C-Suite Strategies Part II: Power Questions for Top Executives

By Andrew Sobel

Welcome to Part II of my special, four-part series on building relationships in the C-suite. (Part I, Adopt the Executive Mindset and Gain Access, is available here). I’m sharing this series to inaugurate the release of my popular eLearning program, Building Your Clients for Life, to individual users (see more below).

A single, trusted relationship with an ambitious top executive can supercharge your business growth. However, these are hard connections to build. C-suite leaders are besieged daily by people who want to sell them something, influence them, or obtain a favor. If you become skilled at using good questions, however, you’ll stand out from the crowd.

Why questions are especially important in building C-Suite relationships

For the most part, senior executives are bright, experienced, and capable. They know their company and their industry well. Consequently, your ability to tell them something they’ve never heard of, or thought about before, is limited.

Where you can consistently shine, however, regardless of your age or experience, is in asking thought-provoking questions that help your client improve their understanding of the challenges they face. So let’s look at techniques to hone and sharpen your ability to use what I call “Power Questions.”

What are power questions?

Power questions are open-ended. They help elevate your conversation to higher-level strategy and goals. They uncover root causes. They can refocus the conversation on the most important issues. They reveal deep, personal knowledge. They engage the other person by making them reflect and, sometimes, self-assess. They are, at their best, surprising.

Conversely: Avoid using questions that are closed-ended (“Are you worried about the new digital platform?”), cliched, stale, and overused.

Let’s look at some different types of power questions you can use with more senior executives:

Aspiration/Gap Questions

You can employ different variations of these three questions to explore a client’s aspirations in a very engaging manner:

  • “What are your aspirations for…?” (“What would you like your business to look like in two or three years?”)
  • “What is the gap between where you are today and where you’d like to be?” (“What’s getting in the way of reaching that aspiration?”)
  • “What capabilities do you need to put in place to support your vision and strategy?”

Framing/Reframing Questions

With junior managers you may focus more on problem solving. With senior executives, however, you need to focus first on issue framing, which uses divergent rather than convergent thinking. You can frame/reframe by exploring four main areas:

  • Explore Strategy: “What are the main strategies or business drivers that this initiative supports?”
  • Explore Enterprise-Wide Implications: “What are the interdependencies that have to be taken into account?”
  • Explore Implementation: “Who are key stakeholders who need to be involved in implementation?”
  • Explore Change Management: “How will this program be managed?” (“What changes in people skills and behaviors do you think need to take place?”)

Agenda Sensing Questions

These are questions designed to tease out an executive’s most important priorities, needs, or goals. Often you need to ask indirect agenda sensing questions (“How are your investment priorities being impacted by X?” or “How are you reacting to Y?”). Sometimes I ask, “Of the various initiatives you have in place, which ones are you investing your personal time and attention in?”

Personal Questions

These help you learn more about your client as a person. For example: “How did you get your start?” or “I’m curious, what was your biggest learning experience as a leader?”

Challenge Questions

Very few people will challenge a senior executive. Ask, “How did you decide on that as a goal?” –perhaps adding, “Some of my clients have reached X%”

Pitfalls to Avoid

  • Lacking confidence when you ask your questions
  • Using too many questions, which is tedious
  • Not paying attention to the answers you get
  • Asking leading questions that try to steer the other person
  • Asking clichéd, overused questions like, “What keeps you up at night?”
  • Sounding mechanical and canned, as though reading from a list

Two weeks from now, in Part III of this series, I’ll share strategies for adding massive “value for time” in your meetings with senior executives. Keep an eye out for it in your inbox.


Just released: my Building Your Clients for Life digital learning program.

I’m finally releasing my acclaimed eLearning program, Building Your Clients for Life, to individual users. Until now, only my major corporate clients, which include many top professional service firms and financial institutions, had access to this program. They have found it so useful they’ve put thousands of their professionals through it.

To inaugurate the launch, for a short period I’m giving my subscribers like you a very special discount—1/3 off the normal price of the course. Just use the discount code subscriber when you check out, instead of the code mentioned on the site.

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At the beginning I was skeptical—will this really work for me? But I found that the format, with short lessons backed up by the workbook, is great. The frameworks are very practical and supported with real examples. I’ve already implemented quite a few of the ideas with my clients.

Maria, course participant

I’ve also produced a short video, here, that gives you an overview of the program.

I encourage you to check out this unique program and take advantage of the one-third off deal—remember to use the code subscriber at checkout. BTW: as a special bonus, in addition to the course itself you’ll get to participate in two live Q&A calls with me. Review the program here. I hope to see you there!

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