Superior Leaders Ask the Tough Questions | TechWell

Superior Leaders Ask the Tough Questions

Leader asking an employee a question

During my career in the military and private sectors, I’ve worked with many leaders—some great, some good, some poor. Great leaders sometimes say inspiring things that are quoted with respect and admiration:

“Ask not what your country can do for you—ask what you can do for your country.” —John F. Kennedy

“I have a dream that one day this nation will rise up, live out the true meaning of its creed: ‘We hold these truths to be self-evident, that all men are created equal.’” —Martin Luther King Jr.

“If loss makes you doubt your belief in justice, then you never truly believed in justice at all.” —Wonder Woman

However, promoting inspiring quotes may do leadership a disservice and make it challenging for up and coming leaders who feel compelled to find clever and memorable things to say. In reality, they should probably focus less on what they’re saying and more on what they’re hearing.

The best leaders I have known listen a lot and ask good questions. Their wisdom comes from experience, and from providing those around them with a context where they can safely speak so the leaders can absorb and reflect on what they say.

These are some good questions I’ve heard leaders ask project managers and product owners:

  • How is team morale? Is there anything I can do to help?
  • Do you have what you need from me to be successful? What else could I provide?
  • What assumptions are we making?
  • What priorities are you working with?
  • What do you think constitutes success for this effort?
  • What risks has the team identified?
  • How confident are you with the estimate? When will you know more?
  • What are the next significant milestones or checkpoints in the schedule?
  • What can I do to make things go more smoothly?
  • What risks are keeping you up at night?
  • What should I be worrying about?
  • What are the advantages, disadvantages, and risks of this approach versus the others you have considered?

An interesting thing about these questions is that they invite conversation. They aren’t yes-or-no questions; they defy single-word answers.

Good leaders also pay attention to context. Asking open-ended questions like the ones above in a room full of people is less likely to generate candid answers than having these conversations in small groups or one-on-one. The best leaders make opportunities to discuss these things with their lieutenants regularly over lunch or coffee. (This is in addition to, not instead of, regular status reporting.)

To get the candor they need, good leaders must be open to disappointing news. Shooting the messenger doesn’t stop bad things from happening; it merely discourages people from sharing bad news promptly.

Good leaders also must have realistic expectations. They don’t expect that things are always going to go well, they forgive honest mistakes, and they build relationships that enable frank assessments and sharing of fears, risks, and uncertainty.

Leadership is more than generating memorable quotes. It is creating an environment where problems can be raised, discussed, and addressed promptly. To do that, effective leaders model the behavior they seek by soliciting candid assessments of the situation from people on the ground, and giving those people every opportunity to be forthcoming with no reason to fear retribution.

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