Questions: The Leadership Power Tool

Volunteer wants, member needs, evolving markets, hectic schedules…there is never a shortage of stuff that keeps us from pausing and asking the questions we should be considering.

“The important and difficult job is never to find the right answers, it is to find the right question.” ~Peter Drucker

Questions are one of the most powerful leadership tools. Questions can serve as a catalyst to help you engage people, focus their energy and efforts around the critical challenges you are facing. Questions can help you to move your organization forward by:

  • Engaging people in revising a project; “Why do we do ___ this way?”
  • Exploring your next opportunity; “How are our member or market needs evolving?”
  • Identifying the next big thing; “What developments are we seeing that will impact our organization or our members in the next three to five years?
  • Solving your challenges; “How might we____?”

Maybe you aren’t ready to step into ‘big’ question discussions. What about the fundamental ones:

  • Who’s the audience?
  • What are we trying to achieve?
  • Why are we taking this on now?

Sometimes we get so wrapped up in the daily stuff or our urgency to jump in and do or fix a situation that we fail to ask even the basic questions. Remember the Five Ws you learned in school…who, what, when where and why? These are critical questions for work, helping people identify the information they need to successfully lead, manage or implement.

The simple act of questioning how, why or what can inspire people to think, explore and engage. These discussions can help you unlock challenges you’re facing, identify new opportunities, develop new understanding and inform smart decision making. Essentially make your organization stronger and more capable of generating new value for your members and community.

So, how do you get started?

Listen. It may sound trite, but check yourself on this. When colleagues or members are talking are you truly listening to what they are saying? Or maybe are you formulating your response, checking your phone, scanning the agenda to see how much longer the meeting might last?

Ask. After you’ve listened, ask a question to ensure your understand what your colleagues are saying. “How do we know ___?” “Why do we ___?” “What is the timeline?”

Enhancing the discussions taking place in your organization now will build comfort for exploring the big questions. Those questions that challenge you or your organization to look beyond what you’ve done, what you know and what people expect. The ones that require trust and a sense of safety for people to be willing to step up and share their ‘crazy’ or ‘half thought out’ idea, ask a ‘dumb’ question or be willing to admit that they just don’t know.

A few resources you might find helpful…

5 Strategy Questions Every Leader Should Make Time For, by Freek Vermeulen, Harvard Business Review Blog, September 3, 2015.

7 Things Great Listeners Do Differently by Travis Bradberry, Forbes/Leadership Online, February 29, 2016.

What’s next?

How much of our time is spent focusing on the present, the things that must be taken care of right now? In our always connected world thinking, exploring and imagining often seem like luxuries we simply don’t have time to take on. But narrowly focusing on today can blind-side you to shifts and opportunities that will impact your industry, profession or organization.

Imagine what might be possible if you spent just one hour a week considering what your organization might do, be or how it could operate in the next one, two or three years.

Most industry changes don’t happen overnight. It may seem that mobile technology, the economy, or competition just pop up, but chances are we just missed the shift. Occasionally looking up, considering what’s going on in and outside of your organization will help you see when a shift might be coming.

Exploring what is going on with your team, colleagues, partners or members can help to expand perspectives of your organization, member (or potential member) needs and build comfort and understanding of what might be coming in the future.

Getting started is not that hard. Smart discussions can engage people, surface perspectives, ideas and opportunities and motivate your team. If you open these discussions, you MUST be prepared to listen. Auto response to future discussions or any talk of change is often to refute, deny, disagree or just simply shut it down. These responses can be harmful. Remember the last time you were asked for your opinion only to have the asker question, ridicule or refute your suggestion? It’s not fun and for many people it is the perfect excuse to step back and decide to keep their head down and just do the easy work.

Being open to new ideas requires some work, a lot of listening and asking questions. You can build these skills. An easy entry point is simply asking a thought provoking question and invite people to share their perspectives, ideas and questions. Questions to consider:

  • What might we do next year that is impossible now? What can we do this year that was impossible last year?
  • What impacts our ability to serve our members, industry or potential market? How are these changing?
  • What is impacting or influencing our members and their work? How might this impact their interest/ability to work with us?

When ideas, concerns, potential challenges or opportunities come up, keep the discussion moving. Ask:

  • What information could help us better understand the issue/opportunity?
  • How might needs or interests change?
  • What can we do now to strengthen our organization to better serve our members/market?
  • What one thing while seemingly impossible could make a tremendous difference?

Not quite ready to lead the charge in future thinking? Take two months to build your personal comfort by developing your awareness and understanding of issues. Commit one hour a week to exploring issues that impact your business/industry, potential trends and forces or related industries. Try checking out online resources, talking with colleagues or others in your field or related fields, or seeing what your competitors are up to.

How Do You Foster Change?

“How do you change the habits of already successful adults?”*

I’ve been struggling with how to help individuals change their habits and try a new approach lately. So when I came across this question, I jotted it down and have not been able to let it go. At first it was the simple challenge of how do you do get adults to change their habits. But it quickly became a more fundamental question. If you cannot encourage individual change, how do you build organization capacity? How do you foster innovation? How do you encourage organizational development?

Individual ability and willingness to change is at the core of organizational change.

  • You can teach people new skills. But, they must be motivated to utilize the skills.
  • You can bring in new ideas. But, colleagues must have an open mind to consider and build the ideas.
  • You can introduce new ways of working. But, colleagues must be willing to try new activities, engagements and structures.

If individuals are not motivated to step out of their personal comfort or interest zone positive change rarely occurs.

So, how can you create space that encourages adults to change their ways?

In her book teaming, Amy Edmondson outlines the concept of a learning frame–an approach to work that aims to accomplish identified goals and simultaneously learn how to do the work better.  (Contrasted to an execution frame, an approach to work that focuses primarily on getting the work done.)

How you frame your efforts influences how others respond and engage. A learning frame encourages collective learning, collaboration, piloting to test new ideas and analysis to learn from the experiments and inform future efforts. It invites people to participate in the effort, values their contributions and cooperation, and encourages learning as a part of the experience. It can nurture their motivation and willingness to engage, learn and ultimately change.

So much of what we do in associations is cyclical–conference/ trade show planning cycle, membership renewal cycle, volunteer engagement campaign cycle. It can be really easy to fall in to a “get it done” attitude or an execution frame.

But, fostering a culture focused on a get it done/execution frame, can lead to an organization culture that views change as a negative experience to be avoided. This can encourage people to hold on to their ways, purposefully tear down new ideas or avoid any change.

If you are taking on a change initiative, would like to foster a culture more comfortable with change or want to enhance the capacity of your organization, consider how you frame your efforts.

  • How do you foster active engagement in work efforts?
  • How do you share goals and vision for efforts?
  • How do you encourage questions?
  • How do you create opportunities for people to share their insights?
  • How do you encourage collaboration?
  • How do you value team member contributions?
  • How do you encourage trying new ideas or steps?
  • How do you acknowledge mistakes and openly discuss what can be learned from them?

How you lead impacts how your team engages at work.

If you have not read Teaming by Amy Edmondson I encourage you to pick up a copy.  It is a great resource for leading teams, change and organizations.

*The question came from a smartly titled post Transforming Culture is Simple: All It Takes Is Changing People by Dr. Larry Senn on


Does your team inspire a following?

Service, innovative programs, community, comfort, ease…the reasons why people engage with your organization vary from person to person. So how do you keep up?

Creating products, services and ultimately a culture that inspire people to engage with your organization takes effort and perseverance.  How do you keep building, serving and facilitating in ways that inspire people to return to your organization?

This type of sustained effort requires teams that get it. You need teams that understand your organization’s purpose, what you are striving to achieve and who you are trying to serve. It requires people who are motivated and enthusiastic about building your success.

Motivated, engaged and enthusiastic teams don’t just happen. The good teams you’ve been a part of, the ones where people share their honest perspectives and “crazy” ideas, disagree respectfully, support each other, and genuinely collaborate. Those teams were fostered.

With the hectic pace of association life we can be tempted to invite people to a conference room or a conference call or assign them a desk in a “collaboratively designed” space and expect teamwork to happen. This rarely results in engaged and successful teams.

If you want a team that: strives to create the best opportunities and resources, provides stellar service and genuinely cares for your members you need to invest in building your team.

As Hank Fortener explains “the people are the work” (How to Build Teams That Won’t Fail Each Other).  Investing time and energy in building your team will reap benefits for you, your team and your organization.

So how do you start or build up your current efforts? Here are a few key things to consider.

Engage with your team
There is a lot of talk about engaged employees. But strong teams also require engaged leaders. Your people need to see you. They need to hear from you, they need to know that you care and understand, they need to know that you get it.

A simple way to build engagement is asking questions that encourage staff to share their ideas, perspectives and concerns with you.
• How do you think we could …?
• What do you need to make this a success?
• Why is this important to you?

Stephen Covey said it best, “listen with the intent to understand, not the intent to reply.”  Listen to what people are telling you. Be open to what they are saying. Ask questions. Listen to what is going on around you – in your organization, in your member’s organizations in the broader community. Make time to listen and take in what is being said and not said.

To focus your attention on listening, I recommend keeping a list of questions in your notebook or electronic device that you can pose to build discussions.
• Why do you think this did or did not work the way we expected?
• What do you think we could do to make ___ better?
• What might slow down our efforts?

Communicate with your team
Communication is a tool for building understanding and engagement – yours and your teams. Good communication requires asking questions, listening and ensuring that your people understand the message you are trying to share. As the Greek philosopher Epictetus said, “we have two ears and one mouth so that we can listen twice as much as we speak.” Good communication is a form of engagement.

Try asking simple questions to gauge your team’s comfort, interest and understanding • How could we improve this plan/idea?
• If you were leading the group, what two things would you do next?
• Can you help me to understand…(your concern, the challenge, the opportunity, etc)?

Good teams require engagement yours and your colleagues. Show that you care and your colleagues will be more likely to invest their time and effort.

Here are a few resources to help you develop your team focus.
HBR Blog: Three Ways To Encourage Smarter Teamwork

Talking Point: Four Ways To Demonstrate Genuine Care

Four Ways to Instill and Promote Transparency at Work

The Question Project

They can’t read your mind!

If you want people to support your efforts and help you move toward success they  need to know what you are trying to achieve.

Not how to do it. They can figure that out.

What are you trying to accomplish? Why are you trying to accomplish it? What challenges might you run in to?

Don’t assume they know or they get it. We are all busy with our own jobs and sometimes the big picture stuff can get lost or distorted along the way.

Inform them. Inspire them. Invite them to be part of the team that builds your next success.

Taking the time to engage your team, to help them understand what you are trying to accomplish and why it is important can help them get behind the effort.

If you still think they know what you want, ask. Then stop talking and listen.

  • Does your team know why your organization exists or why the project is critical?
  • Do they understand the strategic challenges you are facing this year or expect next year?
  • Do they know the project goals?
  • Do they know who the target market is and why?

Save yourself and your team the frustration and headache. Talk with them. Engage them in discussion about who your organization is – what’s your purpose, goals, challenges, opportunities. Help them to be part of your success.

Lining up to Fail?

No one aspires to fail.  Most people would prefer their name not be included in the story explaining a failure.

But, if you want to design new experiences, a unique product or a better way of working, failure is a reality.  Trying something new or different will inevitably result in missteps, challenges and failure.

You can play it safe and try to avoid failures by staying in the protected known space.  Or you can influence the kind of failures that might occur and how you and your organization respond to them.

In her book teaming*, Amy Edmondson identifies three types of failure:

  • Preventable failures – Failure in routine operations typically resulting from a deviation in process in a well understood activity.
  • Complex failures – Failure in complex operations typically resulting from a breakdown in a process or system (can occur when a task is too difficult or process is composed of many elements that can break down when a novel situation is encountered).
  • Intelligent failures – Failure in innovative operations typically resulting in areas where knowledge is less developed, experiments must be run to test ideas and gain new knowledge.

The idea of a continuum of failure can make it a lot easier to discuss failure and intelligent risk taking in your organization.  The categories make it clear that not all failures are the same.  Some should absolutely be avoided, but some failures are a key component of learning and developing expertise.

Preventable failures are the kind that occur in everyday activities – typos in member communications, oversights in scheduling and prepping for meetings, etc.  These generally happen when people are in a hurry or do not have the skills or insight to correctly execute an action.  These are avoidable.

Complex failures tend to happen when systems get so complicated and dense that one missed entry or oversight can result in a system not working.  These happen as we add steps, requirements or activities to systems (approval processes, meeting development, AMS systems, etc) and at some point they breakdown under the sheer weight of it all.  These failures we can work on, we can review systems to ensure they are manageable and that we have appropriate project management.

Intelligent failures occur when you step outside of your mastery space and innovate.  These happen when we test new ideas, when we experiment with new models or products.  These are smart failures.  Managed correctly these are the ones that can help you innovate and succeed.

You want to avoid preventative failures and even complex failures.  However, these will occasionally occur and how you respond to the situations impacts what people will be willing to take on.  A few things for you to consider:

  • Do you embrace the messenger?  You want people to identify problems that they see, so make it ok even expected that staff identify problems/challenges.
  • How do you encourage discussion? If you create space to question and discuss ideas, challenges and risk and listen you can learn from situations (and even identify issues before they become big problems).

Failure free is absolutely crucial in some industries – bridge construction, airplane building come to mind.  But, in associations we typically have wiggle room.  Experimenting and trying new things helps us to remain relevant, keep members engaged and attract smart staff.

Unfortunately, risk taking and failing aren’t openly embraced and celebrated in most organizations.  But these are critical considerations for leading associations in the competitive and evolving space we operate it.

So what can you do to encourage intelligent risk taking?  One of the first steps is fostering an environment that encourages smart risk exploration.  Here are a few things for you to consider:

  • How do your leaders encourage experimenting?  How do leaders encourage people to take on new/innovative activities?  How do you engage people in the desired activities and discussions? How do leaders step out of their comfort zone?
  • What are the perceived consequences of failure in your organization?  How do leaders respond?  How do colleagues respond?  What is the next assignment for the staff involved?  How do you talk about failures?
  • What do you reward?  Do you talk about small wins or only spectacular splashes? Do you celebrate people trying something new (even if it didn’t work just as you planned)?  Do you recognize people for making a difference for a member?

No one wants to fail.  But it happens.  So, create a place where failures are taken in stride, learned from and built on and you will likely find success and people who are willing to journey with you.

“To avoid failure is to limit accomplishment.” ~ Will Rogers

*teaming is a wonderful book exploring how organizations learn and innovate. I highly recommend checking it out.

Are You Leading (with your questions)?

“How did you guys enjoy that?”  I overheard someone pose this question and had to laugh.  How do you respond to this?  “No, we didn’t enjoy it.” That is clearly not the response he was expecting or likely seeking.

I admit I am guilty of using leading questions. “Did you love it?” or “Isn’t he great?” When you are excited or have an opinion, it can be challenging to set aside your perspective and objectively inquire about someone else’s views.

How you frame questions influences how people engage and respond.  Your words can invite people to participate in the discussion – “What do you think about …?” and encourage them to share their perspectives – “Can you describe how that could work?”

Leading questions are framed to guide people to a particular response or way of thinking. Instead of asking about an individual’s experience or their opinion your word choice guides them to an answer. This can happen in several ways:

  • Adding a personal appeal of agreement. “The new session format is the best we’ve tried, don’t you think?” or “This is the worst program we’ve ever offered, isn’t it?”
  • Using an assumption. “Do you think Tim’s team will fail to meet the deadline again?”
  • Phrasing the question so that the easiest response is yes. “Shall we all approve the revised publication proposal?”

Consider the questions you ask for the next 24 hours. If you find that you use leading questions set aside 15 minutes a day to frame questions to use in your discussions and meetings. The more you practice good questioning, the easier it becomes.

Visit The Question Project for sample questions and resources to support your questioning.

“Successful people ask better questions, and as a result they get better answers.” ~ Anthony Robbins

“A question is the most powerful force in the world”*

The google app questions commercial is one of my favorite things lately. I love the simple way it highlights the power of question. “A question can start you on an adventure.”

I also appreciate how it showcases the types of questions well suited for a google search– where is…, how do you say… what is the going rate… questions that typically have one correct response.

Google has transformed how we explore – “I googled it.”  But, when it comes to the complex questions we deal with in our organizations there is rarely one correct response.

Most of the challenges we experience have several potential solutions, some we are aware of, some we aren’t. To learn about our options, investigate the potential and select the best opportunity for our organization we need to engage people.

Successfully engaging people requires good questioning and listening.  You need engaging questions that inspire, challenge and invite people to explore with you.

We all keep crazy schedules, so if you are going to ask people to work with you, make the best use of the time, their expertise and experience. Ask good questions.  Here are a few questions that can help you get started.

  • What do we need to achieve…?
  • How might we…?
  • Why do we need to take this on now?
  • What needs to be true in order for the idea to be successful?
  • What patterns are we stuck in?

Yes, there will be times when it seems that figuring it out yourself would be a whole lot easier.  But, do you really have all the knowledge and insights you need to successfully develop and implement the idea? If not, you will be better served by engaging colleagues, learning along the way and building a team that supports the effort.

“The right questions will empower everyone to think in new ways.” ~Krista Brookman, in How To Ask Better Questions, Fast Company

*google app questions commercial

Invite People to Think

Googling a question may be the quickest way to get an answer, but is it the best way?

If you want to explore a topic, google can help.  If you enter the correct words you can review hundreds or thousands of possibly relevant hits.

But, exploring a challenge with people, even if you don’t use the correct words, can enhance everyone’s knowledge, inspire ideas, open up new opportunities and invite others to support the effort.

Open ended questions help you explore. What, why, how, or tell me about questions invite people to think, to share their insights and expertise, and generate fresh ideas and solutions.  Consider these:

  • What do we know about …?
  • How could we…?
  • Why does this need to work?

Asking closed questions – is, are, will, would, or should questions – generally results in a yes or no response encouraging little or no discussion.

  • Is there a market for this product? (versus What do we know about the potential market?)
  • Are you pleased with the membership drive results so far? (Versus Why do you think the membership drive generated the initial results?)

By asking questions you can encourage an environment that engages people, inspires them to think and encourages them to share their ideas. Isn’t this the kind of place you want to work?

“When faced with a challenge, get smarter.” ~Ed Catmull, Creativity Inc.

Do Your Questions Invite People to Participate?

Engagement seems to be one of the hot topics in business lately. The reasons why it is important are everywhere, but how do you do it?  How do you help people participate? How do you help them become part of the effort?

A key step is asking questions that invite people to participate. Posing good questions can help you engage your team, develop shared perspectives and collective goals, inspire future possibilities and inform smart decision making.

Start with engaging questions.  Pose questions that ask and inspire people to explore their insights and share their perspectives. Engaging questions can foster energy by inviting people to participate, focusing on what is working and what can be achieved.

Here are a few questions to help you get started.

  • Why is this important to you?
  • What information, if you had it, could help develop the solution?
  • What is holding us back on this effort?
  • What have we accomplished so far that is supporting our success?

There’s a great HBR blog post today, Make it OK For Employees to Challenge Your Ideas, that highlights the value of asking questions and listening. If you are going to ask a question, be sure you are really ready to listen.

Have a favorite question, please share it.  Building a question bank is key to becoming a strong questioner.