Do You Ask Strategic Questions?

October 16, 2015 Tammy Heermann

A number of years ago I did my first 360 assessment.  Ugh.  Do you remember the good, the bad and the ugly of your first 360?  Actually it turned out to be the kick in the pants I needed to propel my career. It also kick started my fascination with perceptions around strategic capability. 

I reviewed the results of my assessment with one of our coaches.  We agreed that the result around being perceived as more tactical versus strategic, was a barrier to taking on more senior roles.  Needless to say I was all in to changing this view.  But where was I to begin? 

“If you want to be perceived as more strategic, start by asking different questions in your meetings,” said the coach. I chuckled. How could something so simple, really change perceptions around how strategic others thought I was?  But I was game to give it a try.

Soon after I was invited to a management meeting. I wasn’t part of the management team at that time. I was brought in as one of the subject matter experts. There was a point in the meeting I still remember today. It was both uncomfortable and joyous. We were talking about changing buying behaviours and other market challenges in preface to a strategy review. Something during the conversation was bugging me and I thought it was a good time to try the new strategic questioning advice suggested by the coach. “I’m concerned about how we’re talking about the buying behaviour of our customers. If we believe this is an enduring trend, how are we reshaping our solutions or messaging to address our customer’s emerging needs?” The room went silent. Everyone just stared.  My face turned red and I thought, ‘what have I done?’ In fact, I asked a good question. A question that got everyone thinking in a new way. So I tried a few more. After that meeting, I was invited to subsequent management meetings because I was perceived as adding value – broader strategic thinking value.

Turns out the coach gave me a good starting point. Most people don’t give much thought to the type of questions they ask. We lob out the 5 W’s with reckless abandon. Carefully crafted questions can have the benefit of showing others how you are thinking about the business, about issues and opportunities. They also allow for richer dialogue and less defensiveness. Below are types of questions that will demonstrate to others your strategic capability. 

  • Connection Questions: These questions show that you get the link between things. After all, these intersection points are where things get messy. Connection questions may also serve to bring attention back to the core purpose of the conversation. We get so engrained in execution mode or fighting over whose idea is best, we forget about what we are actually trying to solve for. How might this connect to what <insert person, project, business line, competitor> is doing around this? What outcomes are we trying to achieve? How does this connect to our goals? How does our current conversation relate to what we’ve been asked to do?  While the last two seem so simple, they are a gold mine for pulling rat-holed conversations back up to the higher level goal.
  • Impact Questions: These questions are useful in identifying what the consequences of a course of action will have.  They are also useful for identifying what has not yet been thought through.  Essentially they aid in risk mitigation.  What are the implications of choosing x over y?  How will this decision influence these stakeholders or our intended outcomes? Impact questions show that you’re able to think longer term about the positive and negative repercussions of various decisions. 
  • Tension Questions: These questions show that you understand the complexities and the natural opposing pressures inherent in business. I was recently with a group of high potential women from a global organization. As a kick off to the program an executive spent the morning with the group reviewing the new strategic priorities, sharing his leadership story, and leading a Q&A session. During the Q&A a variety of questions were asked. I paid attention to the types of questions the women asked and the impact it had on the executive. “In your experience, how will we gain the advantage of centralization and the consistencies and efficiencies it affords, with the local market tailoring that our customers demand?”  The executive literally guffawed and said, “Well that’s the million dollar question, isn’t it?” He was visibly impressed. She had succinctly summed up his entire presentation and the mandate for his role. She demonstrated her understanding of the inherent tensions, and the delicate balance their strategy hinged on. Her question stood out in spades in comparison to the questions asked by the others. It showed real strategic acumen.

Asking questions in a new way isn’t the only thing that will increase the perception of your strategic capability.  But it’s a good place to start. Frame your question with a concise statement that shows you have some insight, are making connections, and understand the complicated implications of business decisions.

Contact us to learn more about how we can help your organization achieve its business goals!

About the Author

Tammy Heermann

Tammy Heermann is Senior Vice President, Leadership Transformation with Lee Hecht Harrison. Helping organizations get serious about leadership, she is specifically sought out for her expertise in gender diversity and accelerating female talent.

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