations;

not your 3 AM nightmares;

not your 4 AM regrets

– Mark Dimaisip

I don’t mind telling you that business could always be better.

Or I miss the energies created by surrounding myself with a powerful team.

Or that I am often awake at 4:00.

So maybe that is why Mark Dimaisip’s poem resonated with me, as did the Hidden Brain podcast episode on regret.

Everyone has regrets.

Some say regret is the most common emotion.

Amy Summerville, who runs the Regret Lab at Miami University in Ohio, says:

‘we ruminate thoughts that spring unwanted to mind, and we chew them over without getting anything new out of them, they’re just repeatedly, intrusively, becoming part of our mental landscape.’

We don’t have time for all of my regrets; besides, that is why they invented rye.

But I would like to touch on my three leadership regrets that run rampant in my mind at 4:00 AM

1. Anger

Given the right set of triggers, I have a temper that can flash and lash out.

I’ve written about this and don’t understand where it comes from.

When it happens, it diminishes me, my leadership, my organization, and my people.

I have learned to manage it by being more aware of situations that may trigger the flash and trying to excuse myself, walk away, and disengage.

Read More About Not Being An Ass

2. Mediocrity

Far too often, I have allowed people to push me toward mediocrity.

As leaders, we know the right thing to do, yet people and systems cause us to settle.

And when we settle, nobody is happy.

People-pleasing only creates soup sandwiches, a mess where no one is satisfied.

Read More About Soup Sandwiches

3. Kindness

The business decisions I regret the most are those I wish I had acted out with more kindness.

Too often, I made decisions based on what I, our bosses or the mission demanded.

Decisions are made without humanity and care for the people impacted.

I know some of the decisions I have made hurt people.

That doesn’t make them wrong or even bad decisions.

But I wish I could get mulligans on a few where I could have been more honest, kind, and generous.

Final Thoughts

My experience tells me that your leadership experience would undoubtedly be happier with less anger, less mediocrity, and more kindness.

Happiness is a choice.

Focus on the positives.

Be self-aware.

Practice deliberate, purposeful, and thoughtful actions.

Understand that ambition and success will not lead to a life of fewer regrets.

Don’t get caught up in what you don’t have.

Be mindful and purposeful of the opportunities right in front of you.

An interesting theme ran through several conversations I had over the past few weeks. People are frustrated in volunteer roles. Non-profit leaders can’t figure out how to engage volunteers. They want to know how to motivate people, which can be especially tricky in situations where pay isn’t involved. In this case, for volunteers.

Interestingly, the frustrated volunteers were exactly the type of people the other group was looking for.

After spending a significant amount of time in the non-profit sector and working with military reservists and cadets, I saw several very comprehensive programs established to lead volunteers effectively. Quite frankly, those efforts kept those who didn’t know how to lead employed and gave consultants a decent revenue stream.

(While you’re here, don’t miss this post next: Can You Name the 9 Essential Qualities of a Leader?)

Leading Volunteers vs. Employees

In my opinion, the only difference between leading a volunteer and leading employees is a system of compensation.

I recall a staff meeting when a manager started complaining about volunteers who were given tasks, and when that staff person checked in after a couple of months, the work was not done to her satisfaction. I spoke up and asked, “what would you do if one of your paid supervisors left another employee for months with poorly defined tasks and then got angry when it wasn’t done right?”

The response … “I would discipline them!” Really! The only problem I had was to figure out if this person was the pot or the kettle.

A terrific friend of mine who is a very accomplished businessperson and a community leader of the highest order related to me was asked to participate in a membership drive.

At the inaugural committee meeting, a consultant sat everyone down. Next, they instructed all of the volunteers on what they must do as part of the committee. These volunteers are all very accomplished in their own right. For them, being treated like five-year-olds must be very off-putting.

How would you respond if this was your boss talking to you like that? Let alone how you might respond
as a volunteer.

(Do you have volunteers working alongside paid staff? Then take a look at this post next)

I served with volunteers who, when given authority, responsibility, and were held to account, led the responses to some of the most complex disasters of our time. I saw reservists (when treated like the professional soldiers they were) accomplish superhuman tasks.

How to Motivate People When Pay Isn’t on the Table

If you want to know how to motivate people, paid or not, it might take going back to basics. Consider what motivates you, other than money, and imagine those same things motivate your volunteers.

Here are some ideas.

Whether paid or unpaid, people want to:

• Have honourable and engaging work to do
• Receive clear expectations
• Feel they are part of something bigger than they are
• Be employed at or above their current capacity
• Get respect and appreciation

Could you use a little more guidance with motivating and leading your team? We should talk. Click here to read about my one-on-one coaching and get in touch.

Did you learn a lot about how to motivate people in this post?

Here are three more to read next:

• Stop Trying To Manage Your Boss; 8 Tips To Partnering With Your Boss
• The Biggest Management Lie Ever Told — Micromanagement Is Bad
• 5 Steps You Can Use To Build a “First Team’ Mindset

This post was first published in 2017, but it was updated in 2021 just for you.