Getting Better at Getting Better: The Questions to Ask

Guest blogger Jeffrey Cufaude, Idea Architects, shares a question framework to help you design smart discussions to explore the critical questions associations should be considering.

beautiful question JCufaude

Based on my facilitation experiences, a question that might serve as a catalyst for change as Warren Berger suggests requires clarity.

Without creating the requisite clarity at a conversation’s onset, discussions are unproductive and participants leave frustrated.

This happens quite often in strategy or planning conversations, be they among staff, board members, or volunteer entities.

We regularly lack clarity about:

  • the problem or opportunity we hope to address;
  • its relevant historical background;
  • current data and future forecasts;
  • how analogous industries have addressed it; as well as
  • the results we want to achieve, the timeframe in which we expect to do so, and the resources that doing so requires.

We’ll never leverage the ideas and insights of the thinkers we convene if so much is left ambiguous or to individuals’ perspectives and personalities. Individual brainpower ends up splintered and fragmented among a variety of issues, rather than the people working in parallel to dig deep into common considerations.

Here is a cascading or scaffolding series of questions to help avoid this.

  • What do we want to make better?
  • Why do we want to do so?
  • For whom do we want to make this better?
  • How do they define better?
  • How can past efforts, current data, and future forecasts inform our efforts to make this better as just defined?
  • What might we learn from how others (even outside our field) have addressed comparable issues and intentions?
  • In what tangible ways/metrics will better show up and on what timetable?
  • To achieve these results, what resources will be required and what might we need to stop doing, start doing, or do differently?

Used consistently, this question framework should help you get better at making things better.

What else would you add to this list?

Learn more about Jeffrey Cufaude his fabulous ideas and work at or  @jcufaude


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.

“When the map and terrain differ, the terrain wins.”

If you have ever worked with kids, you know the truth in this statement.  The best laid plans can go out the window in a matter of seconds and you need to figure out how to take the next step quickly, before chaos ensues.

The same is true for associations.  We can create beautiful maps of our plans, but if the environment differs from what we imagined the real terrain will win.

Organizations must be flexible enough to navigate the environment and strong enough to devise and execute a change in plans. This requires:

  • Space for people to think and explore (to be aware of their surroundings)
  • People with the skills and mindsets to identify challenges and devise and champion ideas to address the opportunities and challenges
  • Organizational capability to adopt and execute a change in course

These will help you avoid the unexpected mountain or crevice.

How do you create a culture for innovation?

I spend a lot of time talking with people about how they can foster a culture for innovation – how they can structure and align resources and support to encourage innovation in their team.  And I am regularly surprised at the lack of awareness or disregard for dealing with culture issues.

So when I came across Tom Agan’s CEOs as “innovation organizer” concept (HBR Blog: Can’t Find a Steve Jobs?  Hire an Innovation Organizer Instead) I was intrigued.  He claims that executives should serve as innovation organizers that create “environments ripe for innovation.” Makes sense to me, an exec’s job is not to do all the work, but to foster a space where the work can be done.  Right?

So if, you wanted to encourage an environment or culture supportive of innovation, what things could you consider?

1.What do you reward (with compensation, recognition, promotions, etc)?

  • no changes –  just follow the plan
  • small steps – things members ask for or other groups are offering
  • listening to member needs or market trends and developing new ideas
  • partnering with other groups on new ideas

2. Do you acknowledge what staff attempt to do (pilots or new activities)?  (It is a lot easier to do the same old thing than to develop a new way to try something.)

3. Does your team have the skills they need to innovate (facilitation, collaboration, decision making, etc)?

Are you ready for Bold?

How can we do something so big others will have to follow? 

I like this question, it’s a little cheeky.  But, it opens the door to a space many of us don’t venture into…“how can we do something?” not “what should we do?”

How can we make a bold move? In my experience associations don’t embrace this question. We tend to take incremental steps.  While I am a proponent of using small steps to build your innovation culture, capacity and comfort, sometimes bold is the right move.   

Have you considered how can you build your organization capacity for greatness? 

  • How can you ignite your team?
  • What expertise can you leverage?
  • What should you get rid of?

Where is the Fault?

“Which suffers more breakdowns – our products, our process or our people?  Why?”  (Kill the Company by Lisa Bodell).  Most of us have an opinion about what doesn’t work in our organization. But, do you know what your members think? Do you know what your partners think?  Have you ever asked them?

For many years I asked members questions about my association, our products, services, etc. But, I never used this language. I like how it brings these three components together. Sometimes we forget that all three impact people’s experiences with the organization.  You can create the most amazing Conference/Show, but if registration process requires jumping through four hoops or your staff are challenging to work with, members and prospective members might never make it to your meeting.   

Experiences with all three – products, processes and people- impact member experience. Do you know where the faults are in your system? 

Where are you stuck?

A favorite question to pose when I start a project is “What patterns are we stuck in?”  Some people will look at me quite confused, like they have no idea what I am asking them to consider.  So I ask a follow up question(s):

  • Who did you invite to participate in this project, and why? (Who was in your last project?  Why?)
  • Why are we meeting in this space?
  • Do you engage people outside of your industry/profession in exploring the ­­__ (need, idea, challenge/opportunity)?
  • What are your assumptions about ___ (how your market accesses information, how people view your association, how your teams work together, how members want to engage with you, etc)?

Many projects falter because people hold assumptions that simply aren’t true.  Recognizing your personal/group assumptions is a great step to helping you move beyond them.

“He who asks a question is a fool for five minutes; he who does not ask a question remains a fool forever.” – Chinese proverb

Simple is a Great Place to Start

The power of simple questions is astonishing. How might we…?” is a great example. There is no jargon to confuse people, no judgment to discourage, just a straightforward question to engage your team.

In his HBR Blog post “The Secret Phrase Top Innovators Use” (Sept 17, 2012) Warren Berger noted that many successful companies have taken on difficult challenges by simply asking their team, “how might we…” improve X, re-imagine Y, or find a new way to engage Z?

“How might we…?” challenges your team to imagine, think and explore.  It will likely inspire them more than the other phrases we hear in exploration/brainstorming discussions… “we’ve tried that” or “we’ve always done it this way.”  So, how might you engage your team today? 

Applying innovation in associations

One of the gaps I’ve noticed in discussions about innovation is an understanding that innovation can also be applied internally, within an association. We are all aware that you can focus innovation externally to develop new products and services for members and other stakeholders. External innovation can include new or enhanced products and services, how the product/service is delivered or experienced. These types of innovation are generally what people are referring to when they discuss innovation.

But innovation can also be applied internally. Internal innovation focuses on how your association is structured, your business model or how you operate. This is key for associations. Internal innovation can include how your organization facilitates and engages committees, how employees engage and collaborate, how people raise/explore challenges, the organization structure (siloed, flat, etc.).  Internal innovation focus can help you strengthen your organization.

The two are not mutually exclusive. In fact, I think associations would be more successful with product and service innovation if they also considered internal innovation. Simply layering an innovation management process over your current association operations doesn’t guarantee that your team will effectively engage in innovation.

Organizations need a culture and leadership that are supportive of innovation if they expect staff to engage. Here are a few things to consider as you contemplate focusing on innovation in your organization:

  • Does your association have a working environment that is respectful, inclusive, diverse and motivational?
  • Does your organization culture encourage people to question established ways of doing things?
  • Do you have structures/processes (formal or informal) for people to bring forward questions and concerns, without fear of ridicule or backlash?
  • Do your staff collaborate with each other?
  • Are knowledge and information openly shared among staff and departments?
  • Does your organization accept failures, learn from them and discuss the insights?

If you responded “no,” “I don’t know,” or “maybe” to any of these questions, I would caution you to consider how you can build your innovation capacity and internal innovation focus before you jump into external product and service innovation. You might first want to consider if your staff are ready to step out of their comfort zone and try something new.