Critical Asking

Critical Asking Reduces AmbiguityA challenge of strategy execution is that visionary people (executives and managers) have visions, ideas, goals, and solutions; they need others to realize the benefits. Often, the tactical people react to the request with pushback: “That will never work. We don’t do it that way. We don’t have this. We don’t have that.”

For good reasons, much execution flounders because of a gap in communication. Both sides need to be grounded into reality. Martin Rupert, who works on strategic initiatives for a large confectionary company has a great technique for turning vision into action. Critical Asking helps to explore the assumptions, visions, and rationale from visionary and strategy requestors. The word “critical” is used in the sense of finding deeper truths, and not in the sense of being pessimistic. Its purpose is to bridge the gap between the expectations of requestor and those implementing the request. Martin tells us,

“If the communications and understanding of the strategy does not happen, the chances of success are slim.”

Funneling ambiguity into clarity

Strategy is inherently ambiguous. The word ambiguity means multiple meanings, which is to say that any given strategic situation makes sense to people in different ways. The job of the leader is to help others tolerate and work through the ambiguity.

Martin suggests that we picture the situation as funnel where the wide side opens into the haze of ambiguity. The technique involves iteratively meeting with requestors (visionary and strategy) and those “tactical” people who have to design a solution. Martin serves as an intermediary between the requestors and the delivery team.

Martin Rupert

Martin Rupert

Phase 1 – Clarifying the request

People who operate business units are on the front lines of interacting with customers and operations. They have many needs and are exposed to lots of suggestions for improving their business. Those solutions – and the underlying business needs — are often vaguely stated.

Martin starts off the critical asking process with open-ended questions, such as these:

“What are we going to do? What is the impact? What is the end goal? How do you see this working?”

Martin is searching for the “driver” for the need that reflects the strategy’s insight.  He often probes deeper:

“Why do you say this? Why do you believe this?”

His ultimate goal is to facilitate the vision by building a business case based on facts. He knows that eventually there will need to be a discussion and exploration of true financial benefits and costs. He also knows (from experience) that there can be a huge gap between the tactical people and the people with the vision.

He presses on with questions like the following two:

How will we know that we’ve been successful? Martin reports that, “You can see the gears turning in the requestor’s mind on what success looks like.”

What’s the financial benefit?

Phase 2 – Exposing the idea to implementation team members for critique

Martin then takes his understanding of the request to the implementation team. He overviews the request with them, explain the “what and the why” of the request. He then asks for reactions.  He finds that there are any number of issues related to resources, technology, process, regulations, system capabilities, funding. These issues will need further investigation.

As the implementation team understands the request and its rationale, they can better plan the needed project-level activities.

Phase 3 – Further resolving the ambiguity (shuttle diplomacy)

Phase 3 is a further iteration, where Martin shuttles back and forth between the requestor and the implementation team.  He says,

“Each time, you get a little more insight each side is seeing where the other is coming from.”

Phase 4 – Meeting of the Minds

At some point, Martin judges that both parties are ready to get together. Being the intermediary saves time and gets people to a common understanding more quickly. There is an agreed basis on the basic need, challenges, and issues. He reports,

“That is where you really start hitting the jackpot and making some progress.”

Martin acts as a mediator helping the participants see all sides of the issues.

Tough-minded mediation

Of course, Martin gets pushback on critical asking because he is taking valuable time.  People will ask him, “Why are you asking so many questions?” He responds,

“This is a calculated and disciplined process. If we do not get the ambiguities resolved, how will we know where we are going and how we will get there?” I am asking you indulge me and I believe you will see the results of this effort very shortly.

I asked Martin about his personality. He says,

“I have been labeled as the ‘strange guy’ and been told that I’m ‘a pain.’ That’s OK because I know the value of this process and what it can provide. Seeing results makes the effort worth the iterations again and again. I know we will make progress and the light bulbs will go off on both sides.”

Critical asking saves time, churn and frustration. How might you use it?

Note: Do you have an idea that you want to share with my readership? Contact me and we’ll discuss how to get it published.

Gregs new book available now


About Greg Githens

Author, How to Think Strategically (2019) Executive and leadership coach. Experience in driving change in Fortune 500 and mid-size companies through strategic initiatives and business transformation. Seminar leader and facilitator - high-impact results in crafting and delivering strategy, strategic initiatives, program management, innovation, project management, risk, and capturing customer requirements.
This entry was posted in Ambiguity and Strong-Minded Thinking, Competencies of Strategic Initiative Leaders, Strategy, Ambiguity, and Strong-Minded Thinking, Useful Practices & Management Tools. Bookmark the permalink.

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