Five Vital Leadership Questions

Some managers believe that their job is to have the answers. Indeed, it is the job for a number of corporate positions. But those in leadership positions also need to ask questions.

A recent Harvard Business Review piece observed that the questions corporate leaders ask should be structured like those great teachers ask.

What are they?

First, they are open-ended, so they go beyond quick requests for data, like “what’s our headcount” or “what were revenues in Q1.”

Second, they are designed to fuel creativity and curiosity in solving organizational issues or taking them to a higher level. At their best, they can inspire a rethinking of procedures, products, and structures. They can also uncover assumptions that impede progress. They can protect against the making of decisions that aren’t optimal.

So what are the business strategy questions that should be asked?

  1. “Wait, what?”

The HBR article cites this as a question that requires slowing down and investigating a proposal or procedure in more detail. The structure of many proposals too often includes a limited amount of data, followed by a thumbs up or thumbs down from leadership. But making decisions without thinking through context and assumptions can be dangerous. “Wait, what?” allows for more time to assess all aspects of a project.

  1. “I wonder why” or “I wonder if”

This can be valuable when new proposals hit resistance or roadblocks. If the answer to a question is, for example, “That’s the way we do it” or “That’s procedure,” it’s an indication that innovative products or processes might be stymied. “I wonder if we could use a new procedure?” opens the door to dissolving those roadblocks by asking involved parties to genuinely ponder if a given innovative step could work. The open-ended structure invites involvement, engagement, and mutual thought.

Questions can spark strategic thinking.

  1. “Couldn’t we at least…?” 

This question is particularly useful if divisions or managers are at loggerheads or at opposite ends of a spectrum about how to enact a desire goal. You need some way of achieving a workable consensus. One way may be to ask this question. Could your team at least agree on initial steps and a re-evaluation later, for example? Could preliminary goals be hammered out, with the understanding that revisiting those goals might well occur?

  1. “How can I help?”

If a leader encounters a subordinate or colleague in a challenging position, they might have a desire to rush in with a fix — or provide advice. A better method might be to ask an open-ended question that allows the person to pause and think about the kind of help that might work to meet the challenge.

  1. “What truly matters?”

This is a long-term question that allows a periodic think-through of overall goals and how they comport with company mission and vision. This question may defer some decisions indefinitely. It may also open the door for important ancillary questions, like ones that address the alignment of personal beliefs and goals with company ones.

While many leaders assume their role is to supply answers — and it is — it is equally important to provide questions that spur deeper thought that leads to more eloquent solutions.