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Questions and Team Building

Question and Team BuildingAn army of one isn’t really much of an army is it? And I can assure you that any CEO who views him/herself as an army of one will fail. Whether you like it or not, your success as a CEO will be largely tied to your team building ability. Not only do great CEOs understand how to recruit a top executive team, but they also understand how to build cohesion among team members through collaboration while addressing specific situational and contextual needs. Great CEOs realize the importance of being consistently, purposefully and intensely engaged with their CXOs. They understand how to effectively deploy these highly productive and valuable team members to create tremendous leverage and velocity across the enterprise. In today’s post I’ll share the questions that great CEOs use to align the interests and focus the efforts of their executive team…

It is not uncommon when working with new clients that I find very fractured executive teams where team members more frequently work against one another, rather than with one another (see “Managing Tough Relationships“). I often observe ego centered conflicts among senior executives, which turn into a competition for turf, budget, power, influence, control, and ultimately survival. As a CEO you can either pit your executives against one another, or have them collaboratively engage in supporting one another for the overall good of the enterprise. An executive team that actually embraces the concept of collaboration will substantially out perform a silo-centric executive team focused on empire building.

Great CEOs not only view their interactions with team members as coaching and mentoring opportunities, but also as learning opportunities for themselves. If as a leader you don’t take the time to get to know your team members on a very personal basis you simply won’t build the trust necessary to successfully weather the seasons of leadership. Because all leaders face good times and bad, it is essential that strong, caring, and loyal relationships are established so that candor and collaboration can occur irrespective of the situation at hand.

I read a great post yesterday by Dan Rockwell (@LeadershipFreak) in which he asked: “what’s the most powerful question of all?” My belief is that there is no perfect question, just the right question for the moment. The comment I left on Dan’s post was as follows:

“Thought provoking post to be sure…However my belief is that the most powerful question of all is the one that works within the context of the situation at hand. The question must be appropriate to the person(s) being addressed, the timing must be spot-on, but most importantly it must unlock the door to reveal the needed input/feedback/information.

Relying on any single question to serve as the omnibus catch-all question is dangerous. I’m not sure what the most powerful question in the world is, but I know that the most powerful question of the moment changes frequently…”

Therefore in the text that follows I’ll provide you with a resource that is immediately actionable, and highly productive – a list of questions that can be used across situations, constituencies and reporting lines. I have found that one of the most effective ways for CEOs to lead their senior executives is by helping them refine and justify their reasoning through the use of intelligent questions. This serves to not only align interests and areas of focus, but also to facilitate the exchange of insights, and to acquire useful knowledge and information – it also builds stronger relationships. Contrary to the beliefs of some, dialog is a healthy thing. I strongly recommend to all CEOs that they routinely ask team members the following questions:

  • Why? (my personal favorite and the most powerful one word question on the planet)
  • How can I help you with that? What do you need from me in order to make that happen?
  • That’s an interesting thought, what process did you go through to reach that conclusion?
  • What’s our biggest risk in this, and what’s your fallback position?
  • What if we did nothing at all, what would happen?
  • Why is this important to you?
  • What does this accomplish for us?
  • If we fail in this can we live with that?
  • How does this add value to our <<fill in the blank>>?
  • Can you give me a bit more detail on the logic used to arrive at your <<costs, timing, return estimates, etc.>>?
  • How will this impact <<individual, team, business unit, competitive advantage, brand perception, customer satisfaction, etc.>>?
  • What are the greatest challenges you face in pulling this off, and how do you plan to deal with them?
  • Where do you see “X” account in <<insert time period>> and what can we do to (improve customer satisfaction, increase influence with key stakeholders, increase the life-cycle value,  etc.)?
  • Which markets, partners, clients, or other opportunities can add significant value to our business?
  • What specific steps can you take to increase your area’s contribution margin?
  • Does this add value to our core business? How? Why?
  • Does this effectively and efficiently support our values, vision, and strategy? How? Why?
  • What can you offer as validation of proof of concept?
  • What motivates <<insert person’s name>>? What’s really important to them?
  • What will be the key performance indicators for this? How will we measure them, and what hurdles do we need to hit to be successful?
  • Do you have the necessary resources (financial, technology, talent, infrastructure, etc.) to hit your objectives?
  • How can we improve the risk management, governance, control, and reporting functions for this?
  • Why should we make this investment? How does it drive revenue, profit, brand equity, competitive advantage, etc. What are the potential risks vs. possible rewards and what is the downside of not making the investment?
  • What are your biggest obstacles and barriers to success? What are your plans to deal with them and what do you need from me?
  • Are all your resources properly aligned and connected?
  • What are the weakest points in your area and how do you plan to deal with them?
  • Who are your strongest leaders and how are you developing them to handle more responsibility?
  • What are you doing to attract new talent?

While the aforementioned list of questions is clearly not exhaustive, it offers some insight into where a CEO should focus their efforts and attention…Perhaps best of all it places you in a constant position of being an active listener, learner, and mentor. If you have a favorite question(s) you use to focus and/or refine your team’s thinking that you’d like to share, please leave a comment below…

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    Rance Shuld

    September 22, 2010 at 9:06 am

    I appreciate the straight forward nature of your blog posts. They are both instructive and useful. Thanks for what you do.




      September 22, 2010 at 9:10 am

      Grateful for the kind words Rance – thanks for stopping by and taking the time to comment.



    September 22, 2010 at 10:28 am

    Thanks again Mike. Pasted the questions in my leaders file to pass on to my leadership team. You are always thorough and explicit. I appreciate you taking the time to write extensively than most bloggers. You are excellent at this.



      September 22, 2010 at 10:34 am

      Thanks for the kind words Tom. I hope the questions will be of use to you and your team. Have a great week Tom.


    Dan Rockwell

    September 22, 2010 at 10:56 am


    Thanks for the shout out and for this great post.

    I must confess that you beat me to the punch. I had intended to aggregate all the great questions in the comments from the blog I wrote and present them as a post. I still may, since your list includes many questions not already mentioned.

    I believe a question is more powerful than a statement. Thanks for this list of great questions.

    You have my best regards,

    Leadership Freak,
    Dan Rockwell



      September 22, 2010 at 11:06 am

      Hi Dan:

      I think it's a great idea to aggregate a list of useful questions as I by no means created an exhaustive list with this post. My guess is that the more people spend developing and sharing their questions, the more we'll all be surprised at the numerous things we should be asking that we're not. Thanks for stopping by Dan…


    Tanveer Naseer

    September 22, 2010 at 11:15 am

    Mike, I read Dan's piece and I likened his question to being a 'big-picture' focus one, akin to defining what's your true north on your compass. Of course, as you pointed out, relying on one question won't help you figure out how to navigate around obstacles that inevitably will appear in your path toward that defined true north.

    That's why I think it's good to have a few questions on hand to help define your direction, but then keep your eyes and ears open to figure out what other questions you will need to ask as you move forward to keep you on course to that true north revealed by answering Dan's question.



      September 22, 2010 at 11:24 am

      Agreed – I think Dan's question is a great one for your suggested purpose of finding "true north." Nothing bad ever comes from a leader keeping their focus on finding out how they can best serve others. Thanks for sharing your thoughts and observations Tanveer.


    Joe Rafter

    September 24, 2010 at 6:43 am

    Mike – Great post. I agree with your first question "why?". My days in technology have taught me that you frequently have to ask "why" up to 5 times before you REALLY get the answer. I suggest a book titled. "Asking the Right Questions: A Guide to Critical Thinking" by Neil Browne as an excellent reference.

    The value with asking the right questions at the right time is immense. My experience tells me that knowing what question to ask, when, and leaving your ego at the door (e.g. don't be afraid to ask a question for fear of sounding like you don't know what you are talking about) are key skills for any business leader from CxO through entry level employee.



      September 24, 2010 at 9:01 am

      Hi Joe:

      All great points and thanks for sharing the book recommendation as well. You point about separating ego and pride from the questioning process was also very astute. Thanks for stopping by Joe…


    Sean Glaze

    June 25, 2013 at 3:42 pm

    Hi Mike-

    Really enjoyed the post… and I agree that “your success as a CEO will be largely tied to your team building ability.” As team building and leadership both begin with building AWARENESS, I loved the list of questions you shared to consider –

    Thanks for the reminder to ask better and deeper questions to connect to those around us!

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