5 Questions The Best CEOs Ask

Guest Post by Pam Fox Rollin

Originally posted on Open for Business

It’s not answers that separate the best CEOs from the rest. It’s questions.

From my perch facilitating executive meetings and coaching top teams, here are the questions that I hear from the most effective CEOs — the ones who actually get their organization to take smart and coordinated action — that I seldom see from the not-so-effective:

1.  What are we missing?

The best CEOs understand our human capacity to delude ourselves. They know everyone in the room — including the CEO — perceive the world through powerful filters. We bias our decisions toward recent conversations, opinions from people like us, cultural truisms, and conclusions that drive short-term incentives.

To reveal blind spots, the best CEOs ask questions like these:

• What’s the basis for your recommendation? How might this be wrong?
• What don’t we know about our customers?
• Who haven’t you talked with yet?
• What are we taking as fact, that probably isn’t?
• Who could give us a different view of this?

In my book, 42 Rules for Your New Leadership Role: The Manual They Didn’t Hand You When You Made VP, Director, or Manager, I talk about this as “healthy paranoia” — the practice of self-doubt that ultimately strengthens confidence in your decisions.

2.  Is there a radically simpler way to do this?

The biggest difference between my fast-growth clients and big corporate clients is how they charter action. The fast-growth companies know they have to keep it simple: one objective, a couple key metrics, one agile team with daily huddles, with simple tools for tracking progress. They know their CEO doesn’t care about pretty internal powerpoint decks, endless documentation, or a complete planning process and risk analysis before even launching a pilot.

What do your people think you want from them? Are you willing to discuss an initial rough design? Can you get the people in the room right now and make a decision versus two months of function-by-function turf-protecting analyses? Yes, some of my clients in highly regulated industries (healthcare, financial services, pharmaceuticals) have to slow down and complicate for risk-mitigation. Do you?

3.  How could we get even more value from this?

Most people think smaller than they could. No surprise here. Our brains evolved to seek to avoid danger over daring greatly. Plus, the previous organizations who trained your team members probably penalized unsuccessful experiments more than they rewarded high-potential possibilities.

Your company certainly has opportunities to expand into new markets, reach customers differently, build valuable alliances, and reinvent your supply chain. Yet, your team members may be too risk-averse, too specialized, or too overtasked to notice.

It’s up to you to think big. Or, more usefully, it’s up to you to be the sort of listener who can hear big ideas. And, you’ll have to ask.

4.  Who could lead this?

The least effective CEOs pile tasks onto a few “trusted” “go-to” team members. The best CEOs vigorously create more of these trustworthy leaders.

Here’s how:

• Instead of giving the next initiative to your go-to person, ask which junior team member could be developed by this assignment. Look especially for team members who are often overlooked (“too quiet”, “too young to be credible”, the one without the fancy degree). Invite an executive team member to commit to mentoring the junior team member to successful completion.
• Give an issue or market opportunity to a small, diverse team. Charter the team with a very clear picture of the outcome you’re looking for by when, and encourage the team to engage an internal or external coach to deepen their learning, so they each come out of the process more capable of leading future initiatives.

5.  How am I the problem?

No question more separates the leaders-who-scale from those limited by their egos. The best CEOs don’t try to sell a story that they’re infallible. They know that their power limits their ability to hear and sense what’s actually going on. And that often no one will tell them when they’re full of crap or getting in the way.

So the best leaders ask:

• How could I be more clear?
• What do you want (and not want) from me on this?
• I suspect there are a few things I don’t understand about how this works. What am I missing?

OK, you’ve invested a couple precious minutes in reading this. Now, what will you actually do differently?

Start by paying attention to what you’re asking, and make powerful questions part of your daily leadership practice.

Catch yourself when you drift into playing what Nilofer Merchant brilliantly calls “Chief of Answers.” Instead of training your team to come to you for answers, train them to ask useful questions and find their own answers. Your brain doesn’t scale. The only way to scale is to engage everyone else.

Pro-tip: ask your assistant, chief of staff, or exec team coach to jot down the questions you and your colleagues ask in key meetings. Review this at the end of a week… which questions opened up the most useful conversations? Who is a question-asking rock star and what can you learn from him or her? What kind of questions are missing, including the sort above? What do you intend to ask more during the next week?

Bottom line: If you want your company to produce better results, ask better questions.

Pam Fox Rollin coaches senior executives and top teams in Silicon Valley and globally. Many of her clients have been rockstars in their functions (marketing, technology, ops, finance) who now want to lead more broadly at C-levels. Her company, IdeaShape, also facilitates strategy sessions, business design and innovation retreats, culture development, leadership development cohorts, and teambuilding sometimes with Myers-Briggs and Enneagram for companies including Cisco, Genentech/Roche, LinkedIn, and Stanford Health Care. A Stanford MBA alum, she comes back to facilitate leadership programs and coach executive education. Pam is always up for a good conversation about what matters to you and your organization. You can follow Pam on Twitter or LinkedIn.